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

This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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Our top choices for Cutthroat Harbor Estates hotels

A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

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, (1,002 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is AED 606
AED 682 total
includes taxes & fees
20 Nov - 21 Nov
Looe Key Reef Resort
A waterfront building with a flat roof, large windows, and a balcony.

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)
"We stayed for four nights. The hotel was quiet, clean, and comfortable. The staff was very friendly. Our patio had a beautiful view of the water. We had drinks and pie in the restaurant, and they were delicious. We would definitely stay there again."
United States
David
The price is AED 364
AED 409 total
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

3. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,003 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
1 Dec - 2 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
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, (384 reviews)
"Very clean for Florida keys room - no complaints easy check in and out"
United States
Anthony
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.

7. 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
8.8 out of 10, Excellent, (1,200 reviews)
"Amazing stay"
Canada
Sandra
The price is AED 493
AED 657 total
includes taxes & fees
29 Nov - 30 Nov
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

8. 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, (1,581 reviews)
"Would definitely stay there again"
United States
John
The price is AED 657
AED 740 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn Key West FL
A hotel room with a bed, a nightstand, a lamp, a painting, and a window with curtains.

9. 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, (1,143 reviews)
"This is a very comfortable place to stay"
United States
Wendi
The price is AED 482
AED 666 total
includes taxes & fees
18 Nov - 19 Nov
DoubleTree Resort by Hilton Grand Key - Key West
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, (1,792 reviews)
"Great location and great staff!!"
United States
Kevin
The price is AED 487
AED 763 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Key West Resort & Marina
A hotel with a swimming pool, sun loungers, and palm trees.

11. 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, (2,788 reviews)
"Nice resort very family friendly"
United States
Sigrid A
The price is AED 426
AED 686 total
includes taxes & fees
16 Nov - 17 Nov
Blue Flamingo Resort Key West
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, (1,316 reviews)
"Good place to stay."
United States
Dharmesh Raju
The price is AED 420
AED 688 total
includes taxes & fees
30 Nov - 1 Dec
The Perry Hotel & Marina Key West
A swimming pool with lounge chairs and palm trees.

13. 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, (1,353 reviews)
"Room was very comfortable, staff was very helpful and breakfast was good"
United States
Darlene
The price is AED 428
AED 584 total
includes taxes & fees
18 Nov - 19 Nov
Hilton Garden Inn Key West / The Keys Collection
Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

14. 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, (1,291 reviews)
"Very nice property, we enjoyed our stay!!"
United States
Joshua
The price is AED 649
AED 896 total
includes taxes & fees
30 Nov - 1 Dec
Hyatt Vacation Club at Beach House, 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, (1,038 reviews)
"Great place to stay!"
United States
Eileen
The price is AED 584
AED 760 total
includes taxes & fees
15 Nov - 16 Nov
The Laureate Key West
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

16. 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, (1,339 reviews)
"We were very impressed by the quality of this Hyatt Hotel!!"
United States
Frank
The price is AED 631
AED 875 total
includes taxes & fees
18 Nov - 19 Nov
Hyatt Vacation Club at Windward Pointe, Key West
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the 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 580
AED 1,288 total
includes taxes & fees
16 Nov - 17 Nov
Aqua Lodges at Hurricane Hole Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

18. 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 1,430
AED 2,502 total
includes taxes & fees
15 Nov - 16 Nov
Grand Marina Suite by Brightwild Waterfront
A swimming pool surrounded by palm trees and a natural rock formation.

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, (1,902 reviews)
"Great hotel, great food, great staff, 5 stars, I am looking to book again now."
United States
Robert
The price is AED 431
AED 717 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 rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

Looe Key Reef Resort

2.5 star property
7.2 km from Cutthroat Harbor Estates
View
A waterfront building with a flat roof, large windows, and a balcony.

Sugar Loaf Lodge

2.5 star property
9 km from Cutthroat Harbor Estates
View
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

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 cozy room with a brown leather sofa, a white table, and a ceiling fan.

Old Wooden Bridge Resort and Marina

2.5 star property
13.8 km from Cutthroat Harbor Estates
View
7.8
Good
1,002 reviews
8.2
Very good
1,000 reviews
9.0
Wonderful
1,003 reviews
7.4
Good
3 reviews
8.6
Excellent
384 reviews
The price is AED 606
AED 682 total
includes taxes & fees
20 Nov - 21 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
1 Dec - 2 Dec
The price is AED 1,901
AED 3,585 total
includes taxes & fees
15 Nov - 16 Nov
The price is AED 257
AED 805 total
includes taxes & fees
4 Dec - 5 Dec
  • 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
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, 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

Hampton Inn Key West FL

Hampton Inn Key West FL

8/10 Good
"The view from our room was wonderful. The pool was clean and staff was friendly."
Jennifer 6-night trip
Posted 7 hours ago
Hampton Inn Key West FL

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.