Pet-Friendly Island Homes
Discover a vacation where your four-legged family member is just as welcome as you are.
Perfect for family vacations or relaxing getaways, our rentals keep you close to outdoor adventures, incredible dining, and boutique shopping. Make lasting memories in paradise with your pets by your side.
For full details on requirements & approvals, please review our Pet Agreement.
17 properties available
Welcome to Vela Mar!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceVela Mar is where elevated coastal living meets modern luxury innovation. Designed with intention and inspired by the sophistication of Miami-style smart living, this fully i
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceYour island escape designed for families and friends to slow down, reconnect, and soak in the simple joys of island life. Nestled near Anna Maria’s most scenic shoreline and moments from Pine Avenue,
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.The SpaceStep inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmos
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.Experience Catching Waves — where laid-back island living meets everyday adventure. Just a short stroll to the white-sand beaches of Holmes Beach, this ground-level h
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.Where slow mornings and quiet evenings meet the rhythm of island life.Just a short stroll from Holmes Beach, this thoughtfully designed bungalow invites guests to rest, r
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.Discover Cozy Cabana East, where comfort, care, and connection come together in a thoughtfully designed, single-level home just a short walk from the beach. Blending
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.Experience Anna Maria Aloha — a tranquil island cottage made for rest, renewal, and connection.Nestled on the peaceful North End of Anna Maria Island, just 500 feet f
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.Please note: The home is next to a construction site. There is no set construction schedule, and activity may occur during your stay.The SpaceEvery corner of Point’s H
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.The SpaceMornings begin with sunlight dancing across the canal and coffee enjoyed on the screened porch. Days unfold between the pool, the dock, and the nearby beach—each mom
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.The SpaceSet within Margaritaville’s One Particular Harbour waterfront community, Sunset Margarita blends modern finishes with easy, resort-style living. This third-f
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.The SpaceWhere calm meets connection, Serenity Now offers spacious living, modern comforts, and a private backyard oasis with a heated pool. Thoughtfully designed for ease and bal
Welcome to Cortez Dock & Dine!On Florida’s Gulf Coast (Cortez, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A rare waterfront escape blending Old Florida charm with modern coastal living.Please note: Boat not included with rental. For more information about boat rental
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