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
Next weekend
Oct 16 - Oct 18

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Our top choices for Cutthroat Harbor Estates hotels

A waterfront building with a flat roof, large windows, and a balcony.

1. 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 $169
CA $190 total
includes taxes & fees
Oct 11 - Oct 12
Sugar Loaf Lodge
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

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, (1,000 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is CA $144
CA $161 total
includes taxes & fees
Oct 14 - Oct 15
Looe Key Reef Resort
A hotel room with two beds, a sofa, and a framed flag collection on the wall.

3. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,001 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
United States
Mireya
The price is CA $209
CA $281 total
includes taxes & fees
Nov 3 - Nov 4
Parmer's Resort
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

4. 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 $736
CA $1,388 total
includes taxes & fees
Oct 11 - Oct 12
Atlantic View Luxury Villa with Pool
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 CA $408
CA $979 total
includes taxes & fees
Oct 14 - Oct 15
Starlight Serenity - Hideaway w Stunning Views
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

6. 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 $125
CA $340 total
includes taxes & fees
Oct 12 - Oct 13
Old Wooden Bridge Resort and Marina
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, (1,799 reviews)
"Fantastic marina and ocean location , comfortable room and all the great saltwater pools at the facility"
Sweden
Anders
The price is CA $189
CA $296 total
includes taxes & fees
Oct 15 - Oct 16
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, (1,332 reviews)
"Great hotel and pool!"
United States
Eli
The price is CA $174
CA $236 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Key West / The Keys Collection
Pool

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, (1,112 reviews)
"Close to everything, comfortable stay"
United States
Nancy
The price is CA $181
CA $252 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree Resort by Hilton Grand Key - Key West
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, (1,315 reviews)
"Beautiful place to stay, would definitely stay here again."
United States
Jade
The price is CA $157
CA $264 total
includes taxes & fees
Oct 26 - Oct 27
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, (2,597 reviews)
"Great location"
United States
James
The price is CA $152
CA $307 total
includes taxes & fees
Oct 11 - Oct 12
Beachside Resort & Residences
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

12. 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, (1,161 reviews)
"Awesome location!"
United States
Brian
The price is CA $198
CA $263 total
includes taxes & fees
Oct 12 - Oct 13
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.

13. 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, (1,310 reviews)
"Amazing spa, beautiful property, friendly staff and gorgeous beaches."
United States
Tina
The price is CA $266
CA $364 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Vacation Club at Windward Pointe, Key West
Pool

14. 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, (2,723 reviews)
"Great spot will stay again"
United States
Esteban
The price is CA $178
CA $280 total
includes taxes & fees
Oct 11 - Oct 12
Blue Flamingo Resort Key West
A hotel room with a large bed, a chair, a desk, and a view of a pool and palm trees through a sliding door.

15. 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, (1,553 reviews)
"Amazing stay, no complaints, clean rooms, and great pool area."
United States
Andrew
The price is CA $227
CA $255 total
includes taxes & fees
Oct 13 - Oct 14
Hampton Inn Key West FL
A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

16. 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, (1,032 reviews)
"Great place to stay!"
United States
Eileen
The price is CA $226
CA $294 total
includes taxes & fees
Oct 25 - Oct 26
The Laureate Key West
Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

17. 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, (1,262 reviews)
"Great place to stay with the family"
United States
Rachel
The price is CA $275
CA $374 total
includes taxes & fees
Oct 28 - Oct 29
Hyatt Vacation Club at Beach House, 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, (199 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $162
CA $426 total
includes taxes & fees
Oct 11 - Oct 12
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 $584
CA $1,002 total
includes taxes & fees
Oct 13 - Oct 14
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, (1,873 reviews)
"Great place to stay"
United States
Stephanie
The price is CA $184
CA $297 total
includes taxes & fees
Oct 25 - Oct 26
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 Big Pine Key Flea Market are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Very food"
Manikandan 1-night trip
Posted less than an hour ago
Hyatt Vacation Club at Beach House, 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 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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