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

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 rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

1. 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 NZ$150
includes taxes & fees
5 Oct - 6 Oct
Looe Key Reef Resort
A waterfront building with a flat roof, large windows, and a balcony.

2. 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 NZ$236
includes taxes & fees
29 Sept - 30 Sept
Sugar Loaf Lodge
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

3. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,003 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
United States
Mireya
The price is NZ$343
includes taxes & fees
4 Oct - 5 Oct
Parmer's Resort
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

4. 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 NZ$427
includes taxes & fees
29 Sept - 30 Sept
Old Wooden Bridge Resort and Marina
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 NZ$1,079
includes taxes & fees
30 Sept - 1 Oct
Starlight Serenity - Hideaway w Stunning Views
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

6. 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$1,723
includes taxes & fees
3 Oct - 4 Oct
Atlantic View Luxury Villa with Pool
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 NZ$357
includes taxes & fees
4 Oct - 5 Oct
Hilton Key West Resort & Marina
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, (1,321 reviews)
"Beautiful place to stay, would definitely stay here again."
United States
Jade
The price is NZ$338
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.

9. 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 NZ$300
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.

10. 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 NZ$329
includes taxes & fees
6 Oct - 7 Oct
Hampton Inn Key West FL
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

11. 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 NZ$306
includes taxes & fees
29 Sept - 30 Sept
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.

12. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,563 reviews)
"Great location"
United States
James
The price is NZ$325
includes taxes & fees
29 Sept - 30 Sept
Beachside Resort & Residences

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, (2,696 reviews)
"Great spot will stay again"
United States
Esteban
The price is NZ$334
includes taxes & fees
29 Sept - 30 Sept
Blue Flamingo Resort Key West
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, (1,331 reviews)
"Love the breakfast and pool/ bar area"
United States
Walt
The price is NZ$258
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Key West / The Keys Collection
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 NZ$1,085
includes taxes & fees
29 Sept - 30 Sept
Grand Marina Suite by Brightwild Waterfront
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

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, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is NZ$493
includes taxes & fees
30 Sept - 1 Oct
Aqua Lodges at Hurricane Hole Marina
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, (1,023 reviews)
"We loved the room and location!"
United States
Mailyn
The price is NZ$366
includes taxes & fees
29 Sept - 30 Sept
The Laureate Key West
A swimming pool surrounded by palm trees and a natural rock formation.

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, (1,862 reviews)
"Amazing place !!!"
United States
Gustavo
The price is NZ$332
includes taxes & fees
29 Sept - 30 Sept
Havana Cabana at Key West
A dining area with a wooden table and teal chairs, a sofa with blue cushions, and a painting of a beach scene.

19. 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
Coconut Mallory Marina and Resort Condo

20. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
29.4 km from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is NZ$498
includes taxes & fees
1 Oct - 2 Oct
Island View 1BR Residence With 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.
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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

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Great place to stay"
John 3-night trip
Posted less than an hour ago
Sugarloaf Key Hotel at KOA Resort

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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