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

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

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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)
"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"
United States
Richard
The price is ฿3,973
฿4,470 total
includes taxes & fees
29 Sept - 30 Sept
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
7.6 out of 10, Good, (1,005 reviews)
"Had a great time over the weekend . Great vibe!"
United States
Michel
The price is ฿2,526
฿2,842 total
includes taxes & fees
5 Oct - 6 Oct
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 ฿17,278
฿32,584 total
includes taxes & fees
3 Oct - 4 Oct
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 ฿4,796
฿6,485 total
includes taxes & fees
4 Oct - 5 Oct
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 ฿7,768
฿20,928 total
includes taxes & fees
30 Sept - 1 Oct
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 ฿3,005
฿8,075 total
includes taxes & fees
29 Sept - 30 Sept
Old Wooden Bridge Resort and Marina
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, (1,812 reviews)
"Beautiful property would stay there again"
United States
Molly
The price is ฿4,049
฿6,553 total
includes taxes & fees
29 Sept - 30 Sept
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, (1,138 reviews)
"Felt very comfortable and the Breakfast was very good."
United States
Patricia
The price is ฿4,307
฿5,784 total
includes taxes & fees
29 Sept - 30 Sept
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
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, (1,321 reviews)
"Beautiful place to stay, would definitely stay here again."
United States
Jade
The price is ฿3,872
฿6,396 total
includes taxes & fees
12 Oct - 13 Oct
The Perry Hotel & Marina Key West
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

10. 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, (1,109 reviews)
"The hotel was clean, great customer service, and the food was really good!"
United States
Craige
The price is ฿4,049
฿5,681 total
includes taxes & fees
30 Sept - 1 Oct
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

11. 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, (1,529 reviews)
"Beautiful pool, friendly staff, comfortable rooms"
United States
Jaycie
The price is ฿5,078
฿5,713 total
includes taxes & fees
1 Oct - 2 Oct
Hampton Inn Key West FL

12. 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, (2,696 reviews)
"Great spot will stay again"
United States
Esteban
The price is ฿3,945
฿6,316 total
includes taxes & fees
29 Sept - 30 Sept
Blue Flamingo Resort Key West
A swimming pool with lounge chairs and palm trees.

13. 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, (1,331 reviews)
"Love the breakfast and pool/ bar area"
United States
Walt
The price is ฿3,509
฿4,886 total
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Key West / The Keys Collection
A balcony with wicker furniture, a view of the sea, and a spiral staircase.

14. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,562 reviews)
"Great location"
United States
James
The price is ฿2,626
฿6,146 total
includes taxes & fees
29 Sept - 30 Sept
Beachside Resort & Residences
A beachside resort with a wooden deck, palm trees, and a sunset view.

15. 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 ฿11,026
฿20,518 total
includes taxes & fees
29 Sept - 30 Sept
Grand Marina Suite by Brightwild Waterfront
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, (1,022 reviews)
"We loved the room and location!"
United States
Mailyn
The price is ฿5,309
฿6,911 total
includes taxes & fees
29 Sept - 30 Sept
The Laureate Key West
A dining area with a wooden table and teal chairs, a sofa with blue cushions, and a painting of a beach scene.

17. 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 ฿33,023
฿43,828 total
includes taxes & fees
29 Sept - 30 Sept
Coconut Mallory Marina and Resort Condo
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

18. 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 ฿3,275
฿9,392 total
includes taxes & fees
29 Sept - 30 Sept
Aqua Lodges at Hurricane Hole Marina
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, (1,862 reviews)
"Absolutely going to be staying here again. Our family throughly enjoyed the hotel, amenities and location to Key West"
United States
Silvia
The price is ฿3,706
฿6,277 total
includes taxes & fees
29 Sept - 30 Sept
Havana Cabana at Key West
A poolside area with lounge chairs, a wooden table, and palm trees.

20. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
26.9 km from Cutthroat Harbor Estates
The price is ฿43,524
฿84,422 total
includes taxes & fees
30 Sept - 1 Oct
The Fairhaven House at Solaire Lunara Bay
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 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

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

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

10/10 Excellent
"Great stay! The breakfast was excellent, and the staff was very friendly and attentive. The room was clean and comfortable. Everything was very nice overall."
Fan 2-night trip
Posted 1 hour ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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.