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 32 properties available
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 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 Mango Bay!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Gorgeously Renovated Spacious Home w/Pool, Spa, Game Room, Walk to Beach! 2560 sq. feetHIGHLIGHTS: Kitchen, Dining Area, Living w/ TV 1 King Primary Suite w/ En-Suite Full Bath
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Mango Bay
Mango Bay
Holmes Beach
$360.00 - $1,050.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
Welcome to On Turtle Time!Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.On Anna Maria Island (Holmes Beach, Florida)Beautifully Recently Updated Ground Level Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS: Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV 1 Ki
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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 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 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (11)
Welcome to Seaswept Mermaid!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Salty Pirate (#1678416), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Ple
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Seaswept Mermaid
Seaswept Mermaid
Anna Maria
$370.00 - $1,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
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.2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Seaswept Mermaid (#1850215), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHT
Post Storm Status: Post Storm Status:
Post Storm Status:
This home unfortunately suffered storm damage. Pending ready for guests in 2025.
Salty Pirate
Salty Pirate
Anna Maria
$350.00 - $980.00 / 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 (12)
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.Ground Level Fully Renovated Beach Cottage in Heart of Anna Maria2 Bed (sleeps 4), 1 Bath with Heated Pool directly on Pine Avenue. Short walk to Piers, Shops, and Gulf Side
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The Cottage on Pine
The Cottage on Pine
Anna Maria Pet Friendly
$275.00 - $850.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (4)
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 - $900.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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.This waterfront 3-bedroom home has a private heated pool, spa, and dock! This home's location is second to none, just steps to the bayside beaches and easy walking distanc
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La Buena Vida
La Buena Vida
Anna Maria Pet Friendly
$380.00 - $980.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Covered Porch/Balcony off living area- 1 King Bedroom w/ TV, En-Suite Full Bathroom (shower, tub, double sink), Walk-in
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Serenity Now
Serenity Now
Holmes Beach Pet Friendly
$380.00 - $1,250.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)

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