A marina with boats, a bridge, and high-rise buildings.

Anna Maria Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Anna Maria vacation rentals

A covered outdoor seating area with a table and chairs, large windows, and a view of palm trees and a road.

1. Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit

Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit
Anna Maria
9.4 out of 10, Exceptional, (32 reviews)
"We really enjoyed our stay. The location was perfect- super close to a quiet beach, and close to restaurants and shopping on Pine street. Place was clean and comfortable and had everything we needed to enjoy the beach."
United States
Louise W.
$521 nightly
The price is $581
Oct 7 - Oct 8
Total with taxes and fees
Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit
A beach with clear turquoise water and white sand.

2. 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, (43 reviews)
"Loved the easy access to the beach and the fact that the property had beach supplies available for you to use. We had great service when needed and will definitely visit again !"
United States
Meagan
$474 nightly
The price is $528
Oct 7 - Oct 8
Total with taxes and fees
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
A beach with clear turquoise water and white sand.

3. 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
9.6 out of 10, Exceptional, (31 reviews)
"Old Florida charm of cottage. Beautiful location and only steps to the beach. Staff was wonderful and room was clean."
United States
Christina R.
$497 nightly
The price is $553
Oct 10 - Oct 11
Total with taxes and fees
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
A wooden boardwalk surrounded by dense foliage.

4. 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, (58 reviews)
"Great stay. "
United States
courtneyharned
$462 nightly
The price is $514
Oct 19 - Oct 20
Total with taxes and fees
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
A beach with clear turquoise water and white sand.

5. 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, (33 reviews)
"Great place to stay!Nice walk to the beach!"
United States
Rose Y.
$485 nightly
The price is $540
Oct 17 - Oct 18
Total with taxes and fees
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
A beach with clear turquoise water and white sand.

6. 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, (30 reviews)
"Very short walk to the beach. We enjoyed our stay. "
United States
Stacey D.
$497 nightly
The price is $553
Oct 7 - Oct 8
Total with taxes and fees
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
A beach with clear turquoise water and white sand.

7. 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
9.8 out of 10, Exceptional, (52 reviews)
"Yes! The cottage was nicely decorated and we had everything we needed for our 2 night stay"
United States
J I.
$479 nightly
The price is $534
Oct 7 - Oct 8
Total with taxes and fees
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
A wooden boardwalk leading to a beach with palm trees and a pier in the background.

8. 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
$399 nightly
The price is $444
Oct 12 - Oct 13
Total with taxes and fees
Updated bayside condo with heated pool - across the street from the beach
A living room with a television, a sofa, a chair, and a view of a river.

9. 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, (129 reviews)
"Place is great and clean. Love how smooth everything was. Jenny is easy to communicate as well"
United States
Natalia D.
$523 nightly
The price is $583
Oct 7 - Oct 8
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A wooden boardwalk leading to a beach with palm trees and a pier in the background.

10. Stylish bayside condo with WiFi & pool - close to the beach & restaurants

Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Anna Maria
$399 nightly
The price is $444
Oct 13 - Oct 14
Total with taxes and fees
Stylish bayside condo with WiFi & pool - close to the beach & restaurants
A wooden boardwalk surrounded by dense foliage.

11. Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes

Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
Anna Maria
9.2 out of 10, Wonderful, (14 reviews)
"Close walk to the beach "
United States
Zev C.
$588 nightly
The price is $655
Oct 7 - Oct 8
Total with taxes and fees
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
A beach with clear turquoise water and white sand.

12. Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!

Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
Anna Maria
10.0 out of 10, Exceptional, (29 reviews)
"Cottage 107 was ver clean, comfortable, and had everything we needed. The property was quiet and very family friendly. The beach, just a very short half block walk, is gorgeous. We had a wonderful time!"
United States
Terry R.
$680 nightly
The price is $757
Oct 7 - Oct 8
Total with taxes and fees
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
A stone building with a brick pathway, palm trees, and a stone staircase.

13. The Hideaway - Less than a block from beach!

The Hideaway - Less than a block from beach!
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great. So close to the beach a 3 min walk. We loved everything about it."
United States
JASON G.
$812 nightly
The price is $906
Oct 7 - Oct 8
Total with taxes and fees
The Hideaway - Less than a block from beach!
A beach with clear turquoise water and white sand.

14. 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
10.0 out of 10, Exceptional, (23 reviews)
"Love these cottages, very close to the beach and restaurants!"
United States
Lewis E.
$676 nightly
The price is $754
Oct 12 - Oct 13
Total with taxes and fees
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave.

15. 3BR Cottage with Heated Pool – Walk to Beach & Pine Ave

3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Great sister stayHouse was perfect, pool was enjoyed by us all after a day a the beachMorning and evening at the pool We will be back for our next get together"
United States
Cheryl M.
$817 nightly
The price is $850
Oct 27 - Oct 28
Total with taxes and fees
3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

16. Waterfront dog-friendly home with heated private pool, dock, views, and lanai

Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Anna Maria
$690 nightly
The price is $768
Oct 9 - Oct 10
Total with taxes and fees
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
A coastal hotel with multiple buildings, a beach view, and a pool area.

17. Private Pool / Spa Home - Steps to Anna Maria Island Beach

Private Pool / Spa Home - Steps to Anna Maria Island Beach
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"An absolute gem! This place was perfection and we couldn’t be happier. We are already planning to hopefully come back in 2 years for our next girls trip. It was immaculately clean, beautifully decorated, so close to the beach and great location for shopping/restaurants. They had everything at the property we could think of."
United States
Erin S.
$849 nightly
The price is $887
Oct 19 - Oct 20
Total with taxes and fees
Private Pool / Spa Home - Steps to Anna Maria Island Beach
A tropical garden with a stone pathway, bamboo fence, and a staircase leading to a wooden deck.

18. 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, (22 reviews)
"Perfect location and lovely place! Would definitely stay again!"
United States
Angela W.
$473 nightly
The price is $527
Oct 7 - Oct 8
Total with taxes and fees
Beach Don't Kill My Vibe by Beach Boutique Rentals
A wooden deck with a table and chairs overlooking a calm body of water, a dock with a boat, and a clear sky.

19. Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
ANNA MARIA
9.6 out of 10, Exceptional, (123 reviews)
"We enjoyed our stay. Great location, and beautiful water view. Would defiantly stay again"
United States
Tina H.
$591 nightly
The price is $659
Oct 7 - Oct 8
Total with taxes and fees
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
A modern living room with a grey sofa, a striped armchair, a coffee table, and a bookshelf.

20. 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, (209 reviews)
"We absolutely loved this house and will be back again! The decoration is very cute and the home has many details that you notice that lots of love has been put into it. Literally 1 block from the beach, the location is perfect! They have bikes and beach gear available which was a plus. Beds were very comfortable; the kitchen had everything you need, even coffee pods! We also loved the pool and surroundings."
United States
Carolina
$702 nightly
The price is $782
Oct 21 - Oct 22
Total with taxes and fees
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
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

Charming cottage , close to beach & bay.

Charming cottage , close to beach & bay.

10/10 Excellent
"My family and I had a wonderful stay at Cindy’s place! The location is perfect, and the house was very clean! Cindy was a great communicator and helped make our stay even more enjoyable! We would definitely recommend to any families looking for a fun beach stay!"
Matthew K. 2-night trip
Posted 2 days ago
Charming cottage , close to beach & bay.

Price trends for vacation rentals in Anna Maria

Less expensive
More expensive
This month
Next month
September
March
$588
$561
Month
Price
January
$648
February
$861
March
$887
April
$725
May
$551
June
$691
July
$777
August
$571
September
$540
October
$588
November
$561
December
$708
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Anna Maria. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Anna Maria

Everything you need to know about Anna Maria 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 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Anna Maria vacation 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 low season months. For more hustle and bustle, you may prefer to visit Anna Maria 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 $782 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 rentals

At Expedia, we put the best Anna Maria 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 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 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. 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

Frequently asked questions

Can I find a vacation rental in Anna Maria?

Yes, we give you a choice of vacation rentals close to top points of interest in Anna Maria, or you can go with 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 vacation rentals that Anna Maria has to offer?

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!: Visitors give good reviews to this Anna Maria vacation home rental, which is located near the beach and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Other favorite homes for rent in Anna Maria are Perfect Anna Maria. Dock on Canal - 3 blocks to sugar sand beach. Heated pool. and Coral Cove: Walk to the Beach! Heated pool! Prime North End!.

How many vacation rentals are there in Anna Maria?

With 574 Expedia vacation rentals, you're sure 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 like Lido Beach and Tampa Bay.

What are vacation rentals like in Anna Maria?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Anna Maria. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for family trips.