Holiday houses in Anna Maria

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!

Sea 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.

Payton's Place | Private Heated Saltwater Pool/Spa

Slow down, settle in, and soak up the island pace of life. Your family will be close to everything when you stay at this centrally located private home — just a short stroll to local restaurants, charming shops, and the free trolley stop at the end of the street by the library. The white sand beaches and turquoise Gulf waters are only a 7-minute walk away. Spend your mornings at the beach, your afternoons by the heated saltwater pool, and your evenings under the stars in your private spa.

The Lady Fish by Duncan Real Estate

Nestled on the far North end of Anna Maria Island, with the beach cottage is just around the corner, The Lady Fish is a three-bedroom, two-bathroom vacation home. Guests will enjoy a full gourmet kitchen, perfect for cooking up your catch of the day! The living area is spacious, with plenty of seating for family and friends to take in a movie on the flat panel HDTV. 3 bedrooms offer comfortable sleeping for up to 6 guests. All have TVs. Step outside and enjoy a fantastic outdoor living.

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.

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.

4 BR Pool Home | Sand Volleyball | Near AMI & IMG

Escape to Two Palms, a spacious 4-bedroom, 3-bath retreat in Bradenton, Florida. Perfectly located just minutes from the sugar-sand beaches of Anna Maria Island. Designed with comfort and relaxation in mind, this home offers everything you need for a memorable getaway. Step inside to an open-concept living space filled with natural light and plenty of space to unwind. Outside, enjoy a private salt-water pool and a beach sand backyard featuring a sand volleyball court.

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.

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. 🏖️✨

Salt + Sol | Canal-Front | Golf Cart | Heated Pool

Relax at Salt + Sol, a canal-front retreat on the north end of Anna Maria Island. This bright 4-bedroom home features a private dock, kayaks, paddleboards, bikes, and a 6-passenger golf cart—everything you need for the perfect island escape. Enjoy peaceful water views, quick access to Bean Point and Pine Avenue, and plenty of space for the whole family to unwind. ✨ Pool is complete and available for all guests.

Palm Villa by Beach Boutique Rentals

*Features include* * 2 Bedrooms and 2 full baths * King bed, Queen bed and Queen sleeper sofa * Impeccably remodeled kitchen * Botanical courtyard with beautiful fountain * Stunning tropical landscape * Secluded back patio with outdoor shower * Only steps away from the beach path * Shared laundry and gym facility * Ground level * Dog friendly!

*New* Canal front home with paddle boards, kayaks!

Welcome to your dream beach house—a stunning, professionally decorated oasis set along a picturesque canal. This brand-new, luxurious residence features 6 spacious bedrooms and 5 beautifully appointed bathrooms, making it the perfect getaway for family and friends. spot or a serene place to unwind, this home is sure to exceed your expectations.