Anna Maria Island Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Anna Maria Island vacation rentals

Premium bedding, pillowtop beds, minibar, free cribs/infant beds

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (92 reviews)
"Great location!"
United States
Kevin
$300 nightly
The price is $339
May 25 - May 26
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
2 restaurants, lunch, dinner served; seafood

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (790 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
$260 nightly
The price is $294
May 13 - May 14
Total with taxes and fees
Bridgewalk Resort
Beach nearby, white sand, sun loungers, beach towels

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, (446 reviews)
"Incredible location, great room! Loved everything! Would def come back!"
United States
Laís Fernanda
$271 nightly
The price is $306
Apr 28 - Apr 29
Total with taxes and fees
Haley's at The Anna Maria Island Inn
Exterior

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, (395 reviews)
"Great location - quiet, private, but just a few blocks from the beach, every eatery and nightlife option. Would definitely stay here again."
United States
Christopher
$292 nightly
The price is $330
May 13 - May 14
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Exterior

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
$457 nightly
The price is $494
May 18 - May 19
Total with taxes and fees
Alamanda Villas
Beach nearby, white sand, beach umbrellas, beach towels

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 traveler
$636 nightly
The price is $699
Apr 29 - Apr 30
Total with taxes and fees
Palm Tree Villas
Pool

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, (12 reviews)
"Great location perfect room for 2 people. "
United States
Macey
$290 nightly
The price is $322
May 2 - May 3
Total with taxes and fees
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Beach nearby, sun loungers

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.
$681 nightly
The price is $759
May 2 - May 3
Total with taxes and fees
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
A heated pool

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.
$426 nightly
The price is $474
May 6 - May 7
Total with taxes and fees
Mello on the Beach - Shore Enuff
A heated pool

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.
$451 nightly
The price is $501
May 10 - May 11
Total with taxes and fees
Mello on the Beach - Sea Duced
A heated pool

Mello on the Beach - Sol Mate

Mello on the Beach - Sol Mate
Holmes Beach
9.8 out of 10, Exceptional, (32 reviews)
"Mello was beautiful, close to the beach very welcoming and had all that you may need."
United States
Brendan N.
$451 nightly
The price is $501
May 10 - May 11
Total with taxes and fees
Mello on the Beach - Sol Mate
Terrace/patio

One Bedroom Condo at Beachfront Resort!

One Bedroom Condo at Beachfront Resort!
Holmes Beach
9.2 out of 10, Wonderful, (23 reviews)
"Great beach access. Quiet area."
United States
Travis S.
$604 nightly
The price is $674
Apr 28 - Apr 29
Total with taxes and fees
One Bedroom Condo at Beachfront Resort!
Property grounds

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, (18 reviews)
"Location was absolutely perfect. Place was clean. The amenities were just enough for our short stay. "
United States
David W.
$488 nightly
The price is $544
Apr 28 - Apr 29
Total with taxes and fees
Beach Don't Kill My Vibe by Beach Boutique Rentals
Beach nearby, sun loungers, beach towels

Charming cottage with heated pool, tropical landscaping in prime location.

Charming cottage with heated pool, tropical landscaping in prime location.
Anna Maria
10.0 out of 10, Exceptional, (62 reviews)
"This was the perfect place for our family of 4 to stay. The location is incredible and the space so very clean."
United States
Kasey C.
Charming cottage with heated pool, tropical landscaping in prime location.
Smart TV, Netflix, DVD player, streaming services

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (125 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
$620 nightly
The price is $692
May 3 - May 4
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

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, (48 reviews)
"Host was welcoming. We were so close to the beach! It was amazing! The amenities were very nice. Wanda is wonderful."
United States
Gretchen H.
$459 nightly
The price is $511
Apr 28 - Apr 29
Total with taxes and fees
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
TV, table tennis, offices

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

Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
Anna Maria
9.6 out of 10, Exceptional, (65 reviews)
"The house was very clean and well located. We fully enjoyed our stay and hope to return in the future. "
United States
Emma D.
$911 nightly
The price is $1,016
May 2 - May 3
Total with taxes and fees
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
Sun loungers, beach towels

Anna Maria Sunsets - studio

Anna Maria Sunsets - studio
Bradenton Beach
9.2 out of 10, Wonderful, (261 reviews)
"Great location but it’s just a room so if you’re gone doing things it’s a good spot."
United States
melanie
$257 nightly
The price is $286
May 6 - May 7
Total with taxes and fees
Anna Maria Sunsets - studio
Beach nearby, sun loungers

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, (35 reviews)
"Amazing stay! location was perfect, the unit was clean and the host was so kind/accommodating!"
United States
Kyle K.
$471 nightly
The price is $525
Apr 28 - Apr 29
Total with taxes and fees
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
Beach nearby, sun loungers

Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!

Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
Anna Maria
10.0 out of 10, Exceptional, (26 reviews)
"Great property!"
United States
Jessica S.
$680 nightly
The price is $757
May 3 - May 4
Total with taxes and fees
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
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

Tortuga Inn Beach Resort

Tortuga Inn Beach Resort

10/10 Excellent
"There are many different sizes and types of rooms at Tortuga Resort on Anna Maria, so pay close attention to the room description and location. We had a large, condo type room that was great, with a lanai and a view of the bay! The kitchen was large and had everything you needed. Table for six. Everything was clean. There are multiple pools and they have their own beach front, though you do need to cross the street, as you do with most of the resorts on the southern part of the island. Chaise lounges on the beach; plenty of beach towels; umbrellas provided in the rooms; wonderful sunsets; at least four restaurants within walking distance. Pavilion on beach seems wheelchair accessible. Old Florida feel, which I like. We will return!"
Leslie Ann 5-night trip
Posted 7 hours ago
Tortuga Inn 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 $275 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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