Current Discounts & Promotions



Properties Available 9 properties available
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
Hot HOT 25
Cozy Cabana East
Holmes Beach Pet Friendly
$240.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 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 72
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 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 45
Sunsets on Carissa
Holmes Beach
$355.00 - $900.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
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
Hot HOT 111
On Turtle Time
Holmes Beach Pet Friendly
$220.00 - $700.00 / 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.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
Hot HOT 155
Fins Up
Holmes Beach
$280.00 - $800.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
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
Hot HOT 63
Blue Haven Beach House
Holmes Beach Pet Friendly
$340.00 - $880.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 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 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 61
Island Time
Holmes Beach
$280.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (6)
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
Hot HOT 83
Serenity Now
Holmes Beach Pet Friendly
$378.00 - $1,450.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 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
Hot HOT 82
Mango Bay
Holmes Beach
$360.00 - $1,250.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)

Tell us what you're looking for and someone will contact you with available options.

I agree