Anna Maria Vacation Rentals

Compare 43 vacation rentals.
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USA > Florida > Anna Maria

Make Anna Maria your next getaway

Treat yourself to a seaside getaway filled with sun-soaked days and easy beach breezes when you pay a visit to Anna Maria. Offering postcard-perfect beaches, easy access to deep sea fishing and ocean adventures, as well as the tranquility of a small town, this hidden Florida vacation destination is perfect spot to let the stress melt away as you slip into vacation mode. With family-friendly outings, wonderful nightlife options, and seasonal festivals, there is something for everyone to dive into no matter what time of year you plan to visit our Anna Maria vacation rentals.

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

$441 avg / night
(excludes fees and taxes)
4.47 (98)
21 Palms Unit A
2 Bedroom | 1 Bath | Sleeps 4

21 Palms Unit A - Anna Maria, FL

$202 avg / night
(excludes fees and taxes)
4.11 (35)
Harmony House
3 Bedroom | 2 Bath | Sleeps 8

Harmony House - Anna Maria, FL

$430 avg / night
(excludes fees and taxes)
4.75 (88)
South Bay Inn 2
2 Bedroom | 1 Bath | Sleeps 4

South Bay Inn 2 - Anna Maria, FL

$359 avg / night
(excludes fees and taxes)
4.78 (76)
Sunrise Garden #11
0 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #11 - Anna Maria, FL

$212 avg / night
(excludes fees and taxes)
4.23 (44)

View 38 more homes

Recent Anna Maria guest reviews

The unit is located directly across the street from the beach! You have a view of the Sunshine Skyway Bridge, and the Anna Maria City Pier (currently awaiting reconstruction after a hurricane). The home was great, everything we needed. Some beach chairs would be a lovely addition!
Teresa K. | Jun 2025
The vacation rental itself was lovely—beautiful, bright, and full of natural light. The room was clean, well-maintained, and very comfortable, and the location couldn’t have been better. It was the perfect home base for exploring the area. However, while the space exceeded expectations, the customer service experience left something to be desired. Since all management and support are off-property, getting help with a unique or time-sensitive question proved frustrating. Each representative I spoke with could only repeat the same scripted information I'd already received, which didn't address my situation. For most guests, this might not be an issue, but when something unexpected comes up, a more personalized, responsive approach would make all the difference. Overall, it's a beautiful rental in a fantastic location—just be aware that the support is hands-off and not equipped to handle anything beyond the standard FAQs.
Kevin S. | Jun 2025
This home was immaculate! Very modern, clean, and fresh! Great access to the beach! The pool area is very nice as well as the game room! Our whole family had an amazing time!
Tessa V. | Jun 2025
Anna Maria vacation rental FAQ

Yes, 62 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. 238 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

Where is Anna Maria, FL?

Located at the tip of Anna Maria Island at the south end of Tampa Bay, you'll be surrounded by the tranquility of swaying palm trees while escaping the typical Florida crowds. An easy drive from Bradenton on the mainland and only 44 miles south of the picturesque shores of Madeira Beach, our Anna Maria vacation rentals have the best of it all.

Things to do in Anna Maria, FL

Grab a spot underneath one of the beautiful Australian Pines on Manatee Beach and enjoy a bit of lunch before you head out onto the water with a rented stand-up paddleboard. Stroll down the walking path at Coquina Beach and slip into the beach lifestyle, then treat yourself to a bit of shopping at St. Armands Circle.

Grab the famed Anna Maria Island Trolley to one of the local aquariums to learn about the local marine life, then take a water shuttle along the coast to see some dolphins jumping and snap some photos of the sweeping ocean views. Treat yourself to a seaside happy hour and a plate of fresh, mouthwatering seafood while you watch the waves rolling in during sunset.

With a bevy of family-friendly offerings, vibrant nightlife hotspots, and a seemingly endless array of ocean adventures, our Anna Maria vacation rentals put memory-making fun at your fingertips.

Anna Maria Island travel inspiration

The 8 Best Beach Towns Near Tampa for Every Traveler

7 Charming Anna Maria Beach Cottages for a Seaside Retreat

Unique Weekend Getaways in Florida

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