Anna Maria Island Vacation Rentals

Compare 149 vacation rentals.
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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

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Condo rentals

View 53 Condo rentals
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House rentals

View 34 House rentals
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Duplexes

View 27 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 #4
1 Bed | 1 Bath | Sleeps 4

Sunrise Garden #4 - Anna Maria, FL

$318 avg / night
4.03 (59)
Almost Heaven
2 Bed | 1 Bath | Sleeps 4

Almost Heaven - Bradenton Beach, FL

$290 avg / night
4.07 (30)
Anna Maria's Finest
3 Bed | 3 Bath | Sleeps 8

Anna Maria's Finest - Anna Maria, FL

$677 avg / night
4.09 (100)
Sunrise Garden #8
2 Bed | 1 Bath | Sleeps 6

Sunrise Garden #8 - Anna Maria, FL

$391 avg / night
4.47 (60)
Sunrise Garden #16
1 Bed | 1 Bath | Sleeps 4

Sunrise Garden #16 - Anna Maria, FL

$316 avg / night
3.95 (40)

View 144 more homes

Recent Anna Maria Island vacation rental reviews

Location, location, location!
Honey T. | Mar 2025
Stayed for 3 days to end a great family vacation. House was spacious and a short walk to the beach.
Elizabeth R. | Mar 2025
The closeness to everything
Pamela H. | Mar 2025
Anna Maria Island Frequently Asked Questions

Yes, 41 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. 149 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?

Anna Maria Island travel inspiration

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