Anna Maria Island Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (422 reviews)
"Location was perfect and room did the job nicely for our stay."
United States
Marcellena
$250 nightly
The price is $282
Feb 1 - Feb 2
Total with taxes and fees
Haley's at The Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (73 reviews)
"The room was clean, the beds were comfy, and the view was incredible!"
United States
Amy
$256 nightly
The price is $289
Feb 2 - Feb 3
Total with taxes and fees
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
$297 nightly
The price is $331
Feb 17 - Feb 18
Total with taxes and fees
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.4 out of 10, Exceptional, (6 reviews)
"I loved the location, for a couple the place is wonderful, I would only request, 2 nice beach chairs and an umbrella. Great communication, clean, we will come back for sure. "
United States
Lourdes
$419 nightly
The price is $452
Feb 1 - Feb 2
Total with taxes and fees
Alamanda Villas

Beach Condo with Pool Near Holmes Beach!

Beach Condo with Pool Near Holmes Beach!
Holmes Beach
9.2 out of 10, Wonderful, (36 reviews)
"Lived the location so close to the beach and really enjoyed having the pool close by "
United States
nicki h.
Beach Condo with Pool Near Holmes Beach!

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, (36 reviews)
"Great place for a beach stay on Anna Maria!!!"
United States
John F.
$519 nightly
The price is $579
Feb 1 - Feb 2
Total with taxes and fees
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

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, (38 reviews)
"Location was perfect"
United States
Michael S.
$508 nightly
The price is $567
Feb 1 - Feb 2
Total with taxes and fees
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

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, (18 reviews)
"Amazing property and great location. "
United States
Chris M.
$532 nightly
The price is $593
Feb 6 - Feb 7
Total with taxes and fees
Beach Sunrise Villa! Outdoor Dining, Beach Cart and Gulf Breezes

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 reviews)
"The location was great and it was perfect for a weekend getaway"
United States
Eileen O.
$303 nightly
The price is $338
Feb 1 - Feb 2
Total with taxes and fees
Experience the passion of hospitality, cleaning, and good location!

Steps from Beach and Local Hotspots! Stay at Sunny Side Down!

Steps from Beach and Local Hotspots! Stay at Sunny Side Down!
Bradenton Beach
9.2 out of 10, Wonderful, (20 reviews)
"Wonderful stay ! Our family loved it ! "
United States
Daniel
$670 nightly
The price is $748
Feb 28 - Mar 1
Total with taxes and fees
Steps from Beach and Local Hotspots! Stay at Sunny Side Down!

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 traveler
$654 nightly
The price is $720
Feb 2 - Feb 3
Total with taxes and fees
Palm Tree Villas

Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
Anna Maria
9.8 out of 10, Exceptional, (63 reviews)
"Overall great location within the island. Walking distance to the beach, shops and restaurants. House was well maintained and had plenty of room for our family. "
United States
Jonathan C.
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

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, (356 reviews)
"Great place…"
United States
Debra
$263 nightly
The price is $297
Feb 2 - Feb 3
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

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.
$302 nightly
The price is $338
Feb 16 - Feb 17
Total with taxes and fees
Updated bayside condo with heated pool - across the street from the beach

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, (21 reviews)
"My fiancé and I stayed at the cottages this past weekend and it was one of most relaxing weekend. Everyone there was so nice and helpful. We can’t wait to book another trip soon!!"
United States
Matthew S.
$578 nightly
The price is $644
Feb 7 - Feb 8
Total with taxes and fees
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

Cute Cottage Near Beach and Shops

Cute Cottage Near Beach and Shops
Anna Maria
10.0 out of 10, Exceptional, (4 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.
$494 nightly
The price is $552
Feb 1 - Feb 2
Total with taxes and fees
Cute Cottage Near Beach and Shops

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, (21 reviews)
"Mom and I just stayed for one night and had a lovely trip. "
United States
Brittany B.
$584 nightly
The price is $651
Feb 1 - Feb 2
Total with taxes and fees
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

Stylish bayside condo with WiFi & pool - close to the beach & restaurants

Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Anna Maria
9.6 out of 10, Exceptional, (102 reviews)
"Perfect place to stay, loved it, walking distance to everything you need beach right across the street. Loved it."
United States
jason l.
$251 nightly
The price is $280
Feb 8 - Feb 9
Total with taxes and fees
Stylish bayside condo with WiFi & pool - close to the beach & restaurants

Bayfront Villa: Dock, Walk to Beach and Bridge Street

Bayfront Villa: Dock, Walk to Beach and Bridge Street
Bradenton Beach
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful property. Very well kept. Walking distance from Bridge Street. Bright and well maintained house. We’ll stay here again!"
United States
Margo J.
$570 nightly
The price is $635
Feb 4 - Feb 5
Total with taxes and fees
Bayfront Villa: Dock, Walk to Beach and Bridge Street

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 reviews)
"Great place and very safe.will be back next August for my wifes birthday thanks"
United States
Terry K.
$550 nightly
The price is $614
Feb 20 - Feb 21
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 $282 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.