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
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

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Our top choices for Cutthroat Harbor Estates hotels

Karaoke room

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, (1,002 reviews)
"Great place to stay!"
United States
Sarah
The price is NZ$132
includes taxes & fees
23 Sept - 24 Sept
Looe Key Reef Resort
Exterior

2. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
9 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (1,000 reviews)
"A clean comfortable room, with a lovely view from the back patio! All staff were very helpful."
United States
Marjorie
The price is NZ$228
includes taxes & fees
15 Sept - 16 Sept
Sugar Loaf Lodge
Exterior

3. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,008 reviews)
"A typical "keys style" resort that had everything we needed with a kitchen, deck seating, a dock for our boat. Enjoyed the Complimentary coffee. Will be back with the family + dog"
United States
Matthew
The price is NZ$377
includes taxes & fees
10 Sept - 11 Sept
Parmer's Resort
House | Terrace/patio

4. 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$1,048
includes taxes & fees
5 Oct - 6 Oct
Starlight Serenity - Hideaway w Stunning Views
1 Bedroom Aqualodge # 6 Tarpon | Living area

5. 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, (367 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
The price is NZ$411
includes taxes & fees
7 Sept - 8 Sept
Old Wooden Bridge Resort and Marina
Exterior

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$1,659
includes taxes & fees
10 Sept - 11 Sept
Atlantic View Luxury Villa with Pool
Exterior

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, (1,821 reviews)
"Awesome place to stay at!"
United States
Linda
The price is NZ$320
includes taxes & fees
16 Sept - 17 Sept
Hilton Key West Resort & Marina
Outdoor pool, pool umbrellas, pool loungers

8. 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, (1,486 reviews)
"Staff are very friendly and the pool area is beautiful"
United States
Melisa
The price is NZ$265
includes taxes & fees
22 Sept - 23 Sept
Hampton Inn Key West FL
Outdoor pool, open 7:00 AM to 9:00 PM, pool cabanas (surcharge)

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, (1,084 reviews)
"Excellent place love it"
United States
Jose
The price is NZ$268
includes taxes & fees
15 Sept - 16 Sept
DoubleTree Resort by Hilton Grand Key - Key West
Marina

10. 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, (1,327 reviews)
"very good better than hotel on key west main island"
United States
Boyan
The price is NZ$375
includes taxes & fees
20 Sept - 21 Sept
The Perry Hotel & Marina Key West
Property grounds

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, (1,262 reviews)
"Great hotel to stay 👌"
United States
Mauricio
The price is NZ$407
includes taxes & fees
22 Sept - 23 Sept
Hyatt Vacation Club at Windward Pointe, Key West
Property grounds

12. 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, (1,228 reviews)
"We loved our stay at the Hyatt Vacation Club! The property was very clean as were the rooms and I enjoyed the kitchen and screened in porch area in each suite."
United States
Kailey
The price is NZ$443
includes taxes & fees
5 Oct - 6 Oct
Hyatt Vacation Club at Beach House, Key West
Outdoor pool

13. 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, (1,107 reviews)
"Great accommodation"
United States
Fernando
The price is NZ$270
includes taxes & fees
15 Sept - 16 Sept
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Ocean View 3BR Condo with Rooftop Balcony | Balcony

14. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,490 reviews)
"Enjoyed my stay"
United States
Jerome
The price is NZ$346
includes taxes & fees
10 Sept - 11 Sept
Beachside Resort & Residences
2 outdoor pools, open 7:00 AM to 10:00 PM, pool cabanas (surcharge)

15. 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, (2,654 reviews)
"We had a great time at this hotel, clean room, great views, exceptional hospitality from the staff!"
United States
REBECCA
The price is NZ$305
includes taxes & fees
8 Sept - 9 Sept
Blue Flamingo Resort Key West
House

16. 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$994
includes taxes & fees
8 Sept - 9 Sept
Grand Marina Suite by Brightwild Waterfront
Outdoor pool, open 6:00 AM to 10:00 PM, pool cabanas (surcharge)

17. 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, (1,312 reviews)
"Entire stay was fabulous"
United States
Amanda
The price is NZ$258
includes taxes & fees
21 Sept - 22 Sept
Hilton Garden Inn Key West / The Keys Collection
Front of property

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, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is NZ$486
includes taxes & fees
8 Sept - 9 Sept
Aqua Lodges at Hurricane Hole Marina
Condo | Living area

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
The price is NZ$2,232
includes taxes & fees
7 Sept - 8 Sept
Coconut Mallory Marina and Resort Condo
Outdoor pool, pool loungers

20. 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, (1,849 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 NZ$302
includes taxes & fees
22 Sept - 23 Sept
Havana Cabana at Key West
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 Munson Island.

Top Cutthroat Harbor Estates Hotel Reviews

Recent Reviews in Cutthroat Harbor Estates

The Laureate Key West

The Laureate Key West

10/10 Excellent
"The room was amazing. I had a great oceanview room. The room had a kitchen area,modern bathroom, and was well kept. And parking was included, not like other hotels/resorts charging up to $65 per day. I highly recommend."
Tamba-Kuii 3-night trip
Posted less than an hour ago
The Laureate 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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