Vacation Rentals
40 properties available
Welcome to Shore's Nice!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Renovated Pristine Modern Beach Cottage w/ Peek-A-Boo Bay ViewsHIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom, En-Suite Full Bathroom- 1 King Bedroom- Full Hall
Shore's Nice
Anna Maria
$265.50 - $612.00 / per night
2
bedrooms
2
baths
4
guests
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
Tern Key
Anna Maria
$540.00 - $2,200.00 / per night
4
bedrooms
4
baths
8
guests
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
Sea La Vie Beach House
Anna Maria
$540.00 - $2,200.00 / per night
4
bedrooms
4
baths
8
guests
5
(5)
Welcome to Fins Up!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.New Home w/Private Heated Pool & 4 Min Walk to Beach w/Beach Gear!1250 sq. ft.HIGHLIGHTS: - Kitchen, Dining, Living w/ Soaring Ceilings & Queen Sleeper Sofa & TV- 1 Ki
Fins Up
Holmes Beach
$280.00 - $680.00 / per night
2
bedrooms
2
baths
6
guests
5
(9)
Welcome to Family Tides - Unit BOn Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals1200 sq ft.This home is located in a duplex that has two units. This listing is for the third floor Unit B ONLY with 3 bedrooms and 2 bathrooms and access to the property's shared heated pool, rooftop deck and parking. The individua
Family Tides - B
Bradenton Beach
$260.00 - $880.00 / per night
3
bedrooms
2
baths
8
guests
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 Family Tides - Unit AOn Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals1200 sq ft.This home is located in a duplex that has two units. This listing is for the second floor Unit A ONLY with 3 bedrooms and 2 bathrooms and access to the property's shared heated pool, rooftop deck and parking. The individu
Family Tides - A
Bradenton Beach
$260.00 - $880.00 / per night
3
bedrooms
2
baths
8
guests
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 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 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!
She's Always Right
Holmes Beach
$380.00 - $1,350.00 / per night
4
bedrooms
4
baths
8
guests
5
(12)
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 - $650.00 / per night
2
bedrooms
2
baths
6
guests
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
AMI Peppertree Paradise
Anna Maria
$332.10 - $880.00 / per night
3
bedrooms
2
baths
8
guests
5
(1)
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