Vacation rentals in Anna Maria Island, FL with a pool

Explore 394 vacation rentals, homes, and villas with pools in Anna Maria Island, FL for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Air Condition Homes, Homes with Free Parking and Best Affordable Homes. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $51 per night and homes offering up to 10 bedrooms and 11 bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

394 Homes with Pools in Anna Maria Island

Gulf Breeze

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 22 - 29
$215 night

Gulf Breeze by AMI Locals VRC21-000001 Welcome to Gulf Breeze, a charming three bedroom, two bath home just a short five-minute walk from Holmes Beach! This tropical oasis offers a private pool, lush, landscaped backyard, and easy access to local parks, shops, and restaurants, all within walking or biking distance. Perfect for families or groups seeking sunshine, relaxation, and fun in paradise, Gulf Breeze promises a memorable Anna Maria Island getaway! Highlights • 5-minute walk to the beach • 3 Bedrooms / 2 Bathrooms • 1 King bed, 1 Queen bed, 2 Twin beds • Private pool with lounge chairs • BBQ grill • Balcony with tropical views • Fully equipped kitchen with stainless steel appliances • Near shops, restaurants, and local parks • 2 parking spaces Step outside into your tropical backyard oasis, where a sparkling private pool surrounded by lush palm trees invites you to unwind under the Florida sun. Lounge in the comfortable chairs, grill fresh seafood or burgers and enjoy evening meals outdoors. After a fun-filled beach day, this outdoor space is the perfect spot to relax, reconnect, and soak up the laid-back atmosphere of Anna Maria Island. Inside, the home offers a warm and inviting living space filled with natural light and coastal decor. The open concept layout connects the living room, dining area, and kitchen, creating a perfect gathering space for your group. The fully equipped kitchen features granite countertops, stainless steel appliances, and a large island for quick snacks or morning coffee. The dining table is great for shared meals, while the living room provides plush seating and a TV for movie nights or quiet afternoons. The primary suite, located on its own upper level, feels like a private retreat. It features a king bed, a private balcony with palm-filled views, and an ensuite bathroom with a double vanity and walk-in shower. On the main floor, the second bedroom includes a queen bed, while the third bedroom has two twin beds and direct pool access, ideal for younger guests. These two bedrooms share a hallway bathroom with a shower and tub combination, providing both style and convenience. Room Details • Primary Bedroom (second floor): King bed, ensuite with double vanity and walk-in shower • Second Bedroom (main floor): Queen bed • Third Bedroom (main floor): Twin beds • Hall Bathroom: Shower/tub combo Gulf Breeze includes Wi-Fi, TVs, a washer and dryer, and parking for two vehicles. Its prime location places you within walking distance of the Gulf beaches, local parks, and fantastic restaurants. For larger groups, rent the neighboring property, Sea Breeze, which together provides six bedrooms and four bathrooms. Book Gulf Breeze today and start making unforgettable memories in paradise. With its unbeatable location, private pool, bright interior, and proximity to everything Anna Maria Island has to offer, this home promises a relaxing and fun-filled getaway your entire family will cherish. Reserve now and let your island adventure begin! - This home is strictly an animal-free zone due to severe allergies. Due to this homeowner allergy, we are unable to welcome any animals including service and/or emotional support animals. 2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. Please see our AMI Locals Rental Policies for full details. This home is managed by AMI Locals, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Sea Breeze

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 25 - Sep 1
$162 night

Sea Breeze by AMI Locals VRC21-000002 Welcome to Sea Breeze by AMI Locals, a charming three-bedroom, two-bathroom coastal retreat just a 4-minute walk to the beach on beautiful Anna Maria Island. Nestled in the heart of Holmes Beach, this home blends tropical style with modern comfort and features a private heated pool, lush landscaping, and a relaxing island ambiance. With shops, restaurants, and local attractions just around the corner, Sea Breeze offers the perfect setting for families or small groups to unwind and enjoy their island getaway. Highlights • 4-minute walk to the beach • 3 Bedrooms / 2 Bathrooms • 1 King bed, 1 Queen bed, 2 Twin beds • Private heated pool • Spacious balconies • BBQ grill and outdoor dining area • Close to shops and restaurants • Near Anna Maria Island trolley stop • 3 Parking spaces Spend your days soaking up the Florida sunshine in your private tropical oasis, complete with a heated pool, comfortable lounge seating, and a BBQ grill for outdoor cookouts. Dine under the palms, cool off with a refreshing swim, or take a short stroll to the white sand beaches of the Gulf. Whether you’re exploring the island by foot, bike, or trolley, Sea Breeze makes it easy to relax, reconnect, and recharge. Inside, the home’s bright and inviting atmosphere welcomes you with coastal decor, large windows, and views of swaying palms. The open living area features plush seating and a TV, perfect for cozy movie nights after a day in the sun. The modern kitchen is fully equipped with stainless steel appliances, granite countertops, and a large island with seating. Gather at the dining table to enjoy meals together and share stories from your island adventures. The primary suite is tucked away on the top level, offering a peaceful retreat with a king bed, private balcony, and an ensuite bathroom featuring a double vanity and walk-in shower. Downstairs, two additional bedrooms provide comfort and charm. The second bedroom includes a queen bed, while the third bedroom offers two twin beds with pool access. These rooms share a hallway bathroom with a shower/tub combination. Room Details -Primary Bedroom (2nd Floor): King bed, balcony access, ensuite bath with double vanity and walk-in shower -Second Bedroom (Main Floor): Queen bed, shares hallway bath -Third Bedroom (Main Floor): Two Twin beds, shares hallway bath, pool access Enjoy the convenience of Wi-Fi, a washer and dryer, and three parking spaces. This home is ideally located near Holmes Beach shops and restaurants, with local favorites like The Feast and The Ugly Grouper, just a few blocks away. Walk to the Anna Maria Island trolley stop for easy access to beachside cafes, boutiques, and attractions up and down the island. Comfortable, stylish, and steps from the sand, Sea Breeze by AMI Locals captures the easygoing charm of Anna Maria Island vacation living. Whether you’re swimming in your private pool, barbecuing under the palms, or exploring nearby restaurants and boutiques, this home is your perfect island retreat. Your coastal escape awaits, book your stay at Sea Breeze by AMI Locals today! - *Please note: this home is strictly an animal-free zone due to severe allergies. Due to this homeowner allergy, we are unable to welcome any animals including service and/or emotional support animals. Please see our AMI Locals Rental Policies for full details. This home is managed by AMI Locals, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

307 65th Street

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 22 - 29
$699 night

VRC 18-000047 This stunningly built and decorated 4 bedroom + Bunk Den 4 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico with crystal clear blue waters. Located in prime Holmes Beach, you are within walking distance to the award winning Beach Bistro and many other restaurants, live music , bars and more. The private heated pool features a water-slide that the young (and young at heart) will LOVE and a covered pool deck where you can relax with family and catch the game on TV while cooking out. The gourmet kitchen features high end stainless steel appliances and is fully stocked with service for 12 and all the cooking tools you need to cook for your friends and family. This beautiful home features 5 bedrooms with 1 king Master bedroom featuring a stunning walkout to the back yard where you can escape it all. Imagine sipping your morning coffee or unwinding at the end of the night with a glass of wine. This bedroom also features a stunning en-suite bathroom with double sinks and huge walk in closet There are 2 additional King bedrooms, one queen bedroom and a great bunk room with 2 sets of bunk beds (totaling 4 twin beds). With details like clapboard walls and bead-board ceilings it is sure to excite the little travelers accompanying the grown ups. A huge dining room will feature a large dining table where everyone can gather for morning breakfast before heading to the beach or come together for dinner with sun-kissed noses after a day spent in the sun. The large great room will feature big comfy couches to lounge around with the family, watching a movie or catching up on some Netflix! This house will have a fully stocked garage with beach cart, beach chairs and a beach buggy to get it all down the street to the most beautiful beaches you’ll ever see. Take the free trolley to Bean Point, or down to historic Bridge Street. Eat at restaurants like Beach Bistro, Chateau Anna Maria, grab burger’s at Skinny’s, or watch the sunset at the Sandbar. Go parasailing, take a sunset cruise or paddleboard on the crystal clear blue waters in the Gulf of Mexico. We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you? "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. Quiet hours on the island are recognized from 10p-7a."

Fins Up – AMI Cozy Island Retreat w/ Private Pool & 4-Min Walk To Beach

Holmes Beach, FL, US
2 Bedrooms 6 Guests
Aug 19 - 26
$367 night

Welcome to Fins Up! On Anna Maria Island (Holmes Beach, FL) The Space Your serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenience, and connection. Soaring ceilings, natural light, and soothing tones create an inviting backdrop for days spent at the beach and evenings gathered by the pool. Perfect for: couples seeking renewal, small families craving quality time, or travelers looking for calm, connection, and comfort. Highlights - Private heated pool with sun shelf, covered seating, and outdoor bar - 2 bedrooms / 2 bathrooms + queen sleeper sofa (approx. 1,250 sq. ft.) - Two en-suite bedrooms — ideal for shared comfort and privacy - Open-concept living area with vaulted ceilings and Smart TV - Indoor and outdoor dining areas for 6, bar seating for 4 - Fully equipped kitchen with stainless-steel appliances and quartz countertops - Washer and dryer in-unit - Three blocks from the beach and steps from the free island trolley Interior Spaces A space designed for presence — light, calm, and ease. The open-concept layout connects the kitchen, dining, and living areas under vaulted ceilings, creating a sense of airiness and flow. Sliding glass doors open to the balcony, welcoming the Florida sunshine and gentle island breeze. - King Bedroom: Spacious and restful with Smart TV, en-suite bath featuring a walk-in shower, and direct access to a Juliette balcony — perfect for morning coffee or quiet evenings. - Bunk Room: Full-over-full bunk beds, Smart TV, and en-suite bath with walk-in shower — ideal for kids or guests. - Living Area: Comfortable sofa (queen sleeper), Smart TV, and open sightlines to the kitchen for easy togetherness. Subtle coastal décor, crisp finishes, and thoughtful details make this home a relaxing environment that feels as refreshing as a morning swim. Kitchen & Dining A bright and functional kitchen sits at the heart of the home, bringing everyone together for meals, conversation, and moments that linger. - Stainless-steel appliances: stove, oven, dishwasher, microwave, refrigerator with ice maker - 12-cup coffee maker, blender, toaster, and full kitchenware - Solid wood cabinets and quartz countertops - Dining table with seating for 6 + bar seating for 4 From morning smoothies to seafood dinners, the space is designed to make cooking easy and connection effortless. Layout Overview - Single-level elevated home (approx. 1,250 sq. ft.) - Two bedrooms, both with en-suite baths - Open living, dining, and kitchen area - Balcony overlooking pool and tropical landscaping - Ground-level outdoor living area with private pool and bar seating This thoughtful layout provides privacy when desired and connection when it matters most. Outdoor Living Your own private island sanctuary awaits below. - Heated private pool and surrounding lounge area - Covered patio with outdoor bar, outdoor seating, and Smart TV - Dining space for 6 with shaded relaxation, bar area with seating for 4 - Outdoor shower for a refreshing rinse after the beach - Gas grill and dining area for easy poolside meals - Tropical landscaping that adds to the sense of peace and seclusion It’s a place to pause, breathe, and reconnect — whether lounging in the shade or sharing laughter under the palm trees. Additional Amenities - Central A/C & heat - Smart TVs and high-speed Wi-Fi - Linens, towels, and starter amenities provided - Hair dryer, iron & ironing board - Washer and dryer for guest use - Beach gear credit through VayKLife Gear (chairs, umbrella, bikes, etc.) delivered before arrival Once Upon A Beach provides trusted, hands-on local support — ensuring your stay is seamless, relaxed, and memorable. Parking - There is parking for 1-2 cars in driveway. There is parking for 1 car in garage. - No street or overnight parking permitted At Fins Up, mornings start with sunlight and the sound of palms, and end with a quiet swim beneath the stars. It’s where time slows, balance returns, and every day feels like a breath of fresh air. Write Your Vacation Story. Policies Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. NO SMOKING. NO PETS. Booking & Fee Policy Include all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets. Optional Services (subject to approval) Early check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking. Reservations & Guest Requirements Most stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed. Quiet Hours 10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted. Cleaning & Linens Home is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite. Golf Cart Rentals Explore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests. Pool Pool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Guests may not adjust equipment; violations may result in fines or damages. Property Security Exterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas. Payments & Cancellation Policy Policies updated October 6, 2025 — see full Terms & Conditions for details. Payment Schedule Deposit - Reservations up to 20 days: 50% of total amount due at time of booking. Remaining Balance - Reservations up to 20 days: Remaining 50% due 30 days prior to check-in. Cancellation Policy For Reservations of 20 Days or Less - More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee. - 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee. - Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee. - Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made. Travel Insurance CSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes. Additional Terms No refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted. City of Holmes Beach Vacation Rental License: VRC18-000018 Max Occupancy: 6 Guests | Max Vehicles: 3 Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Mojito Splash

Holmes Beach, FL, US
5 Bedrooms 10 Guests
Sep 12 - 19
$408 night

Mojito Splash by AMI Locals VRC18-000068 Welcome to Mojito Splash, a stunning five-bedroom, three and a half bath waterfront retreat located just a short stroll from Holmes Beach’s white sandy beaches on Anna Maria Island! This beautifully designed home boasts a sparkling pool, dual waterfalls, a stone-edged spa, and a large, covered lanai with a built-in bar and outdoor TV, perfect for relaxing, entertaining, and making lasting memories. Ideally situated near Holmes Beach Towne Center restaurants, shops, and marina, Mojito Splash combines luxury, outdoor fun, and island charm in one perfect vacation destination! Highlights • 5-minute walk to Holmes Beach • 5 Bedroom / 3.5 Bath • 4 King Beds, 1 Twin Daybed • Private saltwater pool and spa • Covered lanai • Outdoor bar and TV • BBQ grill • Close to waterfront restaurants, shops, and marina  • Washer and dryer • 4 Parking Spots Relax outdoors on the expansive sundeck entry, featuring dual waterfalls with seating and a stone-edged spa. The large, covered lanai includes a built-in bar, outdoor dining table, BBQ grill, and an outdoor TV, the perfect space for sunset cocktails or watching your favorite game. Lush landscaping surrounds the area, creating a tranquil oasis for outdoor living. Bike with rentals or drive to local waterfront restaurants, shops, and the marina, or enjoy water activities such as paddle boarding, kayaking, and fishing just steps from your door. Step inside this coastal haven to find an expansive living area featuring comfortable seating for family and friends, a flat-screen TV, and a bright, inviting ambiance. The fully equipped kitchen boasts stainless steel appliances, ample countertops, and a breakfast bar for quick meals or casual snacks. The formal dining table seats eight and offers a perfect setting for dinners or game nights. The primary bedroom on the second floor is a serene retreat with a king bed, a private balcony, and an ensuite bathroom with a walk-in shower, soaking tub, and double vanity, perfect for unwinding after a day of adventure. The second bedroom is a secluded oasis with an ensuite bathroom, and TV. The third and fourth bedrooms each feature king beds, crisp linens, and flat-screen TVs. The fifth bedroom, ideal for kids, includes a twin daybed. The hall bathroom offers an updated shower and tub combo. An on-site washer and dryer allows for easy packing and cleaning, so you’re always ready to go. Room Details • Primary Bedroom (2nd floor): King bed, ensuite bathroom • Second Bedroom (3rd floor): King bed, ensuite bathroom • Third Bedroom (3rd floor): King bed • Fourth Bedroom (3rd floor): King bed • Fifth Bedroom (3rd floor): Twin daybed Book Mojito Splash today and enjoy an unforgettable island escape in ultimate comfort and style. Whether relaxing by the pool, exploring waterfront restaurants, or simply soaking up the sunset views, this home provides everything you need for a memorable Anna Maria Island vacation! - 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home does not allow pets. No cable, just smart TVs with streaming Apps. This home is managed by AMI Locals, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Beach Bliss

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 29 - Sep 5
$505 night

320 64th Street - Holmes Beach - FL - 34217 VRC17-000113 Incredible 3 Bed 3 Bath bungalow, Minutes From The Beach With Backyard Oasis This beautiful 3 bedroom 3 bathroom Bungalow is only minutes from the white sands beach of Anna Maria Island. Only a minute walk to the nearest free trolley stop you can explore all the beauty of the island like Bean Point or just spend the day relaxing in your own backyard oasis. This is one of the best rentals on Anna Maria Island. Only a short walk to the beach, and around the corner to restaurants, pubs & stores. Featuring a huge heated pool to relax in after your busy day, Beach Bliss is a luxurious and welcome retreat in the perfect location on Anna Maria Island. This Bungalow has been fully renovated and no expense has been spared. Take the free trolley to Bean Point, or down to historic Bridge Street. Eat at restaurants like Beach Bistro, Chateau Anna Maria, grab burger’s at Skinny’s, or watch the sunset at the Sandbar. Go parasailing, take a sunset cruise or paddleboard on the crystal clear blue waters in the Gulf of Mexico. We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you? "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property" Guests are allowed up to 2 dogs provided they are housebroken and must be friendly with other dogs and people. Pet must be disclosed up front at the time of inquiring/booking. A one-time non-refundable fee of $150 will be due at the time of booking to accommodate for extra cleaning/pet sanitation. Should we receive complaints from neighbors of barking/disruption we reserve the right to ask you to remove the pet immediately. In addition, a refundable damage deposit of $250 will be collected at the time of booking. If pet odors/waste or any other remediation occurs as a result of their stay, we will withhold all or a portion of the damage deposit. Undeclared pets will be charged $500 and you will be required to vacate the property. By booking this property you are agreeing to the terms and fees associated with bringing an approved pet. We closely monitor all properties. . VRC17-000113 Keywords: luxury, bungalow, hot tub, heated pool, luxury vacation home, close to beach, minutes to beach, steps to beach, loaded with amenities, relaxing, lounge, patio, hideaway,

Caribbean Reef

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 22 - 29
$200 night

Caribbean Reef by AMI Locals VRC18-000084 Welcome to Caribbean Reef, an inviting three-bedroom, two-bathroom Holmes Beach vacation home by AMI Locals, perfectly situated just a four-minute stroll from the sugary white sands of Anna Maria Island’s Gulf Coast. This stylish private villa blends island charm with modern comfort, featuring a heated pool, lush tropical patio, and plenty of space for relaxing after a day at the beach. Ideal for families or small groups, guests will love being close to island favorites like Publix, local shops, and restaurants, all while enjoying a peaceful retreat in the heart of Holmes Beach. Highlights -4-minute walk to Holmes Beach -3 Bedrooms / 2 Bathrooms -2 King beds, 2 Twin beds, 1 Sleeper sofa -Private heated pool and patio -Elevated covered deck -BBQ grill -TVs in every bedroom -Centrally located near Holmes Beach shopping center -Pet friendly - 2 Parking Spaces The lush, tropical backyard is the perfect space to relax, featuring a sparkling heated pool, plenty of lounge seating, and a BBQ grill for outdoor dining. The elevated covered deck offers a shaded retreat for morning coffee or evening cocktails. With just a four-minute walk separating you from the Gulf’s turquoise waters and sandy beaches. Caribbean Reef blends tropical charm with modern comfort. The living room features two couches, artwork, and decor, creating a cozy gathering spot with a TV. The kitchen includes stainless steel appliances, granite countertops, and all the essentials for cooking meals at home. The dining space offers room for the whole group, and the open layout makes it easy to flow between indoor and outdoor living areas. The primary suite offers a king bed, TV, and an ensuite bathroom with double sinks and a walk-in shower. The second bedroom also features a king bed and shares a hallway bathroom with the third bedroom, which has two twin beds. The shared bathroom includes a shower/tub combination. A sleeper sofa in the living room provides additional sleeping space. Room Details -Primary Bedroom: King bed, ensuite with double vanity and walk-in shower -Second Bedroom: King bed, shares hallway bathroom with shower/tub combo -Third Bedroom: Two twin beds, shares hallway bathroom with shower/tub combo -Living Room: Sleeper sofa This villa’s central Holmes Beach location puts you minutes from the Holmes Beach shopping center, restaurants and a short trolley or bike ride to Anna Maria Island attractions. Beach gear, private parking, and a pet-friendly policy make it easy to enjoy your stay from the moment you arrive. With its unbeatable location, private pool, and charming coastal style, Caribbean Reef is the perfect home base for your next Anna Maria Island getaway. Book now and start planning your island adventure! - This home is managed by AMI Locals, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our AMI Locals Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Mermaid’s Crossing

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 22 - 29
$699 night

210 65th Street Holmes Beach, FL 34216 VRC17-000007 At 4 bedrooms and 3 full bathrooms, this is one of the most charming rentals on Anna Maria Island!! Located a few houses from the beach, it is only a two minute walk until white powdery sand is between your toes! Easy on the kids and even easier on you! Around the corner from restaurants, pubs & stores by bike, car or free island trolley. Free trolley stop is only three houses away! Trolley will take you and your family all over Anna Maria Island for sights, food, ice cream and shopping. Makes getting around a breeze! This home features a huge 32 feet long heated pool with waterfall, enormous sun step for kids/babies that don’t swim & spa to relax in after your busy day of walking on the beach. Pool has it’s own table with water seating - great for snacks and drinks! Mermaid Crossing is a luxurious and welcome retreat in the perfect location on Anna Maria Island. This bungalow has been fully renovated with no expense being spared. Boasts luxury with 5 flat screen TVs, stainless steel appliances, beautiful ’wood’ tile floors, granite counter tops, unique beach decor, tropical heated pool and a massive outdoor covered cabana with big screen TV, custom bar & lounging furniture. Outdoor seating for 15 plus. Tropical landscaped back yard is private and fenced in. Indoor dining table seats 8! 2 master suites with en-suites featuring top of the line king sized beds, 3rd room with a king sized bed and the kids room featuring 2 bunks that sleep 5 (4 twins & 1 pull out twin trundle). Decorated in ultimate beach style with tons of loving touches, Mermaid Crossing is the place for a large family gathering or a simple quiet retreat. The homeowners stay here with and without their children (sorry kids!) so this get away is set up with all of the necessities and tons of extras! Garage is stocked with 2 kayaks, 2 bikes w/ drink holders and baskets, wagon, toddler tricycle, toys, 8 beach chairs, 2 large beach umbrellas, beach towels, and beach toys. At the beach expect to see dolphins, manatees, fish, birds, crabs and sometimes jumping rays! Take the free trolley to Bean Point, or down to historic Bridge Street. Eat at restaurants like Beach Bistro, Chateau Anna Maria, grab burger’s at Skinny’s, or watch the sunset at the Sandbar. Go parasailing, take a sunset cruise or paddleboard on the crystal clear blue waters in the Gulf of Mexico. ​​​​​​​We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS, and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you? "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property"

Caribbean Surf

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 19 - 26
$447 night

306 67th Street Unit B Holmes Beach, FL 34217 VRC 19-000277 This beachy 3 bedroom 2 bathroom home is only a short stroll to the beautiful white sand beaches and miles away from any cares. With two rooms having king beds, and the third having two twins this home can accommodate your family of 6 or you and 5 friends Enjoy your dinner in the dining room or out by the pool. Kickback and relax in the living room for game night or movie night. Great room to entertain in and enjoy yourself and your vacation. Take the free trolley to Bean Point, or down to historic Bridge Street. Eat at restaurants like Beach Bistro, Chateau Anna Maria, grab burger’s at Skinny’s, or watch the sunset at the Sandbar. Go parasailing, take a sunset cruise or paddleboard on the crystal clear blue waters in the Gulf of Mexico. "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property" We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you? Guests are allowed up to 2 dogs provided they are housebroken and must be friendly with other dogs and people. Pet must be disclosed upfront at the time of enquiring/booking. A one-time non-refundable fee of $150 will be due at the time of booking to accommodate for extra cleaning/pet sanitation. Should we receive complaints from neighbors of barking/disruption we reserve the right to ask you to remove the pet immediately. In addition, a refundable damage deposit of $250 will be collected at the time of booking. If pet odors/waste or any other remediation occur as a result of their stay, we will withhold all or a portion of the damage deposit. Undeclared pets will be charged $500 and you will be required to vacate the property. By booking this property you are agreeing to the terms and fees associated with bringing an approved pet. We closely monitor all properties.

Sizzling Summer Rates at Surf Side Beach House GULF VIEWS Elevator

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 31 - Sep 7
$1,465 night

6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Right across the street from the beach and the Beach Bistro! Gulf Views available from this beautiful home. This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen with gas stove, wine bar, roof top deck with sweeping views of the Gulf of Mexico, 4 bedrooms each with en-suite bathrooms, custom cabinetry, balcony’s, and so much more. Not to mention its fantastic location-just a 1 minute stroll to the White sandy beaches of Holmes Beach!!! Less than 5 minutes walk to Holmes Beach City Center where you can grab your morning coffee, take the kids for ice cream or shop til you drop! This lovely property offers a private heated pool with a spa, The backyard is an oasis with BBQ grill, tropical landscaping, huge covered section and lots of space to hang out. The large outdoor space features outdoor dining and a lounge area where your group can catch the game on the big screen outdoor TV. ​​​​​​​We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS, and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you? VRC 19-000280 "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property"

Peachy Keen

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Sep 18 - 25
$287 night

Peachy Keen by AMI Locals VPR22-000026 Escape to Peachy Keen, a luxurious family vacation rental on Anna Maria Island! This spacious three-bedroom, plus loft, home is just 200 steps from the Gulf, offering stunning water views and easy access to the island’s best amenities. Wake up to breathtaking sunsets, splash in your private saltwater pool, or enjoy dining under the starry sky. Located within walking distance to local dining, shopping, parks, and water activities, Peachy Keen invites your family and friends to embrace island life in style and comfort! Highlights • 2-minute walk to Holmes Beach • 3 Bedroom + loft / 2.5 Baths • 2 Kings, 2 twin beds, 2 twin daybeds with trundles • Saltwater pool • Screened-in lanai • Outdoor dining area • Ping Pong Table • BBQ grill  • Dog friendly • Short walk to Holmes Beach Towne Center shops and waterfront restaurants • 3 Parking Spaces Enjoy a true coastal vacation with ample outdoor amenities. The private saltwater pool and is perfect for unwinding after beach days. The lush backyard features outdoor dining, a BBQ grill, and tropical views to enhance every meal. Less than two blocks from the beach provide easy access for water activities. Whether swimming, fishing, or enjoying watercraft in the calm bay, every day is an adventure in your private outdoor oasis. Inside, the fully renovated beach house offers an airy, open floor plan filled with natural light and modern touches. The kitchen features stainless steel appliances, a large island, and an inviting dining space suitable for families or friends. The cozy living room, with a sofa and a large TV, is perfect for relaxing after a day of exploring Anna Maria Island. Retreat to the primary bedroom, featuring a luxurious king bed, private balcony, and an ensuite bathroom with a walk-in shower. The second bedroom also offers a king bed, with the third bedroom equipped with two twin beds, perfect for kids or extra guests. The loft provides additional sleeping space with two twin daybeds and trundles. Every bedroom is designed for comfort and restful nights. Room Details • Primary Bedroom (2nd floor): King bed, balcony, ensuite with walk-in shower  • Second Bedroom (3rd floor): King bed  • Third Bedroom (3rd floor): Two twin beds  • Loft (3rd floor): Two twin daybeds with trundles Enjoy outdoor living at its finest, soak in the sun by the private pool or dine under the stars. Spend your days exploring nearby beaches, fishing, kayaking, or paddleboarding. Afterward, make your way down to the shops and waterfront restaurants or enjoy serene sunsets from your private balcony. Book Peachy Keen today and enjoy a luxurious, water-view family retreat in the heart of Anna Maria Island. With its private pool, scenic water access, outdoor dining, and close proximity to beaches and local hotspots, this home provides everything for a memorable Gulf Coast vacation. Reserve your dates now and start creating lifelong island memories! - This home is managed by AMI Locals, an Anna Maria Island property management company. With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our AMI Locals Rental Policies for full details. 3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Coconut Cottage

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 20 - 27
$414 night

Coconut Cottage by Anna Maria Island Accommodations VRC16-000159 Welcome to Coconut Cottage, a stunning coastal retreat just a quick stroll from the turquoise ocean of Holmes Beach! Perfect for families and groups seeking fun and relaxation. This three-bedroom, two and a half bath home offers a private heated pool, a game room, and beach touches throughout. Located near top restaurants, boutique shopping, and Anna Maria beaches, Coconut Cottage is your ideal island escape to create unforgettable memories! Highlights • 5-minute Walk to Holmes Beach • 3 Bedroom / 2.5 Bath • 2 king beds, 1 twin/ twin trundle, 1 queen sleeper sofa • Private heated pool • Outdoor TV and BBQ grill • Hammock • Game room • Jenga • Near free island trolley stop • 3 car parking Relax in your private backyard oasis featuring a heated pool, hammock, outdoor TV, and a grill for fun summer cookouts. Challenge friends to a game of Jenga under the Florida sunshine or unwind with a movie night poolside from our DVD collection. The outdoor veranda provides a peaceful spot to enjoy your morning coffee or evening cocktails. For a break from the sun, enjoy a game of ping pong, puzzles, or on the PlayStation 4 and gather everyone for a friendly challenge. Step inside this charming beach home to discover a relaxed coastal vibe. The living area invites you to unwind on plush seating while catching your favorite TV shows. The fully equipped kitchen features granite countertops and stainless steel appliances, making meal preparation effortless. Enjoy meals indoors or dine outdoors on the covered patio, soaking up the island breeze and tropical scenery. Retreat to the primary bedroom, featuring a king-sized bed, TV, and access to the veranda where you can relax in style with poolside views. The ensuite bathroom offers a spa-like experience with a soaking tub, walk-in shower, and plenty of space. The second bedroom provides a comfortable king bed and ample storage, perfect for rest after a day of adventure. The third bedroom is ideal for kids or additional guests, furnished with a twin over twin trundle and a TV, with access to the veranda. The hall bathroom includes a double vanity and walk-in shower, accommodating everyone effortlessly. The loft area features a queen sleeper sofa, perfect for extra guests or movie nights with the family. Room Details • Primary Bedroom: King bed, ensuite bathroom • Second Bedroom: King bed • Third Bedroom: Twin over twin trundle • Loft: Queen sleeper sofa The Island trolley stop is just a minute’s walk from your doorstep, making it easy to explore Pine Avenue boutiques and the many Gulf beaches. Elevate your stay with manatee and dolphin tours, bike rentals, golf trips, paddle-boarding, fishing charters, or sunset sails. Coconut Cottage offers everything you need for a truly memorable Anna Maria Island vacation! - This property has an active Ring doorbell and additional video surveillance on the exterior public approach areas and the pool equipment. **Please note that the right-side garage is not available for guest use** There are no pets allowed in this home. *Please note: 3 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Accommodations, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Accommodations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise respectful during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions, including fines and/or termination of your rental agreement without a refund.

Gulfside Oasis

Holmes Beach, FL, US
6 Bedrooms 12 Guests
Nov 12 - 19
$694 night

Gulfside Oasis by Anna Maria Vacations Home in Holmes Beach, Florida Escape to Gulfside Oasis, a stunning multi-level vacation home just seconds from Anna Maria Island’s breathtaking Gulf beaches! Offering six spacious bedrooms and five bathrooms, this luxury retreat features a private outdoor entertainment area, a game room with ping pong and foosball tables, and a luxurious heated pool and spa. Perfect for families, friends, or large groups, you will be counting the days until your next visit to this quintessential Florida paradise, just minutes from shops, waterfront eateries, and a drawbridge to the mainland. Highlights • 2-minute walk to Holmes Beach • 6 Bedroom / 5 Bathroom • 5 Kings, 2 twin/ twin bunks, 1 full sleeper sofa • Private pool and spa with in-water seating • Outdoor lounge and dining • BBQ grill • Game room • Short drive or trolley to shops, waterfront restaurants, parks, and local attractions • Washer and dryer • 4 Parking spaces This outdoor oasis offers the best of island luxury. Relax in your private, heated pool with a splash zone, a bubbling in-ground spa, and a sun shelf for all ages. Gather in your lush backyard with outdoor lounge furniture, an outdoor dining set, and a BBQ grill for memorable cookouts. Challenge loved ones to ping pong or foosball in the game room or unwind watching the sunset and tropical views. Just minutes from the Gulf and bay, the backyard adds a peaceful, scenic backdrop for your island adventures. Inside, you’ll find a welcoming, bright living space with a comfortable seating area, large flat-screen TV, and large windows pouring in natural light. The gourmet kitchen features granite countertops, stainless steel appliances, and a spacious island that doubles as a breakfast bar. A charming bistro table and a formal dining area complete the indoor layout, making it effortless for entertainment. Your primary bedroom coastal elegance with high-end furnishings, a private balcony perfect for sunset viewing, and a luxurious ensuite bathroom with a walk-in shower, double vanity, and soaking tub. Four additional bedrooms feature king beds, two with private ensuites and one with hall bath access. The fifth bedrooms includes a jack-and-jill bathroom and two twin over twin bunk beds, provide spacious comfort and privacy. Each room has a TV, plush bedding, and the home features a washer and dryer for convenience. Room Details • Primary Bedroom (3rd floor): King bed, ensuite with walk-in shower and tub • Second Bedroom (3rd floor): King bed, ensuite with walk-in shower • Third Bedroom (2nd floor): King bed, ensuite with walk-in shower • Fourth Bedroom (3rd floor): King bed • Fifth Bedroom (2nd floor): King bed, • Sixth Bedroom (2nd floor): Two twin over twin bunk beds, jack-jill bathroom • Living Room: Full sleeper sofa Relax outdoors in your tropical backyard featuring a large private heated pool, spa, and grassy sundeck. The covered lanai has a full-sized outdoor dining set and a grill, perfect for family dinners or sunset cocktails. Explore nearby beaches, water sports, or enjoy waterside dining just minutes away. Book Gulfside Oasis today for a luxurious, water-view Florida getaway. With stunning outdoor amenities, spacious interiors, and proximity to beaches, shops, and waterfront dining, this home offers all you need for an unforgettable Gulf Coast vacation. Reserve your dates now and start making lifelong memories in this waterfront paradise! - This property participates in our Professional Linen Program. In Anna Maria Vacation’s continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. This property does not allow pets of any kind. 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by Anna Maria Vacations, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Anna Maria Vacations Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Crosswind Cottage

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 19 - 26
$479 night

312 A 61st Street Holmes Beach, FL 34217 VRC19-000277 ​​​​​​​"You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. Quiet hours on the island are recognized from 10p-7a." 312 (A) 61st street - Holmes Beach - FL - 34217 Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind! Take the free trolley to Bean Point, or down to historic Bridge Street. Eat at restaurants like Beach Bistro, Chateau Anna Maria, grab burger’s at Skinny’s, or watch the sunset at the Sandbar. Go parasailing, take a sunset cruise or paddleboard on the crystal clear blue waters in the Gulf of Mexico. Crosswinds Cottage is just a short five minute walk to Anna Maria Island’s world renowned white sandy beaches where you will enjoy time with family and friends while relaxing in the sun! Crosswinds Cottage is a gorgeous Key West style home offering a private heated pool, and plenty of room for family and friends to enjoy luxury accommodations. You are sure to fall in love with everything Crosswinds Cottage has to offer! Perfectly located to provide privacy and relaxation, Crosswinds Cottage is just a short walk to one of the nicest beaches on Anna Maria Island and just a few minutes’ walk to a beautiful city park with a children’s playground, a skate park, and tennis courts. Locally operated restaurants and boutiques with delicious local food and quaint island themed gifts are just around the corner. The location of Crosswinds Cottage, in the heart of Holmes Beach, has something for everyone. With two adult bikes available for your convenience, you can easily explore the rest of the island without a car. The free Island Trolley Service is also available to inspire your adventure! Enjoy the luxurious back yard with a private heated pool and palm trees swaying in the breeze. Here you will find the perfect blend of sun and cool shade with evening starlight twinkling overhead. The covered patio offers plenty of seating to enjoy cocktails or a delicious freshly grilled meal with family and friends. You can also enjoy a private cocktail or a cup of morning coffee on one of the other two private decks located off the living room and the master bedroom. Make memories in the game area playing Ping Pong just next to the pool area. For quiet moments, enjoy four flat screen TVs, all with cable throughout the house. All bedrooms have flat screen TVs and two Smart TVs are located in the living room and large upstairs bedroom. High-speed wireless internet will let you keep in touch with the rest of the world - just remember, you are on vacation and it is time to relax! Professional decorating, a romantic master suite, spa tub, solid wood cabinets, wood floors, volume ceilings and granite surfaces are just some of the fantastic amenities that you can expect from Crosswinds Cottage. There is also an elevator to all floors to accommodate guests or help with luggage. A laundry room is located on the main floor for your convenience. Get ready to make memories at Crosswinds Cottage! **Please keep in mind if the elevator becomes inoperable due to any reason, the stairs will be the only form of transportation to and from your unit** Bedrooms & Bathrooms There are 3 bedrooms and 2.5 bathrooms. This property conveniently sleeps up to 8. The Master bedroom has a King sized bed and so does the second bedroom. The third offers one king bed and a bunk bed comprised of a twin over twin sized bed with a pull out trundle for 3 twin beds total. There is also a queen sleeper sofa in the living room. Exterior Crosswinds Cottage offers a fantastic location that is ideal for your Anna Maria Island getaway. Close to local shops and restaurants and only a short 5-7 minute stroll to the pristine Gulf beaches of the Gulf of Mexico. Offering a private heated pool with a covered lanai and mature tropical landscaping for your convenience. Enjoy quality time outdoors around the pool, grill up a delicious home cooked meal or simply try out some of the delicious local seafood--this versatile offers it all! We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you? Guests are allowed up to 2 dogs provided they are housebroken and must be friendly with other dogs and people. Pet must be disclosed up front at the time of inquiring/booking. A one-time non-refundable fee of $150 will be due at the time of booking to accommodate for extra cleaning/pet sanitation. Should we receive complaints from neighbors of barking/disruption we reserve the right to ask you to remove the pet immediately. In addition, a refundable damage deposit of $250 will be collected at the time of booking. If pet odors/waste or any other remediation occur as a result of their stay, we will withhold all or a portion of the damage deposit. Undeclared pets will be charged $500 and you will be required to vacate the property. By booking this property you are agreeing to the terms and fees associated with bringing an approved pet. We closely monitor all properties.

Native Sun

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 19 - 26
$322 night

Native Sun by AMI Locals VR22-000055 Welcome to Native Sun, a beautifully updated coastal home featuring four bedrooms and three bathrooms one block from Holmes Beach! This island retreat boasts a private pool, lush backyard lounge area, and convenient outdoor dining and BBQ area, ideal for relaxing family vacations or gatherings with friends. Perfectly located near the best restaurants, shops, and a free trolley stop, Native Sun provides everything you need for a memorable Anna Maria Island escape! Highlights • 2-minute Walk to Holmes Beach • 4 Bedroom / 3 Bath • 3 Kings, 1 Twin Bed, 1 Twin-over-twin Bunk • Private pool • BBQ grill • Outdoor shower  • 2-minute Walk to the trolley stop • Washer and dryer • 4 Parking Spaces • Near Marina Drive boutiques, dining, and waterfront attractions  Enjoy outdoor living to the fullest in your lush backyard. Lounge on the poolside deck or sunbathe on the lounging chairs, then fire up the BBQ for a family cookout. An outdoor dining table makes outdoor meals a delight. With a private outdoor shower, the tropical greenery set the perfect Florida scene, this backyard oasis is your ideal spot to unwind. And with the trolley stop just a short stroll away, exploring the island’s beaches and attractions like the Holmes Beach Towne Center boutiques is easy and fun. Inside, you’ll find a cozy, inviting living space with two comfortable sofas, side chairs, and a large flat-screen TV, your perfect spot for family movie nights or relaxing after a day on the beach. The fully equipped kitchen features stainless steel appliances, plenty of cabinets, and a handy island with seating. Adjacent is an elegant dining room table, perfect for dinner parties, game nights, or casual island meals, all bathed in natural light from large sliding doors that lead to the backyard. Retreat in style to the primary bedroom, which offers a king-sized bed, premium bedding, and a flat-panel TV. The second and third bedrooms each feature luxurious king beds, with one boasting its own ensuite bathroom with a walk-in shower. The fourth bedroom has a playful nautical theme, twin-over-twin bunk beds, and a TV for the kids. The hall bathroom includes a shower and tub combo, while a washer and dryer provide added convenience during your stay. Room Details • Primary Bedroom: King bed, ensuite bathroom  • Second Bedroom: King bed • Third Bedroom: King bed, ensuite bathroom • Fourth Bedroom: One Twin bed, One Twin-over-twin bunk bed Book Native Sun today for a relaxing, fun-filled vacation on Anna Maria Island. Whether lounging by the pool, exploring local hotspots, or enjoying gorgeous sunsets, this home offers everything you need for an unforgettable seaside getaway! - There are No pets allowed in this home. 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Locals, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Meant to Bee on AMI

Bradenton Beach, FL, US
2 Bedrooms 6 Guests
Aug 19 - 26
$362 night

310 60th street Unit B- Holmes Beach - 34217 "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property" Relax and unwind in this gorgeous, renovated 2 bedroom, 2 bath home close to everything! Just a few short blocks to the sugar sand beaches, this adorable 2 bed 2 bath home is the perfect place to stay while on AMI. Beautifully updated, the home features a king bedroom with ensuite bath, a queen bedroom + an additional queen pull out off the kitchen. Minutes to downtown Holmes Beach and ½ a mile from historic Pine Avenue on Anna Maria Island. Meant to Bee on AMI Beach House is a fantastic beach retreat for any family, couple or small group of friends. This property offers two bedrooms; One king bedroom and the second bedroom has a queen bed. There are also 2 full baths: One with a walk in shower and the second bathroom off the main living area with a tub/shower combination - perfect for sandy kids after a long day at the beach. The open and generous living area features ample seating for winding down in front of the HDTV. Need room to sleep six? A queen sized murphy bed is available just off the kitchen. Take the free trolley to Bean Point, or down to historic Bridge Street. Eat at restaurants like Beach Bistro, Chateau Anna Maria, grab burger’s at Skinny’s, or watch the sunset at the Sandbar. Go parasailing, take a sunset cruise or paddleboard on the crystal clear blue waters in the Gulf of Mexico. ​​​​​​​We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS, and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you? ( ASK: Guests are allowed up to 2 dogs provided they are housebroken and must be friendly with other dogs and people. Pets must be disclosed up front at the time of inquiring/booking. A one-time non-refundable fee of $150 (per pet) will be due at the time of booking to accommodate for extra cleaning/pet sanitation. Should we receive complaints from neighbors of barking/disruption we reserve the right to ask you to remove the pet immediately. In addition, a refundable damage deposit of $250 will be collected at the time of booking. If pet odors/waste or any other remediation occur as a result of their stay, we will withhold all or a portion of the damage deposit. Undeclared pets will be charged $500 and you will be required to vacate the property. By booking this property you are agreeing to the terms and fees associated with bringing an approved pet. We closely monitor all properties.)

Mango Bay – Luxury Island Home w/ Heated Pool, Spa & Walk To Beach

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 19 - 26
$528 night

Welcome to Mango Bay! On Anna Maria Island (Holmes Beach, FL) Set on a quiet street near the sand, Mango Bay blends open interiors with plenty of outdoor living. Upstairs, the main living floor brings kitchen, dining, and lounge spaces together so conversation flows as easily as the sea breeze. Outside, a backyard oasis features a heated pool, spa, grill, and seating under palms—made for lazy afternoons and easy dinners. Perfect for: Multi-family stays • Friends traveling together • Groups who love pool-to-beach days Highlights - Four king bedrooms + bunk room (sleep space for kids/teens) - Private heated pool & spa with loungers, Adirondacks, and grill - Open kitchen with island seating and dining table - Multiple balconies for morning coffee and sunset chats - Garage/game room with ping-pong - Near the beach (about a 5-minute walk) and close to shops and dining Interior - Living Room: Bright second-floor lounge with large Smart TV, two sofas (one is a sleeper), and sliders to a screened porch overlooking the pool. - Dining Area: Table just off the kitchen—great for family meals or board-game nights. Kitchen & Dining A fully equipped kitchen keeps meals simple and social: - Stove, oven, microwave, refrigerator/freezer - Coffeemaker (12-cup) & Keurig, blender, toaster, full kitchenware - Generous counter space + island seating for 4; dining table for 6 - Screened in dining table, seating for 6 - Table available for meals by the pool Bedrooms - Primary King Suite: Ensuite with soaking tub + walk-in shower; screened private balcony, Smart TV. - Second King Suite: Ensuite with walk-in shower, double vanity, private patio, clothing storage, Smart TV. - Two Additional King Bedrooms: Share a Jack-and-Jill full bath with a walk-in shower, both with Smart TVs, French doors & Juliette balconies. - Custom Bunk Room: Twin-over-twin built-ins off Primary Suite—perfect for kids or teens. Bathrooms: Three full and one half bath, thoughtfully placed for group comfort. Layout Overview - Main Level (Second Floor): Open kitchen/dining/living, wet bar, screened porch, half bath, Jack-and-Jill King bedrooms. - Top Floor: Two King ensuites, plus bunk room. - Ground Level: Covered lanai, pool/spa, grill station, garage/game room with ping-pong. Outdoor Living Step into your backyard retreat. The heated pool features a built-in table for in-water lounging; the spa is set just beside it for easy soaks. Spread out between sun loungers and Adirondack chairs, then fire up the gas grill (propane provided) for dinner outside. Multiple screened balconies give everyone a quiet perch for sunrise coffee or an evening wind-down. Additional Amenities - High-speed Wi-Fi & Smart TVs - Central A/C & heat - Linens, towels, hair dryers, iron/ironing board - Washer/Dryer - Beach gear credit included (chairs, umbrellas, carts, bikes, and more; selection and delivery arranged pre-arrival) Parking Total 3–4 vehicles, depending on size. Start your story where the sunshine meets the shore — at Mango Bay, where every day feels like it was made for you. Policies Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. NO SMOKING. NO PETS. Booking & Fee Policy Include all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets. Optional Services (subject to approval) Early check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking. Reservations & Guest Requirements Most stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed. Quiet Hours 10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted. Cleaning & Linens Home is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite. Golf Cart Rentals Explore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests. Pool & Spa Pool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages. Property Security Exterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas. Payments & Cancellation Policy Policies updated October 6, 2025 — see full Terms & Conditions for details. Payment Schedule Deposit - Reservations up to 20 days: 50% of total amount due at time of booking. Remaining Balance - Reservations up to 20 days: Remaining 50% due 30 days prior to check-in. Cancellation Policy For Reservations of 20 Days or Less - More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee. - 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee. - Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee. - Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made. Travel Insurance CSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes. Additional Terms No refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted. Holmes Beach Vacation Rental License: VRC24-000081 Max Occupancy: 8 Guests | Max Vehicles: 4 Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.

Serenity at Bay Palms

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 23 - 30
$332 night

Serenity at Bay Palms by AMI Locals Discover the charm of Anna Maria Island at Serenity at Bay Palms, a newly updated coastal retreat just a short walk from the stunning Gulf beaches on Anna Maria Island! This four-bedroom, four-ensuite bath home offers modern luxury, a private heated pool with in-ground spa, and easy access to local dining, shopping, and outdoor adventures. Perfect for families and friends traveling together, this stylish home provides comfort, convenience, and coastal elegance in the heart of Holmes Beach. Highlights • 8-minute walk to Holmes Beach  • 4 Bedroom / 4 Bathroom • 2 Kings, 2 XL Twins, 1 Twin/ Full bunk • Private heated pool and in-ground spa  • Foosball Table • Newly updated home • Outdoor patio • BBQ Grill • Near popular restaurants and boutique shops • Close to free island trolley stops • 3 Parking spaces Enjoy resort-style outdoor living with a private heated pool, relaxing in-ground spa, and an outdoor patio equipped with Sonos speakers for summer evenings and backyard entertaining. The home’s bright, open layout features new furnishings, large windows, and a coastal touch throughout. The fully equipped kitchen includes a wine fridge, coffee bar, and barstool seating at the island, ideal for preparing and enjoying meals with family and friends. The spacious living room has two inviting sofas, a large flat-screen TV, and large windows with views of the lush, landscaped backyard, creating a cozy yet airy atmosphere. The dining area seats up to eight guests, set beside the modern kitchen—perfect for family dinners or entertaining friends in style. The home’s split bedroom layout offers maximum privacy, with two primary suites on each side of the house. The first primary bedroom features a king bed, luxurious linens, and a private ensuite with a walk-in shower. The second primary has a plush king bed and a stylish ensuite bath. The third bedroom features two extra-long twin beds and an ensuite with a walk-in shower. The fourth bedroom is ideal for kids with a twin over full bunk bed, also with an ensuite bath. All bedrooms include walk-in showers, modern decor, and smart TVs for ultimate comfort. Room Details • Primary Bedroom: King bed, ensuite with walk-in shower  • Second Primary Bedroom: King bed, ensuite with walk-in shower  • Third Bedroom: Two extra-long twin beds, ensuite with walk-in shower  • Fourth Bedroom: Twin over full bunk, ensuite with walk-in shower This vacation haven offers a washer and dryer, outdoor patio with Sonos speakers, resort-style pool and spa, and ample outdoor space for lounging and dining. The proximity to trolley stops makes exploring Anna Maria Island’s seven miles of beaches, boutiques, and bay activities effortless and enjoyable. Book your stay at Serenity at Bay Palms today and immerse yourself in island life. With close proximity to beaches, shopping, kayaking, paddleboarding, and the island’s charming attractions, this stylish home is the perfect escape for creating unforgettable vacation memories. Slip into relaxation and adventure today! - This property does not allow pets. Please note: 3 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Locals, an Anna Maria Island property management company. This property has an active Ring doorbell at the main entrance. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Starfish Cove

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 19 - 26
$463 night

302 60th Street Holmes Beach, FL 34217 VRC19-000274 At 3 bedrooms and 2 full bathrooms, this is a beautiful choice for your next Anna Maria Island getaway! Two short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Cove is a luxurious and welcome retreat in the perfect location on Anna Maria Island. This home is completely new and has been built with no expense spared. The 4 Flat screen TV’s, Sonos multiroom audiosystem, stainless steel appliances, beautiful tile floors, granite counter tops, free phone/cable/wireless Internet, and a great outdoor living area with pool, spa & patio will exceed the expectations of even the most discerning vacationers. (1 Master Suite, one room with two twin beds and an additional room with a queen sized bed. Take the trolley to Bean Point, or historic Bridge St. Have a bite at Chateau Anna Maria, or the Beach Bistro or grab a burger and enjoy the game at Skinny’s. Go paddle boarding or kayaking in the crystal clear blue waters in the Gulf Of Mexico. Guests are allowed up to 2 dogs provided they are housebroken and must be friendly with other dogs and people. Pet must be disclosed up front at the time of inquiring/booking. A one-time non-refundable fee of $150 (per pet) will be due at the time of booking to accommodate for extra cleaning/pet sanitation. Should we receive complaints from neighbors of barking/disruption we reserve the right to ask you to remove the pet immediately. In addition, a refundable damage deposit of $250 will be collected at the time of booking. If pet odors/waste or any other remediation occur as a result of their stay, we will withhold all or a portion of the damage deposit. Undeclared pets will be charged $500 and you will be required to vacate the property. By booking this property you are agreeing to the terms and fees associated with bringing an approved pet. We closely monitor all properties. "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property" ​​​​​​​We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS, and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you?

Palms By The Bay

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 19 - 26
$498 night

Welcome to Palms by the Bay! This beautiful home features three bedrooms plus bonus room and three bathrooms and is located just a short walk away from the stunning Gulf beaches. Spend your days soaking up the sunshine on the sugary white sand and then retreat back to the backyard oasis for a refreshing dip in the sparkling pool or a relaxing soak in the in-ground spa. You’ll leave feeling rejuvenated and refreshed after your stay at this tropical paradise. As soon as you step inside, you’ll be welcomed by a warm and inviting living space offering plenty of room and beautiful backyard views. Take a seat in one of the comfortable side chairs or sofas and enjoy the company of loved ones as you watch your favorite movies on the TV. The dining area is the perfect place to gather for meals, and the kitchen is a chef’s dream, with stunning granite countertops, custom cabinets, top-of-the-line stainless-steel appliances, and a spacious island with plenty of seating. There are two workspaces which makes work or studying away from home a pleasure. Also enjoy blazing-fast 1-Gig Wi-Fi throughout the home, perfect for streaming, remote work and multiple devices. Each of the three stunning bedrooms plus bonus room are equally appointed with plush bedding, televisions, and dressers, ensuring a peaceful and restful night’s sleep. You’ll find 3 bedrooms plus a bonus room to accommodate up to 6 guests in total. There are two king suites with walk-in showers, one guest room with two twin beds and a bedroom with a queen bed. The hall bathroom hosts a lovely shower and tub combination, and for your added convenience, a washer and dryer are provided, making your stay as seamless and stress-free as possible. HIGHLIGHTS • 1841 sq. ft. • Private pool (28x12 ft.) • Spa • Pet friendly • 100 steps from the canal for fishing • 0.3 miles from beach access • 1 gig Wi-Fi for seamless and fast connectivity BEDROOMS • Sleeps 6 • Primary Bedroom: King Ensuite • Second Bedroom: Queen • Third Bedroom: Twins • Bonus room: King Ensuite BATHROOMS • Primary Bathroom: Walk-in Shower • Second Bathroom: Shower/Tub • Third Bathroom (ensuite): Walk-in Shower With a plethora of activities and amenities, there’s something for everyone. Imagine basking in the glorious sunshine while lounging by the pool or on the sun shelf. You can also showcase your culinary skills by grilling up a delicious meal, catching up on your favorite sports game on the outdoor TV, or taking a stroll to the Gulf beach nearby. At Palms by the Bay, you can have everything you need for a perfect vacation! This property participates in our Professional Linen Program. In Property Manager’s continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high-quality linens; including bedding, bath towels, washcloths, hand towels, bathmats, kitchen towels and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology. Minimum stay: 7 nights and Maximum occupancy: 6 people 3 cars maximum are able to park at this home. Palms by the Bay is a pet friendly property for dogs up to 50 lbs. The non- refundable pet fee is $150.00 per pet and will be charged for each week. Short stays are not prorated. The pet fee does not cover any damage caused by the pet. The pool heat is $150.00 a week. Pool heaters in private homes are locked for your safety and controls must not be tampered with as they are monitored by the pool company. 86° F is the highest heat temperature setting which might not be always reached. Please note if cold days and nights occur, water temperatures will drop and may stay cooler longer. Pool heaters will not operate and will automatically shut down if outside temperatures get too cold. While we take every precaution to ensure that pools are heated as specified, weather conditions may affect the temperature of the pool. Nothing can be done about this issue. Outdoor spas are not hot tubs and require heat at the additional cost. The temperature of a spa is typically set at the same temperature as the pool. In the event of pool equipment malfunction during your stay, Property Manager will expedite repairs as quickly as possible. It may be necessary to close swimming pools for maintenance purposes. No refund or rent adjustment will be made for circumstances beyond our control, malfunctions, or loss of use of equipment or amenities. Please keep in mind that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. VRC16-000361

Starfish Isle

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 19 - 26
$545 night

VRC 21-000046 5803 Holmes Blvd Holmes Beach, FL 34217 At 4 bedrooms and 3 full bathrooms, this is a great option for one or two families to stay at. A few short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Isle is a luxurious and welcome retreat in the perfect location on Anna Maria Island. The 5 Flat screen TV’s, Sonos Multiroom audiosystem with out side speakers, stainless steel appliances, beautiful tile floors, granite counter tops, free phone/cable/wireless Internet, and a great outdoor living area with pool, spa & patio will exceed the expectations of even the most discerning vacationers. (2 Master Suites - one with with en- suite and one with ’Jack and Jill’ bathroom attached to a room with 2 twin beds. An additional room with two twin sized bed. PLEASE NOTE: Each side has it’s own PRIVATE yard, POOL and GRILL - no need to share anything with the neighbours! Take the free trolley to Bean Point, or historic Bridge St. Have a bite at Chateau Anna Maria, or the Beach Bistro or grab a burger and enjoy the game at Skinny’s. Go paddle boarding or kayaking in the crystal clear blue waters in the Gulf Of Mexico. "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property" ​​​​​​​We might be only 7 miles long but Anna Maria has everything you could possibly need for your perfect beach vacation. Traveling with a little one? All our homes come with pack & plays and highchairs. Need more? There are several great rental places that have everything from baby gates to golfcarts, and they will drop them right off at your vacation property for you. No need to pack beach towels we provide those for you. Remember we are laid back and on Island time - Flip-flops and shorts are ok for breakfast, lunch and dinner no need to overpack you will most likely be in your cutest bathing suit or bikini anyways. No need to pay the crazy high fees to check all those bags! With Publix, CVS, and Walgreens right on the island you can grab any sunscreen, hair product anything needed, why haul it all with you? Guests are allowed up to 2 dogs provided they are housebroken and must be friendly with other dogs and people. Pet must be disclosed up front at the time of inquiring/booking. A one-time non-refundable fee of $150 (per pet) will be due at the time of booking to accommodate for extra cleaning/pet sanitation. Should we receive complaints from neighbors of barking/disruption we reserve the right to ask you to remove the pet immediately. In addition, a refundable damage deposit of $250 will be collected at the time of booking. If pet odors/waste or any other remediation occur as a result of their stay, we will withhold all or a portion of the damage deposit. Undeclared pets will be charged $500 and you will be required to vacate the property. By booking this property you are agreeing to the terms and fees associated with bringing an approved pet. We closely monitor all properties.

Casa Bella

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 19 - 26
$238 night

Casa Bella by AMI Locals VRC22-000114 Experience the ultimate island retreat at Casa Bella, a luxurious corner lot vacation home located just three blocks from the pristine Gulf in Holmes Beach. This stunning four-bedroom, three-bath home offers modern coastal elegance, a private pool, and easy access to parks, beaches, and local attractions. Perfect for families and groups seeking relaxation and adventure in Anna Maria Island, Casa Bella is a true seaside paradise with stylish decor and spacious outdoor living! Highlights • 5-minute walk to Holmes Beach • 4 Bedroom / 3 Bathroom • 3 Kings, 2 Twin/ Twin bunks • Private pool with pool loungers  • Screened-in lanai  • Near popular parks • Ping pong table • Washer and dryer • Short drive to Holmes Beach Town Center shopping, dining, and local attractions • 3 Parking spaces Enjoy resort inspired amenities including a sparkling private pool, a screened-in lanai, and a game room featuring a ping pong table. The backyard is perfect for lounging, outdoor games, and socializing, while the nearby parks and promenade provide endless opportunities for outdoor adventures. The home’s coastal decor and open floor plan make it an inviting setting for creating lifelong memories with friends and family. The main living area welcomes you with stunning blue hues, engaging artwork, and plush sectional seating that creates a relaxing atmosphere. The fully equipped kitchen features stainless steel appliances, a custom backsplash, stone countertops, and a coastal dining table, plus outside dining on the balcony. Large sliding doors connect indoor comfort to outdoor living, perfect for vacation relaxation and entertainment. The third-floor primary bedroom is a tranquil oasis with a King bed, private balcony, and an ensuite bathroom with a soaking tub, walk-in shower, and double vanity. The second bedroom on the third floor offers a King bed and a TV, while the third bedroom, also on the third floor, is ideal for kids with two twin over twin bunk beds. The fourth bedroom on the second floor features a King bed and a TV, with easy access to the hallway bathroom that includes a shower and bath combo. Every bedroom offers comfortable linens, ample closet space, and a relaxing retreat to rest after a day of island adventures. Room Details • Primary Bedroom (3rd floor): King bed, balcony, ensuite with soaking tub and walk-in shower  • Second Bedroom (3rd floor): King bed Third Bedroom (3rd floor): Two twin-over-twin bunk beds  • Fourth Bedroom (2nd floor): King bed This home provides a washer and dryer, a screened in porch, a ping pong table in the game room, and plenty of outdoor space for poolside lounging and backyard games. Beach chairs and outdoor seating are included to enhance your stay, while the home’s convenient location makes exploring Anna Maria Island easy and enjoyable. Book your stay at Casa Bella today and immerse yourself in the charm of Holmes Beach. With effortless access to the beach, parks, and local shops and dining, this stylish coastal retreat offers endless opportunities for adventure and relaxation. Slip into island time and create unforgettable vacation memories at Casa Bella on Anna Maria Island! - There are no pets allowed in this home. *Please note: 3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Locals, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our AMI Locals Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

The Shady Mermaid

Holmes Beach, FL, US
2 Bedrooms 6 Guests
Aug 19 - 26
$544 night

Welcome to The Shady Mermaid! A luxury ground-level vacation home just a 3-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen has ample counter space, gas cook top and oven, extra-large fridge/freezer and wine cooler making meal prep a breeze. There is also a wet bar in the dining area with two cooler drawers, a large butler’s kitchen with a large freezer. Delight in your delicious island- inspired homemade meals or Anna Maria Island take-out at the indoor or outdoor dining table, where you can also enjoy the Island breeze. The primary bedroom offers a calming atmosphere perfect for catching up on much-needed sleep and has a TV for late-night entertainment. The second bedroom is perfect for another couple and has plenty of closet space for vacation attire and beach necessities. The primary bedroom has a bathroom which features a soaking tub and walk-in shower. The guest bathroom has a walk-in shower. There is also a baby monitor in the property. Relax in your private backyard oasis, where you and your guests can make a splash in the pool which also functions as a spa and you relax in one of the many seating areas. There is a BBQ grill perfect for grilling locally caught seafood. Explore the beautiful beaches Anna Maria Island offers, swim in the warm turquoise waters, and feel the sugary sand cover your feet. Afterward, browse the fantastic boutiques, coffee shops in Holmes Beach or head to any local restaurants for delicious treats and fresh seafood! Hop on the free trolley and explore the island! Anna Maria Island has many guided tours. Kayak or paddleboard the bay and the calm Gulf of Mexico, where you might even encounter some wildlife! HIGHLIGHTS • 1406 sq. ft. • Private Pool/Spa (12x7 ft.) • Tiki Hut • 0.1 mile from beach access • 0.2 miles from bay access BEDROOMS • Sleeps 6 • Primary Bedroom: King Casper Mattress • Second Bedroom: King • Sleeper Sofa: Queen BATHROOM • Primary Bathroom: Spa Soaking Tub and Walk-in Shower • Second Bathroom: Walk-in Shower EXTERIOR After a long day at the beach, head back to The Shady Mermaid and take advantage of its beautiful outdoor scape. Take a dip in the crystal-clear private heated pool/spa. There is a gas grill and outdoor dining spot to enjoy a bite to eat in a beautiful, tropical landscape. Also, a large Tiki Hut with bar, loungers and outdoor TV where you can enjoy the Game. The pool/spa heat is $100.00 a week. Pool heaters in private homes are locked for your safety and controls must not be tampered with as they are monitored by the pool company. 100° F is the highest heat temperature setting for spa use but it might not be always reached. Please note if cold days and nights occur, water temperatures will drop and may stay cooler longer. Pool heaters will not operate and will automatically shut down if outside temperatures get too cold. While we take every precaution to ensure that pools are heated as specified, weather conditions may affect the temperature of the pool. Nothing can be done about this issue. Outdoor spas are not hot tubs and require heat at the additional cost. The temperature of a spa is typically set at the same temperature as the pool. In the event of pool equipment malfunction during your stay, Property Manager will expedite repairs as quickly as possible. It may be necessary to close swimming pools for maintenance purposes. No refund or rent adjustment will be made for circumstances beyond our control, malfunctions, or loss of use of equipment or amenities. Minimum stay: 7 nights and Maximum occupancy: 6 people There are parking spaces for two cars at The Shady Mermaid. Also, a Golf Cart parking space with outlet. Please keep in mind that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. VRC: 23-000116

Vacation Rentals in Anna Maria Island by Amenities & Features

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Vacation Rentals Near Anna Maria Island

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