Find hotels in Cutthroat Harbor Estates, Summerland Key

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Discover Cutthroat Harbor Estates hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4.0 star property
17.6 mi from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1155)
"Will be staying here every single time we visit! "
United States
Rebecca
$177 nightly
The price is $199
Nov 30 - Dec 1
Total with taxes and fees
The Perry Hotel & Marina Key West
Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4.0 star property
18.4 mi from Cutthroat Harbor Estates
8.0 out of 10, Very Good, (1015)
"Very very nice stay! "
United States
Chloe
$153 nightly
The price is $172
Dec 1 - Dec 2
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 star property
18.3 mi from Cutthroat Harbor Estates
8.0 out of 10, Very Good, (1132)
"Nice hotel 🏨 staff was very helpful."
United States
MICHAEL Z
$112 nightly
The price is $126
Dec 1 - Dec 2
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
Outdoor pool, sun loungers
Havana Cabana at Key West

Havana Cabana at Key West

4.0 star property
18.8 mi from Cutthroat Harbor Estates
8.8 out of 10, Excellent, (1744)
"Wonderful staff, nice rooms, reasonable rates, love the shuttle service!"
United States
Wendy
$177 nightly
The price is $199
Dec 15 - Dec 16
Total with taxes and fees
Havana Cabana at Key West
Outdoor pool
Fairfield Inn & Suites by Marriott Key West at the Keys Collection

Fairfield Inn & Suites by Marriott Key West at the Keys Collection

3.5 star property
18.3 mi from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1002)
"Clean room, friendly staff, good amenities and good location "
United States
Naseem
$132 nightly
The price is $148
Dec 3 - Dec 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Indoor pool, outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas
The Laureate Key West

The Laureate Key West

3.5 star property
18.7 mi from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1009)
"Our favorite place to stay in Key West!"
United States
Kevin
$184 nightly
The price is $207
Dec 1 - Dec 2
Total with taxes and fees
The Laureate Key West
Outdoor pool
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 star property
18.1 mi from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1010)
"It was peaceful and great location"
United States
Kevin
$311 nightly
The price is $350
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Vacation Club at Beach House, Key West
Suite, 1 Bedroom, Kitchen, Sea Facing | Beach/ocean view
Parmer's Resort

Parmer's Resort

2.5 star property
5.7 mi from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1005)
"Breakfast options, a heated pool"
United States
Ricardo
$137 nightly
The price is $154
Nov 30 - Dec 1
Total with taxes and fees
Parmer's Resort
Restaurant
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 star property
5.6 mi from Cutthroat Harbor Estates
8.2 out of 10, Very Good, (1004)
"Tiki hit closed, wish I had known Staff very nice, rooms fine"
United States
James
$99 nightly
The price is $111
Nov 30 - Dec 1
Total with taxes and fees
Sugar Loaf Lodge
6 outdoor pools, free cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
17 mi from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1744)
"Wonderful customer service, beautiful resort, and outstanding amenities"
United States
Patrick
$217 nightly
The price is $244
Nov 30 - Dec 1
Total with taxes and fees
Oceans Edge Key West Resort, Hotel & Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 mi from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (271)
"We will definitely stay here again. Perfect spot to relax. Clean Rooms "
United States
Gregory
$259 nightly
The price is $292
Nov 24 - Nov 25
Total with taxes and fees
Old Wooden Bridge Resort and Marina
Outdoor pool, pool umbrellas, sun loungers
Beachside Resort & Residences

Beachside Resort & Residences

3.5 star property
18.3 mi from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1701)
"Very cool place to vacation "
United States
Gabriel
$158 nightly
The price is $178
Dec 9 - Dec 10
Total with taxes and fees
Beachside Resort & Residences
Outdoor pool, pool umbrellas, sun loungers
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 star property
18.5 mi from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1270)
"Great property and location."
United States
Indraneel
$180 nightly
The price is $202
Nov 30 - Dec 1
Total with taxes and fees
Hampton Inn Key West FL
Exterior
Looe Key Reef Resort

Looe Key Reef Resort

2.5 star property
4.5 mi from Cutthroat Harbor Estates
7.4 out of 10, Good, (1003)
"Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect"
United Kingdom
Clare
$195 nightly
The price is $219
Nov 25 - Nov 26
Total with taxes and fees
Looe Key Reef Resort
2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4.0 star property
18.4 mi from Cutthroat Harbor Estates
8.0 out of 10, Very Good, (1716)
"Great stay!"
United States
Aaron
$145 nightly
The price is $164
Nov 30 - Dec 1
Total with taxes and fees
Blue Flamingo Resort Key West
Outdoor pool
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 star property
18.6 mi from Cutthroat Harbor Estates
9.6 out of 10, Exceptional, (1016)
"Rooms were great, grounds everywhere were fantastic!"
United States
Raymond
$294 nightly
The price is $331
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Vacation Club at Windward Pointe, Key West
Restaurant
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
17.9 mi from Cutthroat Harbor Estates
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
$256 nightly
The price is $288
Nov 30 - Dec 1
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Kayaking
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2.0 star property
14.6 mi from Cutthroat Harbor Estates
8.8 out of 10, Excellent, (158)
"Todo perfect"
Mexico
Rachel
$385 nightly
The price is $433
Dec 12 - Dec 13
Total with taxes and fees
Sunshine Key RV Resort & Marina
Exterior
Little Torch Cottages

Little Torch Cottages

2.0 star property
5.7 mi from Cutthroat Harbor Estates
9.2 out of 10, Wonderful, (9)
"Felt like home. We'd stay here again!"
United States
William
$587 nightly
The price is $661
Dec 6 - Dec 7
Total with taxes and fees
Little Torch Cottages
Apartment | 1 bedroom
Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony

2.0 star property
18.2 mi from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
$341 nightly
The price is $384
Dec 1 - Dec 2
Total with taxes and fees
Island View 1BR Residence With Balcony
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. Learn more about Cutthroat Harbor Estates
Learn more about Cutthroat Harbor Estates
Sugarloaf Shores featuring a bay or harbor

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 Venture Out Keys, 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, Cook Island and Venture Out Keys are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"Staff was super friendly and helpful plus the location was very nice"
Gurinder 1-night trip
Posted 3 days ago
Hyatt Vacation Club at Windward Pointe, Key West

Frequently asked questions

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 can I save on a Cutthroat Harbor Estates hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and 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.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
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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