Holiday rentals in Bimini Bay

Carissa A | Beachside Retreat | Golf Cart | Pool

Carissa Loft A🏝️ 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!

Stunning beach house with heated pool and hot tub!

Welcome to The Colony, a stunning vacation rental on Anna Maria Island, designed to capture the essence of Palm Beach living. This spacious 4-bedroom, 4.5-bathroom house features elegant decor and modern amenities. Step outside to discover a beautiful backyard oasis, complete with a large pool, hot tub, and a well-appointed patio that invites relaxation. Just a 5 minute walk to the pristine beaches of AMI, The Colony is perfectly situated in charming Holmes Beach for an unforgettable getaway.

Canalfront Home with Boat Dock! - A Pirate's Dream

A Pirate’s Dream by AMI Locals Welcome to A Pirate’s Dream by AMI Locals, a grand waterfront retreat that perfectly blends coastal elegance with island adventure on beautiful Anna Maria Island. This four bedroom, three and a half bath vacation home plus loft is designed for families and groups seeking both relaxation and excitement. Located just a five-minute walk from the beach, this Mediterranean inspired home features a private dock, a heated pool, and spectacular bay and canal views,

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.

1/2 Block from Beach- Private Boat Dock & 30' Pool

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.

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*

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

NEW! Steps to Beach, Hot Tub, Pool, Kid Friendly

6-minute stroll to the private beach, heated pool, bubbling spa & ping-pong fun—perfect for families seeking sunshine! 3 bedrooms - 2 kings, 2 fulls +1 trundle twin (sleeps 6) Chef-ready kitchen + outdoor grill Beach chairs, beach umbrellas, + beach wagons Pack ’n play, stroller + high chair included Explore nearby cafés, boutiques and coastal bike paths, then unwind under the stars by the pool. Ready for a worry-free getaway? Click “Reserve” before your dates disappear!

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.

Luxury Canal Home + Heated Pool/Spa, Sleeps 12

Welcome to Hammock Daze, a luxury 4BR/3.5BA canal-front home in the heart of Anna Maria Island. Just a 10-minute walk to the Gulf and steps from Pine Avenue, this resort-style retreat features a heated walk-in pool and spa, peaceful water views from multiple balconies, and a private boat dock. Enjoy beach gear, baby items, an elevator, ping-pong, and spacious living areas—perfect for families and groups seeking an effortless, unforgettable AMI getaway.

Luxury Escape, Pool, Beach, Essentials & Fun!

Welcome to your Anna Maria escape! Our 3-bed luxury home features a heated, private pool and is just minutes from the sugar-sand beach. 🏄🏽‍♀️Beach chairs, and essentials 💦Heated pool ⛱️ Outdoor lounge, grill & sun loungers 🛋️ Spacious open-plan living 🍽️ Gourmet kitchen 🛏️ Three serene bedrooms 🛜Fast Wi-Fi, smart TVs, washer & dryer ⭐️ Superhost service ensures rapid replies and spotless cleanliness Book now and start making island memories!

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.