Anna Maria Island Rentals Near The Beach
Browse our collection of Anna Maria Island vacation rentals that are located within walking distance to the beach. Enjoy being just steps from the sand when you rent on of our luxury AMI rentlas that offer effortless access to the island’s most beautiful beaches. Start your day with a short stroll to the shoreline, spend hours in the sun and surf, and return home with ease to relax in comfort.
These homes are perfectly positioned for those who want to stay close to the beach without sacrificing style or convenience, delivering a seamless coastal experience from sunrise to sunset.
37 properties available
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.The SpaceYour serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenie
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*Step inside Island Girl West, where natural textures, sunlight, and soft coastal hues set the tone for your stay. The open layout invites easy flow between kitchen, dining, and living spaces
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.The SpaceThoughtfully redesigned for simplicity and comfort, On Turtle Time blends the charm of an island cottage with the ease of modern living. Inside, natural light filt
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 Hangin’ on Hammock!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Tucked along a quiet stretch on the north end of Anna Maria Island, this home blends easy island living with space to gather, unwind, and enjoy the water. Fresh paint, u
Welcome to Family Tides – Unit BOn Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides B (Top Unit)*Set above its sister unit in this beautiful duplex, this light-filled home offers space for connection and comfort, with access to shared outdoor amenities designed for
Welcome to Bateman's!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 Bateman’s — where thoughtful design and waterfront living come together.Set along a quiet canal on Anna Maria Island’s north end, this modern coastal h
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 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.The SpaceStep into Coconut Lagoon, where generations of island charm meet easy, family-focused living. Nestled along the beloved Magnolia Avenue—lined with palms, bike
Welcome to Sandy Pants!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 creativity meets coastal calm, Sandy Pants brings modern design and island ease together just steps from the Gulf. Every detail feels intentional — from the na
Welcome to Kokomo!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceDiscover Kokomo, where comfort meets calm in a thoughtfully updated beach cottage just a short walk from the Gulf of Mexico. Designed for rest and reconnection, this home
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
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