Anna Maria Island Vacation Rentals

Compare 136 vacation rentals.
Home > USA > Florida > Anna Maria Island

Make Anna Maria Island your next getaway

Nestled on Florida’s Gulf Coast, Anna Maria Island is a hidden gem where Old Florida charm meets stunning natural beauty. With no high-rises, a relaxed island vibe, and miles of pristine beaches, it’s the perfect destination for a laid-back getaway. Whether you're strolling along historic piers, indulging in fresh seafood, or simply soaking up the sun, Anna Maria Island offers an escape like no other.

Explore Anna Maria Island condo rentals, house rentals, duplexes, and more

housing_type_condo.jpg

Condo rentals

View 49 Condo rentals
housing_type_house.jpg

House rentals

View 31 House rentals
housing_type_duplex.jpg

Duplexes

View 22 Duplexes

Explore more vacation rental amenities in Anna Maria Island

Pool | Lake view | Ocean view | Oceanfront | Sound view | Soundfront | Water view | Waterfront | A/C | Elevator

Anna Maria Island vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Sunrise Garden #8
2 Bed | 1 Bath | Sleeps 6

Sunrise Garden #8 - Anna Maria, FL

$358 avg / night
(excludes fees and taxes)
4.49 (72)
Sunrise Garden #15
1 Bed | 1 Bath | Sleeps 4

Sunrise Garden #15 - Anna Maria, FL

$283 avg / night
(excludes fees and taxes)
3.67 (61)
Sunrise Garden #7
1 Bed | 1 Bath | Sleeps 4

Sunrise Garden #7 - Anna Maria, FL

$305 avg / night
(excludes fees and taxes)
4.03 (69)
Sunrise Garden #11
0 Bed | 1 Bath | Sleeps 4

Sunrise Garden #11 - Anna Maria, FL

$294 avg / night
(excludes fees and taxes)
4.25 (57)
Sunrise Garden #10
1 Bed | 1 Bath | Sleeps 4

Sunrise Garden #10 - Anna Maria, FL

$300 avg / night
(excludes fees and taxes)
4.13 (63)

View 131 more homes

Recent Anna Maria Island vacation rental reviews

Wir hatten einen ziemlich ekligen und verrosteten Grill ! Der wurde am gleichen Tag der Beanstandung ausgetauscht. Die Matratze vom Bett ist sehr weich!!
Michael O. | May 2026
The view is excellent, comfortable bed, large grill for cooking, very close to the beach and stores as well.
Barbara S. | May 2026
Quiet, clean property only a few steps to the beach. The kitchen was well equipped with everything needed for our stay. We loved the table and chairs out front. We hung out and talked with the neighbors everyday. But then we had the option to sit at the table on the small back patio, usually for breakfast, taking in the mornings. We have stayed at the upstairs unit before and while you get a great view up there, there are no stairs to this unit, so it was a nice trade off. The convenience of Walgreens/Publix just a short walk or drive around the corner is very nice. We even walked over a couple times to get dinner at Los Chiludos. Highly recommended! And don't forget the island trolley. We rode it to Bridge St to the Moose Lodge and to do some shopping. The stop is just around the corner, a 3 minute walk. You will not be disappointed staying here. We will definitely be booking this unit again!!
Jessica M. | May 2026
Anna Maria Island Frequently Asked Questions

Yes, 40 of our Anna Maria Island homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 136 of our Anna Maria Island vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Anna Maria Island vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Anna Maria Island team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Anna Maria Island, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Why choose Anna Maria Island?


Book an Anna Maria Island vacation rental

Whether you're lounging under swaying palm trees, exploring quirky shops and gourmet eateries, or soaking in the laid-back island vibes, Anna Maria Island offers the peaceful escape you've been dreaming of. From cozy beachfront cottages to spacious, family-friendly homes, we have the ideal vacation rental for your next island getaway!

Anna Maria Island travel inspiration

The best beach towns near Tampa for every traveler Charming Anna Maria beach cottages for a seaside retreat Unique weekend getaways in Florida

People also search for

Gulf Coast   |   Florida Gulf Coast   |   Manatee County   |   Sunrise Garden Resort - Anna Maria Island   |   The Bayview Inn   |   Waters Edge Condos - Holmes Beach, FL   |   Runaway Bay Condos - Bradenton Beach   |   Hidden Cove Condominiums - Holmes Beach   |   North Beach Village - Holmes Beach   |   Sea Pirate - Holmes Beach   |   La Casa Costiera - Anna Maria Island   |   Holmes Beach   |   Bradenton Beach   |   Anna Maria   |   Cortez   |   Bradenton   |   Florida
Show more