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 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.Beautifully Recently Updated Ground Level Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1
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
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.Ground Level Fully Renovated Beach Cottage in Heart of Anna Maria2 Bed (sleeps 4), 1 Bath with Heated Pool directly on Pine Avenue. Short walk to Piers, Shops, and Gulf Side
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.Renovated Pristine Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1 King Bedroom, En-Suit
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.Less than 2 miles from the Anna Maria Public Beach in the highly desirable brand new Margaritaville’s One Particular Harbour complex, clean, beautiful and bright!Thir
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.Historic ground floor cottage but with all new interior paint and furnishings! Within easy walking distance to the gulf side beaches!DESCRIPTION:Casa Posada is a charming old Florida
Welcome to Island Girl 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.Experience an extraordinary vacation at this stunning half-duplex on Anna Maria Island, ensuring an unparalleled escape.HIGHTLIGHTS:- Short Walk to the Beach- Open Kitche
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.HIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa TV- 1 King Bedroom, En-Suite Full Bathroom w/ walk in shower- 1 Queen Bedroom- Hall Full Bathroom w/ tub shower c
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 Pristine Modern Beach Cottage w/ Peek-A-Boo Bay ViewsHIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom, En-Suite Full Bathroom- 1 King Bedroom- Full Hall
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.A gorgeous home filled with luxurious furnishings, high-end touches, and smart home technology! The home is picture perfect from a Pottery Barn or Restoration Hardware magazine and co
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 Ki
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