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

Hotels in Cutthroat Harbor Estates, Summerland Key

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Our top choices for Cutthroat Harbor Estates hotels

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, (1,000 reviews)
"Great location with a nice pool. Plenty of parking and really friendly staff. Hope to stay here again."
United Kingdom
Christopher
The price is CA $175
CA $197 total
includes taxes & fees
Aug 19 - Aug 20
Looe Key Reef Resort

2. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,005 reviews)
"A very nice property, friendly and helpful staff. Very relaxing stay by the water."
United States
John
The price is CA $153
CA $217 total
includes taxes & fees
Aug 12 - Aug 13
Parmer's Resort

3. 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)
"A clean comfortable room, with a lovely view from the back patio! All staff were very helpful."
United States
Marjorie
The price is CA $167
CA $188 total
includes taxes & fees
Aug 25 - Aug 26
Sugar Loaf Lodge

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, (360 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
United States
Kathy
The price is CA $126
CA $339 total
includes taxes & fees
Sep 1 - Sep 2
Old Wooden Bridge Resort and Marina

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 CA $354
CA $893 total
includes taxes & fees
Aug 17 - Aug 18
Starlight Serenity - Hideaway w Stunning Views

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 CA $926
CA $1,594 total
includes taxes & fees
Aug 25 - Aug 26
Atlantic View Luxury Villa with Pool

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, (1,839 reviews)
"very nice place to go on family vacation, totally recommend"
United States
Alondra
The price is CA $172
CA $278 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Key West Resort & Marina

8. 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, (1,061 reviews)
"The hotel was well maintained."
United States
Chandra
The price is CA $184
CA $254 total
includes taxes & fees
Aug 16 - Aug 17
DoubleTree Resort by Hilton Grand Key - Key West

9. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,397 reviews)
"The best part was, I was able to check in early and very friendly staff"
United States
Nicole
The price is CA $164
CA $319 total
includes taxes & fees
Aug 17 - Aug 18
Beachside Resort & Residences

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, (1,308 reviews)
"Stayed here for our honeymoon it was a great place!!"
United States
Dallis
The price is CA $184
CA $291 total
includes taxes & fees
Aug 12 - Aug 13
The Perry Hotel & Marina Key West

11. 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
8.0 out of 10, Very good, (1,284 reviews)
"Great place to stay for a weekend"
United States
Oscar
The price is CA $178
CA $239 total
includes taxes & fees
Aug 22 - Aug 23
Hilton Garden Inn Key West / The Keys Collection

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, (1,444 reviews)
"Great location!"
United States
Marines
The price is CA $225
CA $253 total
includes taxes & fees
Aug 17 - Aug 18
Hampton Inn Key West FL

13. 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, (1,174 reviews)
"Very good hotel for the price"
United States
Lakshit
The price is CA $332
CA $437 total
includes taxes & fees
Aug 24 - Aug 25
Hyatt Vacation Club at Beach House, Key West

14. 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, (1,068 reviews)
"Great accommodation"
United States
Fernando
The price is CA $163
CA $222 total
includes taxes & fees
Aug 31 - Sep 1
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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, (2,599 reviews)
"Great place to stay."
United States
Robert
The price is CA $175
CA $276 total
includes taxes & fees
Aug 10 - Aug 11
Blue Flamingo Resort Key West

16. 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, (1,212 reviews)
"Amazing place!"
United States
Adam
The price is CA $281
CA $379 total
includes taxes & fees
Aug 30 - Aug 31
Hyatt Vacation Club at Windward Pointe, Key West

17. 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, (193 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is CA $160
CA $414 total
includes taxes & fees
Aug 3 - Aug 4
Aqua Lodges at Hurricane Hole Marina

18. 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, (1,008 reviews)
"Excellent resort our second time there"
United States
Robert
The price is CA $223
CA $290 total
includes taxes & fees
Aug 19 - Aug 20
The Laureate Key West

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 CA $367
CA $753 total
includes taxes & fees
Aug 31 - Sep 1
Grand Marina Suite by Brightwild Waterfront

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, (1,835 reviews)
"We stayed for a week and really enjoyed the pool, shuttle service, and the bar. Very friendly staff!"
United States
Tracie
The price is CA $164
CA $273 total
includes taxes & fees
Aug 16 - Aug 17
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.

Where to stay in Cutthroat Harbor Estates

Find the best Cutthroat Harbor Estates areas and neighborhoods for the activities you enjoy most.

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

Bay Point

Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Coupon Bight Aquatic Preserve and Cook Island are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

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 PARADISEboasts 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 PARADISEis 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 24-48 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 much is the nightly rate at a Cutthroat Harbor Estates hotel?
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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