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

Cutthroat Harbor Estates Hotels, Summerland Key

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Check prices for these dates

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30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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Our top choices for Cutthroat Harbor Estates hotels

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

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)
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
United States
Mariia
The price is AU$190
includes taxes & fees
1 Nov - 2 Nov
Sugar Loaf Lodge
A tropical resort with palm trees, a pool, and a wooden building.

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, (1,000 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is AU$231
includes taxes & fees
9 Nov - 10 Nov
Looe Key Reef Resort
A covered deck with chairs and umbrellas overlooking a beach.

3. 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 AU$259
includes taxes & fees
4 Nov - 5 Nov
Parmer's Resort
A marina with boats docked, a pool area, and a building with a white facade.

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, (1,794 reviews)
"Great location and great staff!!"
United States
Kevin
The price is AU$285
includes taxes & fees
15 Nov - 16 Nov
Hilton Key West Resort & Marina
A swimming pool with lounge chairs and palm trees.

5. 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, (1,349 reviews)
"Room was very comfortable, staff was very helpful and breakfast was good"
United States
Darlene
The price is AU$224
includes taxes & fees
17 Nov - 18 Nov
Hilton Garden Inn Key West / The Keys Collection
A pool area with lounge chairs and gazebos, surrounded by palm trees.

6. 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, (1,125 reviews)
"Very nice, would stay again."
United States
Danee
The price is AU$267
includes taxes & fees
1 Nov - 2 Nov
DoubleTree Resort by Hilton Grand Key - Key West
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

7. 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, (378 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is AU$342
includes taxes & fees
30 Oct - 31 Oct
Old Wooden Bridge Resort and Marina
Pool

8. 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, (2,757 reviews)
"Great place, great environment, friendly staff."
United States
Gabriel
The price is AU$265
includes taxes & fees
1 Nov - 2 Nov
Blue Flamingo Resort Key West
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

9. 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, (1,329 reviews)
"Nice and clean hotel with good amenities and central location"
United States
Leismy
The price is AU$339
includes taxes & fees
28 Nov - 29 Nov
Hyatt Vacation Club at Windward Pointe, Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

10. 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, (1,174 reviews)
"Amazing stay"
Canada
Sandra
The price is AU$240
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 palm trees, surrounded by boats and a sunset in the background.

11. 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, (1,301 reviews)
"Absolutely amazing property and people could not recommend enough helpfully staff and great location"
United States
david
The price is AU$276
includes taxes & fees
1 Nov - 2 Nov
The Perry Hotel & Marina 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, (1,571 reviews)
"Excellent location and the property it’s very clean"
United States
Heylin
The price is AU$310
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Key West FL
A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

13. 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, (1,030 reviews)
"Great place to stay!"
United States
Eileen
The price is AU$294
includes taxes & fees
1 Nov - 2 Nov
The Laureate Key West
A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

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, (1,275 reviews)
"It was clean, helpful staff, amazing location. Second time there and I hope to go back soon."
United States
Milton
The price is AU$367
includes taxes & fees
28 Nov - 29 Nov
Hyatt Vacation Club at Beach House, Key West
A row of floating houses with balconies, connected by walkways, on calm 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, (201 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is AU$417
includes taxes & fees
30 Oct - 31 Oct
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 AU$1,385
includes taxes & fees
15 Nov - 16 Nov
Atlantic View Luxury Villa with Pool
A wooden deck with a hanging hammock and a view of a green landscape.

17. 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 AU$1,112
includes taxes & fees
19 Nov - 20 Nov
Starlight Serenity - Hideaway w Stunning Views
A resort pool with clear blue water, surrounded by palm trees and lounge chairs.

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, (1,892 reviews)
"Great place to stay"
United States
Stephanie
The price is AU$320
includes taxes & fees
19 Nov - 20 Nov
Havana Cabana at Key West
A waterfront property with a large building featuring balconies and a covered area, boats docked in front, and palm trees in the background.

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 AU$863
includes taxes & fees
30 Oct - 31 Oct
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 AU$856
includes taxes & fees
1 Nov - 2 Nov
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 corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
Sugar Loaf Lodge
2.5 star property
8.2
Very good
1,000 reviews
View
A covered deck with chairs and umbrellas overlooking a beach.
Parmer's Resort
2.5 star property
9.0
Wonderful
1,000 reviews
View
A marina with boats docked, a pool area, and a building with a white facade.
Hilton Key West Resort & Marina
4.0 star property
9.0
Wonderful
1,794 reviews
View
A cozy room with a brown leather sofa, a white table, and a ceiling fan.
Old Wooden Bridge Resort and Marina
2.5 star property
8.6
Excellent
378 reviews
View
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.
Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
9.4
Exceptional
1,329 reviews
View

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

Recent Reviews in Cutthroat Harbor Estates

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"Great stay for second time"
Lesley 4-night trip
Posted 1 hour ago
The Perry Hotel & Marina Key West

Frequently asked questions

What are the best family hotels in Cutthroat Harbor Estates?
For a family-friendly hotel in Cutthroat Harbor Estates, consider the ISLAND PARADISE.

The ISLAND PARADISE boasts an exceptional 10.0 review rating, making it a highly recommended choice for families. This hotel offers a playground, a selection of games and books for children, and an outdoor play area, ensuring plenty of entertainment for younger guests. Additionally, rooms are equipped with sofa beds, providing extra sleeping space for families.
What are the top pet-friendly hotels in Cutthroat Harbor Estates?
For top-rated pet-friendly accommodation in Cutthroat Harbor Estates, consider the ISLAND PARADISE.

The ISLAND PARADISE, with a superb 10.0 rating, is an excellent choice for travellers with canine companions as it specifically permits dogs. This accommodation also features a kitchen, providing added convenience for preparing meals during your stay.
What are the most romantic hotels in Cutthroat Harbor Estates for couples?
For a romantic stay in Cutthroat Harbor Estates, ISLAND PARADISE is an excellent choice for couples.

This property boasts a great 10.0 review rating, ensuring a delightful experience. It offers a shared outdoor pool, a private patio or deck, and a porch or lanai, providing ample opportunities for relaxation and enjoyment together. Additionally, a kitchen is available, which can be very convenient for a romantic getaway. For those looking for extra indulgence, a hot tub is also a feature. The property is conveniently located just 1.4 km from Venture Out Keys.
When is the best time to go to Cutthroat Harbor Estates?
The best time to visit Cutthroat Harbor Estates is during the dry season, from November to April, when the weather is consistently pleasant and ideal for outdoor activities.

During these months, you can expect warm, sunny days with lower humidity and very little rainfall. This makes it great for enjoying the beaches, boating, and exploring the natural beauty of the region without the intense heat and afternoon thunderstorms common in the summer. For those seeking a comfortable and active holiday, this period offers the best conditions.

Families often find these months particularly suitable as the cooler temperatures are more comfortable for children to enjoy the outdoor attractions and theme parks nearby. The drier weather also means fewer disruptions to planned activities.

Couples looking for a relaxing escape will appreciate the consistently clear skies and gentle breezes.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline − this is often within 24 to 48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our 'Fully refundable property' filter during your search to find the right Cutthroat Harbor Estates hotel for you.
How can I save on a hotel booking in Cutthroat Harbor Estates with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Cutthroat Harbor Estates hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Cutthroat Harbor Estates?
Hotel prices in Cutthroat Harbor Estates often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates and sort search results by 'Price: low to high' for our cheapest rates.

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