Private Pool Vacation Rentals


Properties Available 32 properties available
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.2150 sq. ft.HIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom - 1 Queen Bedroom - 1 Custom Bunk Room w/ 3 Twin Beds and 2 Double Beds- Sleeper SofaPool Area
Hot HOT 45
Sandy Pants
Holmes Beach
$355.00 - $900.00 / 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 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
Hot HOT 39
Seaswept Mermaid
Anna Maria
$360.00 - $1,400.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
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 41
La Buena Vida
Anna Maria Pet Friendly
$340.20 - $980.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
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 59
Island Time
Holmes Beach
$280.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (6)
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.A newly constructed premier luxury home just across the street from the pristine sugary white sands of Anna Maria Island with views of the gulf from practically every
Hot HOT 73
Mariner's Crossing
Bradenton Beach
$765.00 - $2,800.00 / per night
Bedrooms 8 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 5 (4)
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2825 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower, Double Vanity, & Soaking Tub- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower- 1 Queen
Hot HOT 65
Sea La Vie Beach House
Anna Maria
$560.00 - $2,200.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation RentalsThis spacious, bright, and luxurious island home is ready to bring some laughter and memories to you and your group! This home is located just a quick skip to the beach, local restaurants, shops and centrally located on the island!
Hot HOT 79
She's Always Right
Holmes Beach Pet Friendly
$468.00 - $1,550.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (12)
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, Bikes, Walk to Beach! 2560 sq. feetHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Primary Suite w/ En-Suite F
Hot HOT 79
Mango Bay
Holmes Beach
$360.00 - $1,250.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
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 24
AMI Peppertree Paradise
Anna Maria
$332.10 - $880.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (2)
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 41
A Shore Thing
Anna Maria
$700.00 - $2,600.00 / per night
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 10 guests
Rating 5 (6)
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.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower/Tub- 1 Queen Bedroom w/ TV, En-Suite Full Bathroom
Hot HOT 26
A Wave From It All
Anna Maria Pet Friendly
$54.00 - $880.00 / 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.1950 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower and access to deck- 1 Queen Bedroom w/ TV- 2 T
Hot HOT 43
Sunsets on Carissa
Holmes Beach
$355.00 - $900.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)

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