Anna Maria Island Vacation Rentals

Compare 151 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 36 House rentals
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Duplexes

View 27 Duplexes

Popular amenities for Anna Maria Island vacation rentals

Popular
Dog-friendly Hot tub Internet
South Bay Inn 1
1 Bedroom | 1 Bath | Sleeps 2

South Bay Inn 1 - Anna Maria, FL

$274 avg / night
4.44 (94)
Almost Heaven
2 Bedroom | 1 Bath | Sleeps 4

Almost Heaven - Bradenton Beach, FL

$192 avg / night
4.07 (30)
South Bay Inn 2
2 Bedroom | 1 Bath | Sleeps 4

South Bay Inn 2 - Anna Maria, FL

$348 avg / night
4.77 (75)
Mangrove Oasis
2 Bedroom | 2 Bath | Sleeps 6

Mangrove Oasis - Holmes Beach, FL

$151 avg / night
4.04 (25)
Sunrise Garden #8
2 Bedroom | 1 Bath | Sleeps 6

Sunrise Garden #8 - Anna Maria, FL

$266 avg / night
4.49 (63)

View 146 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

Good mattresses. Pool and hot tub and easy walk to beach
Robert K. | May 2025
This home was everything we could ask for. Spacious and the pool was a great size. We had a mamma manatee and her new baby swim up.in the canal. What a great experience. Highly recommend
Lori M. | May 2025
We loved the amount of space, inside and out. Pool was lovely and we had it to ourselves whenever we went in, even though it is shared. . Perfect for a family of four and close to the beautiful beach and bus stop.
Nelli B. | May 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).

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Yes. 151 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

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

Nearby destinations

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