Anna Maria Island Vacation Rentals

Compare 128 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.

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

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Condo rentals

View 65 Condo rentals
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House rentals

View 34 House rentals
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Apartments

View 17 Apartments

Explore more vacation rental amenities in Anna Maria Island

Pool | Ocean view | Oceanfront | Water view | Waterfront | A/C | Air conditioning | Elevator | Fireplace | Washer/dryer

Anna Maria Island vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Sea Pirate 1
2 Bed | 1 Bath | Sleeps 4

Sea Pirate 1 - Holmes Beach, FL

$439 avg / night
(excludes fees and taxes)
4.57 (44)
Hidden Cove Unit 6
2 Bed | 2.5 Bath | Sleeps 4

Hidden Cove Unit 6 - Holmes Beach, FL

$610 avg / night
(excludes fees and taxes)
4.65 (92)
3rd Floor OceanView Condo Steps to Beach - Shared Pool & Putting Green - On-Site Parking
3 Bed | 2.5 Bath | Sleeps 6

3rd Floor OceanView Condo Steps to Beach - Shared Pool & Putting Green - On-Site Parking - Bradenton Beach, FL

$640 avg / night
(excludes fees and taxes)
Beachview balconies with pool, steps from the beach
6 Bed | 4.5 Bath | Sleeps 12

Beachview balconies with pool, steps from the beach - Bradenton Beach, FL

$2,007 avg / night
(excludes fees and taxes)
Beacon by the Sea- Unit B
3 Bed | 2.5 Bath | Sleeps 10

Beacon by the Sea- Unit B - Bradenton Beach, FL

$663 avg / night
(excludes fees and taxes)
4.7 (10)

View 123 more homes

Recent Anna Maria Island vacation rental reviews

Pool was great and location was great. We had an issue at the house and the service was great. They took care of everything immediately.
Anthony V. | Aug 2026
This is the second time we’ve stayed in that apartment and we love it, just one block to the more beautiful beach and very nice restaurants, we are recommend this apartment
Andrea I. | Aug 2026
Lovely property, no front desk but check in was easy. Super close to shops, restaurants, rentals and the beach. Quiet at night. Nice and clean pool for guests on property. Would definitely come back!
Esteban G. | Aug 2026
Anna Maria Island Frequently Asked Questions

Yes, 37 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. 128 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

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