Private Pool Vacation Rentals

A luxurious private pool surrounded by beautiful palm trees and tropical landscaping. All of the private pools at Once Upon a Beach vacation rentals are heated.

Find the perfect Anna Maria Island vacation rental with a private heated pool and elevate your island getaway. Whether you're looking for a luxury beachfront villa or an affordable family-friendly home, each of our Anna Maria Island rentals offers the ideal balance of comfort, relaxation, and fun. Start your day with a refreshing swim, lounge by your own poolside oasis, and after exploring the island's pristine beaches, unwind in the privacy of your heated pool. Experience the best of Anna Maria Island, where your private pool transforms every moment into a memorable escape. Book your ultimate vacation rental today and dive into the tranquility of Anna Maria Island.


Check out our listing of luxury vacation rentals by bedroom: 2 Bedrooms, 3 Bedrooms, 4 Bedrooms, and 5+ Bedrooms.
Properties Available 29 properties available
Welcome to The Cottage on Pine!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comf
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The Cottage on Pine
The Cottage on Pine
Anna Maria Pet Friendly
$275.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (5)
Welcome to A Wave From It All!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comfo
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A Wave From It All
A Wave From It All
Anna Maria Pet Friendly
$335.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (9)
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Peace and Paradise at Serenity Now – Your Dream Vacation Home on Anna Maria IslandHIGHLIGHTS: Spacious Open Layout: Enjoy a bright, airy kitchen, dining, and
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Serenity Now
Serenity Now
Holmes Beach Pet Friendly
$380.00 - $1,150.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
Welcome to Sandy Pants!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comfortabl
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Sandy Pants
Sandy Pants
Holmes Beach
$355.00 - $785.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (36)
Welcome to Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—with updated pictures as
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Cozy Cabana East
Cozy Cabana East
Holmes Beach Pet Friendly
$280.00 - $680.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
Welcome to AcquaLuxe!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience unparalleled luxury at AcquaLuxe, a stunning canal-front retreat on Anna Maria Island featuring a heated pool, private dock, gourmet kitchen, and upscale amenities designed
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AcquaLuxe
AcquaLuxe
Anna Maria
$750.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (6)
Welcome to Fins Up!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A cozy vacation home with a private heated pool, just a 4-minute walk to the beach, complete with everything you need for an unforgettable stay!HIGHLIGHTS:  Living Space: 1
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Fins Up
Fins Up
Holmes Beach
$310.00 - $710.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
Welcome to Sunsets on Carissa!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.A Stunning Beachside Escape with a Private Heated Pool, Game Room, and Gulf BreezesHIGHLIGHTS: Open Layout: Bright and airy kitchen, dining, and living area with a large TV, per
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Sunsets on Carissa
Sunsets on Carissa
Holmes Beach
$350.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (9)
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A luxurious 2,825 sq. ft. canal-front home featuring a heated pool, spa, and spacious living areas designed for relaxation and comfort.HIGHLIGHTS: Open Concept Living:&nbs
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Sea La Vie Beach House
Sea La Vie Beach House
Anna Maria
$540.00 - $1,950.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Newly Built Luxury Canal-Front Home with Pool, Spa, and Private DockHIGHLIGHTS: Private Single-Family Home: Unique and spacious layout, professionally designed for comfort and luxu
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Tern Key
Tern Key
Anna Maria
$900.00 - $2,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)
Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Island Girl East & Island Girl West*Island Girl East & West offers a luxurious and spacious retreat near Holmes Beach with ample room for up to 10 guests, featuring decks, two gourmet ki
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Island Girl - East & West
Island Girl - East & West
Holmes Beach Pet Friendly
$340.00 - $900.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (3)
Welcome to Bateman's!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover the ultimate in coastal luxury at Bateman's, a stunning canal-front retreat perfect for families and friends seeking an unforgettable Anna Maria Island getaway.2543 sq
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Bateman's
Bateman's
Anna Maria
$560.00 - $2,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (11)

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