Current Discounts & Promotions
10 properties available
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 beachNOW OFFERING UP TO 40% OFF* SUMMER RATES *price reduction a
On Turtle Time
Holmes Beach
$260.00 - $720.00 / per night
2
bedrooms
2
baths
6
guests
5
(3)
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
Sunsets on Carissa
Holmes Beach
$320.00 - $850.00 / per night
3
bedrooms
2
baths
6
guests
5
(4)
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
$300.00 - $750.00 / per night
2
bedrooms
2
baths
6
guests
5
(9)
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
$285.00 - $820.00 / per night
3
bedrooms
2
baths
6
guests
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!
She's Always Right
Holmes Beach
$359.00 - $1,500.00 / per night
4
bedrooms
4
baths
8
guests
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
Mango Bay
Holmes Beach
$395.00 - $1,400.00 / per night
4
bedrooms
3
baths
8
guests
5
(1)
Welcome to Beachy Villa Vista!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2177 sq ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining seating 12, Living w/ TV- Plenty of outdoor deck and patio space including covered lanai- Deck with Gulf &am
Beachy Villa Vista
Holmes Beach
$450.00 - $1,400.00 / per night
5
bedrooms
4
baths
10
guests
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
Serenity Now
Holmes Beach
$395.00 - $1,400.00 / per night
4
bedrooms
3
baths
8
guests
5
(3)
Welcome to Blue Haven Beach House!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Recently updated & AMAZING LOCATION!This LOVELY two story elevated island home has been recently updated with fresh coastal colors, new furniture, and decor. This ho
Blue Haven Beach House
Holmes Beach
$320.00 - $850.00 / per night
3
bedrooms
3
baths
6
guests
5
(8)
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
Cozy Cabana East
Holmes Beach
$240.00 - $750.00 / per night
2
bedrooms
2
baths
6
guests
5
(5)
Tell us what you're looking for and someone will contact you with available options.
Copyright © 2023 • Once Upon a Beach
All Rights Reserved.