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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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—with updated pictures as
Hot HOT 24
Cozy Cabana East
Holmes Beach Pet Friendly
$280.00 - $680.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
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.3,000 sqft of a Beautifully Restored Island Home with Pool, Spa, and Spacious Outdoor Living!HIGHLIGHTS: Kitchen, Dining Area, and Open Living Space: Fully equipped kitchen with
Hot HOT 28
Mango Bay
Holmes Beach
$360.00 - $1,050.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.6 (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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and co
Hot HOT 35
On Turtle Time
Holmes Beach Pet Friendly
$260.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
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.A cozy vacation home with a private heated pool, just a 4-minute walk to the beach, complete with everything you need for an unforgettable stay!HIGHLIGHTS:  Living Space: 1
Hot HOT 16
Fins Up
Holmes Beach
$310.00 - $710.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Peace and Paradise at Serenity Now – Your Dream Vacation Home on Anna Maria IslandHIGHLIGHTS: Spacious Open Layout: Enjoy a bright, airy kitchen, dining, and
Hot HOT 32
Serenity Now
Holmes Beach Pet Friendly
$380.00 - $1,150.00 / per night
Bedrooms 4 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.A Stunning Beachside Escape with a Private Heated Pool, Game Room, and Gulf BreezesHIGHLIGHTS: Open Layout: Bright and airy kitchen, dining, and living area with a large TV, per
Hot HOT 29
Sunsets on Carissa
Holmes Beach
$350.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (9)
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.This spacious and luxurious island home is perfect for creating unforgettable memories with your group! Located just one block from the beach and within walking distance
Hot HOT 70
She's Always Right
Holmes Beach Pet Friendly
$460.00 - $1,250.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (15)
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.Discover island charm and modern comforts at Blue Haven Beach House, an elevated coastal retreat steps from the white sands of the Gulf beaches in Holmes Beach.HIGHLIGHT
Hot HOT 41
Blue Haven Beach House
Holmes Beach Pet Friendly
$300.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (10)

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