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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Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

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Our top choices for Cutthroat Harbor Estates hotels

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

1. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,001 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
United States
Mireya
The price is CA $180
CA $250 total
includes taxes & fees
Nov 1 - Nov 2
Parmer's Resort
A canal with boats docked on both sides, surrounded by lush greenery and trees.

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, (1,002 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is CA $144
CA $162 total
includes taxes & fees
Oct 5 - Oct 6
Looe Key Reef Resort
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

3. 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 CA $191
CA $415 total
includes taxes & fees
Oct 11 - Oct 12
Old Wooden Bridge Resort and Marina
A waterfront building with a flat roof, large windows, and a balcony.

4. 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 accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"
United States
Richard
The price is CA $170
CA $191 total
includes taxes & fees
Oct 5 - Oct 6
Sugar Loaf Lodge
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

5. 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 $737
CA $1,391 total
includes taxes & fees
Oct 9 - Oct 10
Atlantic View Luxury Villa with Pool
A wooden deck with a railing, wicker chairs, and a view of greenery.

6. 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 $328
CA $890 total
includes taxes & fees
Oct 5 - Oct 6
Starlight Serenity - Hideaway w Stunning Views
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, (1,802 reviews)
"Beautiful property would stay there again"
United States
Molly
The price is CA $180
CA $286 total
includes taxes & fees
Oct 12 - Oct 13
Hilton Key West Resort & Marina
A swimming pool with lounge chairs and palm trees.

8. 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, (1,329 reviews)
"Love the breakfast and pool/ bar area"
United States
Walt
The price is CA $159
CA $219 total
includes taxes & fees
Oct 8 - Oct 9
Hilton Garden Inn Key West / The Keys Collection
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, (1,114 reviews)
"Close to everything, comfortable stay"
United States
Nancy
The price is CA $176
CA $246 total
includes taxes & fees
Oct 11 - Oct 12
DoubleTree Resort by Hilton Grand Key - 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
8.6 out of 10, Excellent, (1,153 reviews)
"Felt very comfortable and the Breakfast was very good."
United States
Patricia
The price is CA $191
CA $255 total
includes taxes & fees
Oct 11 - Oct 12
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A swimming pool surrounded by palm trees and a natural rock formation.

11. 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, (1,864 reviews)
"Great place to stay"
United States
Stephanie
The price is CA $182
CA $295 total
includes taxes & fees
Nov 2 - Nov 3
Havana Cabana at Key West
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

12. 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, (1,302 reviews)
"Amazing spa, beautiful property, friendly staff and gorgeous beaches."
United States
Tina
The price is CA $273
CA $371 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Vacation Club at Windward Pointe, Key West
Pool

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, (2,712 reviews)
"Great spot will stay again"
United States
Esteban
The price is CA $168
CA $270 total
includes taxes & fees
Oct 5 - Oct 6
Blue Flamingo Resort Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

14. 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, (1,542 reviews)
"Beautiful pool, friendly staff, comfortable rooms"
United States
Jaycie
The price is CA $241
CA $271 total
includes taxes & fees
Oct 6 - Oct 7
Hampton Inn Key West FL
Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

15. 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, (1,255 reviews)
"Great place to stay with the family"
United States
Rachel
The price is CA $276
CA $374 total
includes taxes & fees
Oct 28 - Oct 29
Hyatt Vacation Club at Beach House, Key West
A balcony with wicker furniture, a view of the sea, and a spiral staircase.

16. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,581 reviews)
"Great location"
United States
James
The price is CA $124
CA $276 total
includes taxes & fees
Oct 5 - Oct 6
Beachside Resort & Residences
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, (1,028 reviews)
"We loved the room and location!"
United States
Mailyn
The price is CA $227
CA $295 total
includes taxes & fees
Oct 5 - Oct 6
The Laureate Key West
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

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, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $130
CA $390 total
includes taxes & fees
Oct 5 - Oct 6
Aqua Lodges at Hurricane Hole Marina
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 $514
CA $924 total
includes taxes & fees
Oct 12 - Oct 13
Grand Marina Suite by Brightwild Waterfront
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

20. 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, (1,316 reviews)
"Beautiful place to stay, would definitely stay here again."
United States
Jade
The price is CA $159
CA $266 total
includes taxes & fees
Oct 26 - Oct 27
The Perry Hotel & Marina 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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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 Big Pine Key Flea Market are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Clean and modern rooms, has covered parking, housekeeping does a good job. Pool was nice, plenty of towels outside. Shuttle to downtown every hour. Management is quick to remedy any issues. Restaurant on premises. I would definetly stay here again."
mark 8-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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