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 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 Bat
Hot HOT 33
Mango Bay
Mango Bay
Holmes Beach
$310.00 - $1,050.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
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.A waterfront luxury home just a few blocks from the pristine sugary white sands of Anna Maria Island and quaint 'downtown' Anna Maria's Pine Avenue!HIGHLIGHTS:- Open la
Hot HOT 12
A Shore Thing
A Shore Thing
Anna Maria
$500.00 - $2,400.00 / per night
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 10 guests
Rating 5 (6)
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBeautifully updated, fresh, and clean elevated 3 Bed, 2.5 Bath which sleeps up to 8 within easy walking distance to Bean Point beaches & Close to Anna Maria's Beloved Pine Avenue1500 square feetHIGHLIGHTS:-
Hot HOT 43
Sol Mate
Sol Mate
Anna Maria Pet Friendly
$324.00 - $880.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (9)
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.Pristine Newly Built Spacious Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point Beaches & Downtown Anna Maria, Bikes Included!3650 sq. ft.HIGHLIGHTS:- Private Single Family H
Hot HOT 21
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)
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
Hot HOT 25
Serenity Now
Serenity Now
Holmes Beach Pet Friendly
$360.00 - $1,250.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)
Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Introducing Island Girl East & West, an extraordinary duplex that guarantees an unforgettable escape to Anna Maria Island.HIGHLIGHTS:- Expansive tropical p
Hot HOT 22
Island Girl - East & West
Island Girl - East & West
Holmes Beach Pet Friendly
$300.00 - $980.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (3)
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.The 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 distance to B
Hot HOT 15
La Buena Vida
La Buena Vida
Anna Maria Pet Friendly
$100.00 - $1,100.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
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.Renovated Pristine Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1 King Bedroom, En-Suit
Hot HOT 9
Cozy Cabana East
Cozy Cabana East
Holmes Beach Pet Friendly
$195.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
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.Ground Level Completely Updated Luxury Historic Home3 Bed (sleeps 6), 2 1/2 Bath with Heated Pool easy walking distance to Pine Avenue and Gulf side beachesHIGHLIGHTS:- Kitchen, D
Hot HOT 22
Coconut Lagoon
Coconut Lagoon
Anna Maria Pet Friendly
$285.00 - $900.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
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
Hot HOT 18
Salty Pirate
Salty Pirate
Anna Maria
$330.00 - $980.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 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.1970 sq. ftHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and Ensuite Full Bath & Walk-In Closet- 1 Queen Bedroom w/ TV- 2 Bunk Beds w/Trundle
Hot HOT 13
AMI Peppertree Paradise
AMI Peppertree Paradise
Anna Maria
$310.00 - $880.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (2)
Welcome to Island Time!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals & Property ManagementGround Level Spacious Home w/Lagoon Style Enclosed Heated Pool & Spa, Walk to the Beach!2600 sq. feetHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and ensuite full bath- 1 Queen Bedroom w/
Hot HOT 21
Island Time
Island Time
Holmes Beach
$250.00 - $710.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)

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