Beach house rentals near Anna Maria Island

4.98 out of 5 average rating, 114 reviews

An aerial view captures a heated private pool surrounded by tropical landscaping. Deck chairs and a lounge chair provide seating options, and stone pathways lead to the pool. The pool curves gracefully, inviting relaxation in a serene outdoor setting.

Home in Bradenton Beach

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

5.0 out of 5 average rating, 9 reviews

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!

Superhost

4.85 out of 5 average rating, 26 reviews

New Beach House 1 Min to Beach! Heated Pool/Spa!

A chic, upscale 5-bedroom, 4.5-bath oasis just steps from the white sands of AMI. Lovingly designed for large families and groups, it features a heated pool, spa, and game area with ping-pong and darts. Relax on spacious verandas under swaying palms or enjoy alfresco dining with a BBQ and covered seating. Inside, the gourmet kitchen offers marble counters and high-end appliances. With king suites, bunk rooms, and generous living space, this retreat blends coastal elegance with modern comfort.

4.91 out of 5 average rating, 131 reviews

Home in Siesta Key

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

Unwind in this spacious 4BR/2BA Siesta Key getaway, set on a quiet street steps from gated, private beach entry. Enjoy a resort-style shared pool when you're not at the shore, then head out to Siesta Key Village restaurants, shops, and the island's top attractions. ✔ 4 Bedrooms (Sleeps 10) ✔ Private Beach Access ✔ Open Design Living ✔ Renovated Chef's Kitchen ✔ Private Patio & Shared Outdoors (Pool, BBQ, Games, Fire Pit, Lounges) ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking Learn more below!

The duplex features a light blue exterior with a welcoming porch adorned with yellow and blue chairs. Lush palm trees and vibrant landscaping enhance the outdoor space, while a clear blue sky adds brightness to the scene. Graveled parking is visible in front of the unit.

4.94 out of 5 average rating, 105 reviews

Do you love the beach?

Seaside Sanctuary is the ground floor unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is thirty steps from one of the most pristine beaches on the Gulf of Mexico. The house is located on a quiet residential street near the north end of the island. The front porch is a great place to watch the sunset. The house is clean, comfortable and well appointed. We welcome well behaved dogs and have a fully fenced yard for your pup to play.

4.93 out of 5 average rating, 27 reviews

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

Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

5.0 out of 5 average rating, 11 reviews

NEW! w/ Pool - The Pearl Unit 2 on AMI

The Pearl (Unit 2) is a newly renovated oasis in the heart of Holmes Beach on Anna Maria Island. Just a 3–5 minute walk to the beach, this sunny AMI duplex home has everything — sparkling saltwater pool, fresh interiors, no stairs, beach gear, and parrots that may say hi on your morning walk! Centrally located and steps away from the AMI trolley to whisk you around the island! Relax, explore, and live your best island life. *pool is shared with one other unit in the duplex home*

An outdoor view showcases a private pool surrounded by lush landscaping and tropical palm trees. The distant beach features soft white sand meeting turquoise waters. A spacious deck, complete with loungers, offers a perfect relaxation spot under clear blue skies.

4.91 out of 5 average rating, 74 reviews

TOES IN THE SAND!

Waves Edge South is one of two very unique homes situated directly on the sugar white sands of Anna Maria Island. Welcome to a dreamy island which oozes the charm of ‘old’ Florida and will remind you of yesteryear when you were young and the pace was a little slower. A place where visitors and residents are as likely to use a bicycle or a golf cart as hop in a car. An Island where the warm waters will soothe your soul and you will leave longing to return once more.

Superhost

5.0 out of 5 average rating, 9 reviews

Flamingo Bay by Duncan Real Estate

Welcome to Flamingo Bay! This beautiful waterfront home with private bay beach and steps to the City Pier! New up-dates! New tiled flooring through the whole property and some up-dates. Absolute waterfront house on the bayside on the north end of Anna Maria. A spacious four bedroom/three and a half bathroom beach house. The master suite expands the entire top floor. It has a king bed and his & her bathroom with views overlooking the bay and the Sunshine Skyway.

5.0 out of 5 average rating, 8 reviews

Beach Baby/4 Min Walk to Beach/ Pool/HotTub /Games

Welcome to Beach Baby – Your Laid-Back Island Escape Just a short stroll from the sugar-white sands, Beach Baby is your perfect Anna Maria Island getaway. Located only six houses from the Gulf and about a 4-minute walk to the stunning Bean Point Beach, this bright and breezy retreat is all about soaking up sunshine, salty air, and easy coastal living. Spend your days beach hopping, biking to local shops, or simply unwinding in your own private backyard oasis.

5.0 out of 5 average rating, 8 reviews

The Lookout by Beach Boutique Rentals

*Features include* * Direct bayfront beach location * 3 bedrooms, 2 bathrooms * Private waterfront swimming pool * Huge covered gazebo outdoor living area * Outdoor dining and lounge spaces overlooking the bay * Cornhole, giant games and stand up paddleboards * Bayfront loungers with umbrellas * Outdoor firepit gathering area * New top-to-bottom designer renovation * Washer and dryer * Beach chairs, umbrella and cart * Minutes to Bean Point and Pine Avenue