A calm lake with several white birds, including herons and pelicans, on the water's edge.

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

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Our top choices for Cutthroat Harbor Estates hotels

A tropical resort with palm trees, a pool, and a wooden building.

1. Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
7.2 km from Cutthroat Harbor Estates
7.8 out of 10, Good, (1,000 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is AED 592
AED 666 total
includes taxes & fees
9 Nov - 10 Nov
Looe Key Reef Resort
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
9 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (1,000 reviews)
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
United States
Mariia
The price is AED 364
AED 409 total
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge
A covered deck with chairs and umbrellas overlooking a beach.

3. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,001 reviews)
"Super cute place and nice people! Would definitely stay again."
United States
Natalie
The price is AED 559
AED 748 total
includes taxes & fees
30 Nov - 1 Dec
Parmer's Resort
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

4. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
2.5 km from Cutthroat Harbor Estates
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is AED 1,901
AED 3,585 total
includes taxes & fees
15 Nov - 16 Nov
Atlantic View Luxury Villa with Pool
A wooden deck with a hanging hammock and a view of a green landscape.

5. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
6.1 km from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is AED 1,248
AED 2,677 total
includes taxes & fees
19 Nov - 20 Nov
Starlight Serenity - Hideaway w Stunning Views
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

6. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
13.8 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is AED 257
AED 805 total
includes taxes & fees
4 Dec - 5 Dec
Old Wooden Bridge Resort and Marina
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

7. Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
29.8 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,570 reviews)
"Would definitely stay there again"
United States
John
The price is AED 691
AED 777 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn Key West FL
A pool area with lounge chairs and gazebos, surrounded by palm trees.

8. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
4.0 star property
29.6 km from Cutthroat Harbor Estates
8.4 out of 10, Very good, (1,132 reviews)
"The hotel was a spectacular place near the airport."
United States
Suset
The price is AED 453
AED 633 total
includes taxes & fees
15 Nov - 16 Nov
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

9. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3.5 star property
29.5 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1,186 reviews)
"Amazing stay"
Canada
Sandra
The price is AED 465
AED 627 total
includes taxes & fees
15 Nov - 16 Nov
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A marina with boats docked, a pool area, and a building with a white facade.

10. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
4.0 star property
27.5 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,795 reviews)
"Great location and great staff!!"
United States
Kevin
The price is AED 434
AED 703 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Key West Resort & Marina
A swimming pool with lounge chairs and palm trees.

11. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
3.5 star property
29.5 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (1,355 reviews)
"Room was very comfortable, staff was very helpful and breakfast was good"
United States
Darlene
The price is AED 423
AED 579 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Key West / The Keys Collection
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

12. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
4.0 star property
28.4 km from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1,314 reviews)
"Good place to stay."
United States
Dharmesh Raju
The price is AED 420
AED 687 total
includes taxes & fees
30 Nov - 1 Dec
The Perry Hotel & Marina Key West
A hotel with a swimming pool, sun loungers, and palm trees.

13. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
29.6 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,775 reviews)
"Nice resort very family friendly"
United States
Sigrid A
The price is AED 459
AED 724 total
includes taxes & fees
15 Nov - 16 Nov
Blue Flamingo Resort Key West
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

14. Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
30 km from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1,337 reviews)
"We were very impressed by the quality of this Hyatt Hotel!!"
United States
Frank
The price is AED 749
AED 1,008 total
includes taxes & fees
29 Nov - 30 Nov
Hyatt Vacation Club at Windward Pointe, Key West
A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

15. The Laureate Key West

The Laureate Key West
3.5 star property
30.1 km from Cutthroat Harbor Estates
9.2 out of 10, Wonderful, (1,031 reviews)
"Great place to stay!"
United States
Eileen
The price is AED 584
AED 760 total
includes taxes & fees
10 Nov - 11 Nov
The Laureate Key West
A waterfront property with a large building featuring balconies and a covered area, boats docked in front, and palm trees in the background.

16. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
27 km from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is AED 1,613
AED 2,707 total
includes taxes & fees
30 Nov - 1 Dec
Grand Marina Suite by Brightwild Waterfront
A row of floating houses with balconies, connected by walkways, on calm water.

17. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
28.8 km from Cutthroat Harbor Estates
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is AED 414
AED 1,095 total
includes taxes & fees
9 Nov - 10 Nov
Aqua Lodges at Hurricane Hole Marina
A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

18. Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
3.5 star property
29.2 km from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1,287 reviews)
"It was clean, helpful staff, amazing location. Second time there and I hope to go back soon."
United States
Milton
The price is AED 961
AED 1,246 total
includes taxes & fees
9 Nov - 10 Nov
Hyatt Vacation Club at Beach House, Key West
A resort pool with clear blue water, surrounded by palm trees and lounge chairs.

19. Havana Cabana at Key West

Havana Cabana at Key West
4.0 star property
30.3 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,899 reviews)
"Great place to stay"
United States
Stephanie
The price is AED 529
AED 828 total
includes taxes & fees
29 Nov - 30 Nov
Havana Cabana at Key West
A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

20. Evershore House Pool Parking Dock

Evershore House Pool Parking Dock
2.0 star property
27 km from Cutthroat Harbor Estates
The price is AED 2,822
AED 5,720 total
includes taxes & fees
24 Nov - 25 Nov
Evershore House Pool Parking Dock
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.
View all properties

Compare top hotels in Cutthroat Harbor Estates

A tropical resort with palm trees, a pool, and a wooden building.

Looe Key Reef Resort

2.5 star property
7.2 km from Cutthroat Harbor Estates
View
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

Sugar Loaf Lodge

2.5 star property
9 km from Cutthroat Harbor Estates
View
A covered deck with chairs and umbrellas overlooking a beach.

Parmer's Resort

2.5 star property
9.2 km from Cutthroat Harbor Estates
View
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

Atlantic View Luxury Villa with Pool

3.5 star property
2.5 km from Cutthroat Harbor Estates
View
A wooden deck with a hanging hammock and a view of a green landscape.

Starlight Serenity - Hideaway w Stunning Views

2.0 star property
6.1 km from Cutthroat Harbor Estates
View
7.8
Good
1,000 reviews
8.2
Very good
1,000 reviews
9.0
Wonderful
1,001 reviews
7.4
Good
3 reviews
10.0
Exceptional
1 review
The price is AED 592
AED 666 total
includes taxes & fees
9 Nov - 10 Nov
The price is AED 364
AED 409 total
includes taxes & fees
30 Nov - 1 Dec
The price is AED 559
AED 748 total
includes taxes & fees
30 Nov - 1 Dec
The price is AED 1,901
AED 3,585 total
includes taxes & fees
15 Nov - 16 Nov
The price is AED 1,248
AED 2,677 total
includes taxes & fees
19 Nov - 20 Nov
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet friendly
  • No WiFi included
  • Yes, Parking

Where to stay in Cutthroat Harbor Estates

Find the best Cutthroat Harbor Estates areas and neighborhoods for the activities you enjoy most.
A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

An aerial view of a bridge over turquoise water.

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

An aerial view of a long bridge over turquoise waters with a few vehicles on it.

Bay Point

Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.

An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Big Pine Key Flea Market are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

8/10 Good
"Really nice spot. Great for families and large groups"
Floyd 2-night trip
Posted 9 hours ago
Blue Flamingo Resort Key West

Frequently asked questions

What's it like in Cutthroat Harbor Estates?
Travelers to Summerland Key's Cutthroat Harbor Estates neighborhood will be sure to enjoy a stay in this neighborhood.
What's the best accommodation in Cutthroat Harbor Estates?
For your stay in Cutthroat Harbor Estates, Just 20 miles from Key West! Oceanfront, dockage, swimming pool is one of the top choices based on our traveler data.
How many hotels will I find in Cutthroat Harbor Estates?
Expedia has 69 hotels and other accommodations in Cutthroat Harbor Estates to choose from, making this an ideal home base for exploring the greater Summerland Key area.
If I need to cancel my hotel reservation in Cutthroat Harbor Estates, will I receive a refund?
Yes! Most hotel reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of booking. Add dates, click "Search", then you can filter by "fully refundable" to view the best deals in Cutthroat Harbor Estates.
Where can I learn more about changing or cancelling my trip to Cutthroat Harbor Estates?
For more details about changing or cancelling your trip to Cutthroat Harbor Estates, click here.
What are the top things to see and do in Cutthroat Harbor Estates?
A few places to visit in the area around Cutthroat Harbor Estates include Venture Key, Out Key, and Venture Out Keys. Crab Key and Pye Key are also worth a visit when you're out sightseeing in Summerland Key.