Holiday rentals with outdoor seating 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!

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

Charming houseB 2 min walk to beach, 4+, baby pets

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 grill! 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!

Reese's Beach Retreat

Welcome to your BEACH oasis, just steps away from some of the most world-renowned beaches on Anna Maria Island! This 3-bedroom, 2-bathroom townhome offers countless ways to soak up the sunshine! It is located just a block and a half from the beach, and you will have access to a spacious garage stocked with bikes, beach chairs, toys, umbrellas, and a beach wagon for easy transport. It's the perfect setup to relax and fully immerse yourself in the beachside experience!

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

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.

A Coastal Retreat Steps From the Sea

Just a short walk to the sugary sands of Holmes Beach! This recently updated condominium has everything you need to enjoy a true getaway. Grab our beach chairs, umbrella, coolers, toys, and amazing beach cart to effortlessly pull the beach necessities across the sand. After a nice float in the ocean, come back to the tropical setting surrounding our heated pool. Welcome to Island Life.

Sea Glass North End • 2bed/2 bath Steps to Beach

Welcome to Sea Glass Cottage—your private retreat on the north end of Anna Maria Island. Just one block from Bean Point’s sugar-white sands, this refreshed coastal home features a private pool, upper deck, and stylish indoor–outdoor living. Enjoy a chef’s kitchen with Wolf and Sub-Zero appliances, an outdoor grill and smoker, and relaxed island charm perfect for families and friends.

NEW! Sea Haven~Heated Pool~Fishing from back yard!

Sea Haven AMI Retreat is a remodeled 3-bedroom, 3-bath canal-front home just a 5-minute walk to Holmes Beach. Enjoy a private dock for fishing, heated pool, BBQ grill, and waterfront lanai views. Inside offers an open kitchen, spacious living area with 75” TV, king suites, bunk room, and beach gear. Pet-friendly and packed with games, it’s the perfect Anna Maria Island escape. 🏖️✨

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.

2 min walk to Holmes Beach - Walk to Shops, Dining

Quiet, tropical townhouse is just a 2-min walk to Holmes Beach, tucked away from the crowds, yet close to dining, shops and everything Anna Maria is known for… 🌴 Location Highlights * 2-minute walk to Holmes Beach * Walkable to shops, dining & coffee * 1-minute walk to the free island trolley * Quiet, family friendly neighborhood