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 beachside dining area with thatched umbrellas, white plastic chairs, and tables.

1. 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 Rp1.805.661
Rp2.031.460 total
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

2. 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 Rp2.994.041
Rp3.368.297 total
includes taxes & fees
20 Nov - 21 Nov
Looe Key Reef Resort
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, (1,000 reviews)
"Super cute place and nice people! Would definitely stay again."
United States
Natalie
The price is Rp2.774.152
Rp3.736.486 total
includes taxes & fees
1 Dec - 2 Dec
Parmer's Resort
A pool area with lounge chairs and gazebos, surrounded by palm trees.

4. 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, (1,142 reviews)
"This is a very comfortable place to stay"
United States
Wendi
The price is Rp2.453.745
Rp3.372.992 total
includes taxes & fees
29 Nov - 30 Nov
DoubleTree Resort by Hilton Grand Key - Key West
A swimming pool with lounge chairs and palm trees, surrounded by a paved area.

5. 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, (1,317 reviews)
"Good place to stay."
United States
Dharmesh Raju
The price is Rp2.098.219
Rp3.422.213 total
includes taxes & fees
30 Nov - 1 Dec
The Perry Hotel & Marina Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

6. 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 Rp3.248.671
Rp3.654.755 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn Key West FL
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

7. 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 Rp9.392.107
Rp17.712.289 total
includes taxes & fees
15 Nov - 16 Nov
Atlantic View Luxury Villa with Pool
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

8. 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, (1,203 reviews)
"Amazing stay"
Canada
Sandra
The price is Rp2.445.850
Rp3.264.462 total
includes taxes & fees
29 Nov - 30 Nov
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

9. 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 Rp3.430.756
Rp4.680.355 total
includes taxes & fees
30 Nov - 1 Dec
Hyatt Vacation Club at Beach House, Key West
A bathroom with a blue and white color scheme, a white sink, a mirror, a shower, and a wooden floor.

10. 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, (2,794 reviews)
"Nice resort very family friendly"
United States
Sigrid A
The price is Rp2.107.099
Rp3.391.504 total
includes taxes & fees
15 Nov - 16 Nov
Blue Flamingo Resort Key West
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

11. 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 Rp1.274.764
Rp3.998.969 total
includes taxes & fees
4 Dec - 5 Dec
Old Wooden Bridge Resort and Marina
A covered outdoor area with a round table and wicker chairs, overlooking a pool and palm trees.

12. 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, (1,340 reviews)
"We were very impressed by the quality of this Hyatt Hotel!!"
United States
Frank
The price is Rp3.577.168
Rp4.841.246 total
includes taxes & fees
18 Nov - 19 Nov
Hyatt Vacation Club at Windward Pointe, Key West
A marina with boats docked, a pool area, and a building with a white facade.

13. 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 Rp2.404.380
Rp3.766.645 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Key West Resort & Marina
A wooden deck with a swing chair and a view of a lake.

14. 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 Rp5.819.408
Rp12.866.648 total
includes taxes & fees
19 Nov - 20 Nov
Starlight Serenity - Hideaway w Stunning Views
A resort pool with clear blue water, surrounded by palm trees and lounge chairs.

15. 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, (1,903 reviews)
"Great hotel, great food, great staff, 5 stars, I am looking to book again now."
United States
Robert
The price is Rp2.516.982
Rp3.988.505 total
includes taxes & fees
29 Nov - 30 Nov
Havana Cabana at Key West
A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

16. 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, (1,041 reviews)
"Great place to stay!"
United States
Eileen
The price is Rp2.885.691
Rp3.757.024 total
includes taxes & fees
16 Nov - 17 Nov
The Laureate Key West
A swimming pool with lounge chairs and palm trees.

17. 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 Rp2.183.869
Rp2.967.384 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Key West / The Keys Collection
A wooden deck with a table and chairs, overlooking a calm water body with boats and a house in the background.

18. 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 Rp2.760.463
Rp6.240.912 total
includes taxes & fees
15 Nov - 16 Nov
Aqua Lodges at Hurricane Hole Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

19. 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 Rp7.067.859
Rp12.361.547 total
includes taxes & fees
18 Nov - 19 Nov
Grand Marina Suite by Brightwild Waterfront
A white two-story house with a balcony and a swimming pool.

20. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
27.1 km from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is Rp21.746.971
Rp37.104.968 total
includes taxes & fees
16 Nov - 17 Nov
Capmar House by Brightwild Huge Home 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.
View all properties

Compare top hotels in Cutthroat Harbor Estates

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

Sugar Loaf Lodge

2.5 star property
9 km from Cutthroat Harbor Estates
View
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

Looe Key Reef Resort

2.5 star property
7.2 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 pool area with lounge chairs and gazebos, surrounded by palm trees.

DoubleTree Resort by Hilton Grand Key - Key West

4.0 star property
29.6 km from Cutthroat Harbor Estates
View
A swimming pool with lounge chairs and palm trees, surrounded by a paved area.

The Perry Hotel & Marina Key West

4.0 star property
28.4 km from Cutthroat Harbor Estates
View
8.2
Very good
1,000 reviews
7.8
Good
1,000 reviews
9.0
Wonderful
1,000 reviews
8.4
Very good
1,142 reviews
9.4
Exceptional
1,317 reviews
The price is Rp1.805.661
Rp2.031.460 total
includes taxes & fees
30 Nov - 1 Dec
The price is Rp2.994.041
Rp3.368.297 total
includes taxes & fees
20 Nov - 21 Nov
The price is Rp2.774.152
Rp3.736.486 total
includes taxes & fees
1 Dec - 2 Dec
The price is Rp2.453.745
Rp3.372.992 total
includes taxes & fees
29 Nov - 30 Nov
The price is Rp2.098.219
Rp3.422.213 total
includes taxes & fees
30 Nov - 1 Dec
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, 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 for the activities you enjoy most.
A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.

An aerial view of a bridge over turquoise water.

Cudjoe Gardens

While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Florida Keys Beaches.

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

Bay Point

While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.

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 there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Cook Island and Big Pine Key Flea Market.

Top Cutthroat Harbor Estates Hotel Reviews

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"Room was very nice size and clean. This hotel is tucked away and feels like a resort. Would definitely stay here again. Had dinner the last night in the hotel restaurant and food and service was great. Hourly free shuttles to the downtown area is super convenient."
Lisa 2-night trip
Posted 7 hours ago
Hilton Key West Resort & Marina

Frequently asked questions

What's it like in Cutthroat Harbor Estates?
Travellers to Summerland Key's Cutthroat Harbor Estates neighbourhood will be sure to enjoy a stay here.
How many hotels are there in Cutthroat Harbor Estates?
Expedia has 69 hotels and other accommodation options 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 bookings are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Add dates, click "Search", then use the filter option "fully refundable" to get the best options available in Cutthroat Harbor Estates.
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.