Pet Friendly Vacation Rentals

A cute little terrier wearing red sunglasses while floating on a surfboard in the ocean. Bring your best friend on your next vacation and stay in one of our luxurious pet friendly vacation rentals on Anna Maria Island!

At Once Upon A Beach, we offer a selection of pet-friendly vacation homes on Anna Maria Island, so your furry family members can join in the fun! Our pet-friendly rentals provide all the comforts of home, with spacious layouts, private pools, and convenient access to Anna Maria Island’s beautiful white sand beaches. Whether you're planning a family vacation or a relaxing getaway, our homes are located near the island’s top attractions, including outdoor activities, local dining, and boutique shopping. Experience the best of Anna Maria Island with your pets by your side and create unforgettable memories in a tropical paradise.

You can also browse our listing of luxury vacation rentals by bedroom: 2 Bedrooms, 3 Bedrooms, 4 Bedrooms, and 5+ Bedrooms.


Properties Available 18 properties available
Welcome to Anna Maria Aloha!On Anna Maria Island (Anna Maria, 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 31
Anna Maria Aloha
Anna Maria Pet Friendly
$240.00 - $680.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (8)
Welcome to Coconut Lagoon!On Anna Maria Island (Anna Maria, FL)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 of Februa
Hot HOT 33
Coconut Lagoon
Anna Maria Pet Friendly
$320.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comf
Hot HOT 32
The Cottage on Pine
Anna Maria Pet Friendly
$275.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (4)
Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Spacious Island Retreat with Rooftop Views, Private Pool, and Steps to Bean Point Beach!HIGHLIGHTS: Kitchen, Dining, Living Area: Open-concept design with vaulted ceili
Hot HOT 26
Point's Hideaway
Anna Maria Pet Friendly
$330.00 - $780.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (5)
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.La Buena Vida is a luxurious 3-bedroom waterfront home on Anna Maria Island, featuring a heated pool, spa, private dock, and easy access to bayside and Gulf beaches, plus shops and
Hot HOT 17
La Buena Vida
Anna Maria Pet Friendly
$380.00 - $880.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
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 20
Cozy Cabana West
Holmes Beach Pet Friendly
$310.00 - $710.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
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 39
She's Always Right
Holmes Beach Pet Friendly
$470.00 - $1,250.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (14)
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 23
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 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 32
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 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 25
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 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 40
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 Sunset Margarita!Bradenton, Florida (Just off Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.Relax and Unwind in a Stunning Coastal Retreat, Just Minutes from Anna Maria Island Beaches!HIGHLIGHTS: Spacious Layout: Third-floor condo with 2 bedrooms and 2 bathro
Hot HOT 19
Sunset Margarita
Off Island Pet Friendly
$205.00 - $410.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (3)

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