An aerial view of a coastal town with a long pier extending into turquoise waters.

Anna Maria Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Anna Maria Island vacation rentals

A wooden boardwalk leading to a beach with a view of the ocean and clouds in the sky.

1. Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (485 reviews)
"perfect"
United States
Danielle
$199 nightly
The price is $225
Oct 7 - Oct 8
Total with taxes and fees
Haley's at The Anna Maria Island Inn
A beach scene with waves gently lapping at the shore and the sun setting in the distance.

2. Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (174 reviews)
"It was just a beautiful stay and love to come back next year!!"
United States
Allison
$583 nightly
The price is $640
Oct 6 - Oct 7
Total with taxes and fees
Palm Tree Villas
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

3. Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (474 reviews)
"Great location and walking distance to the beach"
United States
Francesca
$214 nightly
The price is $241
Oct 6 - Oct 7
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
A wooden boardwalk surrounded by dense foliage.

4. Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
Anna Maria
9.8 out of 10, Exceptional, (58 reviews)
"Great stay. "
United States
courtneyharned
$413 nightly
The price is $460
Oct 4 - Oct 5
Total with taxes and fees
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
A modern bedroom with a large bed, a TV mounted on the wall, a wooden headboard, and a view of the sea through the balcony.

5. Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (140 reviews)
"Right on beach, in a good area. Comfy beds, would stay here again"
United States
Katelyn
$266 nightly
The price is $301
Oct 4 - Oct 5
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
A beach with clear turquoise water and white sand.

6. Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Anna Maria
10.0 out of 10, Exceptional, (43 reviews)
"Loved the easy access to the beach and the fact that the property had beach supplies available for you to use. We had great service when needed and will definitely visit again !"
United States
Meagan
$425 nightly
The price is $474
Oct 4 - Oct 5
Total with taxes and fees
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
A multi-story building with a light blue facade, featuring a restaurant named 'Bridge Street Bistro' and a sign for 'Island Time.'

7. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (835 reviews)
"I loved this hotel"
United States
Raisare
$314 nightly
The price is $355
Oct 6 - Oct 7
Total with taxes and fees
Bridgewalk Resort
A beach with footprints in the sand and waves approaching the shore.

8. Cozy 1-bedroom condo with AC in Bradenton Beach

Cozy 1-bedroom condo with AC in Bradenton Beach
Bradenton Beach
9.4 out of 10, Exceptional, (45 reviews)
"Enjoyed the proximity to beach access, free trolley, and restaurants. "
United States
DanRoxy R.
$270 nightly
The price is $301
Oct 4 - Oct 5
Total with taxes and fees
Cozy 1-bedroom condo with AC in Bradenton Beach
A beach with waves and a sunset sky.

9. Anna Maria Sunsets - studio

Anna Maria Sunsets - studio
Bradenton Beach
9.2 out of 10, Wonderful, (287 reviews)
"We had a wonderful stay! The place was clean, comfortable, and exactly as described. The location was great, and everything we needed was available. The host was friendly, responsive, and made the whole experience easy and enjoyable. We would definitely stay here again and highly recommend it! ⭐️⭐️⭐️⭐️⭐️"
United States
Elizabeth
$263 nightly
The price is $292
Oct 4 - Oct 5
Total with taxes and fees
Anna Maria Sunsets - studio
A wooden beach pavilion with a checkered roof and open sides, overlooking the beach.

10. Anna Maria Sunsets - studio

Anna Maria Sunsets - studio
Bradenton Beach
9.0 out of 10, Wonderful, (270 reviews)
"Loved our stay!"
United States
Vincent
$257 nightly
The price is $286
Oct 8 - Oct 9
Total with taxes and fees
Anna Maria Sunsets - studio
A beach with clear turquoise water and white sand.

11. Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
Anna Maria
9.4 out of 10, Exceptional, (30 reviews)
"Old Florida charm of cottage. Beautiful location and only steps to the beach. Staff was wonderful and room was clean."
United States
Christina R.
$497 nightly
The price is $553
Oct 10 - Oct 11
Total with taxes and fees
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
A beach with umbrellas, a boat, and a sign.

12. Amazing View, Updated Beachfront Condo

Amazing View, Updated Beachfront Condo
Bradenton Beach
9.4 out of 10, Exceptional, (58 reviews)
"Exceptional beach condo, great view and clean."
United States
Paul W.
$554 nightly
The price is $618
Oct 8 - Oct 9
Total with taxes and fees
Amazing View, Updated Beachfront Condo
A beach with clear turquoise water and white sand.

13. Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
Anna Maria
9.6 out of 10, Exceptional, (30 reviews)
"Very short walk to the beach. We enjoyed our stay. "
United States
Stacey D.
$446 nightly
The price is $497
Oct 4 - Oct 5
Total with taxes and fees
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
Aerial Beach

14. Island Life #7 Beach Club AMI RVA

Island Life #7 Beach Club AMI RVA
Bradenton Beach
9.0 out of 10, Wonderful, (91 reviews)
"Love the proximity to the beach. Pool and hot tub are great"
United States
Kimberly H.
$299 nightly
The price is $333
Oct 14 - Oct 15
Total with taxes and fees
Island Life #7 Beach Club AMI RVA
A wooden beach pavilion with a checkered roof and open sides, overlooking the beach.

15. Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1
Bradenton Beach
9.8 out of 10, Exceptional, (233 reviews)
"Great place to stay!"
United States
Donna B.
$335 nightly
The price is $373
Oct 4 - Oct 5
Total with taxes and fees
Anna Maria Beach Condo 1/1
A bedroom with a bed, a desk, and a kitchenette.

16. Club Bamboo South unit 122, Anna Maria Island - Gulf Front Studio, ocean view, maximum occupancy of 3 people.

Club Bamboo South unit 122, Anna Maria Island - Gulf Front Studio, ocean view, maximum occupancy of 3 people.
Bradenton Beach
9.4 out of 10, Exceptional, (87 reviews)
"My family and I enjoyed our stay very much. Can’t beat the location, all rooms by the pool and super close to the beach. I will recommend to my family and friends. Great experience!"
United States
Nancy
$549 nightly
The price is $604
Oct 6 - Oct 7
Total with taxes and fees
Club Bamboo South unit 122, Anna Maria Island - Gulf Front Studio, ocean view, maximum occupancy of 3 people.
Beach

17. Fabulous 1-bedroom condo with AC in Bradenton Beach

Fabulous 1-bedroom condo with AC in Bradenton Beach
Bradenton Beach
9.2 out of 10, Wonderful, (37 reviews)
"Everything about my stay was great! Will definitely be back!"
United States
Darian
$280 nightly
The price is $312
Oct 6 - Oct 7
Total with taxes and fees
Fabulous 1-bedroom condo with AC in Bradenton Beach
A beach with clear turquoise water and white sand.

18. Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Yes! The cottage was nicely decorated and we had everything we needed for our 2 night stay"
United States
J I.
$429 nightly
The price is $478
Oct 4 - Oct 5
Total with taxes and fees
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
Aerial Beach

19. Beachfront Bliss – Anna Maria Island #11 RVA

Beachfront Bliss – Anna Maria Island #11 RVA
Bradenton Beach
9.6 out of 10, Exceptional, (126 reviews)
"Everything is very clean and organized, nice lady on the check in process I will definitely come back"
United States
Raisa
$326 nightly
The price is $364
Oct 4 - Oct 5
Total with taxes and fees
Beachfront Bliss – Anna Maria Island #11 RVA
A beach with clear turquoise water and white sand.

20. Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
Anna Maria
9.8 out of 10, Exceptional, (33 reviews)
"Great place to stay!Nice walk to the beach!"
United States
Rose Y.
$485 nightly
The price is $540
Oct 17 - Oct 18
Total with taxes and fees
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Anna Maria Island Hotel Reviews

Via Roma Beach Resort

Via Roma Beach Resort

8/10 Good
"Beach view and everything is close"
Sandra 6-night trip
Posted 18 hours ago
Via Roma Beach Resort

Find out more about Anna Maria Island

Everything you need to know about Anna Maria Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Anna Maria Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anna Maria Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Anna Maria Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $225 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Anna Maria Island rentals

At Expedia, we put the best Anna Maria Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Anna Maria Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Anna Maria Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Anna Maria Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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