Anna Maria Island Vacation Rentals from $231: Search Short-Term Rentals

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Vacation Rentals in Anna Maria Island

"This was an amazing property and we can’t wait to come back on our next trip to the island."

$276 nightly

Aug 10 - Aug 11

Total includes taxes and fees

"Absolutely loved staying here. Lovely property and exceptional service. The staff was very helpful. Rooms were pristine. I was pleasantly surprised by the decor and modernness of the room. The views were exceptional and the location is fantastic! "

$351 nightly

Jul 20 - Jul 21

Total includes taxes and fees

"The staff is very friendly. Everything is new and very clean. I highly recommend it."

$288 nightly

Jul 24 - Jul 25

Total includes taxes and fees

"This house was perfect for our family of 4. Loved the open concept. The small pool was refreshing and the location was amazing - so close to the most beautiful section of the beach. We will be back! "

$879 nightly

Jul 22 - Jul 23

Total includes taxes and fees

"This property was a dream to stay at! It truly has everything you need. The property was beautiful, all the amenities, great communication with/from owner. Our families had a wonderful vacation and can’t to come back!"

Private beach nearby, sun loungers, beach towels

"Great experience! We loved staying here. This is our second time coming and it never disappoints "

"The Bungalow was spotless, I had a fantastic stay, thank you !!!"

" Very clean great location and property owner very nice and understanding thank you for everything "

$207 nightly

Jul 17 - Jul 18

Total includes taxes and fees

"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"

"Room was clean and comfortable. Spacious enough for 2 people. Nice pool. Will stay here again."

$231 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Fridge, oven, dishwasher, coffee/tea maker

"Wonderful stay ! Our family loved it ! "

"Apartment was clean, airy and comfortable, convenient with elevators and incredible location; the host was very responsive and helpful when we arrived and got a little lost. I highly recommend if you are looking for a nice place to stay in Anna Maria Island. "

$357 nightly

Jul 31 - Aug 1

Total includes taxes and fees

Beach nearby, sun loungers, beach towels

"Family of 4 stayed here comfortably for 3 nights in April. Had an excellent time on the island. And we were really impressed with the property and its location. Cool little trail, steps from the door take you straight to Bean Point."

"Great location, great amenities, and great communication from Mike Norman Realty. "

"Our stay was fantastic. Easy walking access to the beach, trolley and restaurants. "

On the beach, sun loungers, beach towels

"Really enjoy this area of the island. Plenty to walk to and most nearby have recovered pretty well from hurricanes. Nice condo with everything needed for a great week getaway from the cold winter"

"Great location, beautiful pool easy access to everything in plenty of parking "

"The location and amenities are amazing. Would definitely stay here again."

"We have stayed in this house a couple of times and love the location the food, shopping and the beach! The backyard oasis is perfect for lounging after a day at the beach. Frankie is fabulous to work with and keeps the property in beautiful condition. Would certainly recommend!"

"We had an amazing stay! Can’t wait to return!"

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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 $231 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.

Recent reviews of Anna Maria Island properties

5/5 Excellent

"Beautiful, relaxing and peaceful. Exactly what we needed!"

A verified traveler stayed at Anna Maria Beach Resort

Posted 1 day ago

5/5 Excellent

"It is place that I 100% recommend. Receptionist and the handyman, super helpful and available all the time for phone call. The sensation to get out of the bed, open your door and see the ocean at like 30 feet is amazing. A place that I will return for sure."

A verified traveler stayed at Seabreeze at Anna Maria Island Inn

Posted 4 days ago

5/5 Excellent

"The location and the amenities was very good even the property was quite old but we love here very much. The things not so impressed was the staff not helping for some questions make our group a hard time about the day to check out. We have a dolphin tour 9-11. We ask for out at noon they say they don’t know have to call that morning. How can we do that. You open 9:00 we on the boat if you say no what can we do. It only one hour and we are in big room. I think you should give us a little convenience. "

A verified traveler stayed at Tortuga Inn Beach Resort

Posted 7 days ago

5/5 Excellent

"2nd year we have stayed here and we love it! Perfect location! Walking distance to beach, restaurants, bars, and shops! Always clean, spacious, and well taken care of. Our favorite part about staying here is the beach access with chairs and umbrellas provided by the hotel. Definitely recommend. "

A verified traveler stayed at Silver Surf Gulf Beach Resort

Posted 13 days ago

Adorable Beach cottage just steps Bean Point beach!

5/5 Excellent

Island time

"House was very close to beach perfect walk. House was equipped with everything we need and very clean. The only thing is I have older kids age range 16-22. So when we got there they were disappointed in the twin beds when the picture showed bunk queens. So our youngest had to suffer whom is very tall. Other than that absolutely perfect. Maybe update your bedroom description it’s a key thing when trying to provide the right size beds for everyone in your group. "

A verified traveler stayed at Adorable Beach cottage just steps Bean Point beach!

Posted 13 days ago

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Vacation Rentals in Anna Maria Island

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

Bridgewalk A Landmark Resort

Bridgewalk A Landmark Resort

Adorable Beach cottage just steps Bean Point beach!

Adorable Beach cottage just steps Bean Point beach!

Beachfront Home | Pool + Spa | Games | Ocean Views

Beachfront Home | Pool + Spa | Games | Ocean Views

Tradewinds Beach Resort

Tradewinds Beach Resort

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Anna Maria Sunsets - studio

Anna Maria Sunsets - studio

Tropical Paradise On The Beach Permit VRC17-000168

Tropical Paradise On The Beach Permit VRC17-000168

Anna Maria Sunsets - studio

Anna Maria Sunsets - studio

Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!

Steps from Beach & Trolley to Local Hotspots! Stay at Sunny Side Down!

Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Wonderful and updated 2 bedroom/2 bath direct beach front. Panoramic views!

Wonderful and updated 2 bedroom/2 bath direct beach front. Panoramic views!

Escape to Anna Maria Island!

Escape to Anna Maria Island!

~ WE ARE OPEN! ~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~

~ WE ARE OPEN! ~ BEACHFRONT ~ YES, THAT'S YOUR VIEW! ~

PRIVATE POOL 2 bedroom 2 bathroom and just 2 blocks from the beach

PRIVATE POOL 2 bedroom 2 bathroom and just 2 blocks from the beach

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬

🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬

South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool

South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool

Find out more about Anna Maria Island

Find out more about Anna Maria Island

Recent reviews of Anna Maria Island properties

Recent reviews of Anna Maria Island properties

Anna Maria Beach Resort

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Expedia's Latest Trends