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

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Oct 2 - Oct 4
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Oct 9 - Oct 11

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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, (1,005 reviews)
"Had a great time over the weekend . Great vibe!"
United States
Michel
The price is ￥15,877
￥17,861 total
includes taxes & fees
Oct 5 - Oct 6
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, (1,002 reviews)
"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"
United States
Richard
The price is ￥18,727
￥21,069 total
includes taxes & fees
Oct 1 - Oct 2
Sugar Loaf Lodge
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

3. 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 ￥81,439
￥153,584 total
includes taxes & fees
Oct 3 - Oct 4
Atlantic View Luxury Villa with Pool
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, (1,003 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
United States
Mireya
The price is ￥22,607
￥30,568 total
includes taxes & fees
Oct 5 - Oct 6
Parmer's Resort
A wooden deck with a railing, wicker chairs, and a view of greenery.

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 ￥34,418
￥96,171 total
includes taxes & fees
Oct 5 - Oct 6
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, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is ￥30,451
￥56,393 total
includes taxes & fees
Oct 26 - Oct 27
Old Wooden Bridge Resort and Marina
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

7. 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, (1,110 reviews)
"Close to everything, comfortable stay"
United States
Nancy
The price is ￥20,647
￥28,539 total
includes taxes & fees
Oct 7 - Oct 8
DoubleTree Resort by Hilton Grand Key - Key West
A balcony with wicker furniture, a view of the sea, and a spiral staircase.

8. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,573 reviews)
"Great location"
United States
James
The price is ￥12,375
￥28,971 total
includes taxes & fees
Oct 1 - Oct 2
Beachside Resort & Residences
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

9. 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, (1,314 reviews)
"Beautiful place to stay, would definitely stay here again."
United States
Jade
The price is ￥16,756
￥28,434 total
includes taxes & fees
Oct 26 - Oct 27
The Perry Hotel & Marina 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, (1,534 reviews)
"Beautiful pool, friendly staff, comfortable rooms"
United States
Jaycie
The price is ￥26,060
￥29,317 total
includes taxes & fees
Oct 6 - Oct 7
Hampton Inn Key West FL
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

11. 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, (1,139 reviews)
"Felt very comfortable and the Breakfast was very good."
United States
Patricia
The price is ￥18,727
￥25,493 total
includes taxes & fees
Oct 1 - Oct 2
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.

12. 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, (1,800 reviews)
"Beautiful property would stay there again"
United States
Molly
The price is ￥19,977
￥31,905 total
includes taxes & fees
Oct 1 - Oct 2
Hilton Key West Resort & Marina
Pool

13. 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, (2,699 reviews)
"Great spot will stay again"
United States
Esteban
The price is ￥17,256
￥28,264 total
includes taxes & fees
Oct 1 - Oct 2
Blue Flamingo Resort Key West
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, (1,327 reviews)
"Love the breakfast and pool/ bar area"
United States
Walt
The price is ￥17,244
￥23,827 total
includes taxes & fees
Oct 4 - Oct 5
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.

15. 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, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ￥14,515
￥43,206 total
includes taxes & fees
Oct 1 - Oct 2
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.

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, (1,024 reviews)
"We loved the room and location!"
United States
Mailyn
The price is ￥25,022
￥32,578 total
includes taxes & fees
Oct 5 - Oct 6
The Laureate Key West
A beachside resort with a wooden deck, palm trees, and a sunset view.

17. 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 ￥62,366
￥108,403 total
includes taxes & fees
Oct 2 - Oct 3
Grand Marina Suite by Brightwild Waterfront
A dining area with a wooden table and teal chairs, a sofa with blue cushions, and a painting of a beach scene.

18. 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
Coconut Mallory Marina and Resort Condo
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, (1,860 reviews)
"Amazing place !!!"
United States
Gustavo
The price is ￥17,468
￥29,585 total
includes taxes & fees
Oct 1 - Oct 2
Havana Cabana at Key West
Exterior

20. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
29.4 km from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is ￥23,865
￥41,476 total
includes taxes & fees
Oct 1 - Oct 2
Island View 1BR Residence With 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

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

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"I"
Tony 4-night trip
Posted 7 hours ago
Hyatt Vacation Club at Beach House, 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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