Take Advantage of new winter rates on great beach properties on Anna Maria Island. Throughout November, December and January we have availability on some amazing properties for you to escape the cold and celebrate the holidays. Enjoy Thanksgiving or Christmas with your family and friends at the beach. Our properties have all the amenities and space that you need. Anna Maria Island offers incredible beaches with relaxing scenery with crystal clear waters, white sand and incredible wildlife.
Anna Maria Vacations has properties from 2-6+ bedrooms available for competitive rates including; BEACHFRONT, WATERFRONT, BEACH CONDOS, & DOG FRIENDLY RENTALS.
See all our properties to find the best match for your needs.
Winter Vacation Rentals on Anna Maria Island
Beach Hideaway
3 bedrooms/2 bathrooms
Beach Hideaway is a cute as a button, ground level private home that features a tropical oasis for a backyard. Enjoy the secluded pool and spa surrounded by lush tropical landscaping—you will feel like you are on your own private island without ever having to leave the backyard.
The Laguna Beach
3 bedrooms/2 bathrooms
The Laguna Beach is a refreshing and modern beach retreat on the prestigious North end of Anna Maria Island. This newly renovated 3 bedroom and 2 bathroom private home boasts a sparkling brand new pool with a spa, covered lanai, a spacious screened in wrap around deck and so much more! Only 1 block away from the world-renowned beaches of the Gulf of Mexico—you will just fall in love with this ideal location.
Paradise Found
4 bedrooms/4.5 bathrooms
Paradise Found is a gorgeous 4 bedroom and 4.5 bathroom private home tucked away on a quiet residential street overlooking the gorgeous Bay waters. This wonderfully located villa features incredible water views throughout and is only a short 3 minute stroll away from the stunning white sandy beaches of the Gulf of Mexico-enjoy the best of both worlds!
Avenue E by the Sea
4 bedrooms/3.5 bathrooms
Beautiful views of the sparkling Gulf waters can be seen from the living room, kitchen, large covered 2nd floor porch and the roof-top deck- unbelievable!. This luxury home has much more than just views, it offers many extras for your relaxing vacation on Anna Maria Island.
Beachbreeze
6 bedrooms/4 bathrooms
This luxury 6 bedroom home is located West of Gulf Dr and just a short 1-2 minute stroll to the Gulf Beach!! The home location is one of the best on the island- and the home has everything you could want for your fantastic tropical island getaway.
Bayside Paradise
4 bedrooms/3 bathrooms
Bayside Paradise is just as the name describes! Come and spend your vacation at this 4 bedroom and 3 bathroom newly renovated island oasis. Equipped with a large private heated pool overlooking the open Bay waters and a tropical backyard, you simply won’t ever want to leave. Just a short 5 minute walk away from the stunning white sandy beaches of the Gulf of Mexico this home offers it all-whether you are looking to rent a boat and enjoy the Bay or spend your days on the beach!
