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

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Oct 30 - Nov 1
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Nov 6 - Nov 8

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Our top choices for Cutthroat Harbor Estates hotels

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

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)
"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 ￥18,775
￥21,123 total
includes taxes & fees
Nov 1 - Nov 2
Sugar Loaf Lodge
A tropical resort with palm trees, a pool, and a wooden building.

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 ￥22,875
￥25,734 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥20,595
￥28,316 total
includes taxes & fees
Nov 1 - Nov 2
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, (1,125 reviews)
"Very nice, would stay again."
United States
Danee
The price is ￥21,627
￥29,655 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

5. 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, (1,571 reviews)
"Excellent location and the property it’s very clean"
United States
Heylin
The price is ￥30,607
￥34,434 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn Key West FL
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

6. 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, (1,174 reviews)
"Amazing stay"
Canada
Sandra
The price is ￥19,737
￥26,640 total
includes taxes & fees
Nov 29 - Nov 30
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.

7. 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, (1,794 reviews)
"Great location and great staff!!"
United States
Kevin
The price is ￥19,923
￥31,643 total
includes taxes & fees
Nov 17 - Nov 18
Hilton Key West Resort & Marina
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

8. 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, (378 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is ￥14,057
￥38,000 total
includes taxes & fees
Oct 30 - Oct 31
Old Wooden Bridge Resort and Marina
Pool

9. 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, (2,756 reviews)
"Great place, great environment, friendly staff."
United States
Gabriel
The price is ￥18,317
￥29,481 total
includes taxes & fees
Nov 1 - Nov 2
Blue Flamingo Resort Key West
A resort pool with clear blue water, surrounded by palm trees and lounge chairs.

10. 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, (1,892 reviews)
"Great place to stay"
United States
Stephanie
The price is ￥22,719
￥35,577 total
includes taxes & fees
Nov 19 - Nov 20
Havana Cabana at Key West
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

11. 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, (1,329 reviews)
"Nice and clean hotel with good amenities and central location"
United States
Leismy
The price is ￥26,911
￥37,375 total
includes taxes & fees
Nov 28 - Nov 29
Hyatt Vacation Club at Windward Pointe, Key West
A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

12. 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, (1,275 reviews)
"It was clean, helpful staff, amazing location. Second time there and I hope to go back soon."
United States
Milton
The price is ￥29,654
￥40,461 total
includes taxes & fees
Nov 28 - Nov 29
Hyatt Vacation Club at Beach House, 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, (1,349 reviews)
"Room was very comfortable, staff was very helpful and breakfast was good"
United States
Darlene
The price is ￥18,207
￥24,921 total
includes taxes & fees
Nov 17 - Nov 18
Hilton Garden Inn Key West / The Keys Collection
A row of floating houses with balconies, connected by walkways, on calm water.

14. 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, (201 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ￥17,218
￥46,397 total
includes taxes & fees
Oct 30 - Oct 31
Aqua Lodges at Hurricane Hole Marina
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

15. 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 ￥81,646
￥153,973 total
includes taxes & fees
Nov 15 - Nov 16
Atlantic View Luxury Villa with Pool
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, (1,030 reviews)
"Great place to stay!"
United States
Eileen
The price is ￥25,085
￥32,659 total
includes taxes & fees
Nov 1 - Nov 2
The Laureate Key West
A wooden deck with a hanging hammock and a view of a green landscape.

17. 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 ￥61,356
￥123,694 total
includes taxes & fees
Nov 19 - Nov 20
Starlight Serenity - Hideaway w Stunning Views
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

18. 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, (1,301 reviews)
"Absolutely amazing property and people could not recommend enough helpfully staff and great location"
United States
david
The price is ￥19,800
￥31,505 total
includes taxes & fees
Nov 17 - Nov 18
The Perry Hotel & Marina 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.

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 ￥51,200
￥95,938 total
includes taxes & fees
Oct 30 - Oct 31
Grand Marina Suite by Brightwild Waterfront
A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

20. The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
29.8 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is ￥44,838
￥95,169 total
includes taxes & fees
Nov 1 - Nov 2
The Grenada Suite Pool View Private Balcony
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 popular hotels in Cutthroat Harbor Estates

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
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
8.2
Very good
1,000 reviews
View
A covered deck with chairs and umbrellas overlooking a beach.
Parmer's Resort
2.5 star property
9.0
Wonderful
1,000 reviews
View
A marina with boats docked, a pool area, and a building with a white facade.
Hilton Key West Resort & Marina
4.0 star property
9.0
Wonderful
1,794 reviews
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
8.6
Excellent
378 reviews
View
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.
Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
9.4
Exceptional
1,329 reviews
View

Hotels recommended for families in Cutthroat Harbor Estates

A pool area with multiple swimming pools, lounge chairs, and palm trees.

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
10.0 out of 10, Exceptional, (1)
The price is ￥17,741
￥62,813 total
includes taxes & fees
Oct 30 - Oct 31
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

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

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"Great stay for second time"
Lesley 4-night trip
Posted 1 hour ago
The Perry Hotel & Marina 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.

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