Holmes Beach Vacation Rentals

Stay in one of our Holmes Beach vacation rentals and experience the epitome of luxury beach living. Many of our homes are within walking distance to the beach, local restaurants, shops, and attractions, while all of our vacation rentals boast of meticulous design and incredible amenities.

With a laid back atmosphere and a wealth of outdoor activities, Holmes Beach is ideal for everything from a couples retreat to a family vacation. We'd love to help you plan your stay, so be sure to contact us with any questions! 

Not sure if Holmes Beach is right for you? Check out our Bradenton Beach vacation rentals as well as our Anna Maria vacation rentals!


Properties Available 15 properties available
Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Island Girl East & Island Girl West*Island Girl East & West offers a luxurious and spacious retreat near Holmes Beach with ample room for up to 10 guests, featuring decks, two gourmet ki
Hot HOT 19
Island Girl - East & West
Holmes Beach Pet Friendly
$340.00 - $900.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 (3)
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 23
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 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 28
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
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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 Island Girl East!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Island Girl East*Island Girl East offers a luxurious and spacious retreat near Holmes Beach with room for up to 5 guests, featuring decks, a gourmet kitchen, a shared heated pool, and easy access to Anna Mar
Hot HOT 23
Island Girl East
Holmes Beach
$225.00 - $490.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (1)
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 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 27
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 Cozy Cabana 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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—with temporary updated picture
Hot HOT 22
Cozy Cabana West
Holmes Beach Pet Friendly
$297.00 - $710.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
Welcome to Griffins Island Getaway!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Coastal Luxury with a Private Heated Pool, Game Room, and Short Walk to the Beach, EV ChargerHIGHLIGHTS: Spacious & Open Layout: Bright and airy living, dining, and
Hot HOT 66
Griffins Island Getaway
Holmes Beach Pet Friendly
$320.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 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.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 49
Catching Waves
Holmes Beach Pet Friendly
$260.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
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 15
Fins Up
Holmes Beach
$310.00 - $710.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
Welcome to Island Girl West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Island Girl West*Island Girl West offers a luxurious and spacious retreat near Holmes Beach with room for up to 5 guests, featuring wraparound decks, a gourmet kitchen, a shared heated pool, and easy access
Hot HOT 8
Island Girl West
Holmes Beach
$225.00 - $490.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)

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