Search Hotels in Cutthroat Harbor Estates, Summerland Key

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Check prices for these dates

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13 Nov - 14 Nov
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14 Nov - 15 Nov
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13 Nov - 15 Nov
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20 Nov - 22 Nov

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Our top choices for Cutthroat Harbor Estates hotels

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
9 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (1,000 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 ฿3,353
฿3,773 total
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge
A covered deck with chairs and umbrellas overlooking a beach.

2. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,000 reviews)
"Super cute place and nice people! Would definitely stay again."
United States
Natalie
The price is ฿5,152
฿6,939 total
includes taxes & fees
1 Dec - 2 Dec
Parmer's Resort
A store with a counter, various items on display, and a sign for boats and rental gear.

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 ฿5,850
฿6,581 total
includes taxes & fees
16 Nov - 17 Nov
Looe Key Reef Resort
A pool area with lounge chairs and gazebos, surrounded by palm trees.

4. 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 ฿4,566
฿6,276 total
includes taxes & fees
29 Nov - 30 Nov
DoubleTree Resort by Hilton Grand Key - Key West
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, (1,203 reviews)
"Amazing stay"
Canada
Sandra
The price is ฿4,529
฿6,044 total
includes taxes & fees
29 Nov - 30 Nov
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

6. 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, (1,581 reviews)
"Would definitely stay there again"
United States
John
The price is ฿5,216
฿5,868 total
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn Key West FL
A swimming pool with lounge chairs and palm trees, surrounded by a paved area.

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, (1,318 reviews)
"Good place to stay."
United States
Dharmesh Raju
The price is ฿3,904
฿6,368 total
includes taxes & fees
30 Nov - 1 Dec
The Perry Hotel & Marina Key West
Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

8. 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 ฿6,372
฿8,692 total
includes taxes & fees
30 Nov - 1 Dec
Hyatt Vacation Club at Beach House, 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 ฿2,367
฿7,427 total
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, (2,796 reviews)
"Nice resort very family friendly"
United States
Sigrid A
The price is ฿3,921
฿6,311 total
includes taxes & fees
15 Nov - 16 Nov
Blue Flamingo Resort Key West
A covered outdoor area with a round table and wicker chairs, overlooking a pool and palm trees.

11. 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, (1,340 reviews)
"We were very impressed by the quality of this Hyatt Hotel!!"
United States
Frank
The price is ฿6,646
฿9,001 total
includes taxes & fees
29 Nov - 30 Nov
Hyatt Vacation Club at Windward Pointe, Key West
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

12. 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 ฿17,477
฿32,958 total
includes taxes & fees
15 Nov - 16 Nov
Atlantic View Luxury Villa with Pool
A marina with boats docked, a pool area, and a building with a white facade.

13. 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, (1,796 reviews)
"Great location and great staff!!"
United States
Kevin
The price is ฿4,488
฿7,030 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Key West Resort & Marina
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, (1,355 reviews)
"Room was very comfortable, staff was very helpful and breakfast was good"
United States
Darlene
The price is ฿4,165
฿5,636 total
includes taxes & fees
18 Nov - 19 Nov
Hilton Garden Inn Key West / The Keys Collection
A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

15. 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, (1,041 reviews)
"Great place to stay!"
United States
Eileen
The price is ฿5,370
฿6,991 total
includes taxes & fees
15 Nov - 16 Nov
The Laureate Key West
A wooden deck with a table and chairs, overlooking a calm water body with boats and a house in the background.

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, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ฿5,152
฿11,648 total
includes taxes & fees
15 Nov - 16 Nov
Aqua Lodges at Hurricane Hole Marina
A resort pool with clear blue water, surrounded by palm trees and lounge chairs.

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, (1,904 reviews)
"Great hotel, great food, great staff, 5 stars, I am looking to book again now."
United States
Robert
The price is ฿4,674
฿7,407 total
includes taxes & fees
29 Nov - 30 Nov
Havana Cabana at Key West
A wooden deck with a swing chair and a view of a lake.

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 ฿10,808
฿23,896 total
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 ฿13,152
฿23,002 total
includes taxes & fees
19 Nov - 20 Nov
Grand Marina Suite by Brightwild Waterfront
A swimming pool with a green-roofed building, palm trees, and a clear blue sky.

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 ฿8,402
฿19,055 total
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 top hotels in Cutthroat Harbor Estates

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

Sugar Loaf Lodge

2.5 star property
9 km from Cutthroat Harbor Estates
View
A covered deck with chairs and umbrellas overlooking a beach.

Parmer's Resort

2.5 star property
9.2 km from Cutthroat Harbor Estates
View
A store with a counter, various items on display, and a sign for boats and rental gear.

Looe Key Reef Resort

2.5 star property
7.2 km from Cutthroat Harbor Estates
View
A pool area with lounge chairs and gazebos, surrounded by palm trees.

DoubleTree Resort by Hilton Grand Key - Key West

4.0 star property
29.6 km from Cutthroat Harbor Estates
View
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

3.5 star property
29.5 km from Cutthroat Harbor Estates
View
8.2
Very good
1,000 reviews
9.0
Wonderful
1,000 reviews
7.8
Good
1,000 reviews
8.4
Very good
1,143 reviews
8.8
Excellent
1,203 reviews
The price is ฿3,353
฿3,773 total
includes taxes & fees
30 Nov - 1 Dec
The price is ฿5,152
฿6,939 total
includes taxes & fees
1 Dec - 2 Dec
The price is ฿5,850
฿6,581 total
includes taxes & fees
16 Nov - 17 Nov
The price is ฿4,566
฿6,276 total
includes taxes & fees
29 Nov - 30 Nov
The price is ฿4,529
฿6,044 total
includes taxes & fees
29 Nov - 30 Nov
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet-friendly
  • No WiFi included
  • Yes, Parking

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 swimming pool with lounge chairs and palm trees, surrounded by a paved area.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island

10/10 Excellent

lovely welcome on arrival by a chap named Chris on the desk. helped us with everything very friendly and informative! lovely hotel perfect for what we needed a weeks peace after orlando and the shuttle allowed us to dip in and out of all the fun. pool area lovely and our room too , overlooked the pool very clean and comfortable housekeeping great . matt’s kitchen offered a great breakfast again with lovely staff one guy in particular lovely with all his recs . telling us all about henry &...
United Kingdom
Julie
Reviewed October 25, 2026
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.

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.