Anna Maria Island Vacation Rentals

Compare 130 vacation rentals.
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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.

Top Anna Maria Island property types

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Condo rentals

View 66 Condo rentals
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House rentals

View 34 House rentals
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Apartments

View 17 Apartments

Browse more vacation rental amenities in Anna Maria Island

Pool | Ocean view | Oceanfront | Water view | Waterfront | A/C | Air conditioning | Elevator | Fireplace | Washer/dryer

Popular amenities for Anna Maria Island vacation rentals

Popular
Dog-friendly Hot tub Internet
Neolinda 305
3 Bedroom | 2 Bath | Sleeps 6

Neolinda 305 - Holmes Beach, FL

$415 avg / night
(excludes fees and taxes)
4.74 (50)
Playa Casanas South
2 Bedroom | 1 Bath | Sleeps 4

Playa Casanas South - Holmes Beach, FL

$223 avg / night
(excludes fees and taxes)
4.11 (53)
Mermaid Manor
4 Bedroom | 4 Bath | Sleeps 8

Mermaid Manor - Anna Maria, FL

$807 avg / night
(excludes fees and taxes)
4.94 (47)
Nautical Nook at Bayview Inn
1 Bedroom | 1 Bath | Sleeps 4

Nautical Nook at Bayview Inn - Bradenton Beach, FL

$211 avg / night
(excludes fees and taxes)
4.78 (23)
21 Palms Unit A
2 Bedroom | 1 Bath | Sleeps 4

21 Palms Unit A - Anna Maria, FL

$195 avg / night
(excludes fees and taxes)
4.21 (43)

View 125 more homes

Recent Anna Maria Island guest reviews

This rental was absolutely fabulous. Definitely recommend
elizabeth C. | Jul 2026
Our first time to the Island. We spent the week in Unit A and the views were remarkable, the proximity to the beach, Bridge Street shopping and trolley stops was the best. The house was very well kept up and clean. We did call ahead to see if toys etc. were on site and were told no. But we were pleased to find pool toys, a beach tent and beach chairs. Even a pack n play for the infant was tucked away in the closet. All were a pleasant surprise! No beach towels but plenty of pool towels were present. The neighbors in unit B were kind. The covered pool was the best. Would return again for sure. Thanks!
Richard M. | Jul 2026
My husband and I found that it was the perfect space for us to spend a few days exploring the island. Space was nicely decorated and spacious. The location is walkable to both the Bay and the Ocean as well as lots of nice restaurants and shops. There is a trolley stop a block away that will take you around the island. Pool was also nice and very clean.
Jen C. | Jul 2026
Anna Maria Island vacation rental FAQ

Yes, 37 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. 130 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

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Nearby destinations

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