Vacation Rentals
40 properties available
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 or Ride Bikes to Beach!2600 sq. feetHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and ensuite full bath- 1 Queen B
Island Time
Holmes Beach
$280.00 - $710.00 / per night
3
bedrooms
2
baths
6
guests
5
(6)
Welcome to Family Tides!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsThis listing is for the entire home including both units for a total of 6 bedrooms, 4 bathrooms, and private heated pool and rooftop deck for your personal and private use only.2288 sq. ft.HIGHLIGHTS:- 2 Separate Homes in One!- Each one level c
Family Tides
Bradenton Beach
$460.00 - $1,600.00 / per night
6
bedrooms
4
baths
16
guests
5
(7)
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
Tern Key
Anna Maria
$540.00 - $2,200.00 / per night
4
bedrooms
4
baths
8
guests
5
(4)
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
A Shore Thing
Anna Maria
$585.00 - $2,300.00 / per night
4
bedrooms
5
baths
10
guests
5
(6)
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.Less than 2 miles from the Anna Maria Public Beach in the highly desirable brand new Margaritaville’s One Particular Harbour complex, clean, beautiful and bright!Thir
Sunset Margarita
Off Island
$202.50 - $432.00 / per night
2
bedrooms
2
baths
5
guests
5
(1)
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.HIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa TV- 1 King Bedroom, En-Suite Full Bathroom w/ walk in shower- 1 Queen Bedroom- Hall Full Bathroom w/ tub shower c
Catching Waves
Holmes Beach
$220.00 - $648.00 / per night
2
bedrooms
2
baths
6
guests
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
Seaswept Mermaid
Anna Maria
$360.00 - $1,400.00 / per night
4
bedrooms
3
baths
8
guests
5
(7)
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
Island Girl - East & West
Holmes Beach
$342.00 - $950.00 / per night
4
bedrooms
4
baths
12
guests
5
(3)
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.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
On Turtle Time
Holmes Beach
$240.00 - $648.00 / per night
2
bedrooms
2
baths
6
guests
5
(3)
Welcome to Marina View Villa!In Historic Cortez Village (Cortez, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.*NEW TO THE RENTAL MARKET. Pictures & additional amenities coming soon!*HIGHLIGHTS:- Separate Living & Sleeping Floors- 1 King Bedroom w/ TV, En-Suite Shower- Screene
Marina View Villa
Off Island
$210.00 - $550.00 / per night
3
bedrooms
2
baths
6
guests
5
(1)
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
The Cottage on Pine
Anna Maria
$300.00 - $720.00 / per night
2
bedrooms
1
baths
4
guests
5
(4)
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
Mango Bay
Holmes Beach
$350.00 - $1,250.00 / per night
4
bedrooms
3
baths
8
guests
5
(1)
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