Anna Maria Island Vacation Rentals

Compare 141 vacation rentals.
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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.

Top Anna Maria Island property types

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Condo rentals

View 49 Condo rentals
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House rentals

View 32 House rentals
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Duplexes

View 26 Duplexes

Popular amenities for Anna Maria Island vacation rentals

Popular
Dog-friendly Hot tub Internet
Sunrise Garden #4
1 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #4 - Anna Maria, FL

$188 avg / night
(excludes fees and taxes)
4.07 (68)
Sunrise Garden #1
1 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #1 - Anna Maria, FL

$212 avg / night
(excludes fees and taxes)
4.56 (66)
Sunrise Garden #11
0 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #11 - Anna Maria, FL

$208 avg / night
(excludes fees and taxes)
4.27 (51)
Beach Bungalow W
2 Bedroom | 2 Bath | Sleeps 4

Beach Bungalow W - Bradenton Beach, FL

$184 avg / night
(excludes fees and taxes)
3.8 (20)
Sunrise Garden #10
1 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #10 - Anna Maria, FL

$205 avg / night
(excludes fees and taxes)
4.09 (57)

View 136 more homes

Browse more vacation rental amenities in Anna Maria Island

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

Recent Anna Maria Island guest reviews

We love the pool/spa area and the openess of the area of the entire home. Always clean and a family favorite for us!
Dawn L. | Dec 2025
Beautiful house great location. We are returning guests plan on coming back next year.
Patty F. | Dec 2025
We absolutely loved this condo for our group of four. The living room and kitchen were perfect for relaxing together, and the view was incredible. Everything was beautifully decorated—both inside and on the lanai. The bayfront location was ideal and just minutes from the Anna Maria Island beaches, shops, and fantastic restaurants. Our only regret is that we couldn’t stay longer. Just book it—you won’t be disappointed!
Beth B. | Dec 2025
Anna Maria Island vacation rental FAQ

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. 141 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Anna Maria Island, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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

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Nearby destinations

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