Vacation rentals with a pool in Holmes Beach

Luxury 3BD Beachfront Retreat with Heated Pool!

Sandy Bottoms Beach House is a luxury Gulf-front retreat where modern comfort meets Florida’s natural beauty. With three king bedrooms—each with its own en suite bath—this home is designed for families, couples, or groups seeking a premium beach getaway. Step through oversized sliding doors to a private patio with a heated pool, outdoor dining, and a direct trail to the sand. Spend mornings walking the shoreline, afternoons lounging by the pool, and evenings watching unforgettable Gulf sunsets f

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

Let me know if you need a stay for a period not listed. Unbeatable location, HEATED POOL, ultimate makeover & NEW bedrm, bathrm, lounge, & covered patio additions for spacious beauty are a few things that set us apart! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage/parking for 6 cars! Near restaurants, Publix, activities! 30 steps to FREE TROLLEY pick up!

Getaway Family Beach Townhome w/Pool!

Wouldn't you like to get away?🌞 Just steps to the perfect family beach at this condo w/pool. Two bedrooms, two baths (+tub), sleeps six! King bed, queen w/twin bunk over, one convertible queen. Fresh updates: Washer-dryer, flooring, sofa, full kitchen, cable, wifi, beach toys, pack n play, baby gate. Did we mention the heated pool?🏊‍♀️ Next door to Walgreens, restaurants, bike rentals, shops, grocery. So many charming delights to discover on America's best beach, Anna Maria Island (AMI)!🏖

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.

Steps to the beach! Updated Condo at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, coffee maker, blender, balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -We typically have shorter stays available, just ask! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

Short Stroll to the Surf! ~ Make Memories on AMI

Nestled in a charming, quiet community of just 8 units, this beautifully updated beach condo offers the perfect blend of relaxation and convenience. The condo is just a short stroll (about 150 steps!) to the pristine white sand beach, where you can soak up the sun and enjoy the coastal views. Wonderful family getaway or couples escape. Private, covered 2 car parking. Laundry in unit. Beach wagon, chairs and gear available. A hidden gem close to everything you need for a relaxing island stay.

Heated Pool, Elevator, Dock, Waterfront, Fire Pit

Escape to The Blue Ark, a unique 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the private pool&spa, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms, 8 beds and 4.5 bathrooms.

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 spa and the 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

Blanco and Sunset Villas on Anna Maria Island

Back Open Jan '25! Located just 200 steps from the beach you’ll have your feet in the sand in no time. A comfortable living area + fully equipped kitchen. Furnished with island décor and local art. Everything you need including a heated pool, large patio with a Tiki hut, tropical gardens, plus a private outdoor area with a shower for your comfort. Walk to everything – grocery, pharmacy, ice cream, breakfast, pizza, donuts, and the beach which is less than 2 minutes away.

Heated Pool & Spacious Lanai! Steps from Beach!

Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for the perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shopping, dining, and tropical attractions are just a stroll, bike, or trolley ride away. Perfect for families, snowbirds, reunions, and couples!

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.