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
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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Our top choices for Cutthroat Harbor Estates hotels

A waterfront building with a flat roof, large windows, and a balcony.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
9 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (1,002 reviews)
"Hostess was wonderful. The rooms traditional with the most amazing views of the gulf. coffee and hot tea appreciated. both the tiki and the restaurant were closed but will like to try on next trip south. Definitely nice place to stay on way down to key west."
United States
morgan
The price is ￥18,839
￥21,195 total
includes taxes & fees
Oct 13 - Oct 14
Sugar Loaf Lodge
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

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, (1,003 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is ￥15,972
￥17,968 total
includes taxes & fees
Oct 14 - Oct 15
Looe Key Reef Resort
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 ￥81,925
￥154,501 total
includes taxes & fees
Oct 13 - Oct 14
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, (1,002 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
United States
Mireya
The price is ￥23,209
￥31,276 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥43,302
￥106,509 total
includes taxes & fees
Oct 14 - Oct 15
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, (374 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 ￥14,096
￥38,120 total
includes taxes & fees
Oct 26 - Oct 27
Old Wooden Bridge Resort and Marina
A balcony with a view of a pool area, palm trees, and outdoor seating.

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, (1,115 reviews)
"Close to everything, comfortable stay"
United States
Nancy
The price is ￥20,137
￥27,997 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

8. 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, (1,316 reviews)
"Beautiful place to stay, would definitely stay here again."
United States
Jade
The price is ￥17,502
￥29,345 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.

9. 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, (1,165 reviews)
"Awesome location!"
United States
Brian
The price is ￥22,654
￥29,938 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A balcony with wicker furniture, a view of the sea, and a spiral staircase.

10. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,609 reviews)
"Nice pool and room was just what we needed."
United States
Brenna
The price is ￥16,898
￥34,148 total
includes taxes & fees
Oct 13 - Oct 14
Beachside Resort & Residences
A marina with boats docked, a pool area, and a building with a white facade.

11. 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, (1,803 reviews)
"Fantastic marina and ocean location , comfortable room and all the great saltwater pools at the facility"
Sweden
Anders
The price is ￥20,640
￥32,480 total
includes taxes & fees
Oct 26 - Oct 27
Hilton Key West Resort & Marina
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

12. 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, (1,556 reviews)
"Amazing stay, no complaints, clean rooms, and great pool area."
United States
Andrew
The price is ￥25,171
￥28,317 total
includes taxes & fees
Oct 13 - Oct 14
Hampton Inn Key West FL
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, (2,728 reviews)
"Great spot will stay again"
United States
Esteban
The price is ￥18,380
￥29,583 total
includes taxes & fees
Oct 26 - Oct 27
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.

14. 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, (1,268 reviews)
"Great place to stay with the family"
United States
Rachel
The price is ￥35,221
￥46,748 total
includes taxes & fees
Oct 28 - Oct 29
Hyatt Vacation Club at Beach House, Key West
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, (1,334 reviews)
"Great hotel and pool!"
United States
Eli
The price is ￥18,839
￥25,648 total
includes taxes & fees
Oct 29 - Oct 30
Hilton Garden Inn Key West / The Keys Collection
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

16. 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, (1,316 reviews)
"Amazing spa, beautiful property, friendly staff and gorgeous beaches."
United States
Tina
The price is ￥32,941
￥44,182 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Vacation Club at Windward Pointe, Key West
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, (1,035 reviews)
"Great place to stay!"
United States
Eileen
The price is ￥25,171
￥32,771 total
includes taxes & fees
Oct 25 - Oct 26
The Laureate Key West
A hotel room with a large bed, a desk, a chair, a lamp, and a view of the outdoors.

18. 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, (1,880 reviews)
"Great place to stay"
United States
Stephanie
The price is ￥20,640
￥33,247 total
includes taxes & fees
Oct 13 - Oct 14
Havana Cabana at Key West
A row of floating houses with balconies, connected by walkways, on calm 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, (199 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ￥15,768
￥44,807 total
includes taxes & fees
Oct 13 - Oct 14
Aqua Lodges at Hurricane Hole Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

20. 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 ￥51,376
￥96,268 total
includes taxes & fees
Oct 26 - Oct 27
Grand Marina Suite by Brightwild Waterfront
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

Hotels recommended for families in Cutthroat Harbor Estates

A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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 ￥19,781
￥65,414 total
includes taxes & fees
Oct 13 - Oct 14
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

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Clean apartment."
Aleksandrs 3-night trip
Posted 1 hour 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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