4 Bedrooms
Our collection of 4-bedroom vacation homes on Anna Maria Island offers the ultimate in coastal luxury and comfort. Perfect for families or groups, each home is thoughtfully designed with spacious living areas, fully-equipped kitchens, and beautifully appointed bedrooms. Enjoy private outdoor spaces with pools, lounge areas, and breathtaking sunset views. Located just steps from the island’s stunning white sand beaches, these homes provide convenient access to Anna Maria Island’s finest dining, shopping, and outdoor activities. Experience a memorable vacation in one of our premium 4-bedroom beach homes, where relaxation and adventure await.
13 properties available
Welcome to Three Little Birds!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.BRAND NEW TO THE RENTAL MARKET. Three Little Birds is the epitome of luxury; a new completely renovated waterfront luxury home with Gulf of Mexico views and directly across
Welcome to Island Girl East & 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.Introducing Island Girl East & West, an extraordinary duplex that guarantees an unforgettable escape to Anna Maria Island.HIGHLIGHTS:- Expansive tropical p
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Covered Porch/Balcony off living area- 1 King Bedroom w/ TV, En-Suite Full Bathroom (shower, tub, double sink), Walk-in
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 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.A waterfront luxury home just a few blocks from the pristine sugary white sands of Anna Maria Island and quaint 'downtown' Anna Maria's Pine Avenue!HIGHLIGHTS:- Open la
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2825 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower, Double Vanity, & Soaking Tub- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower- 1 Queen
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 AcquaLuxe!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.3137 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King Bedr
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.Gorgeously Renovated Spacious Home w/Pool, Spa, Game Room, Walk to Beach! 2560 sq. feetHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Primary Suite w/ En-Suite Full Bat
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.2543 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation RentalsThis spacious, bright, and luxurious island home is ready to bring some laughter and memories to you and your group! This home is located just a quick skip to the beach, local restaurants, shops and centrally located on the island!
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.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining seating 8, Living w/ TV on MAIN 2nd floor- Multiple screened in porches/lanai areas- 2 Twin XL Bedroom w/ TV, En-Suite Full Ba
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