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.
19 properties available
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
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
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 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
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
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
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 Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBright and Beautifully Updated 3-Bedroom Home with Heated Pool & Spa, Walking Distance to Bean Point Beaches and Pine AvenueHIGHLIGHTS: 1,500 Square Feet: Fresh, modern comfort designed for relaxation. Sle
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 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.Charming Ground-Level Beach Cottage with Heated Pool in the Heart of Anna MariaHIGHLIGHTS: Living & Dining Area: Open-concept space with comfortable seating, a flat-
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
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
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