
Home rentals with a pool near Anna Maria Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Anna Maria Island
Guests agree: these stays are highly rated for location, cleanliness and more.

New Golf cart + 4bd/3b w pool/2100 sq ft home
Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

Carissa B | Beachside Retreat | Golf Cart | Pool
Carissa Loft B🏝️ A well-designed home offering comfortable spaces to relax, reconnect & experience all that AMI has to offer! Step inside to discover a private lower level retreat featuring a queen bed, sofa, TV and game table. Upstairs you'll find the fully stocked kitchen, inviting family room, 2-bedrooms & 2-full baths. The private outdoor oasis features a heated/cooled cocktail pool. 🚙Park the car & let the island adventures begin! The 6-person golf cart is complimentary with your stay!

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.

AMI Ohana Beach Resort B with fabulous salt pool!
The location with Heated Pool is perfectly situated on the island with quick access to the beach (3 minute walk from door to shore without crossing Gulf Drive), Publix grocery store, Walgreens, Manatee Public Beach, shopping, restaurants and more. The free trolley stop is steps away offering an affordable way to explore the whole island. Ohana Beach Retreat is a newly renovated triplex in Holmes Beach on Anna Maria Island. Come enjoy our heated salt water pool in an oasis of palm trees.

Salty Harbor AMI pool retreat near the Beach
Charming Salty 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 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

1/2 Block from Beach- Private Boat Dock & 30' Pool
o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

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.

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"
Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

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.

Cabin 2 at Spinnakers Vacation Cottages
My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

MARYS PLACE Walk to the Beach, Brand New Pool
Indulge in the ultimate beach escape to “Mary’s Place” located on Los Cedros, a *premier location* just north of Pine Avenue in the city of Anna Maria. Mary’s Place is a very short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *ultimate beach house* has been fully renovated in 2025. Enjoy *single-story beach house living* with *seamless flow* between the house and private pool/spa…no steps to climb! Amenities include:

Luxe Island Escape by Beach Boutique Rentals
*Features include* * Huge heated pool and spa * Swim up bar seating * Rooftop deck with sweeping water views * 4 bedrooms, 4 ½ baths * 3 king master suites with attached baths * Indoor/outdoor living on all 3 levels * Patio dining for 6, plus lounge area * Chaise loungers by the pool * Garage game room with ping pong table and TV * 2 blocks to beautiful Bean Point beach! * Beach chairs, umbrella, and cart
Popular amenities for rentals with a pool near Anna Maria Island
House rentals with a pool

The Florida Rooms

Stunning beach house with heated pool and hot tub!

Magnolia Palms: Family Retreat w/ Backyard Oasis

Ocean72 | Heated Pool & Spa | 2BR Near Beach

NEW! Heated Pool, Pickleball, Mini-Golf, Play Room

4 BR Pool Home | Sand Volleyball | Near AMI & IMG

Bayfront Beach access with Heated Pool!

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!
Apartment rentals with a pool

Short Stroll to the Surf! ~ Make Memories on AMI

Island Time!

Steps to the beach! Condo with pool at The Terrace

1/1 STEPS to Beach w/ Heated POOL - Sleeps 4

New Luxury 3/3 Condo in Margaritaville Resort

Beach Escape & Pool, steps to Beach & restaurants

Beach Condo with Quiet, Private Beach

*Shore Thing* Walk to Beach | Intercoastal Views
Other holiday rentals with a pool

Manatee Sanctuary - in the heart of Anna Maria

Payton's Place | Private Heated Saltwater Pool/Spa

TOES IN THE SAND!

New Modern on Beach Longboat Key (5 steps to Sand)

Just renovated, beach view from balcony Unit 203

NEW Canal Family Home - Pool, Kayaks, Game Room

Anna Maria retreat house

La Raya - 3bed/2bath POOL Home
Quick stats about rentals with a pool near Anna Maria Island

Total holiday rentals
Explore 2,340 holiday rentals in Anna Maria Island

Nightly prices starting at
Anna Maria Island holiday rentals start at €9 per night before taxes and fees

Verified guest reviews
Over 35,530 verified reviews to help you choose

Family-friendly holiday rentals
1,990 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 760 rentals that welcome pets

Rentals with dedicated workspaces
1,230 properties have a dedicated workspace

Wifi availability
2,330 of Anna Maria Island holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Anna Maria Island rentals

4.8 Average rating
Anna Maria Island stays are highly rated by guests – averaging 4.8 out of 5!
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- Siesta Beach
- Anna Maria Island Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
- Tampa Convention Center
- Dunedin Beach
- Vinoy Park
- Manasota Key Beach
- Hard Rock Casino
- University of South Florida
- Crescent Beach
- John's Pass
- Tropicana Field
- Englewood Beach
- Fort De Soto Park
- Sand Key Beach
- Anna Maria Public Beach
- MidFlorida Credit Union Amphitheatre





