Anna Maria Vacation Rentals

Compare 43 vacation rentals.
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USA > Florida > Anna Maria

Make Anna Maria your next getaway

Tucked into the northern tip of Anna Maria Island, the city of Anna Maria offers a laid-back coastal lifestyle that feels like Old Florida at its finest. Walkable streets, colorful cottages, quiet Gulf beaches, and friendly locals make this town a favorite for vacationers seeking sand, sunshine, and a slower pace.

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

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House rentals

View 17 House rentals
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Condo rentals

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Apartments

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Popular amenities for Anna Maria vacation rentals

Popular
Dog-friendly Hot tub Internet
Sea's The Day
2 Bedroom | 2 Bath | Sleeps 6

Sea's The Day - Anna Maria, FL

$356 avg / night
(excludes fees and taxes)
4.47 (99)
South Bay Inn 3
1 Bedroom | 1 Bath | Sleeps 2

South Bay Inn 3 - Anna Maria, FL

$278 avg / night
(excludes fees and taxes)
4.72 (100)
South Bay Inn 2
2 Bedroom | 1 Bath | Sleeps 4

South Bay Inn 2 - Anna Maria, FL

$360 avg / night
(excludes fees and taxes)
4.78 (77)
Sunrise Garden #1
1 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #1 - Anna Maria, FL

$226 avg / night
(excludes fees and taxes)
4.55 (60)
21 Palms Unit A
2 Bedroom | 1 Bath | Sleeps 4

21 Palms Unit A - Anna Maria, FL

$196 avg / night
(excludes fees and taxes)
4.11 (35)

View 38 more homes

Recent Anna Maria guest reviews

Fantastic house! We will definitely book this home again. Loved the location and the outdoor areas. The layout of the inside is great too! All the bedrooms are a nice size, the family room was fantastic with enough comfortable seating for our entire group. The kitchen is stocked! We like to make a lot of our meals and this kitchen had everything we needed. We've stayed in a lot of houses and this was one of our favs!
stacie h. | Jul 2025
Secluded area. Very quiet and peacefully. The pool was wonderful. Could walk to the beach in a couple of minutes. The cottage was well maintained and decor was lovely.
BARRETT L. | Jul 2025
We absolutely loved this place! We come to AMI every year and this was totally our vibe! Intimate, great decor, location and pool was amazing! We like to feel like locals and this was it!
April C. | Jul 2025
Anna Maria vacation rental FAQ

Yes, 26 of our Anna Maria 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. 232 of our Anna Maria 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 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 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, 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

Whether you're sipping coffee on your porch, walking to the beach barefoot, or biking to get ice cream on Pine Avenue, Anna Maria invites you to relax, settle in, and stay a little longer.

Why vacation in Anna Maria?

Anna Maria captures everything people love about the Gulf Coast—but without the crowds or high rises. There are no chain stores or tall hotels. Just charming homes, mom-and-pop cafés, white-sand beaches, and warm tropical breezes any time of year.

It’s a top choice for couples looking to unwind, snowbirds escaping winter, and families seeking simple, sunny days by the water. Visitors return every year to enjoy the peace, the people, and the way time seems to slow down here.

Things to do in Anna Maria, FL

What makes Anna Maria unique?

Where to stay in Anna Maria

Anna Maria features some of the most sought-after rental homes on Florida’s Gulf Coast. From pastel-colored cottages and breezy bungalows to luxurious coastal homes tucked into quiet neighborhoods, there’s a wide range of options for guests who want walkability, privacy, and easy access to the beach.

With most rentals just steps from both the Gulf and the bay, you’ll never be far from postcard views and laid-back adventure.

Live like a local in Anna Maria

Anna Maria, Florida isn’t just a place to vacation—it’s a place to slow down, breathe deep, and find joy in the little things. From sunrise walks to evening strolls, ice cream afternoons to sunset beach dinners, it’s a town that feels like home the moment you arrive.

Whether you're here for a weekend, a week, or a whole winter season, Anna Maria welcomes you with open arms and quiet coastal charm.

Anna Maria travel inspiration

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