Private Pool Vacation Rentals

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.


Properties Available 31 properties available
Welcome to Salty Pirate!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Charming Retreat with Heated Pool, and Spacious Living AreasNeed More Space?Expand your island getaway by reserving the sister property next door, Seaswept Mermaid (#1850215)! When
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Salty Pirate
Salty Pirate
Anna Maria
$350.00 - $1,150.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
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 (13)
Welcome to A Shore Thing!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 getaway in this waterfront luxury retreat, perfectly situated just moments from the powdery white sands of Anna Maria Island and the charming boutiqu
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A Shore Thing
A Shore Thing
Anna Maria
$580.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 10 guests
Rating 5 (6)
Welcome to Blue Haven Beach House!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover island charm and modern comforts at Blue Haven Beach House, an elevated coastal retreat steps from the white sands of the Gulf beaches in Holmes Beach.HIGHLIGHT
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Blue Haven Beach House
Blue Haven Beach House
Holmes Beach Pet Friendly
$350.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (9)
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 - $13,550.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.This spacious and luxurious island home is perfect for creating unforgettable memories with your group! Located just one block from the beach and within walking distance
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She's Always Right
She's Always Right
Holmes Beach Pet Friendly
$470.00 - $1,250.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (13)
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.Escape to Coconut Lagoon, a beautifully renovated historic 3-bedroom, 2.5-bath home on Anna Maria Island's sought-after Magnolia Avenue, featuring vintage charm, modern a
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Coconut Lagoon
Coconut Lagoon
Anna Maria Pet Friendly
$320.00 - $810.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
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 (7)
Welcome to Catching Waves!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover the ultimate pet-friendly tropical escape at Catching Waves, a charming coastal duplex in Holmes Beach on Anna Maria Island, offering two bedrooms, two bathrooms,
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Catching Waves
Catching Waves
Holmes Beach Pet Friendly
$260.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 5 (8)
Welcome to Sunset Margarita!Bradenton, Florida (Just off Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.Relax and Unwind in a Stunning Coastal Retreat, Just Minutes from Anna Maria Island Beaches!HIGHLIGHTS: Spacious Layout: Third-floor condo with 2 bedrooms and 2 bathro
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Sunset Margarita
Sunset Margarita
Off Island Pet Friendly
$205.00 - $410.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (2)
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 (9)

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