Vacation Rentals

Relax…you’re on vacation!  You have found the perfect Anna Maria Island vacation paradise, and you are just a reservation away from feeling warm, white sand filter between your toes as the gentle surf of the Gulf of Mexico echoes in the background.  From luxurious, grand and sophisticated, to economical, charming and quaint accommodations…your wish is our goal at Island Real Estate.

Why stay with Island Real Estate?

Anna Maria Island Vacation Rentals



Loads of Amenities

Rental Amenities


Each home offers fully equipped kitchens and air conditioning. Many also feature private heated pools, decks, upgraded appliances, entertainment equipment and high speed internet access.

Search by Amenity

Advanced Rental Search

Advanced Search's for Rentals


View all properties and find your perfect piece of paradise. If you prefer, please call and allow our knowledgeable rental specialists find the perfect accommodation for you, your family or your group.

Full Search

Condo Complex Rentals

Rent A Condo Complex


Amazing choices and big selection of Anna Maria condo rentals. Browse our dozens of condo complex choices and find the one that is right for your family and vacation. 

Search Condos

Need Help Booking Vacations?

Call us toll free within the US at 1-877-778-6066 Toll free from the UK at 0 800 188-8906. 

Island Real Estate has partnered with Red Sky Travel Insurance to provide Sun Trip Preserver® coverage for our guests. Sun Trip Preserver provides cancellation and interruption services as well as emergency assistance and travel services. Click HERE for more information.

Need to rent a car for your trip? Click HERE for a special deal with us through Thrifty Rent-A-Car!



Guest Testimonials

I believe you do a fantastic job, the home is beautiful and roomy. Will use Island Real Estate again for our rental needs....

-Ken & Debra

Owner Testimonials

As you know, I was not originally signed up with Island Real Estate. After enduring a year of problems with my old...

-Michael View Property