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, (428 reviews)
"Location was perfect and room did the job nicely for our stay."
United States
Marcellena
Haley's at The 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, (5 reviews)
"Great location perfect room for 2 people. "
United States
Macey
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (81 reviews)
"Very nice room with great beachside gulf views."
United States
PEGGY
Seabreeze at Anna Maria Island Inn

2 Blocks to Beach- 1-Story Retreat-Tropical Courtyard--Villa "St. John"

2 Blocks to Beach- 1-Story Retreat-Tropical Courtyard--Villa "St. John"
Bradenton Beach
9.8 out of 10, Exceptional, (19 reviews)
"We had a great stay! The condo was in a great location. We enjoyed the short walk to the beach. The unit had everything we needed. We would definitely book another stay the next time we visit!"
United States
Sharon C.
2 Blocks to Beach- 1-Story Retreat-Tropical Courtyard--Villa "St. John"

Mello on the Beach - Sea Duced

Mello on the Beach - Sea Duced
Holmes Beach
9.6 out of 10, Exceptional, (22 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.
Mello on the Beach - Sea Duced

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
7.6 out of 10, Good, (29 reviews)
"It was amazing stay and convenient "
United States
Jennifer P.
The price is €282
includes taxes & fees
3 Mar - 4 Mar
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!
Anna Maria
9.8 out of 10, Exceptional, (39 reviews)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
United States
Michel
Beautiful Bungalow with Pool and Bay Views!

Cute Cottage Near Beach and Shops

Cute Cottage Near Beach and Shops
Anna Maria
10.0 out of 10, Exceptional, (6 reviews)
"The place was great and as presented on the app. Having a designated parking space was very helpful. Close to many great restaurants, shops, the beach, etc. The north shore cafe and waterfront restaurant were both very good and very close in walking distance "
United States
Justin B.
The price is €604
includes taxes & fees
25 Feb - 26 Feb
Cute Cottage Near Beach and Shops

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.2 out of 10, Very good, (43 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 €284
includes taxes & fees
8 Mar - 9 Mar
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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, (101 reviews)
"Everything was great"
United States
lillybet h.
The price is €396
includes taxes & fees
26 Mar - 27 Mar
Updated bayside condo with heated pool - across the street from the beach

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, (35 reviews)
"Loved access to the beaches and restaurants."
United States
Kenneth C.
The price is €317
includes taxes & fees
26 Feb - 27 Feb
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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
10.0 out of 10, Exceptional, (41 reviews)
"Location was perfect"
United States
Michael S.
The price is €480
includes taxes & fees
1 Mar - 2 Mar
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

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, (14 reviews)
"Really nice cottages, and mgt on-site and super responsive and helpful!"
United States
Jerry A.
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Mello on the Beach - Shore Enuff

Mello on the Beach - Shore Enuff
Holmes Beach
10.0 out of 10, Exceptional, (22 reviews)
"During the week the stay was perfect. We were steps from the beach. The property abuts to the public park which meant dramatically increased crowds on the weekend. Very nice stay."
United States
Diana M.
The price is €636
includes taxes & fees
5 Mar - 6 Mar
Mello on the Beach - Shore Enuff

Villa-style condo with pool and beach access - Condo 8

Villa-style condo with pool and beach access - Condo 8
Holmes Beach
9.4 out of 10, Exceptional, (162 reviews)
"We really enjoyed our stay. The facility was very clean. Location is great. Owner was great to work with. "
United States
Carl M.
The price is €386
includes taxes & fees
7 Mar - 8 Mar
Villa-style condo with pool and beach access - Condo 8

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (172 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
Palm Tree 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, (368 reviews)
"Room was clean and great location."
United States
Jennifer
Pelican Post at Anna Maria Island Inn

Mello on the Beach - Gone Coastal

Mello on the Beach - Gone Coastal
Holmes Beach
9.8 out of 10, Exceptional, (21 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: It was amazing, quaint, clean & beautiful. I would definitely go back."
United States
Sylvia P.
Mello on the Beach - Gone Coastal

Beach Don't Kill My Vibe by Beach Boutique Rentals

Beach Don't Kill My Vibe by Beach Boutique Rentals
Anna Maria
10.0 out of 10, Exceptional, (16 reviews)
"We really enjoyed our brief stay here. Very clean. Great location. Very helpful staff/owner. Great location."
United States
Drew N.
The price is €863
includes taxes & fees
25 Mar - 26 Mar
Beach Don't Kill My Vibe by Beach Boutique Rentals

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
9.6 out of 10, Exceptional, (39 reviews)
"Great location and the property was well cared for/clean. Happy to have the pool and be close to the beach as well. "
United States
Liz P.
The price is €539
includes taxes & fees
27 Mar - 28 Mar
Anna Maria Beach Cottage 109G Old-Florida beach cottage,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

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 €334 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.