
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.

Steps to the beach! Updated Condo at The Terrace
Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, coffee maker, blender, balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

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: -We typically have shorter stays available, just ask! -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

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!

Elevator, Heated Pool, Dock, Waterfront, Fire Pit
Escape to The Blue Ark, a unique 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 private pool&spa, 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, 8 beds and 4.5 bathrooms.

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 spa and the 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

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!
Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Heated Pool & Spacious Lanai! Steps from Beach!
Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for the perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shopping, dining, and tropical attractions are just a stroll, bike, or trolley ride away. Perfect for families, snowbirds, reunions, and couples!

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.

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.

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG
🌴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!

Dec Still Open! 2 Blocks to Beach + Heated Pool
Welcome to Salty Sunsets, hosted by Adored Luxe Getaways! Why you’ll love staying here: Salty Sunsets puts you just two blocks from the sand with a private screened porch, 6-seater golf cart, and community pool included. Inside, relax with a fully equipped kitchen, luxe bedding, and all the essentials for an easy island getaway. ☀ 5 minute walk to the beach ☀ 5 minute drive to Pine Ave. shopping & dining ☀ 15 minute drive to Bradenton

Waterfront Retreat | Pool • Spa • Dock | Bridge St
🌴 Anna Maria Island Waterfront Oasis! Private dock + heated pool included. Relax by the pool, sip coffee on the dock, or walk just 5 minutes to the Gulf’s sugar-sand beach. Bright, updated home with stocked kitchen, fast Wi-Fi, smart TVs, and cozy beds—perfect for families or couples. Grill by the pool, dine outdoors, or fish from the dock. Boat/kayak friendly. Beach gear + parking included. Your peaceful island escape awaits.
Popular amenities for rentals with a pool near Anna Maria Island
House rentals with a pool

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

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

83rd St Villas West by Duncan Real Estate

Bayfront Beach access with Heated Pool!

Luxury Beachfront Getaway on Anna Maria Island

Loggerhead - Private Pool + Golf Cart - AMI Oasis

Sunrise Villa - Tropical 3 bedroom home with pool

Walk 2 blocks to Beach + Private Pool + King Beds!
Apartment rentals with a pool

Luxury 3/3 Margaritaville Resort

Beach Escape & Pool, steps to Beach & restaurants

A&A's Paradise near IMG & Anna Maria beaches

Sunset and beach view from your balcony Unit 403

Spectacular beach to bay views from this resort.

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

One-Bedroom Condo on LBK!

Short Stroll to the Surf! ~ Make Memories on AMI
Other holiday rentals with a pool

Beautiful Pool/Spa, Steps to sand, New Golf Cart

TOES IN THE SAND!

Turtle Nest! Private Heated Pool and Access to the

Brand New Remodeled Villa + Large Private Pool!

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

Private Luxurious Ground Level Home

Pirate's Den Bungalow steps from Beach Access!

Unwind Sunshine: steps to locals' favorite beach
Quick stats about rentals with a pool near Anna Maria Island

Total holiday rentals
Explore 2,270 holiday rentals in Anna Maria Island

Nightly prices starting at
Anna Maria Island holiday rentals start at $78 SGD per night before taxes and fees

Verified guest reviews
Over 31,200 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 690 rentals that welcome pets

Rentals with dedicated workspaces
980 properties have a dedicated workspace

Wifi availability
2,260 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
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- Busch Gardens Tampa Bay
- Raymond James Stadium
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