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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Sep 11 - Sep 13
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Sep 18 - Sep 20

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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, (1,000 reviews)
"Great place to stay!"
United States
Sarah
The price is CA $93
CA $105 total
includes taxes & fees
Sep 23 - Sep 24
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, (1,000 reviews)
"A clean comfortable room, with a lovely view from the back patio! All staff were very helpful."
United States
Marjorie
The price is CA $164
CA $185 total
includes taxes & fees
Sep 21 - Sep 22
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, (1,000 reviews)
"Excellent location, quiet hotel, you can enjoy the view sitting under the tree 🌳, I live it"
United States
Yuran
The price is CA $163
CA $229 total
includes taxes & fees
Sep 25 - Sep 26
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, (371 reviews)
"Nice place"
United States
abhimanyu
The price is CA $124
CA $334 total
includes taxes & fees
Sep 28 - Sep 29
Old Wooden Bridge Resort and Marina
A wooden deck with a swing chair overlooking a lush landscape.

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 $336
CA $883 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $714
CA $1,347 total
includes taxes & fees
Sep 20 - Sep 21
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, (1,821 reviews)
"great place"
United States
Elizabeth
The price is CA $146
CA $247 total
includes taxes & fees
Sep 20 - Sep 21
Hilton Key West Resort & Marina
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

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, (1,091 reviews)
"Excellent place love it"
United States
Jose
The price is CA $143
CA $207 total
includes taxes & fees
Sep 27 - Sep 28
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.

9. 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, (1,497 reviews)
"Staff are very friendly and the pool area is beautiful"
United States
Melisa
The price is CA $163
CA $184 total
includes taxes & fees
Sep 16 - Sep 17
Hampton Inn Key West FL
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

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, (1,325 reviews)
"very good better than hotel on key west main island"
United States
Boyan
The price is CA $188
CA $296 total
includes taxes & fees
Sep 24 - Sep 25
The Perry Hotel & Marina Key West
A balcony with wicker furniture, a view of the sea, and a spiral staircase.

11. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,507 reviews)
"Enjoyed my stay"
United States
Jerome
The price is CA $121
CA $268 total
includes taxes & fees
Sep 22 - Sep 23
Beachside Resort & Residences
Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

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, (1,236 reviews)
"Amazing place, friendly staff, very clean"
United States
Jose
The price is CA $218
CA $308 total
includes taxes & fees
Sep 27 - Sep 28
Hyatt Vacation Club at Beach House, Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

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, (1,116 reviews)
"This hotel exceeded my expectations. It was clean, the staff was friendly, the shuttle was a great thing, and the breakfast was good."
United States
Dan
The price is CA $161
CA $220 total
includes taxes & fees
Sep 20 - Sep 21
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

14. 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, (1,272 reviews)
"Great hotel to stay 👌"
United States
Mauricio
The price is CA $235
CA $326 total
includes taxes & fees
Oct 5 - Oct 6
Hyatt Vacation Club at Windward Pointe, Key West

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, (2,662 reviews)
"We had a great time at this hotel, clean room, great views, exceptional hospitality from the staff!"
United States
REBECCA
The price is CA $149
CA $245 total
includes taxes & fees
Sep 27 - Sep 28
Blue Flamingo Resort Key West
A swimming pool with lounge chairs and palm trees.

16. 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, (1,319 reviews)
"We had a wonderful stay! The place was very clean, comfortable, and looked just like the photos. The staff at the front desk were kind, quick to reply, and made check-in simple. We would love to stay here again!"
United States
Marian
The price is CA $145
CA $202 total
includes taxes & fees
Sep 22 - Sep 23
Hilton Garden Inn Key West / The Keys Collection
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

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, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $143
CA $393 total
includes taxes & fees
Sep 20 - Sep 21
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.

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, (1,014 reviews)
"Great place"
United States
Dylan
The price is CA $220
CA $286 total
includes taxes & fees
Sep 12 - Sep 13
The Laureate Key West
A beachside resort with a wooden deck, palm trees, and a sunset view.

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 $412
CA $800 total
includes taxes & fees
Sep 27 - Sep 28
Grand Marina Suite by Brightwild Waterfront
A swimming pool surrounded by palm trees and a natural rock formation.

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, (1,856 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 CA $150
CA $256 total
includes taxes & fees
Sep 27 - Sep 28
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.
View all properties

Where to stay in Cutthroat Harbor Estates

Find the best Cutthroat Harbor Estates areas and neighborhoods for the activities you enjoy most.
A waterfront property with a pool, palm trees, and a building with a white roof.

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.
An aerial view of a bridge over turquoise water.

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.
An aerial view of a long bridge over turquoise waters with a few vehicles on it.

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.
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 Breezeswept Beach Estates isn't home to many top sights, Cook Island and Munson Island are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Rooms, at least the ones with direct beach access, were amazing. Full kitchen and large SF. The beach itself leaves a lot to be desired. small and lots of sea weeds, but very intimate and semi-private. The gym was 90 degrees and no fan. few dumbbells, cardio, and cable station, and stretching yoga area."
Jorge 5-night trip
Posted 1 hour ago
Beachside Resort & Residences

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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