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 Coconut Lagoon!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—with updated pictures as of Februa
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Coconut Lagoon
Coconut Lagoon
Anna Maria Pet Friendly
$320.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
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 Family Tides!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Family Tides A & Family Tides B*Elevate your vacation experience at Family Tides, a beautifully renovated coastal retreat featuring two stacked condo-style homes, offering a total of 6 bedroom
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Family Tides
Family Tides
Bradenton Beach
$540.00 - $1,600.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
Rating 5 (7)
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover coastal elegance at Mariner's Crossing, a premier luxury vacation rental home just steps from the pristine, sugary white sands of Anna Maria Is
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Mariner's Crossing
Mariner's Crossing
Bradenton Beach
$770.00 - $2,900.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 5 (6)
Welcome to Three Little Birds!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Luxury Waterfront Living with Gulf Views, Heated Pool, and Island CharmHIGHLIGHTS: Spacious and Open Layout: Living, dining, and kitchen areas designed for seamless gathe
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Three Little Birds
Three Little Birds
Anna Maria
$620.00 - $2,300.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Welcome to Decked Out!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 the ultimate island retreat at Decked Out, a luxurious 2-bedroom elevated home with high-end furnishings, a heated pool, and prime access to Anna Maria's bay and G
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Decked Out
Decked Out
Anna Maria
$310.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (14)
Welcome to On Turtle Time!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—ensuring a safe, stylish, and co
Hot HOT 28
On Turtle Time
On Turtle Time
Holmes Beach Pet Friendly
$260.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
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
$355.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (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 Casa Mariposa!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 the charm and luxury of Casa Mariposa, a hidden gem that combines 'Old-Florida' elegance with modern amenities. Nestled behind lush gardens and a butte
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Casa Mariposa
Casa Mariposa
Anna Maria
$440.00 - $1,800.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (9)
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 (4)
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.La Buena Vida is a luxurious 3-bedroom waterfront home on Anna Maria Island, featuring a heated pool, spa, private dock, and easy access to bayside and Gulf beaches, plus shops and
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La Buena Vida
La Buena Vida
Anna Maria Pet Friendly
$380.00 - $880.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)

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