House in Holmes Beach, FL
8 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Welcome to Fairwinds, your Anna Maria Island vacation rental where coastal charm meets tropical luxury. This spacious four-bedroom, three-and-a-half-bath home is the perfect spot for families and groups seeking a relaxing island escape, just a short walk from the white-sand Gulf beaches.
Step into your own private paradise, featuring a heated pool with swim-up tiki table, a soothing hot tub, and a fully equipped outdoor kitchen and bar. Whether you’re grilling fresh seafood, lounging under the palms, or soaking in the sun, this backyard oasis is built for making memories.
Inside, the bright open living area invites you to unwind. Enjoy comfy seating, a fully stocked kitchen with stainless steel appliances, and French doors leading to a second-floor balcony perfect for morning coffee or evening cocktails.
The primary suite is a peaceful retreat with a king bed, private balcony, and spa-style ensuite complete with jacuzzi tub and walk-in shower. The other bedrooms offer smart TVs and cozy coastal décor, including a kid-friendly twin room that’s perfect for families.
For entertainment, head to the game room with ping pong, foosball, and even axe throwing for fun-filled nights in.
With its unbeatable location, resort-style amenities, and relaxing atmosphere, Fairwinds is the ultimate Anna Maria Island beach house for your next getaway.
Good Neighbor Policy: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.
VRC25-000034
| Max Vehicles: 4 | Max Day Guests: 2
Step into your own private paradise, featuring a heated pool with swim-up tiki table, a soothing hot tub, and a fully equipped outdoor kitchen and bar. Whether you’re grilling fresh seafood, lounging under the palms, or soaking in the sun, this backyard oasis is built for making memories.
Inside, the bright open living area invites you to unwind. Enjoy comfy seating, a fully stocked kitchen with stainless steel appliances, and French doors leading to a second-floor balcony perfect for morning coffee or evening cocktails.
The primary suite is a peaceful retreat with a king bed, private balcony, and spa-style ensuite complete with jacuzzi tub and walk-in shower. The other bedrooms offer smart TVs and cozy coastal décor, including a kid-friendly twin room that’s perfect for families.
For entertainment, head to the game room with ping pong, foosball, and even axe throwing for fun-filled nights in.
With its unbeatable location, resort-style amenities, and relaxing atmosphere, Fairwinds is the ultimate Anna Maria Island beach house for your next getaway.
Good Neighbor Policy: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.
VRC25-000034
| Max Vehicles: 4 | Max Day Guests: 2
Amenities at Fairwinds Family Getaway with Pool & Hot Tub - by Island Real Estate Vactions
Non-smoking
No pets allowed
Family friendly
Map of Holmes Beach, FL
Ratings and reviews
10 / 10Outstanding·Jul 2026
Property was fantastic. Location was awesome with walking distance to shops and restaurants. Also beach access was 100 yards from front door. The backyard was a vacation Oasis. Pool, hot tub, outdoor cooking area and every game you could imagine. They also had all and I mean all of the beach chairs and gear for young and old. Highly recommend! Thanks for making the 250th! Celebration week special.
10 / 10Outstanding·Jun 2026
Great location. House was fully stocked with everything you could need or want. Communication with rental company was awesome.
10 / 10Outstanding·May 2026
First of all, the management company was excellent to work with! The house was wonderful. We rent vacation homes twice a year and this house was the most stocked house that we’ve rented. It had everything you need and then some. The backyard was amazing. The pool, spa, games, outdoor kitchen, seating, etc. was better than expected. The beach supplies were great. Wagons, coolers, floats, chairs, umbrellas, and then the five minute walk to the beach. We had a great time and will be back.
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Top rated by guests
10Outstanding
(4 Ratings)
"Property was fantastic. Location was awesome with walking distance to shops and restaurants. Also beach access was 100 yards from front door. The backyard was a vacation Oasis. Pool, hot tub, outdoor ..."
Michael W.Don't miss out! Price and availability may change
