Holiday rentals with a pool in Anna Maria

4.98 out of 5 average rating, 121 reviews

Townhouse in Anna Maria

Green Jacaranda AMI Duplex B, 5 min walk to beach

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

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.

4.96 out of 5 average rating, 200 reviews

Be an 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.

Bungalow in Bradenton Beach

A tranquil outdoor space features a wooden dining table surrounded by eight chairs set on a tiled patio. A small, curved swimming pool is framed by lush tropical plants, and umbrellas provide shaded areas. The vibrant greenery creates a serene atmosphere.

4.92 out of 5 average rating, 118 reviews

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

5 out of 5 average rating, 10 reviews

New! Gorgeous home on AMI. Heated pool!

Discover the perfect getaway at this charming 3bed/2.5 bath vacation rental on Anna Maria Island! Centrally located & just a short stroll to the beautiful beach and vibrant Pine Avenue, where shops and dining await. Enjoy the sunny days lounging by the heated pool or challenge your loved ones to a game of ping pong, foosball, or Connect Four. This delightful home is designed for families and friends, offering a cozy atmosphere for unforgettable memories. Book your slice of paradise today!

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.

4.89 out of 5 average rating, 63 reviews

Island in the Sun, luxury beach house,private pool

Welcome to Island in the Sun this newly renovated home on Ami offers charm, comfort, and luxury. No damage from hurricane Helene or Milton. This Anna Maria Island vacation rental is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach and the popular restaurant - The Waterfront. The City Pier Bay Beach offers narrow white sand beaches, views of the of the City Pier, the Skyway Bridge and the boats traveling back and forth in Anna ...

4.93 out of 5 average rating, 123 reviews

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

4.88 out of 5 average rating, 179 reviews

A charming cottage is set against a vibrant blue exterior, featuring a thatched umbrella over a small outdoor seating area with four chairs. Lush green shrubs and sandy pathways enhance the inviting entrance, while palm trees are visible in the background under clear blue skies.

Bungalow in Anna Maria

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

4.9 out of 5 average rating, 10 reviews

Sunset Beach by Duncan Real Estate

Welcome to Sunset Beach! Looking for an island duplex with private pool and tons of charm and personality for your getaway? Look no further. This newly updated vacation rental is perfect for a laid-back getaway. Sunset Beach is just a three-minute walk over to the Gulf Beaches in a quiet residential neighborhood. HIGHLIGHTS 1016 sq. ft. 0.2 mile from bay access 0.2 mile from beach access BEDROOMS Sleeps 6 Primary Bedroom: King Second Bedroom: Two Twins

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.

5 out of 5 average rating, 82 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.

5 out of 5 average rating, 7 reviews

Heated Pool, Steps to the Beach, Luxury Home

Welcome to your Anna Maria escape! Our 3-bed luxury home features a heated, private pool and is just minutes from the sugar-sand beach. • Spacious open-plan living & gourmet kitchen • Three serene bedrooms with premium linens • Outdoor lounge, grill & sun loungers • Fast Wi-Fi, smart TVs, washer & dryer • Beach chairs, and essentials • Superhost service ensures rapid replies and spotless cleanliness Book now and start making island memories!

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, 187 reviews

2-night available 5/21 & 6/18-Boat Dock, 30' Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

5 out of 5 average rating, 5 reviews

NEW! Steps to Private Beach, Heated Pool + Hot Tub

5-minute stroll to the private beach, heated pool, bubbling spa & ping-pong fun—perfect for families seeking sunshine! 5 bedrooms, 3 kings & 2 queens (sleeps 10) Chef-ready kitchen, outdoor grill & fast 654 Mbps Wi-Fi Beach gear, pack ’n play & high chair included Explore nearby cafés, boutiques and coastal bike paths, then unwind under the stars by the pool. Ready for a worry-free getaway? Click “Reserve” before your dates disappear!

Popular amenities for Anna Maria rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 29 reviews

A tranquil outdoor space features a heated pool surrounded by stone pavers. Comfortable lounge chairs are positioned nearby, and a modern fire pit offers seating. The restored stone house stands in the background, framed by palm trees under a clear blue sky.

Home in Bradenton

100 yr Old Stone Home + Pool + 9 miles to beaches

5 out of 5 average rating, 15 reviews

A private pool area is showcased within a screened enclosure, featuring clear waters and sun loungers. Colorful umbrellas in red and green provide shade, while tall palm plants are arranged around the space. The adjacent home showcases large windows, offering views of the inviting outdoor area.

Home in Arlington Park

Sarasota's Luxury Oasis

Superhost

A sunlit pool area features a spacious rectangular pool surrounded by lounge chairs. The fenced backyard includes tropical landscaping and a deck area elevated above the pool. A walkway made of pavers leads to the poolside, creating an inviting outdoor space.

4.85 out of 5 average rating, 68 reviews

AMI Retreat

A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.

4.97 out of 5 average rating, 102 reviews

Salty Harbor AMI pool retreat near the Beach

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.

5 out of 5 average rating, 25 reviews

The Shell House

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, 148 reviews

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

The exterior of the villa showcases a two-story structure featuring a light-colored façade. Lush greenery surrounds the property, complemented by a paved driveway. The spacious balconies are adorned with seating, inviting relaxation among the tropical landscaping. Two garage doors provide convenient parking.

4.91 out of 5 average rating, 34 reviews

5 min Walk to Beach & Dining in a Private Street

Superhost

Beach House Steps from the Water-Anna Maria Island

Condo rentals with a pool

A heated pool is surrounded by a paved patio and lush tropical landscaping. Comfortable seating under an umbrella is positioned nearby, creating a relaxing outdoor space. The building above features a balcony, adding a vertical dimension to the inviting environment.

4.87 out of 5 average rating, 131 reviews

Steps from the beach

The living area features a seating arrangement with two blue sofas and a light coffee table. A ceiling fan is present, along with a beige recliner. Large glass doors open to a lanai, allowing natural light to fill the room, complemented by coastal-themed art on the walls.

4.98 out of 5 average rating, 100 reviews

A Coastal Retreat Steps From the Sea

A sign bearing the name 'Gulf Beach Place' is prominently displayed against a backdrop of palm trees. The area is surrounded by gravel and features a white fence, indicating a welcoming entrance to the condo property.

4.88 out of 5 average rating, 8 reviews

Gulf Beach Getaway-STEPS FROM BEACH

4.88 out of 5 average rating, 40 reviews

A heated saltwater pool and spa are illuminated with calming blue light, surrounded by tropical plants. The pool features a unique Mickey Mouse shape, and the backdrop showcases a welcoming house with vibrant wall art. Soft lighting adds to the serene evening ambiance.

Condo in Anna Maria

Lakefront Ground Floor 1BR Suite Heated Pool & Spa

4.97 out of 5 average rating, 200 reviews

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

Condo in Bradenton

Luxury 3/3 Margaritaville Resort

4.94 out of 5 average rating, 170 reviews

Adirondack chairs in soft blue are positioned on the sandy beach, offering scenic views of the ocean and coastline. The sun reflects off the water, enhancing the tranquil atmosphere, while a distant figure strolls along the shore. Lush greenery borders the sandy area.

Condo in Bradenton Beach

Beach Escape & Pool, steps to Beach & restaurants

4.98 out of 5 average rating, 227 reviews

Condo in Longboat Key

Sun-Kissed Memories: Open Thursday, $250/nt+Fees!

4.96 out of 5 average rating, 103 reviews

Steps to the beach! Condo with pool at The Terrace

Other holiday rentals with a pool

4.86 out of 5 average rating, 35 reviews

Ocean72 | Heated Pool & Spa | 2BR Near Beach

Townhouse in Holmes Beach

A sandy beach extends towards a calm ocean, where turquoise waters meet a clear blue sky. Colorful umbrellas provide shade for beachgoers, who are relaxing on vibrant towels. The shoreline features soft white sand, inviting visitors to enjoy the peaceful environment.

4.93 out of 5 average rating, 58 reviews

Getaway Family Beach Townhome w/Pool!

4.91 out of 5 average rating, 67 reviews

Family Condo with Heated Pool Spa and Mini-Golf

4.94 out of 5 average rating, 70 reviews

A coastal-style duplex is framed by lush tropical landscaping, featuring palm trees and colorful flowering plants. The exterior showcases light-hued siding, a spacious front porch with railings, and two garage spaces below. A clear blue sky enhances the inviting atmosphere of the property.

Cottage in Holmes Beach

Close to the Beach+ Private heated pool and spa!

A private heated pool, approximately 33 feet long, is surrounded by lush greenery. Covered in-pool seating and a small table are visible, along with a patio area featuring an outdoor shower and an umbrella-shaded dining table for six.

4.9 out of 5 average rating, 10 reviews

Turtle Nest! Private Heated Pool and Access to the

4.97 out of 5 average rating, 31 reviews

A living area features a light-colored sofa and armchairs arranged around a chic coffee table. A television is mounted on the wall, and large sliding glass doors provide views of the outdoors. A decorative plant and a lamp add warmth to the space.

Condo in Isla del Sol

Everything You Need - St Pete Condo - Isla Del Sol

The exterior of a light blue house is shown, featuring a large private pool and a spa area surrounded by a stone deck. Lounge chairs and umbrellas are arranged near the pool, with palm trees providing shade in a landscaped yard. Clear skies are visible overhead.

5 out of 5 average rating, 15 reviews

Lakeview Hideaway - Waterfront Anna Maria