Pet Friendly Rentals
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.
16 properties available
Welcome to Point's Hideaway!Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.On Anna Maria Island (Anna Maria, FL)HIGHLIGHTS: Kitchen, Dining, Living w/ TV 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Walk in Shower 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Shower Tub Combo 1 Kin
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBeautifully updated, fresh, and clean elevated 3 Bed, 2.5 Bath which sleeps up to 8 within easy walking distance to Bean Point beaches & Close to Anna Maria's Beloved Pine Avenue1500 square feetHIGHLIGHTS:-
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.Pristine Renovated Home with Private Heated Pool, 6-8 Minute Walk to the Beach!HIGHLIGHTS: Living Spaces: Open-concept design featuring a spacious living area with a
Welcome to On Turtle Time!Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.On Anna Maria Island (Holmes Beach, Florida)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 Ki
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.Renovated, Designer-Inspired Ground-Level Home on Beach Block, Just Steps to the Pristine Beaches of Anna Maria Island!HIGHLIGHTS: Prime Location: Beach block, only 500 fee
Welcome to Casa Posada!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience the charm of old Florida living with modern comforts at Casa Posada, a historic ground-floor cottage just steps from the Gulf-side beaches.1050 sq. ft. of Cozy Cottage Com
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.This waterfront 3-bedroom home has a private heated pool, spa, and dock! This home's location is second to none, just steps to the bayside beaches and easy walking distanc
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.Discover the ultimate pet-friendly tropical escape at Catching Waves, a charming coastal duplex in Holmes Beach on Anna Maria Island, offering two bedrooms, two bathrooms,
Welcome to Island Girl East & 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.Introducing Island Girl East & West, an extraordinary duplex that guarantees an unforgettable escape to Anna Maria Island.HIGHLIGHTS: Expansive tropical pa
Welcome to A Wave From It All!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover your dream vacation at this newly renovated, single-story Anna Maria Island home, featuring a private heated pool, lush outdoor oasis, and a prime location just minut
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.Escape to Coconut Lagoon, a beautifully renovated historic 3-bedroom, 2.5-bath home on Anna Maria Island's sought-after Magnolia Avenue, featuring vintage charm, modern a
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
Tell us what you're looking for and someone will contact you with available options.