Vacation rentals in Bimini Bay

A two-story beach house features a wooden staircase leading to a wrap-around balcony. Lush tropical landscaping surrounds the entrance, and several palm trees are visible. Large windows allow natural light to fill the home, enhancing the inviting facade.

4.98 out of 5 average rating, 41 reviews

Anna Maria Beach House

Come stay at our beautiful beach house in Anna Maria, Florida! Located just a few hundred feet from the beach on Maple Avenue, you can easily walk to the Gulf for a day of family fun on the white sand beaches. The house is also walking or biking distance to center of Anna Maria with great restaurants. Please Note: We want to respect our neighbors. This is not a party house. We have a six person and three car maximum. Please reach out for exceptions. If not, you will be asked to leave.

4.98 out of 5 average rating, 45 reviews

Cottage in Anna Maria

Starfish home, BEST North End, walk to beach, pool

Welcome to an old Florida 'The Starfish Cottage" . Enjoy the private heated pool with lush tropical setting. Inside you'll find an open concept living space where dining area, kitchen and living room have been newly furnished with luxurious deep seat couches and lounge chairs, hardwood floors add to the charm. Fresh linens, bath and beach towels are provided along with basic toiletries. Decor has been collected over time and obtained from local artists for a unique old Florida style.

4.95 out of 5 average rating, 208 reviews

9/14-9/17 Discount 30’ Pool & Dock, Steps to Beach

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

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*

4.89 out of 5 average rating, 61 reviews

Apartment in Anna Maria

Anna Maria 2BR Condo • Walk to Beach, Dining, Pier

Modern 2BR/2BA Condo | Walk to Beach & Dining: Experience the best of Anna Maria Island from this bright, coastal-style condo: just a 5-minute walk to the beach, pier, shops, and local restaurants. You’ll Love: • King and Queen bedrooms + queen sofa bed • Smart TVs, fast Wi-Fi, and a full kitchen • 2 private parking spots • Patio shower for easy beach clean-up Perfect for couples, families, or business travelers seeking a comfortable, modern, and walkable island getaway.

The outdoor area features a spacious pool and a separate spa, surrounded by manicured gardens and palm trees. A covered lanai with steps leads to the upper level of the home, which includes expansive sliding glass doors inviting natural light into the interior.

4.97 out of 5 average rating, 37 reviews

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.

Superhost

4.86 out of 5 average rating, 7 reviews

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!

5.0 out of 5 average rating, 9 reviews

83rd St Villas West by Duncan Real Estate

Welcome to 83rd St Villas West! A stunning ground-level vacation villa just a 6-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen with Cafe appliances, ample counter space, cook top and oven, extra-large fridge/freezer making meal prep a breeze.

A serene canal view is presented, showcasing calm water reflecting vibrant hues of sunset. Lush palm trees and greenery border the serene setting, complemented by a wooden dock extending into the water. The peaceful ambiance invites relaxation and enjoyment of nature.

5.0 out of 5 average rating, 65 reviews

Heavenly Hideaway, 3 bdrm, 5 minute walk to beach

Welcome to Heavenly Hideaway, a beautiful canal-front vacation home located just a few blocks from the beach. With 3 bedrooms and 3 bathrooms, this home is perfect for families and friends seeking an unforgettable getaway on Anna Maria Island. This retreat offers luxury and comfort, close to attractions, shops, and dining. Enjoy a serene outdoor oasis with a private heated pool, a private dock on a canal, and a fire pit for smores.

4.93 out of 5 average rating, 14 reviews

Black Pearl! NEW! Block and half to Beach!

Black Pearl is a brand-new luxury 4-bedroom, 4-bath home just a block and a half from the beaches of Holmes Beach. This modern coastal retreat features a rooftop deck with gorgeous views, a private pool and spa, BBQ grill, ping pong table, and corn hole. Each bedroom offers a queen bed and ensuite bath, making it perfect for families or friends seeking upscale comfort and walkable beach access on Anna Maria Island. 🏖️✨

A spacious living area features two yellow sofas accented with vibrant patterned cushions. A wooden coffee table sits atop a patterned area rug with palm leaves. A colorful abstract wall art piece is displayed above the seating, and a standing lamp adds an inviting touch.

5.0 out of 5 average rating, 40 reviews

L'Oasis East 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.