Anna Maria Island Summer Rentals, Cottages & Cabins

There are a lot of options in Anna Maria Island. If you plan on staying in the Anna Maria Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Anna Maria Island:

• Northshore Beach House near Pine Ave, north end of Anna Maria Island
• Sea You Soon AMI Designer Villa, Holmes Beach, Walk to the Beach!
• Cozy 'Day' Side Cottage with Heated Pool Pet Friendly No size restrictions
• Sand Dollar Beach Side Villa
• Palm Haven Beach Side Villa
• yyVilla #2 Shrimp
• The Surf Shack
• Sun Kissed Villa by SkyRun Anna Maria
• Beach Sunset Villa
• Beach Villa 1B

In 2026, Luxurysicilyvilla offers 159 summer rentals in or around Anna Maria Island. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.

The average price per night for a summer rental in Anna Maria Island is $592. Check the full list of summer accommodations in Anna Maria Island.

There are 159 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Luxurysicilyvilla.

Yes, here are some popular summer holiday rentals in Anna Maria Island that have a private or indoor pool:

• Modern home near Gulf beaches with private heated pool & WiFi
• NORTH BEACH VILLAGE 235 townhouse
• 1 Step Closer 2 Bedroom Villa by RedAwning
• Comfortable island villa with private heated pool, courtyard & easy beach access

Check all holiday rentals with a pool in Anna Maria Island on Luxurysicilyvilla.