House vacation rentals in Holmes Beach

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.

Hidden Haven / Private Pool & Hot Tub

Your dream bayside escape at this charming single-story haven, just a heartbeat away from the pristine shores of Anna Maria Island. Featuring 4 inviting bedrooms and 2 stylish baths, indulge in the luxury of a private pool nestled among vibrant tropical foliage. Sip your morning coffee or toast to sunset cocktails poolside, wander to the sparkling Gulf, discover the delightful shops and eateries in Holmes Beach. This oasis is perfect for sun-kissed relaxation and exciting island escapades!

Coastal houseA 2 min walk to beach, 4+, baby pet

Modern & comfortable 2-bedroom, 2-bathroom stay is a short couple minute walk to the white sand beach of Anna Maria Island. The fully equipped kitchen has modern appliances, and the open layout provides plenty of space to relax. Step outside onto private outdoor space to enjoy a morning coffee, sit and relax, or watch the sunset! Newly outfitted for the 2025 season, with brand-new furnishings, linens, and everything you need for a comfortable stay. Side-by-Side Units – Book One or Both!

Salty Harbor AMI pool retreat near the Beach

Charming Salty 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: -Ask us if your dates don't fit our calendar! -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

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

Luxury Beach Home•Steps to Beach•Essentials

Welcome to 203 By the Sea your beach getaway on Anna Maria Island. Step into a bright home with vaulted ceilings & luxury coastal charm. Relax in the outdoor living room, sip coffee on the deck, or stroll a block to the beach. After a day of sun-kissed skin and sandy toes, use the outdoor shower to cool off and then wind down with a game or movie. With a stocked kitchen, beverage center and beach essentials, you have everything you need to relax & make unforgettable memories.

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly just 5 min. walk to the beach. Private lagoon-style *heated* saltwater/low chlorine pool amid lush landscaping with gorgeous rock waterfall. New appliances, HVAC, 60-inch Sony HDTV, Italian leather reclining sofas, BBQ, beach gear, three king bedrooms, all linens provided. Classic Florida one-level home - no stairs. Managed directly by owners, so no crazy fees.

Ocean72 | Heated Pool & Spa | 2BR Near Beach

Welcome to your island escape! Nestled in Holmes Beach, this stunning retreat at Ocean72 offers the perfect blend of luxury and relaxation. Just a short walk to sugar-white beaches, this home boasts a private heated pool, and spa, lush tropical landscaping, and spacious indoor-outdoor living. Enjoy a fully stocked kitchen, plush beds, and beach gear for your adventures. Ideal for families & groups, this coastal gem is your perfect getaway on Anna Maria Island!

Captain's Quarters at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love my place because of the high ceilings, the location, and the ambiance. It is located in the lush tropical paradise of Spinnakers Vacation Cottages. With a large living room, dining area and large master suite, it is perfect for couples, families (with kids), and furry friends (dogs, with a small pet fee). Captains Quarters also has Private patio!

Peacock Way by Duncan Real Estate

Welcome to Peacock Way!This lovely 1 bedroom duplex side is tucked away on quiet Peacock Lane for a fantastic island getaway with a private pool. The ground level cottage style rental offers a spacious living area with fully equipped kitchen and bistro breakfast area. The property sleeps a total of 4 featuring the king bedroom and the living room sofa that can convert into a full size sleeper. Enjoy all new furnishings after the recent complete remodel!

NEW! Steps to Private Beach, Heated Pool + Hot Tub

5-minute stroll to the private beach, heated pool, bubbling spa & ping-pong fun—perfect for families seeking sunshine! 5 bedrooms, 3 kings & 2 queens (sleeps 10) Chef-ready kitchen, outdoor grill & fast 654 Mbps Wi-Fi Beach gear, pack ’n play & 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!

AMI Sunset~Close to beach! Heated Pool!

A charming three-bed, two-bath beach house on Anna Maria Island, this coastal retreat offers a heated pool, two king rooms, and a fun bunk room. Just steps from the beach, it delivers unforgettable sunrises and sunsets. Beautifully designed for comfort and relaxation, it’s the perfect island getaway for families or friends looking to enjoy the best of AMI.