Holiday Rentals in Anna Maria Island

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Our top choices for Anna Maria Island holiday rentals

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, (442 reviews)
"Incredible location, great room! Loved everything! Would def come back!"
United States
Laís Fernanda
The price is €264
includes taxes & fees
5 May - 6 May
Haley's at The Anna Maria Island Inn

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (788 reviews)
"So nice to walk to restaurants and shops. Very walkable. Clean. Updated and relaxing atmosphere. Parking was really convenient and accessible. Would stay again."
United States
Deborah
The price is €310
includes taxes & fees
28 Apr - 29 Apr
Bridgewalk Resort

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (91 reviews)
"The view was beautiful! "
United States
Jennifer
The price is €364
includes taxes & fees
15 Apr - 16 Apr
Seabreeze at Anna Maria Island Inn

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Bradenton Beach
10.0 out of 10, Exceptional, (10 reviews)
"Great location perfect room for 2 people. "
United States
Macey
The price is €301
includes taxes & fees
13 Apr - 14 Apr
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.0 out of 10, Wonderful, (8 reviews)
"Very clean and the perfect location! Close to the beach, restaurants, and the grocery! We loved the heated pool in February. "
United States
Robert
The price is €441
includes taxes & fees
4 May - 5 May
Alamanda Villas

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, (388 reviews)
"Love this place "
United States
Leeanne
The price is €282
includes taxes & fees
11 May - 12 May
Pelican Post at Anna Maria Island Inn

Beach Condo with Pool Near Holmes Beach!

Beach Condo with Pool Near Holmes Beach!
Holmes Beach
9.0 out of 10, Wonderful, (39 reviews)
"Everything was as expected and the location is great."
United States
Thomas T.
The price is €650
includes taxes & fees
24 Apr - 25 Apr
Beach Condo with Pool Near Holmes Beach!

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (173 reviews)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveller
The price is €570
includes taxes & fees
23 Apr - 24 Apr
Palm Tree Villas

Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!
Anna Maria
9.6 out of 10, Exceptional, (41 reviews)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
United States
Michel
The price is €572
includes taxes & fees
5 May - 6 May
Beautiful Bungalow with Pool and Bay Views!

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, (47 reviews)
"Location was perfect"
United States
Michael S.
The price is €436
includes taxes & fees
6 May - 7 May
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

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, (27 reviews)
"We had such an amazing stay. The place was beautiful and clean, staff was so friendly, and the most amazing location. Steps from the beach! "
United States
Cara E.
The price is €513
includes taxes & fees
5 May - 6 May
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

Updated bayside condo with heated pool - across the street from the beach

Updated bayside condo with heated pool - across the street from the beach
Anna Maria
9.2 out of 10, Wonderful, (102 reviews)
"What a great place! Trolly pickup was two blocks away Walking distance to shops, restaurants and the beach. Can’t wait to visit again soon "
United States
Rhonda k.
The price is €243
includes taxes & fees
29 Apr - 30 Apr
Updated bayside condo with heated pool - across the street from the beach

One Bedroom Condo at Beachfront Resort!

One Bedroom Condo at Beachfront Resort!
Holmes Beach
9.2 out of 10, Wonderful, (22 reviews)
"Great beach access. Quiet area."
United States
Travis S.
The price is €580
includes taxes & fees
15 Apr - 16 Apr
One Bedroom Condo at Beachfront Resort!

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.4 out of 10, Very good, (44 reviews)
"Everything about the property was great, especially the location, which is walking distance away from restaurants and island shops."
United States
Ron H.
The price is €283
includes taxes & fees
29 Apr - 30 Apr
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
Anna Maria
9.8 out of 10, Exceptional, (17 reviews)
"Really nice cottages, and mgt on-site and super responsive and helpful!"
United States
Jerry A.
The price is €658
includes taxes & fees
5 May - 6 May
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.0 out of 10, Very good, (29 reviews)
"Great location, will come back again. Very clean..."
United States
albert V.
The price is €235
includes taxes & fees
14 Apr - 15 Apr
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Mello on the Beach - Shore Enuff

Mello on the Beach - Shore Enuff
Holmes Beach
10.0 out of 10, Exceptional, (22 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: a nice, laid-back stayproperty was very well cared for"
United States
Ellan B.
The price is €474
includes taxes & fees
6 May - 7 May
Mello on the Beach - Shore Enuff

Mello on the Beach - Sea Duced

Mello on the Beach - Sea Duced
Holmes Beach
9.6 out of 10, Exceptional, (24 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a wonderful time staying at Mello for Fathers Day weekend with our two toddlers. We will definitely stay again!"
United States
kelly g.
The price is €474
includes taxes & fees
10 May - 11 May
Mello on the Beach - Sea Duced

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, (23 reviews)
"Host was very friendly and accommodating. The location of the cottage was steps from the beach, great location, can also walk to anywhere on the north end of the island from the cottage. Cottage was clean and comfortable, the grounds where the cottage was neat and well cared for. Perfect place for quick stay as most places require a 1 week minimum."
United States
Michael A.
The price is €471
includes taxes & fees
28 Apr - 29 Apr
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

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, (25 reviews)
"Mom and I just stayed for one night and had a lovely trip. "
United States
Brittany B.
The price is €515
includes taxes & fees
5 May - 6 May
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
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

Find out more about Anna Maria Island

Everything you need to know about Anna Maria Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anna Maria Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anna Maria Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria Island holiday rentals we have selected for you start as low as €264 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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.