Holiday rentals in Bimini Bay

The Florida Rooms

NEW POOL/SPA. Just 10 minutes from the beach, The Florida Rooms is a 3BR, 2BA retreat with NEW RESORT POOL & SPA, outdoor dining and living space, premium beds, rain showers, a full kitchen, and dining for 8. Extra sleeping includes a queen sofa bed and Pack ’n Play. Enjoy a pool table, ping-pong, board games, outdoor string lights, and a fire pit. We include beach gear—chairs, towels, umbrella, and wagon—for easy fun in the sun. Comfort, charm, and convenience await! Pool/spa heating included!

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

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!

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.

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach

You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

Barefoot Mermaid 4, steps to the beach

Welcome to “Barefoot Mermaid 4” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop steps to the restaurants and shops on Pine Ave and the free island trolley service. “Barefoot Mermaid 4” is the Southwest unit of 4 units located within The Gulf Queen Apartments.

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.

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.

Oceanfront Condo | Rooftop Terrace | Arcades |

Picture this: you step onto the rooftop as the Gulf stretches out in front of you — golden hour, warm breeze, a putting green underfoot and nowhere else you'd rather be. Back inside, the kids are deep into NBA Jam while the waves crash just beyond the balcony. Hello Sunshine is a direct oceanfront condo in the heart of Indian Shores, designed like a magazine spread and stocked for the kind of trip people talk about long after they've unpacked.

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.

NEW! Coconuts 106! Beach Front! Heat Pool!

Welcome to Coconuts Beachfront #106! This renovated ground-floor condo features 1 bedroom and 1 bathroom, on the sands of Holmes Beach. Enjoy Gulf views from the living room, kitchen, and private patio, or step out your back slider straight onto the beach. Perfect for couples or small families, this retreat offers comfort, relaxation, and unforgettable days by the shore.

New! Heated Pool • Shopping • Pine Ave • Beaches!

🛍️Modern comfort meets island charm ✨ walk to beaches, boutiques & bites on Pine Ave! 🌴Welcome to Spring Luxe Beach House, your perfectly located getaway on the north end of beautiful Anna Maria Island — just one block from Pine Avenue’s shops, restaurants, and ice cream parlors 🍦, and an easy walk to both the Gulf Beach 🌊 and the Bay 🌅