Anna Maria Island Rentals
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 the 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.
43 properties available
Welcome to Sea La Vie!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover the ultimate in luxury island living at Sea La Vie, a custom-built retreat located on the desirable north end of Anna Maria Island. With 2,933 sq. ft. of elegant living space
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 Family Tides – Unit A!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides A*Family Tides – Unit A is a bright and spacious second-floor condo that offers 3 bedrooms, 2 bathrooms, and access to shared outdoor amenities, including a he
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 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.Charming Updated Ground-Level Home with Private Pool, Just Minutes from the Beach!HIGHLIGHTS: Spacious Living & Dining Areas: Open concept kitchen, dining, and liv
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 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 Salty Pirate!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 Retreat with Heated Pool, and Spacious Living AreasNeed More Space?Expand your island getaway by reserving the sister property next door, Seaswept Mermaid (#1850215)! When
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A luxurious 2,825 sq. ft. canal-front home featuring a heated pool, spa, and spacious living areas designed for relaxation and comfort.HIGHLIGHTS: Open Concept Living:&nbs
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.Discover your dream vacation at this newly renovated, single-story Anna Maria Island home, featuring a private heated pool, lush outdoor oasis, and a prime location just minut
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 Seaswept Mermaid!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Need More Space?Expand your island getaway by reserving the sister property next door, Salty Pirate (#1678416)! When booked together with Seaswept Mermaid you’ll enjoy acc
Tell us what you're looking for and someone will contact you with available options.