Holiday houses 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.

Poolside Oasis on Anna Maria Island!

Remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall and Swim-up Tiki Table, turf putting green ,Weber Grill, patio bar with 55” Outdoor Smart TV! Calypso is outfitted with a cozy Coastal decor, you feel that vacation vibe as soon as you walk in the door. The kitchen offers quartz countertops with Stainless Steel appliances. Both bedrooms have King size beds, living room has a queen sleep sofa. All furniture was brand new in December of 2024

Retreat at Solace West-Hot Tub/Fire Pit/Sunsets

Slow down & trade your winter days for warm sunshine & sandy beaches. Solace West is the perfect place to unplug, and reconnect. Just a short walk to the beach spend your days basking in the sun or hop on the FREE trolley to explore all of Anna Maria Island. Discover charming local spots and enjoy the laid-back island life. After sun-filled days, enjoy an evening soak in the hot tub or relax by the fire. Warm days, peaceful nights, and endless island charm are the escape winter was meant for.

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

NEW!~ Beach Front/Heated Pool! Coconuts 107

Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!Relax with the whole family at this peaceful place to stay.

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

83rd St Villas East by Duncan Real Estate

Welcome to The 83rd St Villas East! A stunning ground-level vacation villa just a 6-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen with Caf appliances, ample counter space, cook top and oven, extra-large fridge/freezer making meal prep a breeze.

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.

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!

L'Oasis East w/Dip Pool

Completely remodeled, this beautifully 2-bedroom duplex, crafted to enhance your living experience. Every detail has been thoughtfully designed to create a serene and inviting atmosphere. New images showcase this stunning transformation, come visit us to see the beauty in person! Additionally, West and East are now available for rent together, featuring convenient adjoining doors through the utility room.

Ocean Views - Spacious Unit, Bonus Loft & Hot Tub

Welcome to "A Wave From It All" – your perfect retreat on Holmes Beach, Anna Maria Island, FL. Nestled within a charming triplex, our end unit offers front-row views of the Gulf of Mexico, ensuring a truly unforgettable stay. With its unbeatable location, spacious accommodations, and top-notch amenities, this is the perfect escape for families, friends, and couples seeking a memorable AMI getaway.