Holiday rentals with a pool in Holmes Beach

Steps to the beach! Condo with pool 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, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, 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!

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!

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

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.

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!

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.

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. 🏖️✨

1/1 STEPS to Beach w/ Heated POOL - Sleeps 4

Spacious and remodeled 1-bedroom condo that sleeps 4 located just STEPS away from the beach. Condo features a large heated swimming pool, private beach access, eat-in kitchen - fully stocked with amenities including coffee maker, WiFi, Smart Tv's, beach accessories, fishing poles, paddle boards, games, & much more! Early Check-in / Late Check-out available upon request.

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.