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
With stunning direct gulf front views, the stylish “Water's Edge 209S” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 4 guests this 2 bedroom 2 bathroom Holmes Beach vacation rental condominium offers one king bed and one queen bed in a beautiful coastal inspired atmosphere. <br /><br />Situated on the Gulf of Mexi
Harrington Cottage is an adorable Anna Maria beach cottage that’s so close to the Gulf of Mexico you can practically smell the sea salt air! Less than a block away you’ll find the white sand beaches of Anna Maria Island, all while staying in this cute 4 bedroom, 3 bath cottage. Enjoy the peace and quiet afforded by the city of Holmes Beach. Harring
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
The perfect spot for an extended island getaway, 523 Loquat is a stunning three bedroom, 3 full bathrooms, canal front Anna Maria Island vacation rental home with accommodations for up 6 guests in casual island style luxury. <br /><br />523 Loquat is located in a coveted vacation destination in the city of Anna Maria just a short walk to Pine Avenu
“EverLasting Sunsets B” is the perfect Anna Maria Island beach rental for a relaxed Florida getaway. When you arrive at this unit you’ll be greeted with a lush tropical landscaping letting you know your vacation has begun!<br /><br /> During your visit you’ll be less than a block from the Gulf of Mexico beaches and endless Florida sunshine! This du
The perfect spot for a memorable island vacation! This ground level vacation rental offers a gorgeous heated pool with a fabulous outdoor common area including gazebo, tropical landscaping, dining areas and plenty of lounge chairs for relaxing. There is also a putting green, custom cornhole and a bocce ball pitch. If you want to enjoy the outdoors,
“dreAMI” 12 Palm Harbor Drive is perfect for a fun and memorable vacation, one of the best rental homes that Anna Maria Island has to offer. “dreAMI” 12 Palm Harbor Drive is a gorgeous home, with three bedrooms three and a half baths this home sports two king beds, and two twin beds and is able to accommodate up to 6 guests. Only monthly stays are
Luxury Anna Maria vacation rental "Beachvergnügen" is a casually sophisticated four-bedroom three-bathroom home nestled a short walk away from Anna Maria’s best gulf beaches with one small road to cross. Accommodating up to 8 guests, "Beachvergnügen" offers three king beds and set of twinsThe North Shore beach access for Bean Point is a favorite am
If you are looking for a family fun vacation destination with all the extras, “Casa Morado” is the perfect place for you! <br /><br />This stylishly updated four bedroom home comfortably sleeps eight guests just a short walk to gulf beaches. Even members of the family with the shortest legs can manage the two blocks walk to pristine gulf beaches! <
Experience the white sandy beaches and gorgeous sunsets of Anna Maria Island at My Big Fat Beach House. My Big Fat Beach House is located just 2 short blocks to the beach and the perfect vacation gathering place for family and friends. Swaying palm trees line the private backyard, guests of all ages will enjoy the saltwater pool/spa, waterfall, ou
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
“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