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

Anna Maria Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Anna Maria holiday 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, (41 reviews)
"Amazing stay! location was perfect, the unit was clean and the host was so kind/accommodating!"
United States
Kyle K.
The price is HK$1,253
HK$3,697 total
includes taxes & fees
14 Sept - 15 Sept
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
A beach with clear turquoise water and white sand.

2. 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 HK$1,277
HK$3,802 total
includes taxes & fees
18 Sept - 19 Sept
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
A beach with clear turquoise water and white sand.

3. 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, (49 reviews)
"Yes! The cottage was nicely decorated and we had everything we needed for our 2 night stay"
United States
J I.
The price is HK$1,277
HK$3,726 total
includes taxes & fees
15 Sept - 16 Sept
Anna Maria Beach Cottage 109G Old-Florida beach cottage,moments from the sand!
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, (56 reviews)
"Great stay. "
United States
courtneyharned
The price is HK$1,244
HK$3,590 total
includes taxes & fees
14 Sept - 15 Sept
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 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 HK$1,309
HK$3,870 total
includes taxes & fees
14 Sept - 15 Sept
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
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, (29 reviews)
"Very short walk to the beach. We enjoyed our stay. "
United States
Stacey D.
The price is HK$1,309
HK$3,870 total
includes taxes & fees
14 Sept - 15 Sept
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
A covered outdoor seating area with a table and chairs, large windows, and a view of palm trees and a road.

7. 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 HK$1,008
HK$4,678 total
includes taxes & fees
30 Sept - 1 Oct
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.

8. 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 HK$1,270
HK$5,779 total
includes taxes & fees
5 Oct - 6 Oct
Emerald Shores East! Walk to Beach!
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 HK$1,595
HK$4,557 total
includes taxes & fees
14 Sept - 15 Sept
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
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.

10. 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 HK$1,694
HK$6,668 total
includes taxes & fees
29 Sept - 30 Sept
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
A wooden boardwalk leading to a beach with palm trees and a pier in the background.

11. 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
The price is HK$685
HK$3,102 total
includes taxes & fees
27 Sept - 28 Sept
Updated bayside condo with heated pool - across the street from the beach
A wooden boardwalk leading to a beach with palm trees and a pier in the background.

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

Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Anna Maria
The price is HK$577
HK$3,036 total
includes taxes & fees
21 Sept - 22 Sept
Stylish bayside condo with WiFi & pool - close to the beach & restaurants
A covered porch with a wooden bench and two green chairs, surrounded by palm trees and a white fence.

13. Dog friendly cottage - One block to the Bay!

Dog friendly cottage - One block to the Bay!
Anna Maria
9.6 out of 10, Exceptional, (15 reviews)
"Great location!"
United States
Jennifer L.
The price is HK$1,206
HK$4,383 total
includes taxes & fees
7 Sept - 8 Sept
Dog friendly cottage - One block to the Bay!
A covered outdoor area with wooden flooring, white railings, and a ceiling fan.

14. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is HK$1,567
HK$6,594 total
includes taxes & fees
9 Sept - 10 Sept
Adorable Cottage with Covered Balconies and Private Pool
An aerial view of a coastal residential area with a beach, houses, and a river.

15. Beachside Duplex w/ Pool and Private Suite

Beachside Duplex w/ Pool and Private Suite
Anna Maria
9.6 out of 10, Exceptional, (5 reviews)
"Amazing relaxing time, perfect accommodations for our budget"
United States
Sandi L.
The price is HK$1,512
HK$6,076 total
includes taxes & fees
7 Sept - 8 Sept
Beachside Duplex w/ Pool and Private Suite
A two-story building with a balcony, signs indicating no beach parking, and bicycles parked outside.

16. Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (37 reviews)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
The price is HK$1,838
HK$6,442 total
includes taxes & fees
11 Sept - 12 Sept
Beautiful Guest House Near the Beach with Private Pool!
A beach with clear turquoise water and white sand.

17. 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 HK$2,062
HK$5,191 total
includes taxes & fees
14 Sept - 15 Sept
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
A living room with a television, a sofa, a chair, and a view of a river.

18. 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)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is HK$2,344
HK$5,064 total
includes taxes & fees
7 Sept - 8 Sept
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A beach with clear turquoise water and white sand.

19. 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, (22 reviews)
"Love these cottages, very close to the beach and restaurants!"
United States
Lewis E.
The price is HK$2,062
HK$5,208 total
includes taxes & fees
14 Sept - 15 Sept
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.

20. 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.
3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
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

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10/10 Excellent
"Fantastic cottage that is a short walk to the beach. The hosts are wonderful and there are tons of amenities. Having the golf cart was a huge bonus!"
Deb L. 5-night trip
Posted 2 days ago
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

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
  • Use the map to find apartments and other holiday homes in the Anna Maria neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Anna Maria while they last

Look no further and take a look at our great range of rental properties in Anna Maria!

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?

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!: This highly rated holiday home rental in Anna Maria is located near the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Anna Maria are Coral Cove: Walk to the Beach! Heated pool! Prime North End! and ANNA MARIA GEM- adorable 3BR/2BA NEWLY REDONE HOUSE -JUST STEPS FROM THE BEACH.

How many holiday rentals are there in Anna Maria?

With 604 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.