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
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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Our top choices for Cutthroat Harbor Estates hotels

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

1. 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 Rp9.385.897
Rp17.700.579 total
includes taxes & fees
16 Nov - 17 Nov
Atlantic View Luxury Villa with Pool
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)
"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 Rp1.795.563
Rp2.020.099 total
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

3. 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 Rp2.629.684
Rp2.958.394 total
includes taxes & fees
9 Nov - 10 Nov
Looe Key Reef Resort
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

4. 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 Rp2.373.808
Rp3.263.878 total
includes taxes & fees
1 Nov - 2 Nov
Parmer's Resort
An aerial view of a large, white, two-story building with a flat roof, surrounded by dense greenery and a body of water in the background.

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 Rp6.297.682
Rp13.369.363 total
includes taxes & fees
30 Nov - 1 Dec
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, (379 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is Rp2.105.706
Rp4.919.435 total
includes taxes & fees
9 Nov - 10 Nov
Old Wooden Bridge Resort and Marina
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, (1,795 reviews)
"Great location and great staff!!"
United States
Kevin
The price is Rp2.290.340
Rp3.637.648 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Key West Resort & Marina
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, (1,571 reviews)
"Excellent location and the property it’s very clean"
United States
Heylin
The price is Rp3.411.570
Rp3.838.016 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn Key West FL
A swimming pool surrounded by palm trees and a natural rock formation.

9. 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, (1,893 reviews)
"Great place to stay"
United States
Stephanie
The price is Rp2.611.728
Rp4.089.894 total
includes taxes & fees
19 Nov - 20 Nov
Havana Cabana at Key West
A pool area with lounge chairs and gazebos, surrounded by palm trees.

10. 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, (1,126 reviews)
"The hotel was a spectacular place near the airport."
United States
Suset
The price is Rp2.419.476
Rp3.334.035 total
includes taxes & fees
1 Nov - 2 Nov
DoubleTree Resort by Hilton Grand Key - Key West
Pool

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, (2,757 reviews)
"Great place, great environment, friendly staff."
United States
Gabriel
The price is Rp2.111.162
Rp3.397.907 total
includes taxes & fees
2 Nov - 3 Nov
Blue Flamingo Resort Key West
Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

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, (1,277 reviews)
"It was clean, helpful staff, amazing location. Second time there and I hope to go back soon."
United States
Milton
The price is Rp3.705.389
Rp4.984.728 total
includes taxes & fees
28 Nov - 29 Nov
Hyatt Vacation Club at Beach House, Key West
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

13. 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 Rp3.329.953
Rp4.562.362 total
includes taxes & fees
28 Nov - 29 Nov
Hyatt Vacation Club at Windward Pointe, Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

14. 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 Rp2.268.939
Rp3.062.569 total
includes taxes & fees
29 Nov - 30 Nov
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A swimming pool with lounge chairs and palm trees.

15. 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 Rp2.093.010
Rp2.864.830 total
includes taxes & fees
17 Nov - 18 Nov
Hilton Garden Inn Key West / The Keys Collection
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

16. 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 Rp1.942.473
Rp5.291.055 total
includes taxes & fees
31 Oct - 1 Nov
Aqua Lodges at Hurricane Hole Marina
A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

17. 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 Rp2.883.783
Rp3.754.540 total
includes taxes & fees
1 Nov - 2 Nov
The Laureate Key West
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 Rp5.901.189
Rp11.057.550 total
includes taxes & fees
31 Oct - 1 Nov
Grand Marina Suite by Brightwild Waterfront
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

19. 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, (1,302 reviews)
"Absolutely amazing property and people could not recommend enough helpfully staff and great location"
United States
david
The price is Rp2.202.082
Rp2.477.342 total
includes taxes & fees
1 Nov - 2 Nov
The Perry Hotel & Marina Key West
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 Rp13.968.610
Rp28.316.198 total
includes taxes & fees
1 Nov - 2 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 popular hotels in Cutthroat Harbor Estates

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A waterfront building with a flat roof, large windows, and a balcony.
Sugar Loaf Lodge
2.5 star property
8.2
Very good
1,000 reviews
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
9.0
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
1,795 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
379 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

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

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

10/10 Excellent
"Great"
Michel 3-night trip
Posted 3 hours ago
Old Wooden Bridge Resort and 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.