Anna Maria Holiday Rentals

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Our top choices for Anna Maria holiday rentals

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 AU$1,164
includes taxes & fees
7 Mar - 8 Mar
Beautiful Bungalow with Pool and Bay Views!

The Hideaway - Less than a block from beach!

The Hideaway - Less than a block from beach!
Anna Maria
The price is AU$1,718
includes taxes & fees
10 Mar - 11 Mar
The Hideaway - Less than a block from beach!

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 AU$799
includes taxes & fees
8 Mar - 9 Mar
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

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 AU$496
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 AU$544
includes taxes & fees
26 Mar - 27 Mar
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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 AU$1,224
includes taxes & fees
9 Mar - 10 Mar
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

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 AU$539
includes taxes & fees
27 Mar - 28 Mar
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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 AU$1,001
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, (41 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.
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!

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 AU$910
includes taxes & fees
12 Mar - 13 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 AU$1,205
includes taxes & fees
7 Mar - 8 Mar
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini 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 AU$910
includes taxes & fees
11 Mar - 12 Mar
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and 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 AU$1,118
includes taxes & fees
31 Mar - 1 Apr
Dog friendly cottage - One block to the Bay!

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 AU$820
includes taxes & fees
8 Mar - 9 Mar
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes

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)
"Host was very friendly and accommodating. The location of the cottage was steps from the beach, great location, can also walk to anywhere on the north end of the island from the cottage. Cottage was clean and comfortable, the grounds where the cottage was neat and well cared for. Perfect place for quick stay as most places require a 1 week minimum."
United States
Michael A.
The price is AU$1,043
includes taxes & fees
28 Mar - 29 Mar
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!

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, (16 reviews)
"We really enjoyed our brief stay here. Very clean. Great location. Very helpful staff/owner. Great location."
United States
Drew N.
Beach Don't Kill My Vibe by Beach Boutique Rentals

Emerald Shores East! Walk to Beach!

Emerald Shores East! Walk to Beach!
Anna Maria
9.8 out of 10, Exceptional, (6 reviews)
"Excellently done everything was perfect "
United States
Luis Alberto C.
The price is AU$1,284
includes taxes & fees
8 Mar - 9 Mar
Emerald Shores East! Walk to Beach!

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)
"Great communication, space was exactly as described and was clean/ready for us! Thank you!"
United States
Larry R.
The price is AU$463
includes taxes & fees
17 Mar - 18 Mar
Freshly Remodeled Island Suite w/ Pool & Pet Friendly

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)
"Location, amenities, pool, cleanliness all were excellent!"
United States
Lauren M.
The price is AU$1,170
includes taxes & fees
9 Mar - 10 Mar
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Gulf View Retreat! Pool, Decks and 2 King Beds!

Gulf View Retreat! Pool, Decks and 2 King Beds!
Anna Maria
9.6 out of 10, Exceptional, (22 reviews)
"Right on the beach"
United States
Hussein M.
The price is AU$1,844
includes taxes & fees
13 Mar - 14 Mar
Gulf View Retreat! Pool, Decks and 2 King Beds!
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, 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 favourite 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 depend 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 AU$1,925 per night. Entering your travel dates in the search wizard might find you 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?

Wake up on the waters of Tampa Bay in a north Anna Maria home.: This highly rated holiday home rental in Anna Maria is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Anna Maria are Waterfront -Canal, Tampa Bay, Large Heated Pool, Tiki Bar, Minutes to the Beach! and Bridgeview: Bay front with sweeping views, sleeps 12!.

How many holiday rentals are there in Anna Maria?

With 525 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 Island Players and Anna Maria Island Museum and Historical Park, 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.