House rentals near Anna Maria Island

5.0 out of 5 average rating, 65 reviews

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

Escape to The Blue Ark, a 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the heated pool, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms + extra sleep space, 8 beds and 4.5 baths.

Superhost

A winding stone path is bordered by lush greenery, leading through the expansive yard surrounded by tall trees. Various native plants are visible, creating a natural and serene environment.

4.8 out of 5 average rating, 270 reviews

Charming Beach house amongst huge Banyon Trees

Charming bright beach house on huge secluded tropical yard voted "A Tropical Paradise", on the quiet residential tip of Anna Maria island . Cozy Porchs and tropical fenced yard sits among grand Banyon Trees with native birds. 3 min's stroll over small fishing bridge to historic Pine Ave w/ quaint eateries /shops or Paddle board / kayak delivery to ami historic trail . 7 min’s walk to bay front beach and AMMA MARIA PIER, or to "Bean Point" voted 1 of the most beautiful beaches in the world.

A two-story beach house features a wooden staircase leading to a wrap-around balcony. Lush tropical landscaping surrounds the entrance, and several palm trees are visible. Large windows allow natural light to fill the home, enhancing the inviting facade.

4.98 out of 5 average rating, 41 reviews

Anna Maria Beach House

Come stay at our beautiful beach house in Anna Maria, Florida! Located just a few hundred feet from the beach on Maple Avenue, you can easily walk to the Gulf for a day of family fun on the white sand beaches. The house is also walking or biking distance to center of Anna Maria with great restaurants. Please Note: We want to respect our neighbors. This is not a party house. We have a six person and three car maximum. Please reach out for exceptions. If not, you will be asked to leave.

4.95 out of 5 average rating, 20 reviews

Hidden Haven / Private Pool & Hot Tub

Your dream bayside escape at this charming single-story haven, just a heartbeat away from the pristine shores of Anna Maria Island. Featuring 4 inviting bedrooms and 2 stylish baths, indulge in the luxury of a private pool nestled among vibrant tropical foliage. Sip your morning coffee or toast to sunset cocktails poolside, wander to the sparkling Gulf, discover the delightful shops and eateries in Holmes Beach. This oasis is perfect for sun-kissed relaxation and exciting island escapades!

A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.

4.95 out of 5 average rating, 124 reviews

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our open calendar -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

The duplex features a light blue exterior with a welcoming porch adorned with yellow and blue chairs. Lush palm trees and vibrant landscaping enhance the outdoor space, while a clear blue sky adds brightness to the scene. Graveled parking is visible in front of the unit.

4.94 out of 5 average rating, 105 reviews

Do you love the beach?

Seaside Sanctuary is the ground floor unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is thirty steps from one of the most pristine beaches on the Gulf of Mexico. The house is located on a quiet residential street near the north end of the island. The front porch is a great place to watch the sunset. The house is clean, comfortable and well appointed. We welcome well behaved dogs and have a fully fenced yard for your pup to play.

4.98 out of 5 average rating, 125 reviews

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

5.0 out of 5 average rating, 11 reviews

NEW! w/ Pool - The Pearl Unit 2 on AMI

The Pearl (Unit 2) is a newly renovated oasis in the heart of Holmes Beach on Anna Maria Island. Just a 3–5 minute walk to the beach, this sunny AMI duplex home has everything — sparkling saltwater pool, fresh interiors, no stairs, beach gear, and parrots that may say hi on your morning walk! Centrally located and steps away from the AMI trolley to whisk you around the island! Relax, explore, and live your best island life. *pool is shared with one other unit in the duplex home*

A private pool is surrounded by tropical landscaping, featuring a clear blue water surface that reflects soft lighting. Several lounge chairs are positioned nearby, providing relaxation space under the palm trees. The serene area is perfect for unwinding after a day at the beach.

4.96 out of 5 average rating, 107 reviews

Beach House w/Private Pool & Spa

Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the beautiful beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. Enjoy the private pool and spa, surrounded by tropical landscaping. Tons of beach gear included! It is located in a great area to explore by bike, ride to Pine Ave., Bayfront Park, the City Pier, etc....

The outdoor area features a spacious pool and a separate spa, surrounded by manicured gardens and palm trees. A covered lanai with steps leads to the upper level of the home, which includes expansive sliding glass doors inviting natural light into the interior.

4.97 out of 5 average rating, 37 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

An outdoor dining area is set with a glass table and six blue chairs, shaded by a blue umbrella. In the background, a swimming pool with surrounding tropical plants invites relaxation, while a spa is visible nearby, offering a serene ambiance.

4.82 out of 5 average rating, 104 reviews

Private pool, only two blocks .3 miles from beach!

Just two blocks away from the beautiful white sands of Holmes Beach. Restaurants & night life even closer. Swimming pool and spa are inviting for both romantic getaways as well as families. You will have access to the entire beautiful two story townhouse. The property has a shared wall, but all space is private and quiet. The outdoors are separated and private as well. Plenty of parking, sun, & fun. New mattresses, new couch, and other furniture.

5.0 out of 5 average rating, 108 reviews

Bean Pt. Bungalow - Half duplex w/private pool

Welcome to Bean Pt. Bungalow! A charming 3/2 villa with a private saltwater pool in the heart of Anna Maria. You're only 0.2 miles from the nearest beach access and 0.2 miles from the Rod and Reel Pier. The home comes equipped with 6 beach chairs and cart. This boutique rental is the perfect place for your next getaway! Primary - King Bed Front bedroom - King bed Bunk room - 4 twin beds

Popular amenities for house rentals near Anna Maria Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene outdoor space features a sparkling pool surrounded by lush greenery and tropical plants. Comfortable lounge chairs are placed along the poolside, and string lights cast a warm glow overhead. A shaded seating area with a gazebo can be seen in the background.

4.91 out of 5 average rating, 426 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

4.95 out of 5 average rating, 207 reviews

Sunshine Cottage: 30’ Pool & Dock, Steps to Beach

4.96 out of 5 average rating, 212 reviews

A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.

Home in Bradenton beach

Sea AMI

5.0 out of 5 average rating, 54 reviews

Palm Paradise~Steps to Shops/Beach~Best location!

A private lagoon pool is surrounded by tropical foliage and lounge chairs. The outdoor space features a gas grill and a shaded patio area under the house. Bright turquoise accents are visible on the exterior, complemented by palm trees and colorful plants.

4.83 out of 5 average rating, 63 reviews

La Raya - 3bed/2bath POOL Home

4.78 out of 5 average rating, 32 reviews

Playa Esmeralda Home! And add a golf cart!

4.88 out of 5 average rating, 51 reviews

AMI 1 Block 2 Beach, Big Heated Saltwater Pool

5.0 out of 5 average rating, 13 reviews

Carissa A | Beachside Retreat | Golf Cart | Pool

Weekly house rentals

5.0 out of 5 average rating, 23 reviews

Pergola Oasis | Walk to Beach + Outdoor Living

Superhost

An outdoor area features a private heated pool surrounded by lush tropical landscaping. Several white loungers are positioned on the deck, and a large umbrella provides shade. The building above offers a covered porch, adding to the inviting atmosphere of the space.

4.95 out of 5 average rating, 19 reviews

AMI Peppertree – Steps to Beach w/ Pool & Oasis

5.0 out of 5 average rating, 29 reviews

New! Gulf Views • Rooftop • Bridge St • Game Room!

4.89 out of 5 average rating, 54 reviews

AMI Dock of the Bay - "On the Water" 1st Floor

5.0 out of 5 average rating, 29 reviews

Walk to Beach + Trolley + Heated Pool + Mini Golf!

An outdoor view showcases a private pool surrounded by lush landscaping and tropical palm trees. The distant beach features soft white sand meeting turquoise waters. A spacious deck, complete with loungers, offers a perfect relaxation spot under clear blue skies.

4.9 out of 5 average rating, 73 reviews

TOES IN THE SAND!

4.97 out of 5 average rating, 39 reviews

Private Pool + Walk 2 blocks to Beach! King Beds!

A serene canal view is presented, showcasing calm water reflecting vibrant hues of sunset. Lush palm trees and greenery border the serene setting, complemented by a wooden dock extending into the water. The peaceful ambiance invites relaxation and enjoyment of nature.

5.0 out of 5 average rating, 65 reviews

Heavenly Hideaway, 3 bdrm, 5 minute walk to beach

Private house rentals

A serene backyard scene is highlighted by a sparkling pool, accompanied by lounge chairs and a hammock nestled among lush trees. The stylish bungalow features a spacious deck, creating an inviting atmosphere for outdoor relaxation. The sky is painted in calming hues as sunset approaches.

4.97 out of 5 average rating, 60 reviews

10 min AMI | 15 min IMG | Heated Pool

5.0 out of 5 average rating, 27 reviews

85" TVs*GLOW in the dark Game Rm*Pool Table*POOL

An outdoor area showcases a heated saltwater pool, surrounded by natural stone tiles. A pergola offers shaded seating above a large dining table, while comfortable lounge chairs are positioned nearby. Lush tropical landscaping and clear blue skies enhance the inviting atmosphere.

5.0 out of 5 average rating, 30 reviews

Manatee Manor by Beach Boutique Rentals

5.0 out of 5 average rating, 48 reviews

Key Lime Cottage | Hot Tub | Steps to Beach

A charming island home is presented on a landscaped property, featuring a paved driveway with ample space for parking. The elevated structure is accessible by a set of stairs, and palm trees add a tropical touch to the surroundings.

4.98 out of 5 average rating, 51 reviews

1 block to Pine Ave + Shopping + Beach + Dining!

5.0 out of 5 average rating, 21 reviews

Luxury Escape, Pool, Beach, Essentials & Fun!

The exterior of the historic home is shown, featuring a wide wrap-around porch adorned with American flags. Several rocking chairs provide seating, surrounded by lush greenery and a gravel pathway leading to the entrance. Sunlight casts a warm glow on the porch area.

4.87 out of 5 average rating, 53 reviews

Welcome to our historic Florida beach HOME

4.96 out of 5 average rating, 48 reviews

The Florida Rooms

Pet-friendly house rentals

4.98 out of 5 average rating, 103 reviews

A well-maintained front yard features lush green grass and a large agave plant. The house, showcasing a contemporary design, is flanked by palm trees. A driveway leads to a two-car garage, with additional landscaped areas adding to the outdoor appeal.

Home in Cortez

Dockside Dreams - Pool, Spa & Waterfront Dock

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

4.98 out of 5 average rating, 202 reviews

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

A tranquil outdoor area features a swimming pool surrounded by lush palm trees and tropical plants. Two loungers invite relaxation beside the water, and a dining table is set for outdoor meals. Sunshine brightens the scene, enhancing the inviting ambiance.

4.98 out of 5 average rating, 163 reviews

Captain's Quarters at Spinnakers Vacation Cottages

A private lagoon-style pool is surrounded by lush tropical landscaping. A small rock waterfall flows into the gently curved pool, which is complemented by comfortable seating. Sunlight filters through the foliage, creating a serene outdoor retreat.

4.96 out of 5 average rating, 158 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

5.0 out of 5 average rating, 102 reviews

Lux Getaway: Pool| Hot Tub| Bocce Ball nr AMI &IMG

An aerial view of the outdoor space reveals a heated saltwater pool shaped like a lagoon, surrounded by lounge chairs and umbrellas. A full-size pickleball court takes center stage, complemented by a nearby mini-golf putting green and a trampoline, all set within lush landscaping.

4.94 out of 5 average rating, 50 reviews

New! Luxurious Retreat w/ Resort Amenities by AMI!

5.0 out of 5 average rating, 15 reviews

The Pink House - Short Walk to the Beach