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

Anna Maria Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Anna Maria vacation rentals

A beach with clear turquoise water and white sand.

1. 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, (42 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
The price is ￥25,159
￥74,550 total
includes taxes & fees
Oct 4 - Oct 5
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
A beach with gentle waves and a sunset.

2. Do you love the beach?

Do you love the beach?
Anna Maria
10.0 out of 10, Exceptional, (163 reviews)
"We really enjoyed this location - steps away from the beach was awesome. Also walking distance from some of our favorite spots (Waterfront, Donut Experiment, North Shore, Poppo’s, Two Scoops). We will be booking this spot on our next trip to Anna Maria."
United States
Zachary Z.
The price is ￥42,813
￥93,227 total
includes taxes & fees
Oct 2 - Oct 3
Do you love the beach?
A covered outdoor area with wooden flooring, white railings, and a ceiling fan.

3. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (53 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is ￥39,091
￥142,758 total
includes taxes & fees
Oct 3 - Oct 4
Adorable Cottage with Covered Balconies and Private Pool
A living room with a television, a sofa, a chair, and a view of a river.

4. 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.
The price is ￥39,200
￥91,832 total
includes taxes & fees
Oct 2 - Oct 3
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A modern kitchen with white cabinets, a marble island, green stools, stainless steel appliances, and a pendant light fixture.

5. Sea Whisper: North End gem w/ pool & dock

Sea Whisper: North End gem w/ pool & dock
Anna Maria
9.6 out of 10, Exceptional, (71 reviews)
"We really enjoyed our stay on AMI. The interior of the house is updated and clean. The pool is very nice and refreshing after a hot day at the beach or kayaking. The living room area is very small with seating only for four though the dining table is large plus bar stool sesting. The screened porch, yard and dock could use some maintenance and upkeep. The dock really needs a ladder and the launch needs to be repositioned for easier access. Overall a good property that met our needs. The owner...
United States
Anonymous traveler
The price is ￥78,685
￥146,228 total
includes taxes & fees
Oct 3 - Oct 4
Sea Whisper: North End gem w/ pool & dock
A beach with clear turquoise water and white sand.

6. 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.
The price is ￥41,380
￥104,665 total
includes taxes & fees
Oct 3 - Oct 4
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
A spacious living area with a high ceiling, a dining table with chairs, a gray sofa, a television, and a staircase leading to an upper level.

7. Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!

Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
Anna Maria
9.8 out of 10, Exceptional, (73 reviews)
"This house is in an excellent location halfway between the bay and the gulf, on a street very close to dining, shopping, etc. and yet quiet. Took only four minutes to walk to coffee shop, eight minutes to the beach and restaurants. House was perfect for our family weekend vacation. We all enjoyed the pool. Washer/dryer on site was convenient. Check in was super easy with door code. Property was clean. Everything worked out well, no issues."
United States
Teresa
The price is ￥38,921
￥140,410 total
includes taxes & fees
Oct 7 - Oct 8
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
A tropical garden with a stone pathway, bamboo fence, and a staircase leading to a wooden deck.

8. 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)
"Great location, accurate description and photos, host was very welcoming."
United States
Justin W.
The price is ￥61,602
￥85,231 total
includes taxes & fees
Oct 5 - Oct 6
Beach Don't Kill My Vibe by Beach Boutique Rentals
A wooden boardwalk surrounded by dense foliage.

9. 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.
The price is ￥32,032
￥92,128 total
includes taxes & fees
Oct 2 - Oct 3
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
A wooden boardwalk surrounded by dense foliage.

10. 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, (57 reviews)
"Great stay. "
United States
courtneyharned
The price is ￥24,978
￥72,376 total
includes taxes & fees
Oct 4 - Oct 5
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
A modern living room with a blue sofa, a TV, and a kitchen area with a white countertop and bar stools.

11. Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!

Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
Anna Maria
9.6 out of 10, Exceptional, (45 reviews)
"My husband and I had a great week staying here. We had everything that we needed for our stay, the house was very comfortable. We loved spending time in the pool and spa!"
United States
Jesse Z.
The price is ￥35,989
￥135,488 total
includes taxes & fees
Oct 26 - Oct 27
Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
A beach with clear turquoise water and white sand.

12. 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.
The price is ￥26,281
￥78,176 total
includes taxes & fees
Oct 4 - Oct 5
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
A beach with clear turquoise water and white sand.

13. 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.
The price is ￥41,398
￥105,042 total
includes taxes & fees
Oct 3 - Oct 4
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
A beach with clear turquoise water and white sand.

14. 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, (30 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.
The price is ￥26,271
￥78,146 total
includes taxes & fees
Oct 4 - Oct 5
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
A beach with clear turquoise water and white sand.

15. Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!

Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
Anna Maria
10.0 out of 10, Exceptional, (39 reviews)
"Perfect beach cottage"
United States
Jane S.
The price is ￥50,533
￥132,381 total
includes taxes & fees
Oct 2 - Oct 3
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
A beachfront property with a two-story house, a sandy beach, and several Adirondack chairs.

16. SEPT. OCT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

SEPT. OCT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
Anna Maria
9.6 out of 10, Exceptional, (216 reviews)
"Fantastic stay! Extremely clean and the location is perfect. The private beach was a great addition to our stay."
United States
Anonymous traveler
The price is ￥43,293
￥115,561 total
includes taxes & fees
Oct 4 - Oct 5
SEPT. OCT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
A beach with clear turquoise water and white sand.

17. 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.
The price is ￥31,978
￥85,034 total
includes taxes & fees
Oct 17 - Oct 18
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
A covered outdoor seating area with a table and chairs, large windows, and a view of palm trees and a road.

18. 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.
The price is ￥18,526
￥91,469 total
includes taxes & fees
Oct 7 - Oct 8
Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit
An aerial view of a coastal residential area with a sandy beach, houses, and a river.

19. Emerald Shores East! Walk to Beach!

Emerald Shores East! Walk to Beach!
Anna Maria
9.0 out of 10, Wonderful, (12 reviews)
"Clean spot and a great stay. Amazing location and 10/10 service / review. "
United States
Christopher B.
The price is ￥25,494
￥115,834 total
includes taxes & fees
Oct 5 - Oct 6
Emerald Shores East! Walk to Beach!
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, (208 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
The price is ￥62,791
￥123,035 total
includes taxes & fees
Oct 21 - Oct 22
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

Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.

Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.

10/10 Excellent
"We stayed in this beautiful , clean, fully equipped and comfortable home during our mini vacation. The place is within 5 minute walk to the beach. I would definitely recommend it to my family and friends."
Justyna N. 4-night trip
Posted 1 day ago
Cozy North end hideaway! 5-min walk to beautiful white sand beach at Bean Point.

Find out more about Anna Maria

Search for holiday rentals in Anna Maria on Expedia! You can easily find your home rentals, villas, holiday apartments in Anna Maria using one of the methods below:

  • View our selection of featured holiday rentals in Anna Maria
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Look no further and take a look at our great range of rental properties in Anna Maria!

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.