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

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Check prices for these dates

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

Our top choices for Anna Maria vacation homes

A modern living room with a grey sofa, a coffee table, and a view of a kitchen and dining area through a doorway.

1. Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B

Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B
Anna Maria
9.8 out of 10, Exceptional, (32 reviews)
"I was impressed with how clean this place is. Location was very close to the beach and all restaurants. Host was very responsive. Definitely will come back!!"
United States
Randa B.
The price is ￥24,159
￥101,411 total
includes taxes & fees
Sep 3 - Sep 4
Dog-Friendly 4 Mins to the Beach and Pine Ave - A Place in Paradise Unit B
An aerial view of a coastal residential area with a sandy beach, houses, and a river.

2. 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 ￥30,626
￥125,788 total
includes taxes & fees
Sep 4 - Sep 5
Emerald Shores East! Walk to Beach!
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.

3. 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 ￥34,515
￥137,655 total
includes taxes & fees
Sep 23 - Sep 24
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
A covered porch with a wooden bench and two green chairs, surrounded by palm trees and a white fence.

4. 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 ￥24,571
￥90,451 total
includes taxes & fees
Sep 7 - Sep 8
Dog friendly cottage - One block to the Bay!
A beach with gentle waves and a sunset.

5. Do you love the beach?

Do you love the beach?
Anna Maria
10.0 out of 10, Exceptional, (160 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 ￥38,422
￥88,617 total
includes taxes & fees
Sep 3 - Sep 4
Do you love the beach?
A modern kitchen with white cabinetry, a central island, bar stools, and a stainless steel refrigerator.

6. Luxury North End Escape | 3 king beds + pool/spa

Luxury North End Escape | 3 king beds + pool/spa
Anna Maria
9.8 out of 10, Exceptional, (9 reviews)
"Great place! "
United States
Kim K.
The price is ￥27,244
￥138,482 total
includes taxes & fees
Sep 7 - Sep 8
Luxury North End Escape | 3 king beds + pool/spa
An aerial view of a coastal residential area with a beach, houses, and a river.

7. 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 ￥30,820
￥125,267 total
includes taxes & fees
Sep 7 - Sep 8
Beachside Duplex w/ Pool and Private Suite
A beach with clear turquoise water and white sand.

8. 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 ￥42,017
￥105,796 total
includes taxes & fees
Sep 14 - Sep 15
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
A stone building with a brick pathway, palm trees, and a stone staircase.

9. 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.
The price is ￥32,359
￥133,607 total
includes taxes & fees
Sep 3 - Sep 4
The Hideaway - Less than a block from beach!
A beach with clear turquoise water and white sand.

10. 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 ￥42,018
￥106,137 total
includes taxes & fees
Sep 14 - Sep 15
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
A backyard with a swimming pool, a thatched umbrella, and a rock feature.

11. Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT

Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT
Anna Maria
9.6 out of 10, Exceptional, (10 reviews)
"A wonderful property for our girls trip . Beach access right across the street. The pool and slide and hot tub were perfect after a day at the beach. Lots of shops and restaurants within walking distance. . Our host Jen was wonderful and our place was very clean and the beds were comfy, We had a great weekend ! would definitely come back to the island again."
United States
Pam R.
The price is ￥34,057
￥182,314 total
includes taxes & fees
Sep 9 - Sep 10
Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT
A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave.

12. 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
A coastal hotel with multiple buildings, a beach view, and a pool area.

13. 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.
Private Pool / Spa Home - Steps to Anna Maria Island Beach
A dining table set with wine glasses, a basket of flowers, and placemats.

14. Vintage Cottage: Pool and Walk to Beach, Pine Ave Shops

Vintage Cottage: Pool and Walk to Beach, Pine Ave Shops
Anna Maria
9.2 out of 10, Wonderful, (14 reviews)
"I booked for the weekend and had a good time with my friend and family members; the property was clean and neat it has everything that you need for a pleasant stay. I would highly recommend it!!!"
United States
IVETTE K.
The price is ￥40,624
￥141,330 total
includes taxes & fees
Sep 22 - Sep 23
Vintage Cottage: Pool and Walk to Beach, Pine Ave Shops
A beach with clear turquoise water and white sand.

15. Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!

Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
Anna Maria
9.8 out of 10, Exceptional, (48 reviews)
"Our stay was amazing! Very short walk to the beach was a bonus. Bathrooms were well stocked having the pool close was great and walking downtown was very close. Definitely will be back."
United States
Cheryl L.
The price is ￥44,810
￥118,615 total
includes taxes & fees
Sep 14 - Sep 15
Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
An aerial view of a coastal residential area with houses, a beach, and a clear view of the ocean.

16. Duplex with Heated Pool! 2 Blocks to Beach! - Turtle Crawl

Duplex with Heated Pool! 2 Blocks to Beach! - Turtle Crawl
Anna Maria
9.6 out of 10, Exceptional, (30 reviews)
"Enjoyed our stay the place was beautiful and very close to everything "
United States
Maria A.
The price is ￥42,082
￥123,978 total
includes taxes & fees
Sep 13 - Sep 14
Duplex with Heated Pool! 2 Blocks to Beach! - Turtle Crawl
A spacious kitchen with a marble countertop, wooden ceiling, and a built-in refrigerator.

17. Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
Anna Maria
9.8 out of 10, Exceptional, (87 reviews)
"Property was extremely clean, as advertised in the listings, and a great experience."
United States
Zach C.
The price is ￥40,661
￥128,389 total
includes taxes & fees
Sep 8 - Sep 9
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
A beach with clear turquoise water and white sand.

18. 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, (38 reviews)
"Perfect beach cottage"
United States
Jane S.
The price is ￥51,291
￥134,526 total
includes taxes & fees
Sep 20 - Sep 21
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
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.
The price is ￥47,903
￥106,719 total
includes taxes & fees
Sep 8 - Sep 9
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
A spacious kitchen with a large island, stainless steel appliances, and a chandelier.

20. Pine Avenue next door!~Heated pool~Steps to Beach

Pine Avenue next door!~Heated pool~Steps to Beach
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Nice size rooms. Pool was in the shade but very clean. All around a great stay"
United States
Kelly F.
Pine Avenue next door!~Heated pool~Steps to Beach
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

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

10/10 Excellent
"MyMy wife and I planned a short getaway to check out a place we’ve never visited. The bungalow was perfect. Clean and could not be in a better location. Right off of Bean Point Beach with several small beach shops, pizza, taco, BBQ, coffee, and ICE CREAM next door! The host was very accommodating. We definitely plan on coming back. Thank you for hosting us and we look forward to our next visit!"
Christopher W. 4-night trip
Posted 9 hours ago
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Find out more about Anna Maria

Anna Maria Vacation Homes information

Number of reviews
631
Accommodation
953 Vacation Homes
Lowest Price
￥88,617
Highest Price
￥182,314