Vacation rentals in Holmes Beach, FL with a pool

Explore 405 vacation rentals, homes, and villas with pools in Holmes Beach, 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.

405 Homes with Pools in Holmes Beach

Sunshine & Good Times

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Sep 26 - Oct 3
$918 night

Be one of the very first to stay in this LUXE, newly constructed custom home. Heated pool & spa, rooftop deck with GULF VIEWS. Grill, custome kitchen, wet bar on thrid level. ALL THE BELLS AND WHISTLES! This stunning 4 bedroom + bonus room (2 additional twin beds), 5 bathroom home only 2-minute walk to the beach with a large heated pool & spa! Equipt with a bar fridge and huge pantry - you’ll have room from off your goodies. This house has everything you could possibly need for the most incredible beach vacation or an extended stay for working from home or homeschooling with a second family room/office/studyon the upper level and high-speed WiFi throughout! Spectacular, sweeping views pf the Gulf of Mexico from the roof top deck. 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?

Paradise Beach House

Holmes Beach, FL, US
6 Bedrooms 12 Guests
Aug 22 - 29
$867 night

403 42nd Street, Holmes Beach FL 34217 VRC19-000276 Stunning 6 bed 6.5 bath ~ Spectacular Pool & Spa ~ Walk to the beach and shops Paradise Beach House ~ Enjoy this 6 bedrooms, 6.5 bathrooms beach home that sleeps up to 14 and is just a short walk to the famous Anna Maria Island beach. Paradise Beach House has all the style and deluxe amenities you could hope for. The home offers high-end kitchen with stainless steel appliances, granite counters and an island that seats four, which is a perfect location for catching up with family and friends as you create the perfect meal. The kitchen opens up to the dining area and the living room so everyone can be close by. There are three elegant king master bedrooms, a queen bedroom and one room with two twin beds. All the bedrooms have en suite bathrooms! The den offers a bunk bed with a trundle, a favorite with the younger kids. It is the perfect room for the kids to have their own space to play games or watch their own TV. Enjoy living in style with the beautiful high-end decor’ and top of the line finishes. The home has 8 TVs, speakers throughout the home that can be controlled by the Sonos app including around the pool and outdoor area. The backyard is a secluded oasis with a wonderful lounge area with where you can soak up the sun or just curl up on with a good book. Cool off in the spectacular pool by day and relax in the hot tub at night. There’s two large outdoor tables for plenty of room for family and friends to enjoy outdoor grilling by the pool. There’s beach chairs, a beach umbrella, beach toys and a beach trolley to make the short stroll to the beach even easier. Plus there’s an outdoor shower making it easy to rinse off after coming back from the beach before getting into the pool. Situated right in the center of Anna Maria Island, it’s a great location for exploring the island by bike or on the free island trolley that stops close by. The shops and restaurants in the City of Anna Maria are a five minute drive to the north end, while quaint Bridge Street and its pier are just a little further to the south. More locally, Holmes Beach offers a choice of sixteen restaurants, a marina and the main shopping center on the island (Publix supermarket, drug stores, beach accessories etc. are all a few minutes’ walk away). The beach stretches for miles in each directions. Feel the powdery sand between your toes and enjoy the warm Gulf waters. Very close to the public beach with restaurants and shops to explore. This property has a maximum of 4 parking spaces. If you have any questions, would like additional information or interested in 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"

Paradise Found

Holmes Beach, FL, US
6 Bedrooms 12 Guests
Aug 18 - 25
$867 night

401 42nd Street Holmes Beach, FL 34217 VRC17-000010 401 42nd Street - Holmes Beach - FL - 34217 6 bedroom 6.5 bathroom - . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, stainless steel appliances, beautiful wood floors, granite counter tops, free phone/cable/wireless Internet. 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 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.

Beach View Retreat

Holmes Beach, FL, US
5 Bedrooms 10 Guests
Aug 18 - 25
$433 night

Beach View Retreat by AMI Locals VRC19-000046 Welcome to Beach View Retreat, a five bedroom, four bath home in Holmes Beach, just one block from Manatee Public Beach. With a private heated pool and spa, rooftop deck with panoramic views, and a prime location where you can walk everywhere. This vacation rental offers the perfect blend of island charm and modern luxury. Highlights • 4-minute walk to Manatee Public Beach • 5 Bedrooms / 4 Bathrooms • 3 Kings, 2 Queens • Rooftop deck with bay and Gulf sunset views • Private heated pool and spa • Outdoor kitchen with grill • Ping pong table • Beach chairs and wagon provided • Walk to Island trolley stop, Publix, Skinny’s Place, and Holmes Beach shops/restaurants • Pet friendly with host approval • 4 Parking spaces The lush backyard oasis features a sparkling pool, hot tub, orange trees, and shaded seating for relaxation. An outdoor kitchen with a grill and dining table makes meals easy, while the rooftop deck is the perfect spot for morning coffee or breathtaking sunsets over the Gulf and the bay. Bring along you furry friends as you enjoy indoor games, ping pong, and beach gear for fun filled days by the shore. The open concept living room boasts coastal inspired decor, plush seating, and multiple balcony access points. The kitchen is fully equipped with stainless steel appliances, ample storage, and a large island with barstools. Gather around the formal wood dining table or relax in the lounge area with a TV. The oversized primary suite includes a king bed, seating area, private balcony, and a luxurious ensuite bathroom with a soaking tub, double vanity, walk-in shower, and closet. Two additional bedrooms upstairs include a king and queen room that share a hall bath with a walk-in shower. On the second floor, two more guest rooms each feature ensuite bathrooms, one with a king bed and the other with a queen. Room Details -Primary Bedroom, 3rd floor: King bed, private balcony, ensuite with walk-in shower, tub, and closet -Second Bedroom, 3rd floor: King bed -Third Bedroom, 3rd floor: Queen bed -Fourth Bedroom, 2nd floor: King bed, ensuite with walk-in shower -Fifth Bedroom, 2nd floor: Queen bed, ensuite with shower/tub combo This home includes a washer and dryer, TVs, ping pong table, and parking. Guests are steps from Holmes Beach restaurants, shops, and Publix grocery store. Hop on the nearby Anna Maria Island free trolley to explore Pine Avenue, Bridge Street, and the island’s seven miles of beaches. With its rooftop deck, private pool and spa, and unbeatable walkable location, Beach View Retreat is the ultimate Holmes Beach vacation rental. Book your stay today and make unforgettable memories on Anna Maria Island! - With host approval before check-in, this property accepts pets. An additional pet fee will apply. See our AMI Locals Rental Policies for full details. There is no outdoor TV provided at this home. *Please note: 4 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. 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.

Angel Sea

Holmes Beach, FL, US
6 Bedrooms 12 Guests
Aug 22 - 29
$867 night

VRC19-000188 4118 5th Ave Holmes Beach, FL 34217 This ideally located 6 Bedroom 3.5 Bathroom is an amazing place to escape and unwind. It is the perfect place to get away with friends or family, offering a large open floor plan and multiple outdoor sitting areas. This little piece of paradise is centrally located to everything you could desire, it is a short 2-3 minutes stroll to the white sand beaches with crystal clear blue waters, restaurants and bars, shops and the island’s free trolley. Whether you are interested in indulging in some local seafood, parasailing, fishing, surfing or listening to live music, you will find tons of fun activities less than 5 minutes from the house. 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. This house features a bright and flowing floor plan framed by large windows and multiple balconies that let in the Florida breeze and sunshine. It is the perfect option for multifamily or mixed group, the house offers 2 spacious king suites each featuring their own private balcony, 2 large king bedrooms, 1 private queen bedroom and a room with 2 twin beds. In addition to these 6 rooms we also offer a sleeper sofa to insure there is always room for everyone. Each room feature a flat screen TVs, high-speed wireless internet., Spectrum cable and free calling within the US, Canada and Mexico. An additional bonus to this Mediterranean dream house is its private elevator which can help with luggage, groceries or just make for easy mobility up and down this beautiful 3 story house. Outside is your own private oasis that is surrounded by gently swaying palms and tropical plants. Whether you want to relax by a large heated pool, soaking in the hot tub, BBQ with family and friends or enjoy a game of corn hole on the sanded game area, this house offers something for everyone. When you need a break from the sun our covered lounge area offers a 52" outdoor TV, relaxing sectional set and outdoor patio table for the whole family to gather around. A stay at Angel Sea would help make anyone’s vacation a success. 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." 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 $200 (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.

Villa Portofino

Holmes Beach, FL, US
5 Bedrooms 10 Guests
Sep 4 - 11
$351 night

Villa Portofino by Anna Maria Vacations VRC18-000050 Experience the perfect family vacation at Villa Portofino, a charming island retreat just a short walk from the pristine beaches of Holmes Beach! Offering five bedrooms, three and a half bathrooms, and a private backyard oasis featuring a sparkling pool, lush tropical landscaping, and outdoor living space, this home provides comfort and luxury for multi generational families, friends, or large groups seeking a relaxing Gulf Coast getaway. Highlights • 6-minute walk to Manatee Beach • 5 Bedroom / 3.5 Bath • 2 Kings, 1 Queen, 4 Twin beds • Private heated pool • Outdoor living space and grill • Multiple balconies • Beach chairs and toys • Close to shops, dining, and local attractions • Washer and dryer • 4 Parking spaces Enjoy your days lounging by the private pool, preparing meals on the gas grill, or relaxing in the outdoor living space surrounded by tropical foliage. Inside, the home features tropical decor, with a fully equipped kitchen perfect for cooking large meals or casual snacks. The second floor primary suite offers a private balcony, a luxurious ensuite with walk-in shower and tub, creating a perfect retreat after a day at the nearby beaches. The upper floor features the main living area decorated with tropical accents, comfy seating, and HDTVs, ideal for family movie nights or relaxing after your beach adventures. The fully equipped kitchen includes wood cabinets, granite countertops, and stainless steel appliances, with a lovely wood dining table that can host family dinners with ocean breezes just outside through glass doors leading to the outdoor space. The two primary bedrooms offer premium beds, balconies, and ensuite bathrooms with double vanities, and walk-in showers, the second floor primary includes an additional standalone tub. The other bedrooms include two spacious twin rooms, each with a TV and ample storage, and a Queen bedroom, all sharing a hall bathroom with a shower and tub combination. All bedrooms are designed for restful nights and family comfort. Room Details • Primary Bedroom (2nd floor): King bed, ensuite with walk-in shower and tub • Second Primary Bedroom (3rd floor): King bed, ensuite with walk-in shower • Third Bedroom (3rd floor): Queen bed, ample storage • Fourth Bedroom (3rd floor): Two twin beds • Fifth Bedroom (3rd floor): Two twin beds Enjoy the convenience of a washer and dryer, multiple outdoor seating areas, pool and beach toys, and beach chairs. Whether relaxing poolside, strolling to the nearby Gulf, or savoring long family dinners on the patio, this home offers everything needed for a memorable island escape. Reserve your stay at Villa Portofino today and discover a tropical paradise with access to stunning beaches, charming local shops, and delicious dining. Book now and create lifelong memories with your loved ones! - The waterfall feature on the pool has been disabled. 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. 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.

Jackie’s Cottage

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Oct 26 - Nov 2
$631 night

Jackie’s Cottage by Anna Maria Island Accommodations VRC18-000190 Welcome to Jackie’s Cottage, a stunning one level canal front home with a private wet dock and dry dock, now showcasing recently updated interiors with modern furnishings and coastal decor. Just a block and a half from the pristine Gulf beaches, this four bedroom, three bath vacation escape offers a serene water-centric retreat. You’ll enjoy breathtaking water views, direct access to the boat slip for water adventures, and a location close to the trolley stop for exploring all of Anna Maria Island’s scenic seven miles. Highlights • Canal front home • 5-minute Walk to the beach • 4 Bedroom / 3 Bath • 2 Kings, 1 Queen, 2 Twin beds • Private heated pool • BBQ grill and water views • In-unit washer and dryer • One block from the nearest free Anna Maria Island trolley stops • Near Marina Drive for local shops, restaurants and more • 3 car parking Relax in your tropical backyard oasis and find yourself swimming in the private pool, surrounded by comfortable loungers, or docking your boat on the spacious slip with room for two jet skis. The outdoor dining area with a BBQ grill and lush landscaping creates the perfect setting for relaxing dinners and viewing sunsets. Water toys, fishing gear, and rentals are just steps away for endless water fun or unwind with a book in the waterfront serenity. Step inside this beautifully upgraded home and enjoy a fresh, modern design. The main living area features large windows framing spectacular water views, plush seating with a TV, and a stylish, updated kitchen with a farm sink, sleek countertops, and stainless-steel appliances. The kitchen offers a bar with seating for casual meals, while the adjacent dining area with a large water-facing table is perfect for family gatherings or entertaining friends in a tropical setting, making every meal a special occasion. Retreat to the primary bedroom, which boasts a king bed, a TV, and exclusive access to the water-facing patio. The luxurious ensuite features a walk-in shower and ample closet space. The second bedroom, with a king bed, TV, and water views, shares a hall bathroom with a walk-in shower. The third bedroom offers two twin beds with nautical decor, and the fourth bedroom features a queen bed, TV, and plenty of space for restful sleep. The hall bathroom has a combined shower and tub, and a washer and dryer provide convenience for all guests. Room Details • Primary Bedroom: King bed, ensuite bathroom • Second Bedroom: King bed, shared ensuite bathroom • Third Bedroom: Two twin beds • Fourth Bedroom: Queen bed Book Jackie’s Cottage today and indulge in the ultimate water-front lifestyle on Anna Maria Island. With recent interiors, stunning water views, a private dock, and proximity to beaches, shops, and dining, this home is your ideal retreat for relaxation and adventure. Reserve now and start creating lifelong memories in this perfect island escape! - DISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary. No pets are 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 Anna Maria Island 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 Anna Maria Island Accommodations 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.

Island Hideaway - Hosted By Skyrun Anna Maria

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Sep 15 - 22
$249 night

Top Reasons to Book: - Private Heated Pool with Lounge Seating (FREE POOL HEAT!) - Pet Friendly (2 pet max, fee applies) - Balcony Overlooking the Pool & Surrounding Landscape - Gas Grill for Easy Home-Cooked Meals - Sleeps Up to 7 Guests – Perfect for Families or Friends - Prime Location in the Heart of Holmes Beach - Short Walk to Anna Maria Island Beaches - Professionally Managed Welcome to Island Hideaway, your peaceful Holmes Beach retreat on Anna Maria Island. This beautifully updated 3-bedroom, 2-bath coastal retreat blends modern design with laid-back island living—perfect for families and friends seeking comfort and style. Inside, a bright open floor plan features a fully equipped kitchen, dining area, and open living room with a Smart TV and high-speed Wi-Fi. A private washer and dryer make it easy to keep beach towels fresh throughout your stay. Step outside to enjoy your heated pool, balcony with seating, and gas grill—perfect for poolside meals or relaxing evenings under the palms. Bedrooms & Baths: - Primary Suite: King bed, ensuite bath with soaking tub, stand-up shower & smart amenities - Guest Room 1: Queen bed - Guest Room 2: Twin-over-twin bunk + twin trundle (Sleeps up to 7 guests) Just a short stroll to Holmes Beach, and close to local favorites like The Sandbar, The Beachcomber, and the Holmes Beach Pier, Island Hideaway offers the ideal blend of comfort, convenience, and coastal charm. Important Notes: - Pool heat is included during your stay at no additional cost. - Dog friendly home: A maximum of 2 dogs is allowed. A $125 per pet fee applies to cover additional cleaning and can be requested through our guest portal.

Magarita-Ville

Holmes Beach, FL, US
6 Bedrooms 12 Guests
Aug 18 - 25
$415 night

Margarita-Ville by Anna Maria Island Accommodations VRC16-000136 Experience the ultimate island escape at Margarita-Ville, a stunning six-bedroom, four and a half bath vacation home designed for large families or groups seeking a memorable getaway! Just a two-minute walk from the beach, this beautifully landscaped estate offers glimpses of the water from balconies, your private pool with a spa, a Tiki bar, outdoor TV, and ample outdoor dining and lounging areas, perfect for relaxing days and lively evenings. Located near locally owned shops, waterfront restaurants, and just a short walk to the trolley stop, Margarita-Ville blends convenience with elegance for an unforgettable Anna Maria Island vacation! Highlights • 2-minute walk to Manatee Public Beach • 6 Bedroom / 4.5 Baths • 4 Kings, 1 Queen, 1 twin with trundle, 1 Queen sleeper sofa • Private heated pool and spa • Elevator access • Tiki bar with an outdoor TV • Outdoor dining space and BBQ grill • Foosball and pool table • Short walk or trolley ride to shops, waterfront restaurants, and local attractions • 4 Parking Spaces Unwind in your personal aquatic oasis, relax in the private heated pool, soak in the hot tub and enjoy the Florida sun. Gather under the covered Tiki bar with a TV and plenty of seating or fire up the BBQ grill for casual family dinners or sunset parties. Enjoy the lush backyard in your secluded retreat or play a game of pool or foosball, easily accessible to the outdoors. Inside, the welcoming layout features a large flat-screen HDTV, plush seating, and serene island decor. The kitchen boasts stainless steel appliances, granite countertops, and an island with seating for four. Seamlessly connecting with a formal dining table for eight, ideal for family meals or entertaining indoors. The open floor plan encourages everyone to gather comfortably, whether indoors or outside on the patio. Relax in the primary bedroom, located on the third floor, with a king-sized bed, private balcony, and ensuite bathroom with a walk-in shower. Three additional bedrooms, one on the second floor and two on the third floor, include king beds, each with their own flat-screen TV and luxurious linens, two with en-suite bathrooms and walk-in showers. On the third floor, find the fifth bedroom with a stunning queen bed, while the final bedroom offers a twin bed plus a twin trundle, ideal for kids or additional guests. The living room offers a queen sleeper sofa for more space. The hall bathroom features a walk-in shower, and a half bath and laundry room add convenience to your stay. Room Details • Primary Bedroom (3rd floor): King bed, ensuite with walk-in shower • Second Bedroom (3rd floor): King bed, ensuite with walk-in shower • Third Bedroom (2nd floor): King bed, ensuite with walk-in shower • Fourth Bedroom (2nd floor): King bed, ensuite with walk-in shower • Fifth Bedroom (3rd floor): Queen bed • Sixth Bedroom (3rd floor): Twin bed with twin trundle • Living Room: Queen sleeper sofa Book Margarita-Ville today and enjoy a luxurious home in the heart of Anna Maria Island. Whether you are floating in the pool, exploring nearby beaches and restaurants, or enjoying breathtaking sunsets, this home has everything you need for an unforgettable Gulf Coast vacation. Reserve your dates now and start creating lifelong island memories! - This home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. 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. 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 Island Accommodations 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.

Coming in Hot

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Oct 16 - 23
$652 night

Coming in Hot by AMI Locals VRC22-000171 Live the island dream at Coming in Hot, a stunning newly built four-bedroom, four and a half bath retreat located in Holmes Beach, just one minute from the sugar-white sands of Anna Maria Island! With a rooftop deck offering panoramic Gulf views, a resort-style pool and spa, multiple balconies, and a ping pong table, this pet-friendly vacation rental is designed for endless fun and relaxation! Highlights -1-minute walk to Holmes Beach -4 Bedrooms / 4.5 Bathrooms -3 King beds, Full-over-Full bunk with Twin trundle -Rooftop deck -Resort-style pool and spa -Ping pong table -Multiple balconies -Dog friendly with host approval -Outdoor grill and dining area -Central location near shopping and dining -4 Parking Spaces Step outside to your private oasis, where you’ll find a sparkling heated pool, soothing spa, and lush landscaping for a secluded feel. Multiple lounge areas invite you to relax in the sun or shade, while the BBQ grill and covered dining patio set the stage for poolside meals and happy hours. Head up to the rooftop deck for breathtaking sunrise yoga sessions or unforgettable sunsets over the Gulf. Inside, the open concept living area is bathed in natural light, featuring plush seating, a TV, and sliding glass doors that open to Gulf breezes. The chef’s kitchen is fully stocked with stainless steel appliances, quartz countertops, and a large island with breakfast bar seating. Gather for meals at the dining table or step outside to enjoy dinners on the balcony. Each of the four bedrooms offers premium linens, TVs, and plenty of storage space. The primary bedroom boasts a king bed, private balcony, and an ensuite bathroom with a walk-in shower and double vanity. The second and third bedrooms offer king beds and ensuite bathrooms with walk-in showers, the third bedroom with private balcony access. The last bedroom, ideal for kids or additional guests, includes a full-over-full bunk bed with a twin trundle, balcony access, and an ensuite bathroom with a shower/tub combo. Room Details -Primary Bedroom: King bed, ensuite with double vanity and walk-in shower -Second Bedroom: King bed, ensuite with walk-in shower -Third Bedroom: King bed, ensuite with walk-in shower -Fourth Bedroom: Full-over-Full bunk with Twin trundle, ensuite with shower/tub combo From your doorstep, you’re just moments from Holmes Beach and a quick trolley ride to explore all of Anna Maria Island’s treasures. Stroll Holmes Beach Towne Center boutiques, enjoy fresh seafood at local restaurants, rent kayaks or bikes, or book a fishing charter and dolphin tour. Whether relaxing poolside, playing ping pong, or watching legendary Gulf sunsets from your rooftop deck, Coming in Hot promises an unforgettable Anna Maria Island experience. Book your stay today and start making lifelong memories at Coming in Hot! - 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. 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. 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.

Just Beachy

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 29 - Sep 5
$1,036 night

128 49th St Holmes Beach VRC 21-000019 this stunning 4 bedroom + bonus Guest Suite ( additional king bedroom with en- suite over the garage great for multi-generational or nanny quarters), 5.5 bathroom home only 2-minute walk to the beach with a large heated pool, spa, and poolside bathroom. 2 king suites, one queen bedroom with a jack and jill bathroom into the full size bedroom, . This house has everything you could possibly need for the most incredible beach vacation or an extended stay for working from home or homeschooling with a separate study with a desk and high- speed WiFi 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"

A Pirate’s Dream

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 18 - 25
$674 night

Welcome to A Pirate’s Dream, a grand waterfront retreat that perfectly blends coastal elegance with island adventure on beautiful Anna Maria Island. This four bedroom, three and a half bath vacation home plus loft is designed for families and groups seeking both relaxation and excitement. Located just a five-minute walk from the beach, this Mediterranean inspired home features a private dock, a heated pool, and spectacular bay and canal views, creating a luxurious setting for your next island getaway. Highlights • 5-minute walk to Holmes Beach • 4 Bedrooms / 3.5 Bathrooms • 4 King beds, 4 Twin beds • Private dock • Heated private pool with sun shelf and picnic table • Outdoor kitchen with grill, TV, and bar • Game room with ping pong, Connect Four, and Cornhole • Balcony water views and multiple lounge areas • 4 Parking spaces Relax and unwind in your own tropical paradise, surrounded by tranquil canals and swaying palms. Enjoy the heated pool featuring a built in picnic table and sun shelf, perfect for cooling off or lounging in the Florida sunshine. The outdoor kitchen boasts a high end grill, stone finishes, and a TV, while the tiki bar sets the scene for memorable evenings with friends and family. With a private dock that accommodates boats up to 38 feet, you can kayak, paddleboard, or watch for dolphins and manatees right from your backyard. Inside, Mediterranean elegance meets modern comfort. The open concept living room invites you to relax on plush leather sofas while streaming your favorite shows on the large TV. The chef’s kitchen is fully equipped with stainless steel appliances, granite countertops, custom cabinetry, and a breakfast bar with seating. Gather around the dining table for six or take your meals outdoors on the balcony to enjoy the view. Each bedroom provides the perfect retreat with luxurious bedding, TVs, and ceiling fans. The primary suite on the second floor offers a king bed, balcony access, and a spa-inspired ensuite bathroom with a marble walk-in shower. The second bedroom features a king bed and private ensuite, while the third and fourth bedrooms share a jack-and-jill bathroom with a walk-in shower. The third bedroom also includes a private balcony. Upstairs, the loft with two twin bunk sets and a Smart TV creates a cozy hideaway for kids or teens. Room Details • Primary Bedroom (2nd floor): King bed, balcony, ensuite bathroom with walk-in shower • Second Bedroom (3rd floor): King bed, ensuite bathroom with walk-in shower • Third Bedroom (3rd floor): King bed, balcony, jack-and-jill bathroom with walk-in shower • Fourth Bedroom (3rd floor): King bed, jack-and-jill bathroom with walk-in shower • Loft (3rd floor): Two sets of twin bunk beds, balcony access The first-floor game room is perfect for family fun, featuring a ping pong table, lounge area, and an extra fridge for poolside drinks. The laundry room includes a washer, dryer, and granite utility sink for convenience. Located near restaurants such as Skinny’s Place inc. and Hurricane Hanks, or close to Publix Super Market, this waterfront home keeps you close to Anna Maria Island’s best dining, shopping, and outdoor experiences while maintaining the privacy of your own tropical oasis. From morning coffee on the balcony to sunset cocktails by the tiki bar, A Pirate’s Dream offers the ultimate Anna Maria Island vacation rental experience. Embrace the laid-back luxury of island life, where every day feels like a treasure waiting to be discovered. Book your stay today and set sail on your perfect coastal escape! - 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. Garage is off-limits to any vehicles, including Golf Carts No Pets are allowed in this home These premises are monitored by video surveillance in select exterior areas. 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 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 termination of your rental agreement without a refund.

Coral Castle

Holmes Beach, FL, US
5 Bedrooms 10 Guests
Dec 1 - 8
$1,104 night

Coral Castle by AMI Locals VRC16-000158 Welcome to Coral Castle, a luxurious waterfront retreat in the heart of Anna Maria Island, where you can spot gentle manatees gliding by from your private dock! This five-bedroom, three-and-a-half-bathroom haven is just a three-minute walk to the powdery sands of Manatee Beach. With a private pool, spa, rooftop deck, and private dock, this coastal gem blends upscale comfort with tropical charm, perfect for families or groups seeking a dream island getaway. Highlights • 3-minute walk to Manatee Beach • 5 Bedroom / 3.5 Bath • 3 Kings, 2 Fulls • Rooftop deck with Gulf and Bay views • Heated pool and in-ground spa • Private dock for up to 20ft boat • Outdoor dining area and grill • Beach chairs provided • Washer and dryer • 5 Parking Spaces The rooftop deck invites guests to take in jaw-dropping views of the Gulf and Bay. It’s the perfect spot to sip morning coffee or watch the sunset with a chilled drink in hand. Outside, the tropical backyard features a heated pool, spa, lounge seating, and a BBQ grill, ideal for relaxing after a day of beach fun or boating. Best of all, keep an eye out for manatees cruising by from the private dock, a magical touch to your island escape! Step inside this spacious island-style home, where the airy living area features plush seating, TV, and sliding doors that lead to the outdoor patio. The gourmet kitchen includes stainless steel appliances, ample counter space, and a wine fridge. Share meals at the dining table or outside under the stars on the covered patio. This home features three king bedrooms, including a primary suite with a private balcony, walk-in closet, and spa-style ensuite with a soaking tub and walk-in shower. The additional two full bedrooms are connected by a Jack-and-Jill bathroom with a shower/tub combo, perfect for kids or additional guests. Room Details • Primary Bedroom: King bed, ensuite bathroom with soaking tub and walk-in shower • Second Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower • Third Bedroom: King bed, Jack-and-Jill bathroom with walk-in shower • Fourth Bedroom: Full bed, shares Jack-and-Jill bathroom with shower/tub combo • Fifth Bedroom: Full bed, shares Jack-and-Jill bathroom with shower/tub combo Enjoy mornings from the dock or head just a few minutes down the street to explore Pine Ave and Bridge Street’s local shops and restaurants. Whether you’re boating, relaxing in the spa, or enjoying the rooftop views, Coral Castle offers a perfect blend of luxury and island adventure. Book Coral Castle now and start making unforgettable family memories in paradise! - This home is managed by AMI Locals, an Anna Maria Island property management company. This property does not allow pets of any kind. 5 cars maximum are able to park at this home. One side of the garage is available for guest use. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. These premises are under active video surveillance in public approach areas and the dock. 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.

You, Me and the Sea AMI

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 22 - 29
$255 night

You, Me, and the Sea AMI by AMI Locals VRC21-000081 Welcome to You, Me, and the Sea AMI by AMI Locals, your perfect family retreat on beautiful Anna Maria Island. Just a one-minute walk to the soft Gulf sands, this elevated three-bedroom, two-bath vacation home blends modern coastal design with laid-back island comfort. Thoughtfully designed for families and multi-generational groups, it offers spacious living, a private pool with spa, and a prime Holmes Beach location close to everything that makes island life unforgettable. Highlights • 1-minute walk to Holmes Beach • 3 Bedrooms / 2 Bathrooms • 2 Kings / 1 Queen / 1 Full-over-Full bunk with Twin trundle • Private pool with in-ground spa • Balcony with outdoor dining and BBQ grill • 2-minute walk to the Anna Maria Island trolley stop • Parking available for 4 vehicles Step into paradise with your very own private heated pool and spa, surrounded by lush tropical greenery that invites total relaxation. The balcony features a shaded dining area and grill, perfect for sharing alfresco meals and sunset cocktails after a fun-filled beach day. Inside, you’ll find a bright open floor plan designed for comfort and togetherness. The living room offers cozy seating and a TV for movie nights, while the fully equipped kitchen features stainless steel appliances, generous counter space, and a dining table set for family gatherings. A small workspace next to the kitchen provides a convenient spot to catch up on emails or jot down vacation plans, making this home functional as it is relaxing. Whether preparing breakfast or enjoying evening dinners, this space makes island living effortless. The primary suite is ideal for parents and kids, featuring a king bed, full-over-full bunk bed with twin trundle, and an ensuite bathroom with a double vanity and walk-in shower. The second bedroom includes a king bed, while the third bedroom offers a queen bed. Both share a hallway bathroom with a walk-in shower, making it easy for everyone to have their own space and comfort. Room Details • Primary Bedroom (2nd floor): King bed, Full-over-Full bunk with Twin trundle, ensuite bathroom with walk-in shower • Second Bedroom (2nd floor): King bed • Third Bedroom (2nd floor): Queen bed • Hall bathroom with walk-in shower This home provides a washer and dryer, Wi-Fi, and beach essentials for guest use. Guests can easily explore Anna Maria Island with the island trolley, just steps away. Located near restaurants such as Skinny’s Place and Double Deez Chicago Style Restaurant, or parks like Grassy Pointe Preserve, you’ll have local dining and outdoor activities at your fingertips for the perfect island experience. From peaceful mornings on the balcony to sunset swims in the pool, You, Me, and the Sea AMI by AMI Locals offers everything you need for an unforgettable Anna Maria Island vacation rental. Make lifelong memories with your loved ones and book your stay today! - This home is managed by AMI Locals, an Anna Maria Island property management company. 4 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. 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 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.

Coral Escape

Holmes Beach, FL, US
6 Bedrooms 12 Guests
Aug 26 - Sep 2
$495 night

Coral Escape by AMI Locals VRC18-000089 Welcome to Coral Escape by AMI Locals, a stunning 6-bedroom, 4-bathroom coastal retreat just a 3-minute walk from the beach on beautiful Anna Maria Island. Perfect for families and large groups, this luxury beach home blends spacious comfort, modern design, and fun amenities; including a private pool and spa, balconies, and a game area with a pool table. Conveniently located near the Anna Maria Island trolley stop, you’ll have easy access to local restaurants, boutiques, and the laid-back charm of Holmes Beach. Highlights • 3-minute walk to the beach • 6 Bedrooms / 4 Bathrooms • 5 King beds, 1 Twin-over-Twin bunk bed • Private heated pool and spa with natural rock features • Outdoor dining area and wet bar • Pool table and balconies • Near island trolley stop • Dog-friendly with host approval and pet fee • 6 Parking space (4 in Driveway, 2 in Garage) Your tropical paradise begins outdoors with a sparkling private pool and spa, surrounded by lush landscaping and natural rock accents. Enjoy sunny days lounging by the water, then gather in the covered outdoor area, complete with a pool table, wet bar, and dining table for alfresco meals. Whether you’re relaxing with a cool drink, taking an evening dip under the stars, or enjoying a game of pool, Coral Escape is designed for unforgettable days in the Florida sun. Inside, you’ll find a bright, open floor plan perfect for entertainment. The main living area features a spacious dining table for eight, a granite kitchen island with bar seating, and a modern kitchen equipped with stainless steel appliances and everything needed to prepare family meals. The living room offers plush seating, a TV, and easy access to the home’s balconies where you can feel the ocean breeze. Each bedroom in Coral Escape is designed for rest and relaxation after a day of beach adventures. The primary suite, located on the second floor, offers a king bed and a private ensuite bathroom with a walk-in shower. A second king bedroom on the same level shares a hallway bathroom with a shower/tub combination. On the third floor, guests will find four additional bedrooms; three with king beds and one with a twin-over-twin bunk bed; along with two more beautifully appointed bathrooms featuring walk-in showers. Room Details -Primary Bedroom (2nd Floor): King bed, ensuite bath with walk-in shower -Second Bedroom (2nd Floor): King bed, shares hall bath with shower/tub combo -Third Bedroom (3rd Floor): King bed, ensuite bath with walk-in shower -Fourth Bedroom (3rd Floor): King bed, shares hall bath -Fifth Bedroom (3rd Floor): King bed, shares hall bath -Sixth Bedroom (3rd Floor): Twin-over-Twin bunk bed, shares hall bath Enjoy the convenience of Wi-Fi, in-home laundry, and parking for up to four vehicles. The island trolley is just around the corner, making it easy to explore Holmes Beach, Pine Avenue, and local favorites like The Feast and Hurricane Hanks. After a day of exploring, return home to your private oasis and unwind in style. With host approval before check-in, dogs are welcome. Offering space, luxury, and location, Coral Escape by AMI Locals is the ultimate destination for families and groups looking for a luxury Anna Maria Island vacation rental. Whether you’re splashing in the pool, relaxing in the spa, or gathering for sunset dinners outdoors, every moment here feels like paradise. Your dream island getaway awaits, book your stay at Coral Escape by AMI Locals today! - 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. 6 cars maximum is 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.

Sand Dollar (AMV)

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 18 - 25
$253 night

Sand Dollar by Anna Maria Vacations Home in Holmes Beach, Florida VR16-000501 Escape to Sand Dollar, a blissful island retreat nestled in Holmes Beach, featuring four bedrooms and three bathrooms, and a private backyard oasis with a pool, BBQ grill, and ample outdoor seating! Located less than five minutes from pristine Gulf beaches, this family-friendly home offers easy access to the scenic 7-mile island, local shops, and outdoor adventures. Perfect for families or groups seeking relaxation and fun in a stylish, elevated setting, Sand Dollar promises unforgettable island memories. Highlights • 4-minute walk to Holmes Beach • 4 Bedroom / 3 Bath • 1 King, 1 Queen, 4 Twin beds • Private pool • Balconies • Outdoor lounging area and BBQ grill • Elevator access • Close to Holmes Beach Towne Center shops, dining, and local attractions • Washer and dryer • 4 Parking spaces Enjoy outdoor living with your private pool, outdoor seating, and BBQ grill perfect for breezy dining. Take the elevator to the main living area, which features a family room with comfortable sofas and a TV that opens to a balcony for relaxing in the island breeze. Inside, the modern kitchen with a large island is designed to facilitate casual meals or entertaining friends with tapas and wine. Explore the nearby beaches or head to Holmes Beach Towne Center for local dining and shopping. The inviting interior combines coastal charm with modern comforts. The family room offers a cozy spot to unwind after a beach day, with easy access to the balcony overlooking lush palms. The fully equipped kitchen is ideal for preparing meals, with thoughtful details like a large island and bar stools. Gather at the dining area for meals or drinks, extending the indoor-outdoor living experience. Relax in the spacious primary bedroom with a king-sized bed, balcony access, and an ensuite bathroom with a walk-in shower and soaking tub. The second bedroom offers a queen bed and an ensuite bathroom, providing privacy and comfort. The third and fourth bedrooms, each with two twin beds, have easy access to the hall bathroom with a walk-in shower. A laundry room with washer and dryer and a half bath complete the layout, ensuring a relaxing and hassle-free stay. Room Details • Primary Bedroom: King bed, ensuite with walk-in shower and soaking tub  • Second Bedroom: Queen bed, ensuite with walk-in shower  • Third Bedroom: Two twin beds • Fourth Bedroom: Two twin beds Enjoy the convenience of a washer and dryer, elevator access, and close proximity to the beach, shops, and local attractions. Relax poolside, explore the island by bike or trolley, or unwind with a family fishing charter. Positioned perfectly to explore Anna Maria Island’s seven miles of pristine beaches and scenic spots, Sand Dollar offers the perfect family island adventure. Reserve your stay at Sand Dollar today and enjoy a luxurious, family-friendly escape on Anna Maria Island. From beach days and boat trips to evenings on the balcony or around the pool, this island retreat promises unforgettable memories. Book now to start your perfect Gulf Coast vacation! - This property does not allow pets. 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.

Blissful Bungalow

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 18 - 25
$239 night

Blissful Bungalow by AMI Locals VRC21-000131 Welcome to Blissful Bungalow by AMI Locals, a stylish three bedroom, two and a half bath vacation home that perfectly captures the charm of Anna Maria Island. Just an 8-minute walk to the pristine Gulf beaches, this beautifully updated ranch-style retreat offers a private pool, lush tropical landscaping, and an inviting outdoor entertainment area. Designed for comfort and relaxation, it’s the perfect coastal escape for families and friends eager to enjoy the laid-back island lifestyle of Holmes Beach. Highlights • 8-minute walk to Holmes Beach • 3 Bedrooms / 2.5 Bathrooms • 2 King beds, 1 Twin-over-Queen bunk bed • Private pool and outdoor shower • BBQ grill • Near the island trolley stop • Close to shops and restaurants • 3 Parking Spaces Step into your private tropical oasis featuring a sparkling backyard pool and BBQ grill surrounded by lush greenery. Lounge in the sun with a cold drink or enjoy evening meals under the island breeze. With a trolley stop nearby, it’s easy to explore the island’s best beaches, eateries, and attractions without ever needing to drive. Inside, natural light fills the living room, offering cozy seating and sliding glass doors with pool views. The fully equipped kitchen features stainless steel appliances, granite countertops, a wine fridge, and bar seating; perfect for preparing meals or sharing morning coffee. Dine together around the indoor table under soft ambient lighting. The primary suite provides a peaceful retreat with a king bed, workstation nook, and private patio access. Its ensuite bathroom includes a walk-in shower, double vanity, and walk-in closet. The second bedroom also features a king bed and a private ensuite bathroom with a shower and tub combination. The third bedroom, furnished with a twin over queen bunk bed, has convenient access to the half bath, ideal for kids or extra guests. Room Details • Primary Bedroom: King bed, backyard access, ensuite bathroom with walk-in shower • Second Bedroom: King bed, ensuite bathroom with shower and bathtub combination • Third Bedroom: Twin-over-Queen bunk bed, hallway access to half bath Guests will appreciate convenient amenities like a washer and dryer, Wi-Fi, and complimentary beach essentials for guest use. Ideally situated near restaurants such as The Ugly Grouper and Hurricane Hanks, this home also offers easy access to Fun and More Rentals, where you can rent golf carts, paddleboards, and bikes to explore the island your way. Enjoy the peace of your private backyard retreat or hop on the island trolley just steps away to discover all seven miles of Anna Maria Island, from boutique shops along Pine Avenue to scenic kayak tours through the mangroves. With its breezy style, modern amenities, and unbeatable location, Blissful Bungalow by AMI Locals is your invitation to experience luxury island living at its most relaxed. From poolside afternoons to sunset strolls on Holmes Beach, every moment feels like paradise. Book your stay today and make lasting memories on beautiful Anna Maria Island! - *This home does not allow pets of any kind 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.

Holmes Beach - Pool - Minutes to Beach - Sleeps 8

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 18 - 25
$691 night

Experience the best of Holmes Beach in this well-appointed 4-bedroom home, offering comfort, convenience, and everything you need for an unforgettable Florida vacation. • Minutes away from the beach! • Heated Private Pool • Outdoor Patio/Dining • BBQ Grill • Board Games • Fully Stocked Kitchen • Drip Coffee Maker • TVs in each bedroom • Private Balcony • Family/Kid Friendly • Washer & Dryer • Ample Parking • High Speed WIFI VRC 16-000759 Welcome to your slice of paradise in Holmes Beach — where laid-back island vibes meet comfort and style! This beautiful 4-bedroom, 4-bathroom coastal retreat comfortably accommodates up to 8 guests, making it perfect for family vacations, couples’ getaways, or a relaxing trip with friends. Designed for both privacy and togetherness, each bedroom offers its own bathroom — no sharing required — so everyone can unwind in comfort after a sun-soaked day. Located just moments from the beach, you’ll have easy access to sugar-white sands, turquoise waters, and breathtaking Gulf sunsets. Whether you’re here for beach days, boating adventures, local dining, or simply slowing down and reconnecting, this Holmes Beach getaway offers the perfect home base for making unforgettable coastal memories. To make exploring even more fun, guests can enjoy a kayak for water adventures and a bike with a children’s seat, perfect for cruising around the island together and soaking in the relaxed coastal atmosphere. MAIN SPACES OF THE HOME: – 4 BEDROOMS & 4 BATHROOMS – BEDROOM 1: * King-sized Bed * Smart TV * Nightstand & Lamps * Direct Balcony Access * Ensuite Bathroom BEDROOM 2: * King-sized Bed * Smart TV * Nightstand & Lamps BEDROOM 3: * Queen-sized Bed * Smart TV * Nightstand & Lamps BEDROOM 4: * Queen-sized Bed * Smart TV * Nightstand & Lamps – 4 BATHROOMS – * Ensuite Bathroom with a Tub & Walk-in Shower * Ensuite Bathroom with Shower/Tub Combo * Full Bathroom with Walk-in Shower * Half Bathroom – CHEF’S KITCHEN – * Fully Stocked * High-end Stainless Appliances * Ample Cabinetry * Large Island w/ High Seating * Coffee Maker: Drip – LIVING ROOM – * 75” Smart TV * Large Plush Sofa * Open Floor Plan – OUTDOOR FUN & AMENITIES – * Heated Private Pool * Outdoor Patio/Dining * BBQ Grill * Beach Essentials: Chairs, Umbrellas & Towels! * Kayak * Bike w/ Children’s Seat The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Free Island Trolley: The Anna Maria Island free trolley is a popular local option! This daily, air-conditioned service runs from 6 a.m. to 10:30 p.m., arriving approximately every 15–20 minutes. It connects Coquina Beach to the Anna Maria City Pier with several stops throughout Holmes Beach, including Manatee Public Beach and the Island Shopping Center. Golf Carts: Multiple golf cart rental services are also available nearby, making it easy and fun to get around the island like a local! Check-in is at 4pm Check-out is at 10am - No pets allowed. - Stays of 28 days or more may incur an additional cleaning fee. - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - An exterior camera is installed solely to monitor our cleaning team for quality and security purposes. - Parking is available for 4 vehicles in the driveway. Please note that street parking is not allowed. - If you’re interested in a long-term stay, please reach out to inquire about availability - The pool can be heated to about 20-25 degrees above the ambient temperature; please keep in mind that when the weather is cooler may not be as warm as you might expect. For example, if the ambient nightly temperature is only 55 degrees, then the pool might heat up to 75-80 degrees. We recommend the pool is heated in the months between October to May each year. We require at least a 3-day notice before your arrival if you’d like the pool heated. Pool must be heated for the entirety of your stay. Thank you! - Guests must be 21 years or older to book this property. - Pool/Beach Towels: Pool and beach towels are provided for your convenience. After use, please return all towels to ensure they are available for the remainder of your stay. Thank you for helping us keep everything organized and ready for everyone to enjoy! - Beach Items: We’re happy to offer a selection of beach supplies for guest use! Beach chairs, umbrellas, and beach toys are available. We hope this makes your beach days even more relaxing and enjoyable! - This home features a pull-out sofa bed for additional sleeping space. Fresh linens can be found in the upstairs bedroom closet left of the staircase. As part of our checkout process, we kindly ask that you remove any used linens and return the sofa bed to its original position. We appreciate your help in preparing the space for our next guests! GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out. License number: VRC 16-000759

Peacock Crossing

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Sep 3 - 10
$244 night

Peacock Crossing by AMI Locals VRC22-000116 Welcome to Peacock Crossing, a stylishly renovated island retreat tucked away on a quiet street in the heart of Holmes Beach. This beautifully updated three-bedroom, two-bathroom family home is just a short stroll to the beach and offers all the essentials for a perfect vacation. Including a private heated pool, swim-up bar, and coastal-modern furnishings. Whether you’re traveling with family or friends, this home has everything you need for a relaxing stay on Anna Maria Island. Highlights • Beach Access at the End of 52nd Street • 8-minute walk to Holmes Beach • 3 Bedroom / 2 Bath • 1 King, 1 Queen, 2 Twin Beds • Heated pool with sun shelf and swim-up table • Grill and outdoor dining area • Washer and dryer • Beach wagon and beach chairs • Dog friendly • 2 Parking Spaces Outside, your private tropical backyard oasis awaits. Take a dip in the heated pool with sun shelf and in-water cocktail table, then grill up a fresh seafood dinner and dine under the stars. Surrounded by lush palm trees and coastal landscaping, the backyard offers the perfect space for soaking up the island lifestyle. Step inside and you’ll be welcomed by a bright, open concept living space filled with coastal decor, comfortable seating, and a flat-screen TV for relaxing after a day in the sun. The updated kitchen includes stainless steel appliances, granite countertops, and all the essentials for preparing home-cooked meals. A dining table for six sits nearby, offering a great place for casual meals or game nights with the family. Each bedroom is thoughtfully appointed with beach-inspired design, luxury bedding, and TVs. The primary suite features a king bed and an ensuite bathroom with a walk-in shower. The second bedroom offers a queen bed, while the third bedroom includes two twin beds. A second full bathroom is located off the hallway, and the home is also equipped with a full-size washer and dryer for added convenience. Room Details -Primary Bedroom: King bed, flat-screen TV, ensuite bathroom with walk-in shower -Second Bedroom: Queen bed, flat-screen TV -Third Bedroom: Two Twin beds, flat-screen TV Guests will enjoy access to a washer and dryer, Wi-Fi, and beach essentials for guest use. Conveniently located near restaurants such as The Ugly Grouper and Hurricane Hanks, this home also offers easy access to Fun and More Rentals, where you can rent golf carts, paddleboards, and bikes to explore the island your way. Hop on the island trolley nearby to explore seven miles of beaches, boutique shops, and island attractions. From morning swims in the heated pool to sunset strolls on Holmes Beach, Peacock Crossing by AMI Locals delivers the perfect balance of modern comfort and island charm. Enjoy coastal living at its finest and book your stay today to experience the best of Anna Maria Island vacation rentals! - 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 note: 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. 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. In accordance with City of Holmes Beach zoning regulations, all reservations for this property must follow a Saturday-to-Saturday booking schedule with a seven-night minimum stay. 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.

Beachfront Paradise

Bradenton Beach, FL, US
8 Bedrooms 16 Guests
Aug 20 - 22
$2,134 night

Beachfront Paradise by Exclusive Vacations TPL19-000058, DWE5105473 Escape to Beachfront Paradise, part of our Exclusive Collection. Offering an exquisite eight bedroom, six-and-a-half bath waterfront estate with spectacular ocean views and private beach access! This boutique luxury home boasts a heated pool and spa, perfect for large family gatherings, or groups craving relaxation and adventure. Located near Bridge Street’s vibrant shops, restaurants, and entertainment, Beachfront Paradise delivers an unrivaled island experience with stunning water vistas and outdoor living spaces that redefine beachfront luxury! Highlights • Beachfront Home • 8 Bedroom / 6.5 Bath • 7 King beds, 1 full over full bunk • Private pool and spa • Outdoor BBQ grill • Corn hole • Golf cart, bikes, and beach gear provided • Located near shops, waterfront dining, fishing piers, and scenic parks • Two laundry rooms • 4 Parking spaces Exclusive Amenities: • 6 Seat Club Car Cru Golf Cart for Guest Use • Luxury Beach Bikes for Guest Use • Luxury Beach Chairs, 2 Beach Umbrellas and a Beach Cart for Guest Use • Upgraded Bed and Bath Linens and Toiletries • Portable Pack and Play Unwind outdoors in your waterfront oasis, soak in the hot tub viewing the ocean, relax by the private pool, or dine under the stars at the outdoor dining table. Watch Dolphins, Manatees, and colorful watercraft pass by as you enjoy unforgettable sunsets from the rooftop deck or beachside patio. The outdoor BBQ area provide the perfect setting to host family cookouts or simply unwind after a day of water adventures. Inside, the home boasts an open, modern design with breathtaking Gulf views from every corner. The main living floor features elegant furnishings, multiple seating areas, and large sliding glass doors that lead to outdoor patios and the rooftop deck, perfect for celebrating sunsets, sunrises, or just relaxing with ocean breezes. The spacious kitchens is outfitted with premium appliances, a wine refrigerator, ample cabinets, and a big island with seating for five, ideal for preparing island-inspired meals or entertaining with friends and family. The primary suite, on the third floor, is a luxurious retreat with a king bed, a private balcony, and an ensuite bath including a double vanity, walk-in shower, and a soaking tub overlooking the water. Five additional bedrooms all feature King beds, with three having ensuite bathrooms with walk-in showers. The large bunk room with full over full bunk beds is perfect for kids or additional guests. Every bedroom is decorated with plush linens and offers stunning water or tropical decor, ensuring restful nights in paradise. A hall bathroom with a walk-in shower and a half bath provide convenience for everyone. Room Details • Primary Bedroom (3rd floor): King bed, ensuite with walk-in shower • Second Bedroom (3rd floor): King bed, ensuite with walk-in shower  • Third Bedroom (3rd floor): King bed, ensuite with walk-in shower  • Fourth Bedroom (3rd floor): King bed, ensuite with shower/tub combo  • Fifth Bedroom (3rd floor): King bed • Sixth Bedroom (2nd floor): King bed, ensuite with walk-in shower  • Seventh Bedroom (2nd floor): King bed, Jack-n-Jill ensuite bathroom  • Eighth Bedroom (2nd floor): Full over full bunk, Jack-n-Jill ensuite bathroom Book Beachfront Paradise today and indulge in the ultimate Anna Maria Island vacation. With stunning ocean views, luxurious outdoor amenities, and proximity to world-class beaches and attractions like Bridge Street and the fishing pier, this estate offers the perfect blend of relaxation, adventure, and luxury. Reserve your stay now and start creating lifelong memories in this coastal haven! - This property is managed by AMI Locals, an Anna Maria Island property management group. 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. Use of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request. 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. 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. This property allows pets - there will be an additional pet fee associated. 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.

7 Doors Down

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 26 - Sep 2
$451 night

This casual and comfortable three-bedroom duplex comes with a private, heated pool. And proximity to the beach with no streets to cross to reach the beach access! A convenient location close to the heart of Holmes Beach is the perfect choice for vacationers to relax and unwind when visiting Anna Maria Island. With coastal decor, an open floor plan, and a fully updated kitchen with stainless steel appliances this lovely duplex is perfect for enjoying time with the family. Slip into ultimate relaxation by your sparkling private pool where the patio is furnished with lounge chairs and couches. Indulge in the Florida lifestyle, soak up the sun on the beach or refresh in the pool. End the day with a nightcap poolside or watch your favorite shows on the large flatscreen TV. Stay connected with the free Wi-Fi and share your photos with friends back home. HIGHLIGHTS • 1065 sq ft. • Pet friendly • Private pool (19x15 ft) • Centrally located near Holmes Beach Plaza • 0.3 miles from bay access • 0.1 miles from beach access BEDROOMS • Sleeps 6 • Primary Bedroom: King Ensuite • Second Bedroom: Queen • Third Bedroom: Queen BEDROOMS • Primary Bathroom: Walk-in Shower • Second Bathroom: Shower/Tub EXTERIOR Enjoy the rectangular shaped 19 ft by 15 ft, pool with spa jets in a tropical setting. There are plenty of chairs and sun loungers to make it a perfect day in the sun! Optional pool heating, up to 86 F, is available at a weekly fee of 150 . Please contact us 48 hrs before arrival to add pool heat to your booking. Pool equipment is locked for safety and controls must not be tampered with. Pool alarms are mandated per city licensing ordinance and cannot be disarmed. Pools are professionally serviced weekly. Debris due to tropical climate might occur in between service days. Pool equipment does not run 24 hours and water temperature can vary as pool heaters operate ONLY when the pool pump is running. Please note if cold days/nights occur, water temperatures will drop and may stay cooler longer. When the ambient temperature falls below 60 degrees F, the pool heater may not function and even switch off. Property Manager will expedite repairs of reported malfunctions, but no refund will be made for circumstances beyond our control. There is one covered parking space under the car port and an additional parking space in the driveway. If you are looking to accommodate a larger party, there is also the adjoining "1 Step Closer", a two bedroom and two bath duplex right next door. With both properties you will expand the property to a five bedroom and 4 bath. You can rent both sides and bring the whole extended family to sleep 12 in total. Don’t forget to bring your furry family member. 7 Doors Down is dog friendly. There is a non-refundable fee of $150.00 per pet per stay and dogs any size are welcome. The pet fee does not cover any damage caused by the pet. 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. VRC18-000008 125 52nd St A, Holmes Beach

Attitude by Lattitude

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Sep 1 - 8
$361 night

Attitude By Latitude by Anna Maria Island Accommodations VRC16-000182 Welcome to Attitude by Latitude, three bedrooms, two and a half bathrooms coastal getaway just a short walk from the stunning Gulf beaches. Perfect for families or friends, this home offers a private heated pool, a fully stocked game room, and a covered outdoor entertainment area. With shopping, dining, and the Anna Maria Island Trolley all within walking distance, your ideal beach vacation starts here. Highlights -4-minute walk to Holmes Beach -3 Bedrooms / 2.5 Bathrooms -1 King bed, 1 Queen bed, 2 Twin beds, 1 Twin Daybed with trundle, 1 Queen sleeper sofa -Private heated pool with waterfall -Game room with pool table, ping pong, and foosball -Elevator -Covered patio with bar, fridge, BBQ grill, and TV -Outdoor shower -Laundry room with washer and dryer -3 Parking spaces Spend your days lounging by the sparkling pool or gather under the shaded patio for meals from the built in grill. The outdoor entertainment area includes a bar, fridge, comfortable seating, and a TV, making it the perfect place for evening gatherings. Challenge your group to friendly competition in the game room, equipped with a pool table, ping pong table, and foosball. Inside, the living room features two plush sofas, colorful artwork, and a large TV for cozy movie nights. The fully equipped kitchen boasts stainless steel appliances, custom cabinetry, and all the cookware essentials you need. Seating is available at the kitchen island, formal dining table, and the outdoor deck, giving you multiple spots to enjoy meals together. The private primary suite occupies the entire third floor and includes a king bed, a sitting area with two chairs, a twin daybed with a trundle, a TV, a work desk, and a private balcony with Gulf breezes. The luxurious ensuite bathroom features a soaking tub, walk-in shower, and a walk-in closet. The second bedroom offers a queen bed, while the third bedroom has two twin beds. These guest rooms share a hall bathroom with a shower/tub combo. A half bath is also available, along with a queen sleeper sofa in the living room for additional sleeping space. Room Details -Primary Bedroom, 3rd Floor: King bed and twin daybed with a twin trundle, private balcony, ensuite with soaking tub and walk-in shower -Second Bedroom, 2nd Floor: Queen bed -Third Bedroom, 2nd Floor: Two twin beds -Bonus, Living Room: Queen sleeper sofa This home includes a laundry room with washer and dryer, an elevator for easy access to all floors, and driveway parking for up to three vehicles. The location makes it simple to walk to the beach, explore local shops and restaurants, or hop on the free trolley to discover all corners of Anna Maria Island. Attitude by Latitude by Anna Maria Island Accommodations is the ultimate Holmes Beach getaway. Book your stay today and experience the island lifestyle in style! - There are no pets allowed in this home. 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 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 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.

Dolphin Resort - 123

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 18 - 25
$325 night

🏖️ Dolphin Resort | Private Pool, Spa, Tiki Bar, Game Room & 3 Min Walk to Beach 💖 Why You’ll Love Dolphin Resort Welcome to Dolphin Resort, your private island retreat where beach days roll into relaxing evenings around your own tropical tiki bar. Just four houses from the white sands of Holmes Beach, this 3-bedroom, 2.5-bath getaway pairs laid-back coastal living with fun-filled amenities the whole family will enjoy. Whether you’re grilling poolside, shooting pool in the game room, or sipping coffee on the porch, Dolphin Resort offers the perfect balance of privacy, play, and Florida charm. 👨‍👩‍👧 Perfect For Families or groups of up to six guests seeking a beachside escape with the bonus of a private pool, game room, and easy walk to shops, dining, and the Gulf. 🎞️ Imagine This... Your mornings begin with coffee on the colorful front porch, where the island breeze sets the tone for the day. The beach is calling you - just a short 3-minute stroll away, perfect for an early swim or beach combing session. After soaking up the Gulf sunshine, retreat to your private backyard oasis. The sparkling heated pool, bubbling spa, and shaded tiki bar invite you to slow down and savor island life. Fire up the grill for lunch or dine al fresco in the covered lounge area. Kids splashing in the pool? Grab a drink and relax in the built-in seating while keeping an eye on the fun. Just steps away, the bonus game room offers a pool table and space to unwind between beach runs. Inside, the open-concept living area is bright and welcoming, with a fully equipped kitchen—featuring both Keurig and Italian espresso makers—perfect for quick breakfasts or preparing the day’s catch. Gather for dinner on the back porch or settle into the cozy living room for a movie night before retreating upstairs to your private bedrooms. 🛌 Where You’ll Sleep • Bedroom 1 (Primary Suite, 3rd Floor): King Bed (1), Ensuite Bathroom with Shower, TV • Bedroom 2 (3rd Floor): Queen Bed (1), Hall Bathroom, TV • Bedroom 3 (3rd Floor): Queen Bed (1), Hall Bathroom, TV 📍 Explore the Area With the beach just four houses away, your days can be filled with sun, sand, and Gulf breezes. You’re also just 0.4 miles from Holmes Beach Shopping Plaza, offering cafés, restaurants, live music, and boutiques—all within walking distance. For more island adventure, rent bikes, try paddle boarding, or hop on the free trolley to explore Anna Maria Island’s charming sights. 📝 Your Island Escape Awaits Dolphin Resort offers more than just a place to stay—it delivers the laid-back, beachy lifestyle you came for. With private poolside living, fun amenities, and unbeatable proximity to Holmes Beach, this home makes it easy to unplug, unwind, and create lasting memories with family or friends. Your reservation includes peace of mind with our signature CottageClean™ program: a 6-hour deep clean and 35-point inspection completed before every arrival, ensuring your home is sparkling, sanitized, and ready for your stay. Need to Know: The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. The bonus game room with a pool table is located on the ground level. This home has stairs—please contact us if anyone in your party has difficulty with stairs. Beach towels, chairs, and a beach cart are provided. We also supply starter packs of kitchen and toiletry essentials to make your arrival seamless. Free high-speed WiFi is included. The primary guest making the reservation must be at least 26 years of age.

Beachside Oasis

Bradenton Beach, FL, US
5 Bedrooms 14 Guests
Aug 18 - 20
$521 night

Beachside Oasis Home in Bradenton Beach, FL TPL18-000049 / DWE5105831 Welcome to Beachside Oasis, a beautiful Bradenton Beach vacation home perfectly located just a two-minute walk from the Gulf beaches. With five bedrooms and three and a half bathrooms, this spacious retreat accommodates up to 14 guests and is designed for large families and groups seeking sun, fun, and relaxation on Anna Maria Island. Enjoy a private heated pool, rooftop deck with Gulf and Bay views, and game room entertainment; all within walking distance of local restaurants and shops. Highlights • 2-minute walk to the beach • 5 Bedrooms and 3.5 Bathrooms • 3 king beds, 1 queen, 2 twin bunk beds • Rooftop deck with Gulf views • Private heated pool with covered lanai • Golf cart included • 4 open-air decks with outdoor seating • Game room with ping pong, foosball, and arcade • Short walk to dining and shopping • 2 outdoor security cameras • 4 Parking spaces Beachside Oasis truly lives up to its name with endless spaces for outdoor living and family fun. Lounge by the heated private pool surrounded by tropical landscaping, grill fresh seafood on the outdoor BBQ, or share meals in the shaded poolside dining area. The rooftop deck offers breathtaking panoramic views of both the Gulf and the Bay. On the ground floor, the game room is a highlight for all ages, featuring ping pong, air hockey, foosball, electronic basketball, a dart board, and even a classic arcade console with 50 retro games. The second floor hosts the home’s main living areas, filled with natural light and coastal decor. The kitchen shines with stainless steel appliances, custom cabinetry, and a vibrant teal backsplash, complemented by a large island with breakfast seating. The dining room seats eight comfortably, while the living room offers plush seating and a TV for relaxing after a day at the beach. A secondary living space with another TV and direct access to a furnished balcony provides extra room for everyone to unwind. Each bedroom at Beachside Oasis provides the perfect mix of comfort and style, ensuring restful nights after long beach days. The primary suite features a king bed and a private ensuite bathroom with a walk-in shower. Two additional bedrooms each offer king beds, while another bedroom includes a queen bed for added flexibility. The fifth bedroom features two twin bunk beds with a trundle, making it ideal for younger guests. A queen sleeper sofa in the living area provides extra accommodations for larger groups. Room Details -Primary Bedroom: King bed, Ensuite bath with walk-in shower -Second Bedroom: King bed, Ensuite bath with walk-in shower -Third Bedroom: King bed, Shared bath with tub-shower combo -Fourth Bedroom: Queen bed, Shared bath -Fifth Bedroom: Two twin bunk beds -Living Area: Queen sleeper sofa -Additional Half Bath Guests enjoy Wi-Fi, TVs, three DVD players, and ample parking. The home is located near local favorites like Double Deez Chicago Style Restaurant and sits conveniently between both island bridges for quick access to the beach. With its rooftop views, private heated pool, and unbeatable proximity to the beach, Beachside Oasis is the perfect home base for your next Anna Maria Island getaway. Spacious, inviting, and full of fun amenities, it’s the ideal choice for families and groups looking to enjoy both comfort and coastal adventure. Book your stay today with us and experience your own beachside oasis! - Please note: This property has two security cameras outside

Vacation Rentals in Holmes Beach by Amenities & Features

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Vacation Rentals Near Holmes Beach

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