Holiday rentals with outdoor seating in Holmes Beach

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!

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!

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.

Enjoy Endless Fun with a Private Pool at Key

Key Largo Cottage by Anna Maria Island Accommodations VRC18-000120 Discover the ultimate family getaway at Key Largo Cottage, a charming bungalow style vacation rental perfectly situated along Anna Maria Island’s peaceful streets. This spacious home features three bedrooms, three modern bathrooms, and a private heated pool with a swim up table and calming waterfall, all just a short stroll from the white sandy beaches of the Holmes Beach. Ideally located near top waterfront restaurants,

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.

AMI Ohana Beach Resort B with fabulous salt pool!

The location with Heated Pool is perfectly situated on the island with quick access to the beach (3 minute walk from door to shore without crossing Gulf Drive), Publix grocery store, Walgreens, Manatee Public Beach, shopping, restaurants and more. The free trolley stop is steps away offering an affordable way to explore the whole island. Ohana Beach Retreat is a newly renovated triplex in Holmes Beach on Anna Maria Island. Come enjoy our heated salt water pool in an oasis of palm trees.

Lake by the Beach by Duncan Real Estate

Welcome to Lake by the Beach! This newly renovated and updated, lakeside family home in Holmes Beach, an easy walk to the glorious white beaches of Anna Maria Island. Enjoy the serene water view from almost every room. This house is very comfortable, with a fully equipped kitchen, large dining area, plush furnishings, flat screens, wireless, all linens and beach towels. The house has a split layout with one wing dedicated to the main suite and the other side of the house with a king ...

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.

Anna Maria retreat house

Elevated home with all the amenities. Walking distance to the beach, chairs and towels provided. Relax in the backyard patio, including pool with waterfall . The shaded balcony overlooks the pool if you need to escape the sunshine. There’s a free trolley that runs all day in AMI if you don’t want to take the car out. The house is located across the street from Bimini Bay, enjoy a jog through these side streets in the morning. Local shops and restaurants that will not disappoint .

LUX BEACH HOME*Gulf Views*Rooftop lounge*Steps2Bch

Experience elevated coastal luxury in this stunning beach retreat, just steps from the sand. Soak in breathtaking Gulf views from the second and third levels through expansive walls of glass, unwind by the resort-style pool and spa, and enjoy the rooftop lounge accessed by a striking spiral staircase. Designer furnishings, premium appliances, and sophisticated finishes create an unforgettable stay. Luxury, comfort, and spectacular views come together for the ultimate beach escape.

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

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. 🏖️✨