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

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Sep 11 - Sep 13
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Sep 18 - Sep 20

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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
7.6 out of 10, Good, (1,002 reviews)
"Great place to stay!"
United States
Sarah
The price is ₩101,859
₩114,591 total
includes taxes & fees
Sep 7 - Sep 8
Looe Key Reef Resort
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

2. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,010 reviews)
"A typical "keys style" resort that had everything we needed with a kitchen, deck seating, a dock for our boat. Enjoyed the Complimentary coffee. Will be back with the family + dog"
United States
Matthew
The price is ₩225,950
₩298,119 total
includes taxes & fees
Sep 10 - Sep 11
Parmer's Resort
A waterfront building with a flat roof, large windows, and a balcony.

3. 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)
"A clean comfortable room, with a lovely view from the back patio! All staff were very helpful."
United States
Marjorie
The price is ₩160,191
₩180,222 total
includes taxes & fees
Sep 7 - Sep 8
Sugar Loaf Lodge
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

4. 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, (367 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
The price is ₩121,141
₩325,585 total
includes taxes & fees
Sep 7 - Sep 8
Old Wooden Bridge Resort and Marina
A wooden deck with a railing, a chair, 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 ₩313,210
₩843,786 total
includes taxes & fees
Sep 7 - Sep 8
Starlight Serenity - Hideaway w Stunning Views
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

6. 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 ₩696,628
₩1,313,749 total
includes taxes & fees
Sep 9 - Sep 10
Atlantic View Luxury Villa with Pool
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, (1,821 reviews)
"Awesome place to stay at!"
United States
Linda
The price is ₩153,433
₩253,084 total
includes taxes & fees
Sep 16 - Sep 17
Hilton Key West Resort & Marina
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
8.6 out of 10, Excellent, (1,109 reviews)
"Great accommodation"
United States
Fernando
The price is ₩156,287
₩213,676 total
includes taxes & fees
Sep 16 - Sep 17
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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, (2,655 reviews)
"We had a great time at this hotel, clean room, great views, exceptional hospitality from the staff!"
United States
REBECCA
The price is ₩147,604
₩241,775 total
includes taxes & fees
Sep 7 - Sep 8
Blue Flamingo Resort Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

10. 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, (1,486 reviews)
"Staff are very friendly and the pool area is beautiful"
United States
Melisa
The price is ₩186,548
₩209,867 total
includes taxes & fees
Sep 20 - Sep 21
Hampton Inn Key West FL
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

11. 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, (1,085 reviews)
"Excellent place love it"
United States
Jose
The price is ₩147,914
₩211,835 total
includes taxes & fees
Sep 15 - Sep 16
DoubleTree Resort by Hilton Grand Key - Key West
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

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, (1,262 reviews)
"Great hotel to stay 👌"
United States
Mauricio
The price is ₩255,875
₩348,435 total
includes taxes & fees
Sep 22 - Sep 23
Hyatt Vacation Club at Windward Pointe, Key West
A balcony with wicker furniture, a view of the sea, and a spiral staircase.

13. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,491 reviews)
"Enjoyed my stay"
United States
Jerome
The price is ₩129,297
₩274,183 total
includes taxes & fees
Sep 7 - Sep 8
Beachside Resort & Residences
A swimming pool with lounge chairs and palm trees.

14. 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, (1,313 reviews)
"Entire stay was fabulous"
United States
Amanda
The price is ₩152,814
₩209,783 total
includes taxes & fees
Sep 14 - Sep 15
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.

15. 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, (1,327 reviews)
"very good better than hotel on key west main island"
United States
Boyan
The price is ₩189,940
₩296,698 total
includes taxes & fees
Sep 20 - Sep 21
The Perry Hotel & Marina 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, (1,009 reviews)
"Such a nice hotel to stay at!"
United States
Jayce
The price is ₩214,036
₩278,664 total
includes taxes & fees
Sep 7 - Sep 8
The Laureate Key West
Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

17. 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, (1,229 reviews)
"We loved our stay at the Hyatt Vacation Club! The property was very clean as were the rooms and I enjoyed the kitchen and screened in porch area in each suite."
United States
Kailey
The price is ₩280,105
₩375,694 total
includes taxes & fees
Oct 5 - Oct 6
Hyatt Vacation Club at Beach House, Key West

18. Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
29.3 km from Cutthroat Harbor Estates
The price is ₩314,828
₩470,791 total
includes taxes & fees
Sep 7 - Sep 8
Ocean Front One Bedroom Residence
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

19. 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, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ₩144,172
₩387,840 total
includes taxes & fees
Sep 7 - Sep 8
Aqua Lodges at Hurricane Hole Marina
A dining area with a wooden table and teal chairs, a sofa with blue cushions, and a painting of a beach scene.

20. Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
29.4 km from Cutthroat Harbor Estates
2.0 out of 10, (1 review)
"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."
United States
Paris
The price is ₩1,331,467
₩1,767,128 total
includes taxes & fees
Sep 6 - Sep 7
Coconut Mallory Marina and Resort Condo
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

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 Munson Island are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

The Laureate Key West

The Laureate Key West

10/10 Excellent
"Love that we were able to use both pools. Kitchenette was helpful to cook small meals and beds were comfortable"
Edgar 6-night trip
Posted 5 hours ago
The Laureate 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.
How many hotels will I find in Cutthroat Harbor Estates?
Expedia has 70 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.