Beach house holiday rentals in Bimini Bay

Location! Beach Access/Trolley/ Restaurants!

📣‼️Location, Location! Welcome to “Island Pearl” 🐚 on Anna Maria Island, where you can leave the car behind! This stylish retreat features a heated pool and is nestled in the heart of the action! 🌴The Trolley Stop is at the end of our block and Bridge Street Pier, a block over. 🏖️Beach access is situated just across the street! Fish from the Bay or catch a sunset while dining at the infamous Beach House Restaurant on Gulf Drive. Many restaurants, bars, and shopping are just a short walk away! 🛍️💃

Location · Family · Hospitality

Luxury 3BD Beachfront Retreat with Heated Pool!

Sandy Bottoms Beach House is a luxury Gulf-front retreat where modern comfort meets Florida’s natural beauty. With three king bedrooms—each with its own en suite bath—this home is designed for families, couples, or groups seeking a premium beach getaway. Step through oversized sliding doors to a private patio with a heated pool, outdoor dining, and a direct trail to the sand. Spend mornings walking the shoreline, afternoons lounging by the pool, and evenings watching unforgettable Gulf sunsets f

Value · Location · Comfort

Best Deal Ever starts 9/16~Pool, Steps to beach!

Unbeatable location. HEATED POOL. Ultimate makeover. Everything like new! Big patio. 3 balconies. Nothing compares! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage & covered parking for 5 cars! Close to restaurants, Publix, activities! Steps to FREE TROLLEY! Beach chairs, cart, toys, towels, incl! Weber gas grill. 4 wide screen TV's! Cable, Netflix, more!!!

Location · Family · View

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!

Location · Family · Kitchen

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.

Family · Value · Getting around

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience 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.

Family · Value · Cleanliness

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*

Location · Family · Amenities

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.

Value · Family · Beach

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.

Family · Value · Bathroom

Golf Cart, Bimini Cove by SeaBreeze Vacation

You’ll fall in love with this incredible bay front 5 bedroom/6 full bathrooms home with a separate suite, having 2 full-size kitchens on the sought-after north end of Anna Maria Island! Short distance to the white sandy beaches and only minutes to restaurants and shops. The space is very modern and airy, with high ceilings and upscale furnishings. Heated pool, private dock, gas BBQ grill, and all the amenities you need to live a VIP island experience!

Location · Family · View

Serendipity |Hot Tub | Golf Cart | Elevator | Pet

Welcome to Serendipity, a luxury 4-bedroom beachfront home on the North End of Anna Maria Island, steps from Bean Point Beach. Enjoy direct beach access, a beachfront hot tub, elevator to all floors, and an included 6-passenger golf cart. King beds in every bedroom, pet-friendly (pre-approval required), plus bikes, paddleboards & kayak included. Perfect for unforgettable island sunsets and relaxed coastal living.

Value · Location · Amenities

Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!

Value · Location · Nearby