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 Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Newly Built Luxury Canal-Front Home with Pool, Spa, and Private DockHIGHLIGHTS: Private Single-Family Home: Unique and spacious layout, professionally designed for comfort and luxu
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 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 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 Sunsets on Carissa!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.A Stunning Beachside Escape with a Private Heated Pool, Game Room, and Gulf BreezesHIGHLIGHTS: Open Layout: Bright and airy kitchen, dining, and living area with a large TV, per
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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and co
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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comfortabl
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.A cozy vacation home with a private heated pool, just a 4-minute walk to the beach, complete with everything you need for an unforgettable stay!HIGHLIGHTS: Living Space: 1
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 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.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and co
Welcome to Griffins Island Getaway!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Coastal Luxury with a Private Heated Pool, Game Room, and Short Walk to the Beach, EV ChargerHIGHLIGHTS: Spacious & Open Layout: Bright and airy living, dining, and
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
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