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
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

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
$299 nightly
The price is $333
May 6 - May 7
Total with taxes and fees
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
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, (94 reviews)
"Great location!"
United States
Kevin
$306 nightly
The price is $346
May 26 - May 27
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
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)
"Location was perfect and room did the job nicely for our stay."
United States
Marcellena
$228 nightly
The price is $258
May 4 - May 5
Total with taxes and fees
Haley's at The Anna Maria Island Inn
Exterior

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.2 out of 10, Wonderful, (9 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
$426 nightly
The price is $460
May 6 - May 7
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
May 6 - May 7
Total with taxes and fees
Palm Tree Villas
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, (398 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
$266 nightly
The price is $300
May 13 - May 14
Total with taxes and fees
Pelican Post 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, (792 reviews)
"This is a great place in the middle of everything clean rooms up-to-date perfect"
United States
Frank
$266 nightly
The price is $301
May 12 - May 13
Total with taxes and fees
Bridgewalk Resort
Beach nearby

Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!
Anna Maria
9.6 out of 10, Exceptional, (41 reviews)
"Súper Super comfortable and tidy"
United States
SOFIA D.
$558 nightly
The price is $622
May 5 - May 6
Total with taxes and fees
Beautiful Bungalow with Pool and Bay Views!
Exterior detail

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.
$292 nightly
The price is $326
May 17 - May 18
Total with taxes and fees
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
A heated pool

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, (31 reviews)
"Great location, will come back again. Very clean..."
United States
albert V.
$242 nightly
The price is $269
May 6 - May 7
Total with taxes and fees
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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.
$577 nightly
The price is $647
May 3 - May 4
Total with taxes and fees
One Bedroom Condo at Beachfront Resort!
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.
$462 nightly
The price is $514
May 6 - May 7
Total with taxes and fees
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
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
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 reviews)
"Everything was clean, quiet, beautiful, definitely we will come back."
United States
Percy O.
$290 nightly
The price is $324
May 20 - May 21
Total with taxes and fees
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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 10 - May 11
Total with taxes and fees
Mello on the Beach - Shore Enuff
Beach nearby, sun loungers

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, (44 reviews)
"very nice, clean, comfortable"
United States
Andrew
$479 nightly
The price is $534
May 3 - May 4
Total with taxes and fees
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
Beach nearby, sun loungers

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.
$497 nightly
The price is $553
May 1 - May 2
Total with taxes and fees
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
A heated pool

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
9.2 out of 10, Wonderful, (62 reviews)
"We appreciated that the property was pet friendly and such a cozy place for our party of four. Property was clean and a pleasant stay. "
United States
Cindy
$318 nightly
The price is $355
May 3 - May 4
Total with taxes and fees
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Property grounds

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, (104 reviews)
"Love the condo and the location"
United States
Rachelle F.
$289 nightly
The price is $322
May 25 - May 26
Total with taxes and fees
Updated bayside condo with heated pool - across the street from the beach
A heated pool

Mello on the Beach - Looney Dunes

Mello on the Beach - Looney Dunes
Holmes Beach
10.0 out of 10, Exceptional, (16 reviews)
"Great property! Super clean, great location, and great communication! It’s also close to the beach! Would definitely stay here again!"
United States
Morgan H.
$426 nightly
The price is $474
May 4 - May 5
Total with taxes and fees
Mello on the Beach - Looney Dunes
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna Maria Island Hotel Reviews

Anna Maria Beach Resort

Anna Maria Beach Resort

2/10 Terrible
"This is not a resort. It is a motel on the beach. We paid over $1000 a night for what was supposed to be a beach front room with no view of the beach. We literally got the worst room in the house and complaints fell on unsympathetic ears. The shower control was missing. The seal for the shower door was falling off and the bathroom is like a phone booth. Lack of pool towels because guests hoard them. Non-guests using the loungers and umbrellas on the beach and even a non-guest woman with a dog at their only picnic table with no one in sight to enforce their policies. Be aware, this resort offers $100 a day day passes, meaning you may not have the facilities YOU paid $1000 a night for. Your only food options are a vending machine with Saran wrapped sandwiches and Pringles. This place does not deserve Marriott resort pricing. What few restaurants there are on the island don't take reservations during peak times, and there is over a 2 hour wait for walk ups. There are simply not enough restaurants for the number of AirB&Bs and hotels. We ended up going inland and still had to wait 30 minutes. Imagine spending $1000 a night for a beach front room and missing the sunset because there was no place to eat near your "resort." As for the island, to call it charming and rustic is a compliment. It's really tacky and low class and way overburdened. It has a nice beach and would be a good day trip, but forget about staying here."
Bill 2-night trip
Posted 14 hours ago
Anna Maria 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 $258 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.

Explore a world of travel with Expedia