Vacation rentals in Holmes Beach, FL with free parking

Explore 625 vacation rentals, homes, and villas with free parking in Holmes Beach, FL for your next getaway or business trip. With on-site parking included in your stay, enjoy the comfort and privacy of a home filled with premium amenities such as Air Condition Homes, Homes with Pools and Best Affordable Homes. Throughout your stay, come and go with ease, knowing parking is always convenient and close at hand. 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 personalized stay designed for your comfort. With 24/7 local support and high-speed Wi-Fi, you can also stay connected and protected throughout your trip. Plus, Marriott Bonvoy members earn points on every stay, making each trip more rewarding than the last. Book your next stay with ease and enjoy the convenience of free parking.

625 Homes with Free Parking in Holmes Beach

Lil’ Nauti

Holmes Beach, FL, US
1 Bedrooms 4 Guests
Aug 24 - 26
$414 night

Nostalgic, eclectic, and built to recharge. Lil’ Nauti is a one-bedroom one-bathroom pet-friendly vacation rental on Anna Maria Island. Formerly the Aquarius Motel and then Anna Maria Island Beach resort, Mello on the Beach is located directly on Manatee Beach and the Gulf of Mexico. This vibrant condo includes a colorful kitchenette, terrace access and private patios for serious mello-ing out. Rooms are perfectly appointed with fully equipped kitchens, full-size washers and dryers, clothes steamers, and even pet accessories! Guests are provided with an amenity starter kit that includes shampoo, conditioner, and body wash. Additional items provided include dishwasher pods, laundry soap, and k-cup coffee service. Mello on the Beach has everything you need to enjoy a truly relaxing vacation. All rentals are equipped with pool and beach towels, beach chairs, beach umbrellas, personal coolers, and much more! Take a dip in our refreshing pool which includes use of lounge chairs, umbrellas, as well as bathroom and shower facilities. After your long day soaking up the sun, fun awaits the whole family on the activity lawn. Take in a game of cornhole, ladderball, or just sit back and relax by the firepit. Want to explore all Anna Maria Island has to offer? Mello on the Beach has all your transportation needs covered. Take a short stroll across the street to enjoy breakfast at the Holmes Beach Café where locals come to experience some of the best pancakes Manatee County has to offer. Come for breakfast but stay for lunch, shopping, or a rum cocktail at their popular tiki bar. Just a hop in the other direction is another local favorite; Skinny’s offering the best burgers in the area. Looking to venture a little further? Mello on the beach offers on-site bike access for all our guests. These bicycles are one of the best ways to explore the beautiful and vibrant Anna Maria Island. And if biking isn’t your thing, just hop on the Anna Maria Island free trolley which runs 7 days a week from historic Bean Point to the south end of Coquina Beach. places to stay on anna maria island anna maria island rentals anna maria island accommodations anna maria island motels

Seabreeze D

Holmes Beach, FL, US
2 Bedrooms 4 Guests
Aug 20 - 27
$114 night

Seabreeze D VRC16-000111 Welcome to Seabreeze D, a charming two-bedroom, two-bath vacation condo perfectly situated in the heart of Holmes Beach on Anna Maria Island. This inviting second level retreat offers water views from the balcony, a bright open living area, and access to a refreshing community pool. Just a quick three-minute stroll to the pristine Gulf beaches, you’ll also be within walking distance to local favorites like Skinny’s Burger joint, Publix, and nearby shops and cafes. Making Seabreeze D the ideal home base for couples or small groups ready to relax and explore the island’s laid back coastal lifestyle. Highlights • 3-minute walk to Manatee Beach • 2 Bedroom / 2 Bath • 2 Queen beds • Balcony • Community pool and lounge chairs • Covered parking • Laundry Facility • Near local shops, waterfront restaurants, and grocery stores • 2 Parking Spaces Relax and dine outdoors on your balcony, overlooking the lush surroundings and cooling ocean breezes. The community pool area offers plenty of lounge chairs, a BBQ grill, and outdoor seating, perfect for making memories after beach days. Walk to the beach, explore the local shops and waterfront restaurants, or rent watercraft and paddle boards to enjoy Anna Maria Island’s scenic waters. Inside, the condo boasts a bright, open living area with a comfortable sectional sofa and a large flat-screen TV, perfect for movie nights or relaxing evenings. The modern kitchen offers a full suite of appliances, cookware, and a dining table, making it easy to prepare family favorites or island snacks. Large sliding doors lead to your balcony, where you can soak up the ocean breeze and water views. Retreat to the primary bedroom, furnished with a plush queen bed, bright decor, a TV, and an ensuite bathroom with a walk-in shower. The second bedroom, also with a queen bed and coastal accents, offers a peaceful space for rest. The hall bathroom, with its shower/tub combo and generous storage, services both bedrooms comfortably. Room Details • Primary Bedroom (2nd floor): Queen bed, ensuite with walk-in shower • Second Bedroom (2nd floor): Queen bed Book Seabreeze D today and experience a relaxing island getaway on Anna Maria Island. With its water views, outdoor amenities, and close proximity to beaches and dining, this condo is the ideal home base for your island adventures. Reserve now and start making lifelong memories in paradise! - This home is managed by Anna Maria Island Accommodations, an Anna Maria Island property management company. Please see our Anna Maria Island Accommodations Rental Policies for full details. There are no pets allowed in this home. 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. 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.

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"

Hidden Pearl

Holmes Beach, FL, US
2 Bedrooms 6 Guests
Aug 20 - 27
$311 night

Hidden Pearl is a completely renovated 2-bedroom, 2 1/2-bathroom condo. Hidden Pearl is in a beautifully maintained complex boasting a sparkling heated pool all-year round. This condo is located in Holmes Beach and is only a short walk away from the beach, shopping, and dining. The Gulf View Townhouses is only a 4-unit complex. All outdoor shared amenities will be shared amongst the 4 units. HIGHLIGHTS • 1430 sq. ft. • Balcony • Shared heated community pool (21x12 ft) • Fully equipped kitchen • 0.1 mile from the beach BEDROOMS • Sleeps 6 • Primary Bedroom: Ensuite King • Second Bedroom: Queen • Living Room: Queen Sleeper Sofa BATHROOMS • Primary Ensuite: Walk-in Shower • Second Bathroom: Walk-in Shower • Half bath EXTERIOR The Gulf View Town House Community has a large heated pool that is shared between the units in the community and plenty of poolside seating. Hidden Pearl comes well stocked with everything you could need for your perfect beach vacation including beach chairs, beach umbrellas, a beach wagon, tent, cooler, portable grill and sand toys. All of the beach amenities can be located in the downstairs storage closet. There is a tandem covered parking space assigned to the unit. Due to limited clearance, this Condominium Association does not permit trailers, large trucks, or RV under covered parking (clearance 7.3"). This Condominium Association only allows gas golf carts as there is no charging available at the property for electric carts, or EV charging. Thank you for your understanding and we apologize for any inconvenience. In accordance with the Condominium Association, this property requires a 7-night minimum stay. Please keep in mind that you are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. VRC16-000063

Paradise Found

Holmes Beach, FL, US
6 Bedrooms 12 Guests
Aug 20 - 27
$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 20 - 27
$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.

Pool Access, Walk to Manatee Beach: Coastal Condo

Holmes Beach, FL, US
2 Bedrooms 6 Guests
Aug 22 - 29
$181 night

3rd-Floor Unit | Central A/C | Screened-In Porch w/ Bay View Leave your worries behind and bring your flip flops and swimsuit to this 2-bedroom, 2-bath vacation rental in Holmes Beach! Soak up the sun at Anna Maria Public Beach — just a half mile from the property — or stay in the complex and lounge at the community pool. No matter what you choose to do, you’re bound to experience pure relaxation at this ideally located condo! -- THE PROPERTY -- CND510579 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Living Room: 1 sleeper sofa INDOOR LIVING - Smart TV (living room) - Flat-screen TVs w/ cable (bedrooms) - Bright beach decor - 4-person breakfast bar, pass-through window OUTDOOR LIVING - Screened-in porch, bay view - Community pool access KITCHEN - Refrigerator, stove/oven, dishwasher - Dishware/flatware, cooking basics - Drip coffee maker GENERAL - Laundry machines - Central A/C & heating, ceiling fans - Linens/towels, complimentary toiletries - Free WiFi ACCESSIBILITY - Single-story condo on 3rd floor - Exterior stairs required PARKING - Garage (1 vehicle) -- THE LOCATION -- - 0.6 miles to Anna Maria Public Beach & Manatee Public Beach - 4 miles to Pine Avenue - 55 miles to Tampa - 15 miles to Sarasota-Bradenton International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story condo on the 3rd floor requires exterior stairs to enter Licence number: CND5105792

Walk to Beach: Home w/ Porch on Anna Maria Island!

Holmes Beach, FL, US
2 Bedrooms 6 Guests
Aug 20 - 27
$198 night

Map out your coastal Florida escape to this warm and welcoming 2-bedroom, 2-bathroom vacation rental located on Anna Maria Island! This tastefully furnished residence offers a modern interior, a full kitchen, a private screened-in porch, as well as access to a heated community pool for soaking up the sun! Whether you're in Holmes Beach to tan on the Gulf of Mexico, fish in the bay, or explore one of the many quaint towns along the coast, this updated condo is the perfect Florida home base! -- THE PROPERTY -- STR # CND5105378 | Central A/C | Community Pool | 7-Day Minimum Stay | Keyless Entry Ideal for coastal family getaways and beach enthusiasts alike, this modern Holmes Beach condo offers all the essentials and a prime location to enjoy the Gulf of Mexico! Bedroom 1: King Bed | Bedroom 2: 2 Twin Beds | Living Room: Sleeper Sofa STEP OUTSIDE: Screened-in porch w/ patio furniture, lighting & privacy, community pool access INTERIOR LIVING: Recently updated modern interior, dining table, 2 cable TVs w/ Roku (1 in Bedroom 1), beach-themed furnishings, storage w/ beach chairs, umbrellas & beach cart KITCHEN: Fully equipped, granite countertops, cooking basics, Keurig coffee maker, drip coffee maker, tea kettle, toaster GENERAL: Free WiFi, central A/C, washer/dryer, linens & towels, free WiFi FAQ: Stairs required for access, 7-day minimum stay, 1 exterior security camera (facing out) PARKING: Carport (2 vehicles), guest parking (first-come, first-served) -- THE LOCATION -- SOAK UP THE SUN: Manatee Public Beach (0.5 miles), Anna Maria Public Beach (0.6 miles), Coquina Beach (3.6 miles), Bayfront Park (3.9 miles), Bean Point Beach (4.2 miles), Longboat Key Beach (4.6 miles), Lido Key Beach (16.1 miles), Siesta Key Beach (24.9 miles) GOLF THE DAY AWAY: Timber Creek Golf Course (7.1 miles), Pinebrook Ironwood Golf Course (8.8 miles), Manatee County Golf Course (8.9 miles), IMG Academy Golf Club (10.6 miles), River Run Golf Links (12.5 miles), Longboat Key Golf Club (14.1 miles), The Highlands Golf Course (23.2 miles) LOCAL ATTRACTIONS: Anna Maria Island Historical Society (3.5 miles), The John and Mable Ringling Museum of Art (15.7 miles), Sarasota Jungle Gardens (17.1 miles), Siesta Key Drum Circle (25.4 miles), Alligator & Wildlife Discovery Center (38.6 miles), The Florida Aquarium (54.3 miles), Busch Gardens Tampa Bay (59.7 miles) EXPLORE NATURE: Neal Preserve (1.7 miles), Perico Preserve (2.1 miles), Robinson Preserve (3.2 miles), Leffis Key Preserve (3.4 miles), Robinson Preserve (7.5 miles), Emerson Point Preserve (14.3 miles) AIRPORTS: Sarasota-Bradenton International Airport (16.0 miles), St. Pete–Clearwater International Airport (44.1 miles), Tampa International Airport (52.3 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs and may be difficult for guests with limited mobility - NOTE: The property has a 7-day minimum stay - NOTE: Electric cars/golf carts are not allowed to be charged on premises - NOTE: Your safety matters. This property features 1 exterior security camera above the front door facing the stairwell. The camera is outward facing and does not look into any interior spaces. The camera records video when motion is detected by the device. It will record when it first senses motion and 5 seconds after the last motion is detected Licence number: CND5105378

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"

You, Me and the Sea AMI

Holmes Beach, FL, US
3 Bedrooms 6 Guests
Aug 22 - 29
$252 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.

Holmes Beach - Pool - Minutes to Beach - Sleeps 8

Holmes Beach, FL, US
4 Bedrooms 8 Guests
Aug 20 - 27
$690 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

Gulf Haven East! 5- minute walk to the Gulf!

Holmes Beach, FL, US
2 Bedrooms 4 Guests
Aug 26 - Sep 2
$128 night

Gulf Haven East by AMI Locals Escape to paradise at Gulf Haven East, a charming two-bedroom, dog-friendly vacation home nestled just a five-minute walk from the sugary sands of Manatee Beach in Holmes Beach! This cozy island retreat offers modern comforts and a lush patio perfect for relaxing or sunset cocktails. Located close to Holmes Beach Towne Center, this home provides an unbeatable location for your next family, romantic, or small group beach getaway in Anna Maria Island. Highlights • 5-minute walk to Holmes Beach • 2 Bedroom / 1 Bath • 1 King, 1 Queen • Beach chairs included • Private patio • BBQ grill • Washer and dryer • Dog friendly • 1 Assigned parking space • Convenient location near dining and shopping Unwind outdoors in your private patio space, perfect for morning coffee or evening cocktails. Fire up the BBQ grill after a day in the sun or take a short stroll to local restaurants and shops. With beach chairs provided, you’ll be ready for those last-minute trips to the shore. Inside, the home is filled with natural light and coastal decor. The open living area features a comfortable sectional, a smart TV perfect for movie nights, and soothing tropical touches. The fully stocked kitchen boasts modern appliances, cookware, and utensils, making meal prep and cooking easy. Whether dining inside or outside on the patio, this space invites relaxation and quality time with loved ones. The primary bedroom offers a plush king bed and ample storage, creating a peaceful retreat. The second bedroom includes a cozy queen bed with comfortable decor. Both bedrooms share access to a hallway bathroom with a shower/tub combo, providing convenience and privacy. Both spaces are designed for restful nights after sunny days exploring Anna Maria Island. Room Details • Primary Bedroom: King bed • Second Bedroom: Queen bed • Shared Hall Bathroom: Shower/tub combo Just steps from the beach and water activities, this home makes it easy to enjoy the best of Anna Maria Island’s scenic beauty and outdoor adventures. Book Gulf Haven East today for a laid-back escape in Holmes Beach. With its outdoor amenities and walkable beaches, this home has everything you need for a memorable Gulf Coast vacation. Reserve your dates now and start creating lifelong memories in paradise! Planning a group getaway with family or friends? Gulf Haven East and Gulf Haven West are neighboring duplex vacation rentals that can be booked side by side, giving larger groups the opportunity to stay close together while enjoying separate private accommodations. Contact our team for availability when booking both homes for your Anna Maria Island vacation. - This home is managed by AMI Locals, an Anna Maria Island property management company. 1 car 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. Weight limit of 50lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. 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. This property requires a 7-night minimum stay as set forth by Holmes Beach’s Land Development Code.

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

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Vacation Rentals Near Holmes Beach

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