
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.

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.

Limited Availably w/ Private Boat Dock & 30' Pool
✨ 4.95★ GUEST FAVORITE! Canal Front & 1/2 Block to Beach Experience the ultimate AMI getaway! This 4.95-star tropical oasis features a wide canal with a 30' boat/fishing dock, a massive 16'x30' private pool, and is just a 1/2 block to the beach. Walk to everything:• 3-min walk to Bay Beach, 15 to Bean Point• Steps to Pine Ave shopping & City Pier• Stroll to Waterfront Restaurant & Two Scoops. Bring your boat, lounge poolside, or hit the sand. Perfect island living with 200+ rave reviews!

The Florida Rooms
NEW POOL/SPA. Just 10 minutes from the beach, The Florida Rooms is a 3BR, 2BA retreat with NEW RESORT POOL & SPA, outdoor dining and living space, premium beds, rain showers, a full kitchen, and dining for 8. Extra sleeping includes a queen sofa bed and Pack ’n Play. Enjoy a pool table, ping-pong, board games, outdoor string lights, and a fire pit. We include beach gear—chairs, towels, umbrella, and wagon—for easy fun in the sun. Comfort, charm, and convenience await! Pool/spa heating included!

Green Jacaranda /Bean Point Beach 5 min walk/pool
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

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.

Island Time: Open July 7 - 10!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

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

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach
You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

NEW!~ Beach Front/Heated Pool! Coconuts 107
Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!Relax with the whole family at this peaceful place to stay.

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.

L'Oasis West w/Dip Pool
Completely remodeled, this beautifully 2-bedroom duplex, crafted to enhance your living experience. Every detail has been thoughtfully designed to create a serene and inviting atmosphere. New images showcase this stunning transformation, come visit us to see the beauty in person! Additionally, West and East are now available for rent together, featuring convenient adjoining doors through the utility room.

Ocean72 | Heated Pool & Spa | 2BR Near Beach
Welcome to your island escape at Ocean72 in Holmes Beach! Just a short walk to sugar-white beaches, this coastal retreat features a private heated pool & spa, lush tropical landscaping, and seamless indoor-outdoor living. Enjoy a fully stocked kitchen, plush beds, and beach gear. Guests also have the option to add a private golf cart for easy island exploring and beach trips.
Popular amenities for rentals with a pool near Anna Maria Island
House rentals with a pool

Heated Pool, Hot Tub, Game Room, Steps to Beach!

Casa Cay by Duncan Real Estate

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!

Bayfront Beach access with Heated Pool!

Heated Pool, 5 miles to the Beach, Sleeps 8

Modern Home Heated Pool near Siesta & Downtown

Pool & Sand Volleyball | 3 Kings | Near AMI & IMG

Waterfront Pool Home Steps to Beach
Condo rentals with a pool

On the Beach; Siesta Key SunBum Studio

Luxury 3/3 Margaritaville Resort

Beach Escape & Pool, steps to Beach & restaurants

Direct Beach Access & Pool | 2B Full Oceanview

#terraceLIFE | 2 Blocks to Beach | Heated Pool

Beach Front at “The Shore”

Oceanfront Condo for Beach Lovers

Steps to the beach! Condo with pool at The Terrace
Other holiday rentals with a pool

Coconut Vacation Rentals/1BR/Pool/Steps to Beach!

Getaway Family Beach Townhome w/Pool!

The Toasty Coconut in Anna Maria

Stunning beach house with heated pool and hot tub!

The Cottage on Pine - Pine Ave Cottage w/ Pool

Sea Shack - 2bd/2ba POOL Home

Is this Heaven? No, it's Longboat Key

Anna Maria retreat house
Quick stats about rentals with a pool near Anna Maria Island

Total holiday rentals
Explore 2,330 holiday rentals in Anna Maria Island

Nightly prices starting at
Anna Maria Island holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 33,900 verified reviews to help you choose

Family-friendly holiday rentals
2,020 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 740 rentals that welcome pets

Rentals with dedicated workspaces
1,280 properties have a dedicated workspace

Wi-Fi availability
2,330 of Anna Maria Island holiday rentals include Wi-Fi 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!
Destinations to explore
- Rentals with an EV charger Anna Maria Island
- Beachfront rentals Anna Maria Island
- Bungalow rentals Anna Maria Island
- Pet-friendly rentals Anna Maria Island
- Apartment rentals Anna Maria Island
- Luxury rentals Anna Maria Island
- Cottage rentals Anna Maria Island
- Villa rentals Anna Maria Island
- Condo rentals Anna Maria Island
- House rentals Anna Maria Island
- Rentals with a fireplace Anna Maria Island
- Resort rentals Anna Maria Island
- Rentals with beach access Anna Maria Island
- Rentals with a sauna Anna Maria Island
- Rentals with outdoor seating Anna Maria Island
- Waterfront rentals Anna Maria Island
- Family-friendly rentals Anna Maria Island
- Rentals with lake access Anna Maria Island
- Rentals with a hot tub Anna Maria Island
- Beach house rentals Anna Maria Island
- Rentals with a patio Anna Maria Island
- Rentals with a fire pit Anna Maria Island
- Townhouse rentals Anna Maria Island
- Fitness-friendly rentals Anna Maria Island
- Hotel rooms Anna Maria Island
- Rentals with breakfast Anna Maria Island
- Rentals with a kayak Anna Maria Island
- Rentals with a washing machine and dryer Anna Maria Island
- Beach condo rentals Anna Maria Island
- Rentals with pools Manatee County
- Rentals with pools Florida
- Rentals with pools United States
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Coquina Beach
- Lido Key Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
- Tampa Convention Center
- Vinoy Park
- Sand Key Beach
- Dunedin Beach
- Cortez Beach
- Hard Rock Casino
- Tropicana Field
- Manasota Key Beach
- St Pete Beach
- Anna Maria Public Beach
- Englewood Beach
- Jannus Live





