2 Bedrooms

Anna Maria Island 2 Bedroom Rentals


Find the perfect quaint 2 bedroom vacation rental on Anna Maria Island in Florida! Search our wide selection of AMI rentals to find the perfect Florida beach house for your next romantic getaway!

Keep Searching: Search All Rentals On Anna Maria Island, AMI 3 Bedroom Rentals, AMI 4 Bedroom Rentals, AMI 5 Bedroom Rentals, Bring your furry friend too and search our Pet Friendly Rentals on AMI


Properties Available 11 properties available
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
Hot HOT 65
Cozy Cabana East
Holmes Beach Pet Friendly
$310.00 - $675.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
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
Hot HOT 53
Decked Out
Anna Maria
$340.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (10)
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
Hot HOT 13
Fins Up
Holmes Beach
$300.00 - $675.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
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 beachNOW OFFERING UP TO 40% OFF* SUMMER RATES   *price reduction a
Hot HOT 25
On Turtle Time
Holmes Beach Pet Friendly
$290.00 - $648.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
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
Hot HOT 15
Sunset Margarita
Off Island Pet Friendly
$225.00 - $432.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (1)
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
Hot HOT 113
Shore's Nice
Anna Maria
$295.00 - $612.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (9)
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
Hot HOT 32
The Cottage on Pine
Anna Maria Pet Friendly
$340.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (3)
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
Hot HOT 43
Casa Posada
Anna Maria Pet Friendly
$279.00 - $450.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 (3)
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
Hot HOT 32
Island Girl East
Holmes Beach
$250.00 - $495.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (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
Hot HOT 20
Island Girl West
Holmes Beach
$250.00 - $495.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
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
Hot HOT 261
Catching Waves
Holmes Beach Pet Friendly
$290.00 - $648.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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