0 Bedrooms for 1 Guest
Price $10 - $1000+

4,305 Anna Maria Vacation Rentals & Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Anna Maria vacation rentals from 11 rental sites including HomeAway, Booking.com, TripAdvisor, and more, ranging from $25 to $2450 a night. 

    Information about Anna Maria

    About Anna Maria

    40 miles south of Tampa is Anna Maria, a beautiful island that is bordered by the Gulf of Mexico to the west and Sarasota Bay to the south. This vacation hotspot was formerly discovered by the Timucan and Caloosan Native Americans, followed by the Spanish explorers. Nowadays the island is known for its white sand beaches, amazing weather, and its small year-round population of less than 2000 people. It’s the perfect tropical vacation getaway without having to fly to the Caribbean.

    Things to Do in Anna Maria

    Anna Maria offers visitors a charming old coastal village feeling when they visit this beautiful place filled with history and sightseeing. To learn more about the town’s interesting history, stop by the Anna Maria Historical Society on Pine Avenue, where admission is free and guests can read up on the fascinating informational archives about the island. Anna Maria is known for having gorgeous beaches year-round at the northern tip of the island; parking tends to be challenging and some of them are more secluded, making them more easily accessible by foot or bike. Check out the beaches on the Gulf of Mexico, Bean Point, and the Tampa Bay beaches at Bay Front Park. Go for a stroll on Anna Maria City Pier, which was built in 1911 and boasts stunning views of the beaches and marine wildlife. The City of Anna Maria hosts various events throughout the year on Pine Avenue that feature great food, live music and vendors. Some of the annual events include Food and Wine on Pine, Sandbar Easter Egg Hunt, Bay Fest, and Christmas on Pine. If you’re looking to do something other than go to the beach, other activities include catching a performance at Players Theater, checking out literature at Little Free Library, and taking a fitness or dance class at the Community Center. Go shopping on Bridge Street, which is located at the other end of the island in Bradenton Beach and has lots of shopping and dining options, offering great views of the Gulf of Mexico and Sarasota Bay.

    Day Trips Near Anna Maria

    If you’re traveling with family and are looking for some kid-friendly options, Orlando is two hours north east of Anna Maria Island and is home to Disney World, SeaWorld, and Universal Theme Parks. Tampa is an hour north of Anna Maria Island and has plenty of fun things to do, including the Florida Aquarium, Big Cat Rescue sanctuary, Raymond James Stadium, and Lowry Park Zoo.

    Anna Maria Accommodation

    There are many beautiful homes that are available to rent for your vacation in Anna Maria. The Pine Avenue area is a popular place for a home rental and offers close proximity to the beach and the main shopping and restaurants. The Holmes Beach area is located right on the Gulf of Mexico and has lots of cute cottages, bungalows, and larger beach homes that offer stunning ocean views and are just steps from the sand. The Bradenton Beach area is on the opposite side of the island from the main Anna Maria center and has gulf front condos that offer direct beach access and unobstructed views.

    Transportation in Anna Maria

    Due to the island’s geography and some of the beaches being harder to access by foot, one great way to travel around Anna Maria is by renting a bicycle. Another fun form of transportation is renting a luxury golf cart rental, which are available in a variety of styles and sizes that are street legal and offer a comfortable, leisurely way to get around the island. If you rent a vehicle from Lux Carts, 10-percent of proceeds are donated to local charities including the Anna Maria Island Elementary School.

    Vacation Rentals in Anna Maria

    Find the best Anna Maria vacation rentals with Tripping.com. Choose from 4,329 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $2450 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 2,872 of homes in Anna Maria offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 2,570 rentals with pool or jacuzzi, or relax with the family in one of the 3,385 homes with cable TV.

    For all those dog lovers and cat lovers, Anna Maria offers 830 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

    Search properties from 11 rental sites in Anna Maria where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 1,577 HomeAway rentals, 1,037 Booking.com short term rentals and 692 TripAdvisor vacation rentals.