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
After you stay at the "Sea Pirate 2" you’ll want to make it your vacation destination year after year! This two bedroom one bathroom Holmes Beach vacation rental home sleeps six guests with one queen bed, two twin beds and queen sleeper sofa. "Sea Pirate 2" offers a fun and fresh island feel with exciting colors and endless style. Find everything f
"The Coconuts Beach Resort 108" offers a fun and fresh coastal feel with endless style. Find everything for the perfect beach vacation for four, or a romantic couple’s tropical retreat.After you stay at the "The Coconuts Beach Resort 108" you’ll want to make it your vacation destination year after year! This one bedroom one bathroom direct beach fr
With stunning direct gulf front views, the stylish “Gulf Place 23” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 6 guests this 2 bedroom 2 bathroom Holmes Beach vacation rental condominium offers one king bed, two twin beds and a queen sleeper sofa in a beautiful coastal inspired atmosphere. <br /><br />Situated o
“Hideaway” is a fantastic Anna Maria Island vacation rental in Holmes Beach offering space for up to six guests just a few blocks from the beach! <br /><br />During your stay you’ll find everything you need for a laid back island getaway. Inside this Holmes Beach rental you’ll enjoy updated decor with a coastal flair. <br /><br />The main living sp
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,
Paradise found indeed! Walk into the open floor plan and look out over the private heated pool, canal, dock and views of open water. This vacation retreat has 3 bedrooms and 3 bathrooms as well as smart Tv's in the living room, each bedroom and the outside patio. The kitchen is renovated for the chef in your party with updated appliances. Also with
Find the perfect Anna Maria Island vacation spot at “Sugaree”! This renovated duplex is comfortable, stylish and close to the beach too! When you visit “Sugaree” you’ll find everything you’ll need for up to six guests.<br /><br />Inside this Holmes Beach rental you’ll find a spacious main living area and well-appointed bedrooms. <br /><br />In the
Gulf View Cottage is a charming, recently renovated home with a rooftop deck offering sweeping views of the Gulf. Relax and enjoy the private, heated pool while experiencing the ultimate Florida vacation!As you arrive at Gulf View Cottage, you'll notice its unique shape, spacious driveway, and beautiful tropical plants in the front yard. Step insid
Classic Key Royale canal front home with a private pool located at 632 Emerald Lane, Holmes Beach, Anna Maria Island is the home of your vacation dreams. Nestled in a quiet community away from the hustle and bustle of the city, you can truly relax and unwind. <br /><br />Amazing three bedroom and two and a half bath canal front vacation rental home
Fall in love with Anna Maria Island paradise when you vacation at “Over the Moonl”! This gorgeous three bedroom, private heated pool getaway accommodates up to six guests with a king bed, a queen bed and two twin beds in this ground level single family home located in the coveted north end of Anna Maria. <br /><br />The city of Anna Maria boasts so
“Palm Isle 3211” is the perfect Anna Maria Island beach rental for a cozy couple’s getaway, or even a casual vacation for up to four guests. This one bedroom villa beach rental offers a premium location near beaches, shopping and dining. Enjoy a well-appointed unit with nice updates and a laid back feel.<br /><br /> When you visit “Palm Isle 3211”
With stunning direct Bimini Bay views, the stylish “High Tides and Good Vibes Westbay Point and Moorings Unit 265” 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 two king beds and a queen sleeper sofa in a beautiful coastal inspired