Holiday Rentals in Anna Maria

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Our top choices for Anna Maria holiday rentals

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
7.6 out of 10, Good, (29 reviews)
"It was amazing stay and convenient "
United States
Jennifer P.
The price is €278
includes taxes & fees
3 Mar - 4 Mar
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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.
The price is €305
includes taxes & fees
26 Mar - 27 Mar
Updated bayside condo with heated pool - across the street from the beach

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.2 out of 10, Very good, (43 reviews)
"Everything about the property was great, especially the location, which is walking distance away from restaurants and island shops."
United States
Ron H.
The price is €284
includes taxes & fees
8 Mar - 9 Mar
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Beautiful Bungalow with Pool and Bay Views!

Beautiful Bungalow with Pool and Bay Views!
Anna Maria
9.8 out of 10, Exceptional, (39 reviews)
"Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!"
United States
Michel
The price is €667
includes taxes & fees
11 Mar - 12 Mar
Beautiful Bungalow with Pool and Bay Views!

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, (35 reviews)
"Loved access to the beaches and restaurants."
United States
Kenneth C.
The price is €311
includes taxes & fees
17 Mar - 18 Mar
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Beachside Duplex w/ Pool and Private Suite

Beachside Duplex w/ Pool and Private Suite
Anna Maria
9.4 out of 10, Exceptional, (3 reviews)
"Amazing relaxing time, perfect accommodations for our budget"
United States
Sandi L.
The price is €777
includes taxes & fees
28 Feb - 1 Mar
Beachside Duplex w/ Pool and Private Suite

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
10.0 out of 10, Exceptional, (41 reviews)
"Location was perfect"
United States
Michael S.
The price is €479
includes taxes & fees
1 Mar - 2 Mar
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

Cute Cottage Near Beach and Shops

Cute Cottage Near Beach and Shops
Anna Maria
10.0 out of 10, Exceptional, (6 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.
The price is €600
includes taxes & fees
11 Mar - 12 Mar
Cute Cottage Near Beach and Shops

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, (40 reviews)
"Great location and the property was well cared for/clean. Happy to have the pool and be close to the beach as well. "
United States
Liz P.
The price is €494
includes taxes & fees
27 Mar - 28 Mar
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

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, (46 reviews)
"Perfect area walking Beautiful little place"
United States
Kimberly S.
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

The Hideaway - Less than a block from beach!

The Hideaway - Less than a block from beach!
Anna Maria
The price is €1,080
includes taxes & fees
10 Mar - 11 Mar
The Hideaway - Less than a block from beach!

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, (14 reviews)
"Really nice cottages, and mgt on-site and super responsive and helpful!"
United States
Jerry A.
The price is €764
includes taxes & fees
1 Mar - 2 Mar
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Dog friendly cottage - One block to the Bay!

Dog friendly cottage - One block to the Bay!
Anna Maria
9.6 out of 10, Exceptional, (11 reviews)
"Great stay. "
United States
Mandy R.
The price is €660
includes taxes & fees
24 Mar - 25 Mar
Dog friendly cottage - One block to the Bay!

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, (22 reviews)
"Mom and I just stayed for one night and had a lovely trip. "
United States
Brittany B.
The price is €557
includes taxes & fees
11 Mar - 12 Mar
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill

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, (26 reviews)
"Easy walk to the beach and restaurants. Allowed us to check in early since the place was available. "
United States
Nancy E.
The price is €615
includes taxes & fees
7 Mar - 8 Mar
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

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, (123 reviews)
"Great place and great location........"
United States
chris w.
The price is €614
includes taxes & fees
12 Mar - 13 Mar
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Anna Maria
9.8 out of 10, Exceptional, (179 reviews)
"As the summary says, very charming at a fabulous location. Would definitely stay again."
United States
Jeremy A.
The price is €730
includes taxes & fees
4 Mar - 5 Mar
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

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, (32 reviews)
"Excellent location! Super clean rooms and resort. Peaceful and quiet weekend of relaxation! Definitely recommended! "
United States
Anonymous traveller
The price is €510
includes taxes & fees
8 Mar - 9 Mar
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

Coast is Clear! Heated pool/spa~Close to shops

Coast is Clear! Heated pool/spa~Close to shops
Anna Maria
Coast is Clear! Heated pool/spa~Close to shops

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, (22 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.
The price is €614
includes taxes & fees
28 Mar - 29 Mar
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, 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 Hotel Reviews

Find out more about Anna Maria

Everything you need to know about Anna Maria holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Anna Maria holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Anna Maria holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Anna Maria. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Anna Maria holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Anna Maria holiday rentals we have selected for you start as low as €316 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Anna Maria rentals

At Expedia, we put the best Anna Maria holiday 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 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 holiday.

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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Anna Maria?

Yes, there are holiday rentals close to the most popular sights in Anna Maria, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Anna Maria. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best holiday rentals that Anna Maria has to offer?

Waterfront -Canal, Tampa Bay, Large Heated Pool, Tiki Bar, Minutes to the Beach!: This highly rated holiday home rental in Anna Maria is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Other favourite homes for rent in Anna Maria are Naut 2 Shabby Cottage-Awesome Pool Area, Pine Ave location close to everything and Wake up on the waters of Tampa Bay in a north Anna Maria home..

How many holiday rentals are there in Anna Maria?

With 450 Expedia holiday rentals, you're guaranteed to find just the right place for your Anna Maria stay.

What can I see and do in Anna Maria?

Cultural attractions include Anna Maria Island Museum and Historical Park and Island Players, whereas Anna Maria Beach and Bean Point Beach are a couple of picturesque spots to enjoy the outdoors. While in the area, you can also visit popular places such as Lido Beach and Tampa Bay.

What are holiday rentals like in Anna Maria?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Anna Maria. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.