Anna Maria Island Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Our top choices for Anna Maria Island vacation 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, (399)
"Beautiful location. Walking distance to beach. "
United States
Maria
$148 nightly
The price is $167
Dec 18 - Dec 19
Total with taxes and fees
Haley's at The Anna Maria Island Inn

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
10.0 out of 10, Exceptional, (3)
"The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay."
United States
Traci
$426 nightly
The price is $460
Dec 13 - Dec 14
Total with taxes and fees
Alamanda Villas

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (328)
"Fabulous stay! Super clean!"
United States
Sarah
$225 nightly
The price is $254
Dec 17 - Dec 18
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
9.2 out of 10, Wonderful, (57)
"It was good. Place is walking distance to everything. The staff were helpful."
United States
Judith
$304 nightly
The price is $339
Dec 14 - Dec 15
Total with taxes and fees
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (56)
"Nice Place "
United States
Rafael
$198 nightly
The price is $223
Dec 14 - Dec 15
Total with taxes and fees
Seabreeze at Anna Maria Island Inn

Beach Sunrise Villa! Outdoor Dining, Beach Cart and Gulf Breezes

Beach Sunrise Villa! Outdoor Dining, Beach Cart and Gulf Breezes
Bradenton Beach
9.6 out of 10, Exceptional, (15)
"Clean, great communication, convenient location. "
United States
Teri
$272 nightly
The price is $304
Dec 13 - Dec 14
Total with taxes and fees
Beach Sunrise Villa! Outdoor Dining, Beach Cart and Gulf Breezes

Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!
Anna Maria
9.8 out of 10, Exceptional, (37)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
United States
Michel
$352 nightly
The price is $392
Dec 15 - Dec 16
Total with taxes and fees
Beautiful Bungalow with Pool and Bay Views!

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (172)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveler
$584 nightly
The price is $640
Dec 14 - Dec 15
Total with taxes and fees
Palm Tree Villas

Experience the passion of hospitality, cleaning, and good location!

Experience the passion of hospitality, cleaning, and good location!
Bradenton Beach
10.0 out of 10, Exceptional, (10)
"Wonderful place we will returm"
United States
ken b.
$280 nightly
The price is $312
Dec 21 - Dec 22
Total with taxes and fees
Experience the passion of hospitality, cleaning, and good location!

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, (99)
"Very comfortable and modern, great location across the street from bay side beach, a block to restaurant/coffee/ice cream"
United States
Jeffrey B.
$261 nightly
The price is $291
Dec 20 - Dec 21
Total with taxes and fees
Updated bayside condo with heated pool - across the street from the beach

Beachside Duplex w/ Pool and Private Suite

Beachside Duplex w/ Pool and Private Suite
2.5 star property
Anna Maria
9.0 out of 10, Wonderful, (2)
"We have stayed here over the years and have enjoyed the perfect location to the beach. The house is a bit dated and needs a few upgrades but overall the house was very clean and comfortable. Please note there were no beach umbrellas supplied but did have plenty of beach chairs. You may want to plan on alternate shade options once there as the sun is intense and can be challenging. We would stay there again as the price was very affordable. "
United States
Mark T.
$348 nightly
The price is $388
Dec 13 - Dec 14
Total with taxes and fees
Beachside Duplex w/ Pool and Private Suite

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, (36)
"Location was perfect"
United States
Michael S.
$462 nightly
The price is $514
Dec 14 - Dec 15
Total with taxes and fees
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (25)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
United States
Paris K.
$387 nightly
The price is $432
Dec 15 - Dec 16
Total with taxes and fees
Beautiful Condo on Pine Ave, 2 Blocks to Beach

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.8 out of 10, Excellent, (41)
"Wonderful relaxing place to be, and very private"
United States
Christy L.
$259 nightly
The price is $289
Dec 14 - Dec 15
Total with taxes and fees
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Sunset View Pet Friendly w/Pool Beach Home

Sunset View Pet Friendly w/Pool Beach Home
2.0 star property
Bradenton Beach
10.0 out of 10, Exceptional, (27)
"The cutest little place! We loved how close it was to the beach and that it was pet friendly. Plenty of spots to sleep without feeling on top of each other. It was perfect for what we needed! "
United States
Ashley O.
$749 nightly
The price is $837
Jan 7 - Jan 8, 2026
Total with taxes and fees
Sunset View Pet Friendly w/Pool Beach Home

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.6 out of 10, Excellent, (39)
"Very close to the beach and restaurants!"
United States
Danay G.
$304 nightly
The price is $339
Dec 14 - Dec 15
Total with taxes and fees
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Anna Maria Island - 2/1

Anna Maria Island - 2/1
Bradenton Beach
9.6 out of 10, Exceptional, (185)
"We loved our stay at this location. It was clean, comfortable beds, no issues with the resort. Kitchen was well stocked with equipment. The pool is great and the beach is just across the street. We plan on staying at this location again!!"
United States
Deana C.
$273 nightly
The price is $304
Dec 13 - Dec 14
Total with taxes and fees
Anna Maria Island - 2/1

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, (34)
"Great place for a beach stay on Anna Maria!!!"
United States
John F.
$479 nightly
The price is $534
Dec 14 - Dec 15
Total with taxes and fees
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

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, (29)
"For our small family of 3 this was the perfect little condo that is located in my favorite area of the island. Everything we needed was a short bike ride away. "
United States
Amanda D.
$282 nightly
The price is $315
Dec 14 - Dec 15
Total with taxes and fees
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Sugary Sands 1 Bed Condo and One Block to Beach!

Sugary Sands 1 Bed Condo and One Block to Beach!
Bradenton Beach
9.4 out of 10, Exceptional, (22)
"Great place and very safe.will be back next August for my wifes birthday thanks"
United States
Terry K.
$491 nightly
The price is $548
Dec 13 - Dec 14
Total with taxes and fees
Sugary Sands 1 Bed Condo and One Block to Beach!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Anna Maria Island Hotel Reviews

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 $167 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.