Luxury Vacation Rentals on Anna Maria Island
Anna Maria Island offers a serene escape with its white sandy beaches, crystal-clear waters, and relaxed, laid-back atmosphere. Our luxury vacation rentals on the island provide a perfect home away from home, whether you're seeking a cozy beachfront cottage, an elegant villa, or a spacious family-friendly retreat. Each property is carefully designed to offer comfort and convenience, with easy access to Anna Maria Island’s best attractions. Experience the beauty of Anna Maria Island and create lasting memories with Once Upon A Beach’s exceptional vacation homes. Immerse yourself in the ultimate island lifestyle with our premier rentals.
Looking to accommodate a specific number of guests? You can also browse our listing of luxury vacation rentals by bedroom: 2 Bedrooms, 3 Bedrooms, 4 Bedrooms, and 5+ Bedrooms.
At Once Upon a Beach, we treat every home as if it were our own and every guest like family. When you book your next vacation with us, you'll receive unparalleled service and a stress-free experience from our team of Anna Maria Island locals and experts. We're proud to be locally-owned and operated, and to provide you with a boutique and intimate style of care. We'd love to help you find your next vacation rental today!
40 properties available
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 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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comfo
Welcome to A Shore Thing!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 ultimate island getaway in this waterfront luxury retreat, perfectly situated just moments from the powdery white sands of Anna Maria Island and the charming boutiqu
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
Welcome to Casa Mariposa!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 and luxury of Casa Mariposa, a hidden gem that combines 'Old-Florida' elegance with modern amenities. Nestled behind lush gardens and a butte
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover coastal elegance at Mariner's Crossing, a premier luxury vacation rental home just steps from the pristine, sugary white sands of Anna Maria Is
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.Experience Peace and Paradise at Serenity Now – Your Dream Vacation Home on Anna Maria IslandHIGHLIGHTS: Spacious Open Layout: Enjoy a bright, airy kitchen, dining, and
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*Island Girl West offers a luxurious and spacious retreat near Holmes Beach with room for up to 5 guests, featuring wraparound decks, a gourmet kitchen, a shared heated pool, and easy access
Welcome to The Oasis at Palmetto!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 unparalleled relaxation at this coastal chic retreat, just steps from direct beach access to the pristine Gulf of Mexico. This stunning 4-bedroom, 3.5-bathroom h
Welcome to Island Girl East!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Island Girl East*Island Girl East offers a luxurious and spacious retreat near Holmes Beach with room for up to 5 guests, featuring decks, a gourmet kitchen, a shared heated pool, and easy access to Anna Mar
Welcome to Family Tides!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units; Family Tides A & Family Tides B*Elevate your vacation experience at Family Tides, a beautifully renovated coastal retreat featuring two stacked condo-style homes, offering a total of 6 bedroom
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
Tell us what you're looking for and someone will contact you with available options.