Anna Maria Island Vacation Rentals

Compare 160 vacation rentals.
USA > Florida > Anna Maria Island

Make Anna Maria Island your next getaway

Looking for a charming beach getaway? Anna Maria Island, Florida, is a hidden gem nestled on the Gulf Coast, offering pristine beaches, vibrant sunsets, and a laid-back island vibe. With its sugar-white sands and crystal-clear waters, this idyllic destination promises the perfect setting for relaxation and adventure.

Explore Anna Maria Island condo rentals, house rentals, duplexes, and more

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Condo rentals

View 56 Condo rentals
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House rentals

View 42 House rentals
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Duplexes

View 26 Duplexes

Popular amenities for Anna Maria Island vacation rentals

Popular
Dog-friendly Hot tub Internet
Sunrise Garden #1
1 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #1 - Anna Maria, FL

$209 avg / night
4.54 (56)
Sunrise Garden #14
1 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #14 - Anna Maria, FL

$198 avg / night
4.11 (56)
Seagrass Sunsets
2 Bedroom | 2 Bath | Sleeps 6 (4 Adults Max)

Seagrass Sunsets - Bradenton Beach, FL

$268 avg / night
4.73 (55)
A Gulf Front Getaway
1 Bedroom | 1.5 Bath | Sleeps 4

A Gulf Front Getaway - Holmes Beach, FL

$277 avg / night
4.8 (65)
Sunrise Garden #11
0 Bedroom | 1 Bath | Sleeps 4

Sunrise Garden #11 - Anna Maria, FL

$200 avg / night
4.13 (38)

View 155 more homes

Browse more vacation rental amenities in Anna Maria Island

Pool | Electric vehicle charger | Lake view | Ocean view | Oceanfront | Sound view | Soundfront | Water view | Waterfront | A/C

Recent Anna Maria Island guest reviews

This condo was amazing. There were only two of us staying, but it could easily handle more. We love the two stories. First of all, having two amazing ocean views instead of one was great. Having the bedrooms upstairs is a great separation of someone wants to watch TV downstairs. 2 1/2 bathrooms was also a great perk. We pack light, so we love the washer and dryer. Very nice touch. We love Anna Maria Island, and this location was so nice because it is not too far into the island. Easy access when you leave and go outside the island. Vacasa was so easy to work with. This was our first experience with them. Overall, just a great experience all around, at a very beautiful location. We will be back.
Robert G. | Dec 2024
There is nothing more relaxing then relaxing in the pool with a nice warm breeze and the silence is the neighborhood. Would highly recommend. Also easy walking distance to beach and dining.
Chris C. | Dec 2024
We spent a lovely week in this condo in early December. I was happy to see how much progress had been made in Holmes Beach coming back from the 2 hurricanes this past fall. The location is perfect, right on the beach, with direct access and wonderful views from the downstairs and uptake Stairs decks. It is very nicely furnished and well-appointed. We were happy to discover a pod coffee maker in a cabinet, as we had brought our favorite pods just in case. I will reiterate what some other guests have said about the hardness of the beds in the second bedroom. My adult daughter was not amused.
Linda R. | Dec 2024
Anna Maria Island vacation rental FAQ

Yes, 52 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. 160 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.

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

Explore Anna Maria Island

Stroll along the beautiful beaches of Anna Maria Island, where you can soak up the sun, build sandcastles, or take a dip in the warm Gulf waters. With three stunning public beaches—Bean Point, Manatee Public Beach, and Coquina Beach—you'll find the ideal spot to unwind and enjoy the breathtaking views.

Fun activities for everyone

Whether you’re seeking adventure or relaxation, Anna Maria Island has something for everyone:

Discover nature and wildlife

Nature enthusiasts will love the island’s parks and nature reserves. Explore the scenic trails of the Anna Maria Island Historical Society and spot wildlife at the nearby Leffis Key or Robinson Preserve, where you can enjoy hiking, biking, and birdwatching.

Plan your perfect getaway

With its friendly atmosphere, stunning landscapes, and countless activities, Anna Maria Island is the ideal destination for families, couples, or solo travelers. Whether you’re planning a romantic escape, a family vacation, or a fun-filled adventure with friends, this enchanting island will leave you with unforgettable memories.

Book your Anna Maria Island vacation rental today and experience the magic of this beautiful Florida paradise.

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

Nearby destinations

Gulf Coast   |   Florida Gulf Coast   |   Manatee County   |   Sunrise Garden Resort - Anna Maria Island   |   Runaway Bay Condos - Bradenton Beach   |   The Bayview Inn   |   Waters Edge Condos - Holmes Beach, FL   |   Hidden Cove Condominiums - Holmes Beach   |   Beach View Condominiums   |   La Casa Costiera - Anna Maria Island   |   Starfish Beach Cottages - Anna Maria Island   |   North Beach Village - Holmes Beach   |   Sea Pirate - Holmes Beach   |   Bradenton   |   Cortez   |   Anna Maria   |   Bradenton Beach   |   Holmes Beach   |   Florida
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