2 Bedrooms
Discover the perfect 2-bedroom vacation rental on Anna Maria Island, Florida! Browse our extensive selection of Anna Maria Island vacation homes to find the ideal Florida beach house for your next romantic getaway, complete with stunning locations, luxury amenities, and close proximity to the island's best dining, shopping, and attractions.
11 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 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 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.Charming Ground-Level Beach Cottage with Heated Pool in the Heart of Anna MariaHIGHLIGHTS: Living & Dining Area: Open-concept space with comfortable seating, a flat-
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 Shore's Nice!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 Modern Beach Cottage with Peek-A-Boo Bay ViewsHIGHLIGHTS: Spacious Living Areas: Open-concept kitchen, dining, and living area with a TV and designer furnish
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 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 Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Pristine Renovated Home with Private Heated Pool, 6-8 Minute Walk to the Beach!HIGHLIGHTS: Living Spaces: Open-concept design featuring a spacious living area with a
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 wraparound decks, a gourmet kitchen, a shared heated pool, and easy access
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 Casa Posada!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 of old Florida living with modern comforts at Casa Posada, a historic ground-floor cottage just steps from the Gulf-side beaches.1050 sq. ft. of Cozy Cottage Com
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