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

View 13 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

$355 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

$275 avg / night
(excludes fees and taxes)
4.72 (99)
South Bay Inn 2
2 Bedroom | 1 Bath | Sleeps 4

South Bay Inn 2 - Anna Maria, FL

$358 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)
4.54 (59)
21 Palms Unit A
2 Bedroom | 1 Bath | Sleeps 4

21 Palms Unit A - Anna Maria, FL

$195 avg / night
(excludes fees and taxes)
4.11 (35)

View 38 more homes

Recent Anna Maria guest reviews

I enjoyed my stay at this location. The condo was exceptionally clean and well kept. Actually quite spacious for 2 people. They provided plenty of towels and toilettries for my short stay. The location is fanastic, just 50 steps to a walk way with direct access to the bay side of AMI offering the most spectaculart sunrise views. It is also close to shopping, restaurants and the amazing Bean Point Beach. Highly Recommend staying here. Pool was also very clean.
Jennifer W. | Jul 2025
We loved the Wee Cottage. Quaint with a taste of Old Florida. Such a thoughtful and joyful vacation experience close to the beach.
Ansley M. | Jul 2025
Very convenient and great location
sonya J. | Jun 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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7 charming Anna Maria beach cottages for a seaside retreat

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