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
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
Nestled into a gorgeous resort style setting, Anna Maria Island vacation rental home “Blue Lagoon 5 – Sandpiper” is a fun vacation destination with endless character. Accommodating up to 6 guests this 2 bedroom 2 bathroom vacation rental home offers 1 king bed, 2 twin beds and a 1 queen sleeper sofa and all the amenities of a beachy home away from
LESS THAN A 5MIN WALK TO THE GULF BEACHES - Find the perfect Anna Maria Island vacation spot at “Starfish Beach Cottage 2”! This newly renovated duplex is comfortable, stylish and close to the beach too! When you visit “Starfish Beach Cottage 2” you’ll find everything you’ll need for up to four guests. Inside this Holmes Beach rental you’ll find a
Anna Maria Island vacation rental home “EverLasting Sunsets A and B” is a fabulous ground level duplex perfect for any family getaway. Enjoy 3 bedrooms and 2 bathrooms with 2 king beds and 1 queen bed providing everyone space for a comfortable vacation.<br /><br />With separate units “EverLasting Sunsets A&B” is a great way to vacation with fam
Enjoy a week in tropical island luxury when you visit the beautiful “Gulfview Townhomes Unit 4"! The perfect Anna Maria Island vacation rental condominium, “Gulfview Townhomes Unit 4" is a refreshing departure from the ordinary Florida holiday. Sleeping up to six guests just a short walk to pristine gulf beaches, this Holmes Beach vacation rental i
Stylishly decorated and spaciously accommodating, you’ll fall in love with Florida living when you stay at the gorgeous vacation rental 1107 Edgewater Circle in Perico Bay Club. Come for the sun, but stay for the view from this beautiful two bedroom, two bathroom condominium sleeping up to four guests!Perico Bay Club is a prestigious gated communit
Relax and unwind in the luxurious Anna Maria Island vacation rental home “Beach Pearl”. This five star rental has everything experienced vacationers look for in a home from the perfect location to well-appointed amenities. Just a block and a half from the powder sand beaches of Anna Maria City, “Beach Pearl” is the quintessential Anna Maria Island
Located directly on the Gulf of Mexico beach, “Hidden Cove” is a beautiful beachfront Holmes Beach vacation rental condo perfect for 4 guests! Well equipped with everything you need for a beach vacation; this 2 bedrooms and 2.5 bathrooms townhome style vacation rental has 1 king bed and 2 twin beds.<br /><br />Immerse yourself in the beach life exp
A comfortable stay with a peekaboo view of the Gulf of Mexico, private pool, and rooftop deck included!With a recently updated kitchen, this Holmes Beach property is decorated with a beach cottage style, giving it a relaxing vibe that you’re sure to enjoy. This island getaway is only a few steps away from the beach, just a little jaunt across Gulf
This three bedroom three and a half bath villa is located just a few blocks from the white sandy beaches of Anna Maria Island. This spacious vacation home offers an open floor plan, perfect for all family and friends to gather for laughter and wonderful memories. This dreamy vacation home has a remodeled kitchen features such as granite countertops
DISCLOSURE!!: There is currently an ongoing disagreement regarding the beach access path on 78th Street. In the meantime, we ask that you use the beach access trail that is located on 77th street, directly behind the home you will be staying in.For this you will need to walk down 78th Street to reach Gulf Dr. Using Gulf Dr make your way towards 77t
Discover the allure of Anna Maria Island's northern end with the delightful "Mango Beach House." This idyllic beach cottage features 3 bedrooms and 2 bathrooms, comfortably accommodating up to 8 guests with 2 King beds, 1 Queen bed, and 2 Twin beds (bunkbed).<br /><br />Relax on the secluded sugar sand beach of Bean Point, which is just a short str