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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Anna Maria holiday homes

Smart TV

1. Tiny Tides: Adorable Cozy House!

Tiny Tides: Adorable Cozy House!
Anna Maria
9.4 out of 10, Exceptional, (6 reviews)
"The weather and peacefulness of the island. "
United States
karen l.
Tiny Tides: Adorable Cozy House!
TV, ping pong, offices

2. 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)
"Everything was clean, great location right near the beach, the kids loved everything and the pool was amazing! Wish the propane tanks got replaced before we checked in as we would have loved to use the grill."
United States
Emily I.
The price is £639
includes taxes & fees
22 Sept - 23 Sept
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
Terrace/patio

3. 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 £435
includes taxes & fees
24 Sept - 25 Sept
Dog friendly cottage - One block to the Bay!
Outdoor dining

4. 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 £480
includes taxes & fees
11 Oct - 12 Oct
Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit
Beach nearby

5. 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 £581
includes taxes & fees
22 Sept - 23 Sept
Beachside Duplex w/ Pool and Private Suite
Beach nearby, sun-loungers

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 £503
includes taxes & fees
22 Sept - 23 Sept
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
Coffee/tea maker, fridge, microwave, oven

7. 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, (10 reviews)
"Great place! "
United States
Kim K.
The price is £643
includes taxes & fees
22 Sept - 23 Sept
Luxury North End Escape | 3 king beds + pool/spa
Beach nearby

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 £562
includes taxes & fees
5 Oct - 6 Oct
Emerald Shores East! Walk to Beach!
Exterior

9. 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.
The price is £601
includes taxes & fees
29 Sept - 30 Sept
Private Pool / Spa Home - Steps to Anna Maria Island Beach
Exterior

10. 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, (215 reviews)
"It was great!"
United States
Megan
The price is £562
includes taxes & fees
4 Oct - 5 Oct
SEPT. OCT. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
Beach nearby, sun-loungers

11. 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 £505
includes taxes & fees
25 Sept - 26 Sept
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
Coffee/tea maker, fridge, microwave, oven

12. 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
The price is £602
includes taxes & fees
27 Sept - 28 Sept
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Beach nearby, sun-loungers

13. 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, (49 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 £560
includes taxes & fees
25 Sept - 26 Sept
Anna Maria Beach Cottage 110 Traditional beach cottage, moments from the sand!
Outdoor pool, a heated pool

14. 4 King Beds + Guest House • Heated Pool/Spa

4 King Beds + Guest House • Heated Pool/Spa
Anna Maria
The price is £647
includes taxes & fees
27 Sept - 28 Sept
4 King Beds + Guest House • Heated Pool/Spa
3 bedrooms, iron/ironing board, free WiFi, bed sheets

15. Hammock Dreams - Canal Home with Pool and Dock Near Beach

Hammock Dreams - Canal Home with Pool and Dock Near Beach
Anna Maria
9.6 out of 10, Exceptional, (17 reviews)
"Very happy with accommodation."
United States
Julie T.
The price is £596
includes taxes & fees
4 Oct - 5 Oct
Hammock Dreams - Canal Home with Pool and Dock Near Beach
On the beach

16. Do you love the beach?

Do you love the beach?
Anna Maria
10.0 out of 10, Exceptional, (162 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 £519
includes taxes & fees
22 Sept - 23 Sept
Do you love the beach?
Marina

17. 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 £499
includes taxes & fees
22 Sept - 23 Sept
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
Beach nearby

18. 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)
"The house was recently remodeled and in amazing condition. It was very clean and the shed had tons of beach gear to use."
United States
Ashley S.
The price is £585
includes taxes & fees
20 Oct - 21 Oct
Duplex with Heated Pool! 2 Blocks to Beach! - Turtle Crawl
Dining

19. Luxury Coastal Retreat with Pool and Rooftop Deck!

Luxury Coastal Retreat with Pool and Rooftop Deck!
Anna Maria
8.0 out of 10, Very good, (3 reviews)
"Great house! Very comfortable, clean and a block from the beach. Mattresses could be a bit better, but overall amazing stay!"
United States
Tania S.
The price is £740
includes taxes & fees
22 Sept - 23 Sept
Luxury Coastal Retreat with Pool and Rooftop Deck!
Beach nearby, sun-loungers

20. 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 £626
includes taxes & fees
4 Oct - 5 Oct
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/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

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

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

10/10 Excellent
"We had a wonderful stay with Dan and Goose. The house is stocked with anything you could ever imagine needing. I cannot say enough great things about our stay and would recommend Dan and Goose to everyone. We will be back!"
Tiffiny D. 3-night trip
Posted 3 hours ago
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Find out more about Anna Maria

Anna Maria Holiday Homes information

Number of reviews
2
Accommodation
954 Holiday Homes
Lowest Price
£353
Highest Price
£353

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