Anna Maria Island Vacation Rentals

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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, (449 reviews)
"Great location, clean and quiet. "
United States
Sara
The price is CA $298
CA $377 total
includes taxes & fees
May 17 - May 18
Haley's at The 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
10.0 out of 10, Exceptional, (20 reviews)
"Great location perfect room for 2 people. "
United States
Macey
The price is CA $210
CA $451 total
includes taxes & fees
May 19 - May 20
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (98 reviews)
"Great location!"
United States
Kevin
The price is CA $373
CA $472 total
includes taxes & fees
May 25 - May 26
Seabreeze at Anna Maria Island Inn

Beach Condo with Pool Near Holmes Beach!

Beach Condo with Pool Near Holmes Beach!
Holmes Beach
9.0 out of 10, Wonderful, (40 reviews)
"Everything was as expected and the location is great."
United States
Thomas T.
Beach Condo with Pool Near Holmes Beach!

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 traveller
The price is CA $347
CA $1,027 total
includes taxes & fees
May 19 - May 20
Palm Tree Villas

Across from the beach - Bella by the Sea by SeaBreeze Vacation

Across from the beach - Bella by the Sea by SeaBreeze Vacation
Bradenton Beach
9.8 out of 10, Exceptional, (9 reviews)
"Excellent location and excellent customer service."
United States
Maxine S.
The price is CA $230
CA $800 total
includes taxes & fees
May 18 - May 19
Across from the beach - Bella by the Sea by SeaBreeze Vacation

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
The price is CA $381
CA $717 total
includes taxes & fees
May 31 - Jun 1
Alamanda Villas

Anna Maria Island Bungalow with Pool! Across the street from Beach, near Pine Av

Anna Maria Island Bungalow with Pool! Across the street from Beach, near Pine Av
Anna Maria
9.2 out of 10, Wonderful, (62 reviews)
"The pool was very nice. The beach is really not a beach, there is really no place to sit on the sand. Nice view and conveniently located. The bedroom is very small but clean. Overall nice place to stay! "
United States
Todd
The price is CA $260
CA $823 total
includes taxes & fees
May 18 - May 19
Anna Maria Island Bungalow with Pool! Across the street from Beach, near Pine Av

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.8 out of 10, Excellent, (50 reviews)
"Location was EXCELLENT just off of Pine Ave and steps away from the ocean and shops. Cute old Florida village with a lovely pool and it was perfect for us. "
United States
Kelly Q.
The price is CA $177
CA $425 total
includes taxes & fees
May 19 - May 20
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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, (49 reviews)
"The host was very welcoming and helpful. The cottage was adorable, clean and very well appointed. Steps from the beach. I will recommend and would love to come again."
United States
Gayla A.
The price is CA $375
CA $845 total
includes taxes & fees
Jun 5 - Jun 6
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

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)
"Love these cottages, very close to the beach and restaurants!"
United States
Lewis E.
The price is CA $452
CA $1,029 total
includes taxes & fees
May 20 - May 21
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

One Bedroom Condo at Beachfront Resort!

One Bedroom Condo at Beachfront Resort!
Holmes Beach
9.2 out of 10, Wonderful, (23 reviews)
"Loved being able to walk easily to beach "
United States
Elizabeth H.
The price is CA $309
CA $934 total
includes taxes & fees
Jun 7 - Jun 8
One Bedroom Condo at Beachfront Resort!

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, (402 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
The price is CA $354
CA $448 total
includes taxes & fees
May 17 - May 18
Pelican Post at Anna Maria Island Inn

Cute Cottage Near Beach and Shops

Cute Cottage Near Beach and Shops
Anna Maria
10.0 out of 10, Exceptional, (10 reviews)
"Clean cozy house"
United States
Dale
Cute Cottage Near Beach and Shops

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
7.8 out of 10, Good, (31 reviews)
"This apartment is adorable! Super cute and had everything we needed.The location is close to restaurants and the beach. My only suggestion would be to put a queen size bed in instead of a double. We were a bit cramped. The pool was clean and warm. And the price for the location was incredible! I searched for weeks and found this little gem!"
United States
Denise
The price is CA $213
CA $470 total
includes taxes & fees
May 25 - May 26
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.8 out of 10, Excellent, (42 reviews)
"Everything was clean, quiet, beautiful, definitely we will come back."
United States
Percy O.
The price is CA $213
CA $472 total
includes taxes & fees
Jun 2 - Jun 3
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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, (40 reviews)
"Loved access to the beaches and restaurants."
United States
Kenneth C.
The price is CA $177
CA $420 total
includes taxes & fees
May 17 - May 18
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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, (27 reviews)
"We really enjoyed our stay here. It was a perfect spot to enjoy the pool or the ocean. Just a quick walk down to the beach. They had all the beach equipment you could need. That also was a highlight because we didn’t have to pack much. Plenty of places to eat nearby also just a short walk away. The best part was the staff made sure the kids had an eventful Easter morning. They put out hundreds of eggs in the middle of the night and when our kids woke up they were so...
United States
jacob
The price is CA $286
CA $758 total
includes taxes & fees
May 19 - May 20
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (800 reviews)
"Very close to beach shops and restaurants Beautiful suite with kitchens."
Canada
Mary
The price is CA $419
CA $474 total
includes taxes & fees
Jun 2 - Jun 3
Bridgewalk Resort

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, (45 reviews)
"We loved our stay on Anna Maria island. The location was perfect, accommodations clean and welcoming as was the staff who wereboth helpful, professional, and kind. We would certainly stay here again."
United States
Nicholas N.
The price is CA $296
CA $754 total
includes taxes & fees
May 30 - May 31
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
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

Find out more about Anna Maria Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Anna Maria Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.