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House rentals near Anna Maria Island

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Top-rated house rentals near Anna Maria Island

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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.

Home in Holmes Beach

4.95 out of 5 average rating, 111 reviews

Breezy Harbor AMI pool retreat near the Beach

Stunning Fall 2024 renovation done! Charming Breezy Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immediately feel stress melting away. You'll love grilling in the lush yard and a 6-min walk to the beach or the AMI trolley stop. A supermarket is a couple of streets over. The home is perfect for families, couples, 1-50Lb pet, and working remotely. Ample Parking for 2 vehicles and toys. *Ask us for shorter stays and always discuss your pets with us*

An aerial view showcases a spacious outdoor area featuring a private pool and lounge chairs, surrounded by a gated patio. A light blue house stands in the background with multiple windows, providing a connection between indoor and outdoor spaces. Lush greenery lines the property.

Home in Holmes Beach

4.93 out of 5 average rating, 30 reviews

Luxury 3BD Beachfront Retreat with Heated Pool!

Sandy Bottoms Beach House is a luxury Gulf-front retreat where modern comfort meets Florida’s natural beauty. With three king bedrooms—each with its own en suite bath—this home is designed for families, couples, or groups seeking a premium beach getaway. Step through oversized sliding doors to a private patio with a heated pool, outdoor dining, and a direct trail to the sand. Spend mornings walking the shoreline, afternoons lounging by the pool, and evenings watching unforgettable Gulf sunsets f

Top guest favorite

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

Home in Holmes Beach

5 out of 5 average rating, 48 reviews

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

Let me know if you need a stay for a period not listed. Unbeatable location, HEATED POOL, ultimate makeover & NEW bedrm, bathrm, lounge, & covered patio additions for spacious beauty are a few things that set us apart! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage/parking for 6 cars! Near restaurants, Publix, activities! 30 steps to FREE TROLLEY pick up!

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 Holmes Beach

4.96 out of 5 average rating, 195 reviews

Sea AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Top guest favorite

A private heated pool is surrounded by lush tropical landscaping and tall palm trees. Two lounge chairs are positioned near the pool, and a shaded area is provided by a large umbrella. White fencing encloses the yard, enhancing privacy in the outdoor space.

Home in Anna Maria

5 out of 5 average rating, 22 reviews

Birdsong-Steps to Bean Point Beach Heated Pool!

Welcome to Birdsong, a picture-perfect 2-bed, 2-bath home situated in Anna Maria, Florida. Recently refreshed with coastal décor, this inviting property is ideal for families or small groups seeking a relaxing getaway. With just a short 3-minute walk to the beach, Birdsong provides an excellent blend of comfort & convenience, allowing you to fully immerse yourself in the beauty of Anna Maria Island. The fenced backyard features a heated pool, outdoor dining, BBQ grill, beach chairs, & cart.

Top guest favorite

The backyard features a saltwater pool surrounded by artificial turf, creating a refreshing oasis. Sunlight brightens the outdoor space, accentuated by lush tropical landscaping. The elevated home showcases multiple balconies, while palm trees lend to the coastal atmosphere of the property.

Home in Anna Maria

4.93 out of 5 average rating, 15 reviews

Bayfront Beach access with Heated Pool!

Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views of Tampa Bay & the iconic Skyway Bridge. The backyard oasis features a refreshing saltwater pool & fully fenced backyard, complete w/artificial turf & outdoor shower. Just steps away, you'll find full access to a stunning white sandy beach & the crystal-clear waters of Tampa Bay! Conveniences have been carefully considered, creating the most ideal vacation destination!

A spacious pool area features a large, oval-shaped swimming pool surrounded by multiple lounge chairs. The light-colored patio is lined with tropical plants. A shaded umbrella stands near the seating area, complemented by the inviting blue exterior of the single-level beach house.

Home in Holmes Beach

5 out of 5 average rating, 18 reviews

One Level Large Home 2 Minute Walk to the Beach!

Welcome to our Blue Grotto on the beautiful Anna Maria Island. We hope you will enjoy your stay in our 1850 sq ft beach house with 3 bedrooms and 2 baths. Our property features a living area and a full kitchen with dining area which makes it great for spreading out. Our little slice of heaven is perfect for family vacays, fishing or golfing trips or that annual girls trip! You are only 6 houses to the beach or right out the back door to the large pool (extra charge for heating).

Home in Anna Maria

5 out of 5 average rating, 9 reviews

Casa Cay by Duncan Real Estate

Welcome to Casa Cay! This Bay front pool home on Anna Maria Island is an absolute paradise! With its prime location on the North end with stunning views of the bay and the Sunshine Skyway Bridge, and direct access to a private bay beach, it offers the quintessential Island experience. The layout of the house, featuring three bedrooms and three bathrooms, including two suites with Ensuite bathrooms, is perfect for families or groups of friends looking for comfort and privacy.

Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.

Home in Bradenton Beach

4.96 out of 5 average rating, 110 reviews

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street

Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!

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.

Home in Bradenton

4.91 out of 5 average rating, 388 reviews

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

Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

Top guest favorite

An aerial view showcases a serene coastal area, emphasizing the proximity to a sandy beach just a short walk away. The vibrant blue water contrasts with the green palm trees and white homes lining the streets, creating a peaceful atmosphere typical of Anna Maria Island.

Home in Anna Maria

5 out of 5 average rating, 79 reviews

New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean

This brand new rebuild on Anna Maria Island located within Anna Maria city has 3 Bedroom, 3 Bathroom home plus loft is professionally decorated throughout, with state-of-the art quartz counter tops, JennAir professional stainless-steel appliances, wide plank wood tile floors, bead board ceilings. All bathrooms have basket weave marble and quartz counters and there is a Whirlpool Washer & Dryer. The house has everything necessary for a perfect beach vacation.

Top guest favorite

An aerial view captures a serene private pool encompassed by a stone patio, with several lounge chairs arranged nearby. Lush greenery and tropical plants border the scene, while a dark pond reflects the surrounding nature, enhancing a tranquil outdoor space.

Home in Bradenton

5 out of 5 average rating, 110 reviews

AMI Beaches + IMG Sports + Hot Tub & Pool!

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

Popular amenities for house rentals near Anna Maria Island

Free parking on premises

Air conditioning

House rentals with a pool

A serene pool area features a crystal-clear pool with built-in spa, surrounded by sun loungers. Lush palm trees line the water's edge, providing shade. The view includes a deep water canal flanked by tropical landscaping and modern homes, under a bright blue sky.

Home in Anna Maria

4.9 out of 5 average rating, 86 reviews

AMI Boathouse

A serene backyard features a heated pool surrounded by lounge chairs and shaded areas. Tropical plants and flowers add color, while the setting sun casts a warm glow. Umbrellas provide shade over the seating, creating a welcoming space for relaxation and outdoor enjoyment.

Home in Bradenton

4.97 out of 5 average rating, 100 reviews

Orange Oasis: Clean, heated pool, near beaches.

A spacious covered lanai contains a large wooden dining table surrounded by six dark wicker chairs. A ceiling fan provides airflow in the area. Large windows offer views of the private heated pool and tropical landscaping, while the light-colored tile flooring adds a clean, bright appearance.

Home in Holmes Beach

5 out of 5 average rating, 12 reviews

Private heated pool,2 minute walk to the beach! W

The outdoor area features a private heated pool with a separate spa, surrounded by lush gardens and palm trees. Comfortable lounge chairs are positioned along the poolside, and a grill area is visible, creating a serene and inviting space for relaxation.

Home in Anna Maria

4.97 out of 5 average rating, 33 reviews

Casa Mariposa – AMI Retreat w/ Pool, Spa & Beach

An aerial view of a charming ground-level vacation home is presented, featuring a light-blue exterior and a metallic roof. Surrounded by lush tropical landscaping, a clear pool reflects the sunlight, and a patio area with lounge chairs is visible in the background.

Home in Anna Maria

5 out of 5 average rating, 16 reviews

Sea Shack - 2bd/2ba POOL Home

Top guest favorite

A tropical backyard features a heated saltwater pool surrounded by palm trees and vibrant landscaping. Lounge chairs are arranged beside the pool, and an outdoor covered seating area with colorful chairs provides a relaxing retreat. A light-colored home stands in the background.

Home in Holmes Beach

4.98 out of 5 average rating, 43 reviews

Loggerhead - Private Pool + Golf Cart - AMI Oasis

Top guest favorite

A spacious living area is defined by high ceilings and an open layout, featuring two comfortable sofas facing a wall-mounted television. Large glass doors provide a view of the lush backyard, while decorative plants add a touch of greenery to the room.

Home in Holmes Beach

4.98 out of 5 average rating, 49 reviews

Unwind Sunshine: steps to locals' favorite beach

Top guest favorite

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Sarasota

5 out of 5 average rating, 31 reviews

Sarasota Escape | Minutes to Beaches + Downtown

Weekly house rentals

Top guest favorite

An outdoor dining area is set with plates and glasses, accompanied by a lantern centerpiece. The space overlooks a private heated pool surrounded by tropical plants. A grill is positioned nearby, enhancing the convenience for outdoor meals.

Home in Anna Maria

5 out of 5 average rating, 41 reviews

Veselka - Canal front w private heated pool & dock

Top guest favorite

A view through large windows showcases lush greenery and palm trees, with glimpses of the ocean in the background. Two comfortable chairs with decorative pillows are positioned invitingly by the window, creating a cozy space to enjoy the scenic surroundings.

Home in Holmes Beach

5 out of 5 average rating, 37 reviews

Seconds to the Beach! Clean & Cozy NO flood damage

Top guest favorite

A spacious outdoor living area is shown, featuring a seating arrangement with floral-patterned cushions and a wooden coffee table. A dining table, set for six, is positioned nearby. The screened lanai offers views of the pool, surrounded by greenery and clear blue skies.

Home in Bradenton

5 out of 5 average rating, 83 reviews

NEW saltwater pool/spa! Amazing outdoor space!

Top guest favorite

A large heated saltwater pool is enhanced by colorful floating rings. A waterfall feature adds a calming effect while lounge chairs are positioned nearby. The patio area is visible, furnished with multiple seating options, and surrounded by lush greenery and sunny skies.

Home in Bradenton

5 out of 5 average rating, 57 reviews

Heated Pool |Game Room|SmartTVs|King Beds|Sleeps14

Home in Holmes Beach

5 out of 5 average rating, 3 reviews

Dolphin Resort | Pool, Spa, Game Room & Beach

Top guest favorite

A warm outdoor space features a heated pool surrounded by tropical landscaping. Comfortable black lounge chairs are positioned nearby, providing a relaxing area for guests. Soft lighting illuminates the space, creating a serene atmosphere in the evening.

Home in Holmes Beach

5 out of 5 average rating, 51 reviews

Perfect Hideaway- Heated Pool, 5 min Walk to Beach

Top guest favorite

The image depicts a bright, two-story beach house with light blue siding, surrounded by palm trees and lush greenery. A white picket fence lines the front, offering a sense of privacy. The sky is clear with soft clouds, conveying a tranquil coastal atmosphere.

Home in Holmes Beach

5 out of 5 average rating, 60 reviews

Luxury Home Steps to Quiet Beach on 78th St

Top guest favorite

A spacious living area features two yellow sofas accented with vibrant patterned cushions. A wooden coffee table sits atop a patterned area rug with palm leaves. A colorful abstract wall art piece is displayed above the seating, and a standing lamp adds an inviting touch.

Home in Holmes Beach

5 out of 5 average rating, 17 reviews

L'Oasis East w/Dip Pool

Private house rentals

A lagoon-style pool is surrounded by a patio featuring lounge chairs and an umbrella, offering a shaded spot for relaxation. Lush palm trees line the space, and the elevated home is visible in the background, completing the serene outdoor setting.

Home in Anna Maria

4.89 out of 5 average rating, 61 reviews

Island in the Sun, luxury beach house,private pool

Top guest favorite

An aerial view showcases SunSalt Cottage surrounded by lush greenery and palms. The large private saltwater pool is visible, along with the tiki hut and outdoor seating area. The nearby beach and distant ocean can be seen beyond the charming homes of Anna Maria Island.

Home in Anna Maria

4.95 out of 5 average rating, 20 reviews

SunSalt Cottage~5 min to Beach, Shops & Food~Pool

Top guest favorite

A private heated pool reflects soft sunset colors, surrounded by tropical landscaping. The spacious deck includes loungers and an outdoor dining area. A covered balcony above provides a view of the pool, while a flat-screen TV is mounted on the wall near the seating area.

Home in Holmes Beach

5 out of 5 average rating, 27 reviews

Sunkissed&Salty: Prime Location!

Home in Anna Maria

5 out of 5 average rating, 4 reviews

Villa Maria: 1 Block to Pine, Beach 3 Blocks, Pool

A private heated pool is surrounded by tropical palms, featuring a gently curved shape with clear blue water. Two white adirondack chairs are positioned nearby on a paved patio, inviting relaxation in a tranquil outdoor setting.

Home in Anna Maria

5 out of 5 average rating, 12 reviews

The Shell House

A private backyard features a curved pool surrounded by tropical landscaping. A thatched tiki hut provides shade over a dining table, while a large umbrella shades additional seating. A flamingo float is visible in the water, enhancing the relaxed outdoor atmosphere.

Home in Holmes Beach

4.78 out of 5 average rating, 18 reviews

Steps Away from the Sandy Shores of Holmes Beach!

Top guest favorite

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.

Home in Anna Maria

4.95 out of 5 average rating, 94 reviews

Do you love the beach?

Top guest favorite

The private saltwater pool is surrounded by lush palm trees, providing a serene atmosphere. A swim-up table is visible in the water, along with a shallow sunning shelf. A spacious wrap-around deck features a dining area and comfortable lounge chairs, ideal for relaxation.

Home in Anna Maria

5 out of 5 average rating, 45 reviews

༄ Sunset Shore on Anna Maria Island ༄

Pet-friendly house rentals

A bright living area is highlighted by a large window with views of lush greenery. A light wood floor complements the modern furnishings, which include a blue couch with yellow cushions, a wood coffee table, and a round dining table for four.

Home in Holmes Beach

4.81 out of 5 average rating, 27 reviews

+ Anna Maria Seaside Escape +

Home in Anna Maria

4.88 out of 5 average rating, 86 reviews

FantaSea

Home in Anna Maria

4.5 out of 5 average rating, 4 reviews

Coastal beach home w/pool 200 steps to beach

Top guest favorite

A light-filled living area features a comfortable, neutral-toned sofa adorned with textured pillows. A wooden coffee table rests on warm-toned flooring. The space includes a cozy lamp and a small dining area with two stools, complemented by natural decor elements on the walls.

Home in Holmes Beach

5 out of 5 average rating, 11 reviews

NEW Charming Coastal, so close to beach!

A private backyard features a clear blue pool adjacent to a hot tub, surrounded by vibrant tropical foliage. Two light blue chairs are positioned nearby for relaxation, and a basketball hoop stands at the edge of the pool, offering a fun activity for guests.

Home in Bradenton Beach

4.9 out of 5 average rating, 10 reviews

House w/ Private Pool & Hot Tub - Bridge Street

Top guest favorite

A private backyard swimming pool is surrounded by tropical landscaping and six lounge chairs positioned for sunbathing. The pool features clear blue water, with a paved patio area and a white fence providing privacy. Palm trees and decorative plants enhance the inviting outdoor setting.

Home in Bradenton

4.94 out of 5 average rating, 48 reviews

Gone Coastal - Heated pool, close to the beach

Home in Bradenton

New place to stay

BRAND NEW Pool Paradise | Put-put! Games! Fire Pit

Home in Bradenton

4.95 out of 5 average rating, 21 reviews

Private Pool + Game Room + King Suite - Near AMI

Quick stats about house rentals near Anna Maria Island

Total rentals
1.5K properties
Total number of reviews
19K reviews
Family-friendly rentals
1.4K properties are a good fit for families
Pet-friendly rentals
590 properties allow pets
Rentals with a pool
1.2K properties have a pool
Rentals with dedicated workspaces
660 properties have a dedicated workspace

Destinations to explore