Your dates are popular!% of our inventory is booked.Book Now!
105 properties returned
Sort by:Random
Name
Beds
Beds
Sleeps
Sleeps
Random
Price
Price
Following a beautifully sculpted path will lead you to a tropical archway of two large coconut trees, there you’ll fine your own piece of island paradise. “Anna Maria Cottage” is an island oasis that's more than worthy of its name sake. This island cottage, placed perfectly near the beaches of Anna Maria, is a treat for the eyes. Inside you’ll find
Ready to find your piece of island paradise? Look no further than “Wave N’ Sea”. This beautiful, sunny Anna Maria home is a spacious three-bedroom two-bathroom rental that can accommodate up to six guests. With a new, and private, heated pool, an oversized yard with tropical landscaping, and less that two blocks from the beach, “Wave N’ Sea” is tru
Nestled into a gorgeous resort style setting, Anna Maria Island vacation rental home “Blue Lagoon 6 – Osprey” is a fun vacation destination with endless character. Accommodating up to 4 guests this 2 bedroom 2 bathroom vacation rental home offers 1 king bed, 1 queen bed and all the amenities of a beachy home away from home. <br /><br />Inside “Blue
Everything you expect from a relaxing stay can be found at this Anna Maria Island vacation rental condominium. If you’ve never experienced Gulf of Mexico beaches you are in for a real treat. Enjoy powder white sand, crisp blue water, gorgeous sunsets and great beach combing all waiting right outside your door! If you visit in the winter months, enj
“Pirate’s Cove” is a great island oasis to enjoy during your stay, the perfect cove for your vacation getaway. One of the only "Any Day" arrival properties on the island.This elevated home is built for family vacations, as it has the room to allow for a relaxing vacation giving everyone their space. “Pirate’s Cove” has an extensive layout, with mul
Inside this Holmes Beach vacation rental you’ll find a well-appointed condominium to kick your feet up in island style. The living room offers a flat screen television, comfortable furniture and the dining area seating four. In the kitchen you’ll find all the basics including a dishwasher. Off the kitchen there is a private balcony.Accommodating up
FLIP FLOP INN - 201 57th Street Holmes BeachIf you are searching for luxury on your Island vacation, this home is your dream come true. Tucked away on a quiet street on Anna Maria Island, this Mediterranean-style Townhouse is your perfect family vacation destination.This lovely home is located only one and a half blocks from white sand beaches and
When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Piece of Paradise”. This fun four bedroom, three bathroom Holmes Beach vacation rental spaciously sleeps up to 8 guests in comfort and style. After spending a week at this fabulous Holmes Beach vacation rental home within walking di
Holmes Beach vacation rental "The Coconuts Beach Resort 101" is the perfectly charming cozy spot great for four guests, or a more intimate couples getaway. You will fall in love with the lively decor in this quaint condo. The open space of the kitchen, living and dining area are great for chatting with friends and relaxing. In the bedroom find two
Searching for a suitable home to enjoy your luxury island vacation? Flip Flop Inn certainly makes the list, a Mediterranean-style townhouse tucked away on one of Anna Maria Island’s peaceful streets. When you enter the home, you’ll be greeted with a bright and airy main level, just upstairs you’ll find a dining area and open living space beneath th
“Martinique” is directly on the coast providing the quintessential beach experience complete with powder white sand, blue water, fresh gulf breezes and amazing sunsets. You’ll want to spend all day soaking up the sun and salt water! Relax with a good book, cool drink or chat with friends around the heated community pool. Enjoy premium linen service
This perfect vacation rental villa “Harrington Bungalow 5” is located just a short walk from the beautiful beaches of Anna Maria Island. This bungalow is in a great group of six vacation rentals previously managed by the Harrington House Bed and Breakfast. Owner just added a private heated pool!<br /><br />It offers two bedrooms, two bathrooms and