Holiday houses in Anna Maria

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.

Manatee Sanctuary - in the heart of Anna Maria

Welcome to Manatee Sanctuary – a spacious 3 bed/ 2 bath canal-front retreat with a private heated pool and hot tub, located in the quiet and highly sought-after North End of the island. This serene and private oasis offers everything you need for a relaxed and memorable beach vacation. The home features an open-concept living and dining area, fully stocked kitchen, and an upstairs porch ideal for morning coffee or evening relaxation. The backyard opens onto a peaceful saltwater canal.

West Bradenton Cottage *No Cleaning Fees or Chores

West Bradenton Cottage is clean, affordable, and great for singles or couples. 8 miles from Anna Maria Island, Holmes Beach, with Coquina Beach and Longboat Key just further down, 2-3 miles from downtown, Riverwalk, GT Bray Park, IMG Acadamy, less than a mile from the country club, 2 miles from Village of the Arts, and 9 miles from Sarasota Bradenton National Airport. Close to Manatee Memorial and HCA Hospitals. Cute, quaint, and cozy, with electric grill on porch, laundry, & fire pit.

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*

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!

Pergola Oasis | Walk to Beach + Outdoor Living

Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sandy beaches of Anna Maria Island, this home features a private covered pergola with outdoor lounge seating and dining, creating the perfect space to relax day or night. Steps from shops and eateries, with nearby bike and golf cart rentals, plus access to community amenities including a boat ramp, kayak launch, fishing dock, and tennis & pickleball courts.

Barefoot Mermaid 2, steps to the beach

Welcome to "Barefoot Mermaid 2" 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 2" is the Northwest unit of 4 units located within The Gulf Queen Apartments.

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.

The Beach House 2 by Duncan Real Estate

Welcome to The Beach House 2! Price Reduction due to construction on Tuna St through April 30, 2026 arrival! Enjoy newly renovated absolute beachfront on the North end of Anna Maria. Directly on the Gulf of Mexico, North of Pine Avenue on beautiful Anna Maria Island, The Beach House 2 is a spectacular beach retreat. This Old Florida beach house on the outside, the interior has been remodeled and updated with all the comforts of a family home.

Under the Foxtails by Beach Boutique Rentals

*Features include* * Private heated pool with covered patio * Ground-level convenience * 3 bedrooms and 3 full bathrooms * Primary suite with king bed and ensuite bath * Second bedroom with king bed * Third bedroom with twin bunk beds – perfect for kids * Vaulted ceilings and skylights * Outdoor area with gas grill and ping pong * Lounge chairs by the pool * Washer and dryer * Beach chairs, umbrella, and cart * Small dog friendly!

NEW! Meet Me At Sunset! 3 Homes from the Beach!

🌅 Meet Me at Sunset is a 4BR/4.5BA beach-boho villa just 3 homes from the Gulf 🌊. Enjoy a heated pool & spa, private balconies, ping pong 🏓, outdoor grill 🍽️, and dog-friendly stays 🐾. Walk to Pine Avenue shops & dining 🛍️, hop on the AMI trolley 🚎, or bike the island 🚲. Beach chairs & cart provided 🏖️. Perfect for families or friends seeking the ultimate Anna Maria Island getaway ☀️🍹.