Holiday rentals with a hot tub in Anna Maria

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.

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.

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.

NEW Saltwater Pool + Spa | Mins to AMI Beaches/IMG

Spend your days playing in the pool and soaking up the sun at this coastal escape! The huge screened lanai includes a pristine heated saltwater pool with a spillover spa and sun ledge, and large covered outdoor living and dining space. The updated 3 bedroom, 2 bath interior is bright and spacious, with a lot of natural light and nearly every room flows out to the pool. Located in a quiet neighborhood with quick access to AMI beaches, IMG, walking trails, parks, shopping & restaurants!

Coral Beach by Duncan Real Estate

Welcome back to Coral Beach! Amenities Include: - Bedroom 1 King Ensuite - Bedroom 2 King Ensuite - Bedroom 3 Queen - Work Space Y - Bathroom 1 Walk-in Shower - Bathroom 2 Walk-in Shower - Bathroom 3 Shower/Tub - Hot Water - Beach Access 0.3 miles - Ground Level Y - Central A C - Cental Heat - Ceiling Fan Living Area - Sqft under a c 1,908 - Free Parking - Parking Spots 4 - Front Security Camera - Self Check In - Keyless Entry - Bath Towels - Beach Towels - Quality Linens - Hair Dryer

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🏝️.

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated PRIVATE pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

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. 🏖️✨

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

NEW Canal Family Home - Pool, Kayaks, Game Room

Just minutes from Anna Maria Island's turquoise water and powder-white beaches, Sandpiper Retreat is your home base for the ultimate Gulf Coast getaway. Wake up to canal views, paddle out to Robinson Preserve at sunrise, then dive in your private heated pool and spa when you come home. A dedicated game room with pool table, foosball, and ping-pong keeps everyone happy once the sun finally sets.

Ocean72 | Heated Pool & Spa | 2BR Near Beach

Welcome to your island escape at Ocean72 in Holmes Beach! Just a short walk to sugar-white beaches, this coastal retreat features a private heated pool & spa, lush tropical landscaping, and seamless indoor-outdoor living. Enjoy a fully stocked kitchen, plush beds, and beach gear. Guests also have the option to add a private golf cart for easy island exploring and beach trips.