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.
41 properties available
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 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.Renovated, Designer-Inspired Ground-Level Home on Beach Block, Just Steps to the Pristine Beaches of Anna Maria Island!HIGHLIGHTS: Prime Location: Beach block, only 500 fee
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 Seaswept Mermaid!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Salty Pirate (#1678416), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Ple
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 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 Island Girl 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.A spectacular vacation half-duplex that promises an unparalleled escape on Anna Maria Island.HIGHLIGHTS: Short Walk to Beach Kitchen, Dining, Indoor/Outdoor Living 1 King
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.2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Seaswept Mermaid (#1850215), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHT
Welcome to Point's Hideaway!Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.On Anna Maria Island (Anna Maria, FL)HIGHLIGHTS: Kitchen, Dining, Living w/ TV 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Walk in Shower 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Shower Tub Combo 1 Kin
Welcome to Decked Out!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 retreat at Decked Out, a luxurious 2-bedroom elevated home with high-end furnishings, a heated pool, and prime access to Anna Maria's bay and G
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.New Home w/Private Heated Pool & 4 Min Walk to Beach w/Beach Gear!1250 sq. ft.HIGHLIGHTS: Kitchen, Dining, Living w/ Soaring Ceilings & Queen Sleeper Sofa & TV 1 King
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.1950 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower and access to deck- 1 Queen Bedroom w/ TV- 2 T
Tell us what you're looking for and someone will contact you with available options.