Anna Maria Island Vacation Rentals

Compare 150 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 52 Condo rentals
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House rentals

View 36 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
South Bay Inn 3
1 Bed | 1 Bath | Sleeps 2

South Bay Inn 3 - Anna Maria, FL

$383 avg / night
(excludes fees and taxes)
4.71 (97)
Mangrove Cottage
2 Bed | 2 Bath | Sleeps 6

Mangrove Cottage - Anna Maria, FL

$787 avg / night
(excludes fees and taxes)
4.3 (83)
21 Palms Unit A
2 Bed | 1 Bath | Sleeps 4

21 Palms Unit A - Anna Maria, FL

$278 avg / night
(excludes fees and taxes)
4.11 (35)
A Gulf Front Getaway
1 Bed | 1.5 Bath | Sleeps 4

A Gulf Front Getaway - Holmes Beach, FL

$449 avg / night
(excludes fees and taxes)
4.81 (67)
Anna Maria's Finest
3 Bed | 3 Bath | Sleeps 8

Anna Maria's Finest - Anna Maria, FL

$741 avg / night
(excludes fees and taxes)
4.06 (104)

View 145 more homes

Recent Anna Maria Island vacation rental reviews

We enjoyed staying in both A and B bungalow. We loved the decor and close proximity to the beach. Both areas were very clean with everything supplied that we needed for our stay.
Kristi A. | May 2025
The house was very clean and we loved how close it was to the beach. Nice that it had beach towels and chairs too. The backyard was great to sit out and relax.
June T. | May 2025
Our second stay at this very cute, well maintained and clean property. It offers great amenities and is in the perfect location! It is located right across the street from the beach and a very short walk (literally a few minutes) to restaurants, shops and live music on Bridge Street, but still a very quiet area for relaxing. We really appreciated the shared beach chairs and other beach supplies on the property to use. Shared washers and dryers on the property are nice to have when needed. We really enjoyed having a pool when we need a break from the beach and it was very clean. Highly recommend this property!
Kurtiss H. | May 2025
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. 150 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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