House holiday rentals 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!

Beautiful Beach house! Heated pool and spa!

Discover your dream getaway at this beautifully decorated vacation rental in Anna Maria Island. This stunning 4-bedroom, 4.5-bathroom home offers luxury and comfort, featuring a spacious open-concept living area, modern kitchen, and elegant furnishings. Enjoy the private pool and hot tub, and the beach is just a 5-minute walk away. The highlight is the rooftop deck, where you can soak in breathtaking sunsets. Experience the perfect blend of style and convenience for your unforgettable vacation!

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.

Villa Mar- 2BD Waterfront Home in Holmes Beach, FL

Welcome to Villa Mar- our charming 2BD/2BA waterfront retreat in Holmes Beach, FL. The property sleeps up to 6 people with two bedrooms w/ one king & queen bed, and a queen Murphy chest in the living area. Enjoy the water views 24/7 and a dock perfect for boating or fishing enthusiasts. Spacious outdoor area with dining table & grill. Fully-equipped kitchen, beach amenities, and comforts like Roku, Alexa, WiFi, & Nest. Just 4 blocks from the beach, surrounded by parks, dining and shops in AMI.

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.

La Cocolia located north end of Ami, Lagoon Pool

Need a Great Ami Getaway? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house called “La Cocolia” lovingly translated as the "little crab". This property is ready to host you and your family as you enjoy this newly renovated and decorated 2 bedrooms, 2 bath island beach house. La Cocolia offers privacy, comfort, luxury, and relaxation. Its location is ideal … on a quiet street, north of Pine Ave and just a few flip flop steps away from ...

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.

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.

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 ☀️🍹.

Bean Pt. Bungalow - Half duplex w/private pool

Welcome to Bean Pt. Bungalow! A charming 3/2 villa with a private saltwater pool in the heart of Anna Maria. You're only 0.2 miles from the nearest beach access and 0.2 miles from the Rod and Reel Pier. The home comes equipped with 6 beach chairs and cart. This boutique rental is the perfect place for your next getaway! Primary - King Bed Front bedroom - King bed Bunk room - 4 twin beds

Magnolia Palms: Family Retreat w/ Backyard Oasis

Escape to Magnolia Palms, a 3-bedroom, 2-bath family retreat near the beach. Enjoy a private pool, putting green, kids play gym, pergola lounge, and rec room with pool table. Premium mattresses, a fully stocked kitchen, family-friendly toys, beach gear, and thoughtful essentials ensure comfort, fun, and lasting memories for adults and children alike.

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 🌅