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 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.Discover your dream vacation at this newly renovated, single-story Anna Maria Island home, featuring a private heated pool, lush outdoor oasis, and a prime location just minut
Hot HOT 54
A Wave From It All
A Wave From It All
Anna Maria Pet Friendly
$320.00 - $792.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
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
Hot HOT 25
Sunsets on Carissa
Sunsets on Carissa
Holmes Beach
$339.44 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
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
Hot HOT 55
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 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
Hot HOT 30
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 AMI Peppertree Paradise!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Enjoy a sun-soaked getaway at AMI Peppertree Paradise, where comfort, convenience, and island charm come together for the perfect Anna Maria Island vacation rental!1970 s
Hot HOT 39
AMI Peppertree Paradise
AMI Peppertree Paradise
Anna Maria
$335.00 - $792.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (2)
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
Hot HOT 46
Sea La Vie Beach House
Sea La Vie Beach House
Anna Maria
$540.00 - $2,100.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)
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
Hot HOT 22
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 (1)
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.Charming Updated Ground-Level Home with Private Pool, Just Minutes from the Beach!HIGHLIGHTS: Spacious Living & Dining Areas: Open concept kitchen, dining, and liv
Hot HOT 27
On Turtle Time
On Turtle Time
Holmes Beach Pet Friendly
$237.02 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
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.This 2150 sq. ft. beach block retreat features a heated pool and a lush tropical oasis, offering the perfect blend of space, comfort, and island charm.HIGHLIGHTS: Prime Beach Block
Hot HOT 38
Sandy Pants
Sandy Pants
Holmes Beach
$333.59 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (33)
Welcome to Seaswept Mermaid!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Need More Space?Expand your island getaway by reserving the sister property next door, Salty Pirate (#1678416)! When booked together with Seaswept Mermaid you’ll enjoy acc
Hot HOT 14
Seaswept Mermaid
Seaswept Mermaid
Anna Maria
$370.00 - $1,050.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
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
Hot HOT 37
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 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
Hot HOT 27
Tern Key
Tern Key
Anna Maria
$900.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)

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