Cutthroat Harbor Estates Hotels, Summerland Key

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Check prices for these dates

Tonight
12 Nov - 13 Nov
Tomorrow
13 Nov - 14 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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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, (1,001 reviews)
"We stayed for four nights. The hotel was quiet, clean, and comfortable. The staff was very friendly. Our patio had a beautiful view of the water. We had drinks and pie in the restaurant, and they were delicious. We would definitely stay there again."
United States
David
The price is NZ$199
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge
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, (1,003 reviews)
"Super cute place and nice people! Would definitely stay again."
United States
Natalie
The price is NZ$363
includes taxes & fees
1 Dec - 2 Dec
Parmer's Resort
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, (1,002 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is NZ$331
includes taxes & fees
20 Nov - 21 Nov
Looe Key Reef Resort
A marina with boats docked, a pool area with lounge chairs, and a white gazebo.

4. 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, (1,792 reviews)
"Great location and great staff!!"
United States
Kevin
The price is NZ$341
includes taxes & fees
18 Nov - 19 Nov
Hilton Key West Resort & Marina
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

5. 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, (1,200 reviews)
"Amazing stay"
Canada
Sandra
The price is NZ$319
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.

6. 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, (1,353 reviews)
"Room was very comfortable, staff was very helpful and breakfast was good"
United States
Darlene
The price is NZ$283
includes taxes & fees
18 Nov - 19 Nov
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.

7. 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, (1,315 reviews)
"Good place to stay."
United States
Dharmesh Raju
The price is NZ$340
includes taxes & fees
30 Nov - 1 Dec
The Perry Hotel & Marina Key West
A pool area with lounge chairs and gazebos, surrounded by palm trees.

8. 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, (1,143 reviews)
"This is a very comfortable place to stay"
United States
Wendi
The price is NZ$323
includes taxes & fees
18 Nov - 19 Nov
DoubleTree Resort by Hilton Grand Key - Key West
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

9. 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, (384 reviews)
"Very clean for Florida keys room - no complaints easy check in and out"
United States
Anthony
The price is NZ$391
includes taxes & fees
4 Dec - 5 Dec
Old Wooden Bridge Resort and Marina
A hotel with a swimming pool, sun loungers, and palm trees.

10. 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, (2,787 reviews)
"Nice resort very family friendly"
United States
Sigrid A
The price is NZ$333
includes taxes & fees
16 Nov - 17 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.

11. 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, (1,291 reviews)
"Very nice property, we enjoyed our stay!!"
United States
Joshua
The price is NZ$454
includes taxes & fees
16 Nov - 17 Nov
Hyatt Vacation Club at Beach House, Key West
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, (1,580 reviews)
"Would definitely stay there again"
United States
John
The price is NZ$359
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn Key West FL
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, (1,339 reviews)
"We were very impressed by the quality of this Hyatt Hotel!!"
United States
Frank
The price is NZ$422
includes taxes & fees
18 Nov - 19 Nov
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.

14. 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, (1,038 reviews)
"Great place to stay!"
United States
Eileen
The price is NZ$369
includes taxes & fees
15 Nov - 16 Nov
The Laureate Key West
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, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is NZ$627
includes taxes & fees
16 Nov - 17 Nov
Aqua Lodges at Hurricane Hole Marina
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

16. 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 NZ$1,741
includes taxes & fees
15 Nov - 16 Nov
Atlantic View Luxury Villa with Pool
A swimming pool surrounded by palm trees and a natural rock formation.

17. 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, (1,902 reviews)
"Great hotel, great food, great staff, 5 stars, I am looking to book again now."
United States
Robert
The price is NZ$379
includes taxes & fees
2 Dec - 3 Dec
Havana Cabana at Key West
A wooden deck with a hanging hammock and a view of a green landscape.

18. 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 NZ$1,272
includes taxes & fees
19 Nov - 20 Nov
Starlight Serenity - Hideaway w Stunning Views
A beachside resort with a wooden deck, palm trees, and a sunset view.

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 NZ$1,215
includes taxes & fees
15 Nov - 16 Nov
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 NZ$992
includes taxes & fees
30 Nov - 1 Dec
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
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
1,001 reviews
View
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
Looe Key Reef Resort
2.5 star property
7.8
Good
1,002 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
1,003 reviews
View
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.
Atlantic View Luxury Villa with Pool
3.5 star property
7.4
Good
3 reviews
View
A wooden deck with a hanging hammock and a view of a green landscape.
Starlight Serenity - Hideaway w Stunning Views
2.0 star property
10.0
Exceptional
1 review
View

Hotels recommended for families in Cutthroat Harbor Estates

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

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1,001)
The price is NZ$199
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge

Our guide on 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

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island

10/10 Excellent

Very welcoming, clean & comfortable
Australia
ERIN
Reviewed October 7, 2025
The Perry Hotel & Marina Key West

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.

What's a favourite hotel to stay 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 traveller data.

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.

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