
Waterfront vacation rentals near Anna Maria Island
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals near Anna Maria Island
Guests agree: these stays are highly rated for location, cleanliness, and more.

Beach Front at βThe Shoreβ
Welcome to The Shore βa beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to Johnβs Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

Private Island Old FL Waterfront Heaven on Earth
Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool
Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!
Enjoy easy living in this updated tropical home! Your private screened lanai is perfect for seamless indoor/outdoor relaxing, with a heated pool and covered dining/lounge area with a 58" outdoor TV! The interior of the home is bright and open with cheerful coastal decor and plenty of room to spread out. We provide everything you need with a well-stocked kitchen, gas grill, game room, beach gear, towels, EV Charger! In a quiet neighborhood with quick access to AMI beaches IMG, parks, and trails!

Sea Wave-[BRAND NEW 2026] Waterfront Oasis
Welcome to Sea Waves, our newly renovated home which is the First Floor of a 2-story property at the North-end of Anna Maria Island. It includes 3 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natural view of Bimini Bay. Smart TV, WiFi, free Netflix, washer/dryer, and a full kitchen are available. You can sailboat directly to Bimini Bay, walk to Pine Ave and City Pier, or eat in nearby restaurants. Our private home has everything you need for a perfect beach vacation in AMI!

Island Time on LBK: Open Sunday $203/nt + Fees!
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...!

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
ππWelcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! ποΈExperience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Cortez ~ Grouper Cottage. BRING YOUR BOAT!
This waterfront home with a private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottageβset in a private, tranquil setting, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

Newly Remodeled Beachfront Studio - On the sand!
ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

KING Bed + Anna Maria Island Beaches + Beach Gear!
βοΈπ¦©Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

Limited Availably w/ Private Boat Dock & 30' Pool
* It doesn't get much better than being right on the water, located on a wide canal, and Β½ 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.

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Welcome to your dream oasis near the world-famous Siesta Key! β¨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenienceβan ideal spot to embrace relaxed Florida living at its finest. π΄
Popular amenities for waterfront rentals near Anna Maria Island
Waterfront apartment rentals

Sweet Retreat at Shorewalk!

Pass a grille Gulf Way Beachfront Parking WiFi 13

Beach Front Condo!

Longboat Key-OCEAN FRONT- on the beach

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Popular Beachside Studio w Relaxing Patio & Palms!

Serenity on the Manatee
Waterfront house rentals

Dock of the Bay by Duncan Real Estate

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

AMI Cortez Beach Retreat "Views" Resort-style Pool

Waterfront Wares Creek Cottage with dock access

Hook Wine and Sinker ~ Walk to Beach/Rooftop Deck

My Sunny home on the Bay.

Manatee Sanctuary - in the heart of Anna Maria

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI
Waterfront condo rentals

Relax in a Newly Renovated Beach Front Paradise

On the Beach; Siesta Key SunBum Studio

Luxury 3/3 Margaritaville Resort

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Spectacular beach to bay views from this resort.

Oceanfront Condo for Beach Lovers

Holmes Beach - literally a few steps to the beach

*Shore Thing* Walk to Beach | Intercoastal Views
Other waterfront vacation rentals

AMI Boathouse

Beachfront Corner Condo | Sunset Gulf Views

Luxury 3B/3B waterfront home w/ pool + boat access

Luxury 2BR Oceanfront Condo + Rooftop Patio

Getaway Family Beach Townhome w/Pool!

Bayfront Beach access with Heated Pool!

ΰΌ Sunset Shore on Anna Maria Island ΰΌ

Seaside Inn a waterfront in Paradise
Quick stats about waterfront rentals near Anna Maria Island

Total vacation rentals
Explore 820 vacation rentals in Anna Maria Island

Nightly prices starting at
Anna Maria Island vacation rentals start at G$2,092Β GYD per night before taxes and fees

Verified guest reviews
Over 13,570 verified reviews to help you choose

Family-friendly vacation rentals
690 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 200 rentals that welcome pets

Vacation rentals with a pool
690 properties feature pools

Rentals with dedicated workspaces
480 properties have a dedicated workspace

Wi-Fi availability
820 of Anna Maria Island vacation 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 guestsβaveraging 4.8 out of 5!
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- Waterfront rentalsΒ Manatee County
- Waterfront rentalsΒ Florida
- Waterfront rentalsΒ 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
- Vinoy Park
- Caspersen Beach
- Tampa Convention Center
- Dunedin Beach
- Sand Key Beach
- Cortez Beach
- Hard Rock Casino
- Manasota Key Beach
- St Pete Beach
- Anna Maria Public Beach
- Englewood Beach
- Jannus Live
- Tropicana Field





