Anna Maria Island 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 35 House rentals
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Duplexes

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Popular amenities for Anna Maria Island 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)
Safari Suite
1 Bedroom | 1 Bath | Sleeps 4

Safari Suite - Bradenton Beach, FL

$205 avg / night
(excludes fees and taxes)
4.65 (60)

View 146 more homes

Recent Anna Maria Island guest reviews

We loved the ample space in the condo and all the amenities that it offered. Steps from the pool and beach made it very easy to access and get to and from with all of our things. The location to restaurants and shopping was very convenient.
Brandi B. | Jul 2025
This unit is right on the beach which is amazing. Unfortunately, from the downstairs porch you do not have a great view because of some Sea Oat trees. The beds are nice and comfortable, and the bedrooms and bathrooms are roomy and well equipped with towels, shower soap, shampoo and conditioner. Each bedroom also has a deck you can sit on, very nice. The kitchen is roomy and has a blender, 3 coffee machines (??) and a coffee pod machine too, which was a nice bonus. We flew in and were banking on the beach supplies, unfortunately there was only one functioning beach chair, the other was rotted and broken. Vacasa did not respond to help with this issue, so we bought a chair ($49,99 + tax) and gifted it to future guests to enjoy. The unit was beautiful, quiet while we were there, but no one was next door, and comfortable. It is a great place to make memories.
Celeste C. | Jul 2025
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
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).

Browse dog-friendly homes >

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
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