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, (1165)
"Will be staying here every single time we visit! "
United States
Rebecca
$184 nightly
The price is $206
Dec 16 - Dec 17
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, (1032)
"Very very nice stay! "
United States
Chloe
$154 nightly
The price is $173
Dec 15 - Dec 16
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, (1144)
" Dry friendly and good breakfast and excellent value for money "
United States
Meenakshi
$143 nightly
The price is $161
Dec 14 - Dec 15
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, (1752)
"Pretty much everything you could hope for out of a resort. Staff was great, amenities were nice, the room was clean. We loved out stay"
United States
alec lawrence
$177 nightly
The price is $199
Dec 8 - Dec 9
Total with taxes and fees
Havana Cabana at Key West
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, (1018)
"Our favorite place to stay in Key West!"
United States
Kevin
$184 nightly
The price is $207
Dec 3 - Dec 4
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, (1025)
"Yes Nice room great service and nice property"
United States
Soham
$345 nightly
The price is $388
Dec 18 - Dec 19
Total with taxes and fees
Hyatt Vacation Club at Beach House, Key West
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, (1008)
"Tiki hit closed, wish I had known Staff very nice, rooms fine"
United States
James
$99 nightly
The price is $111
Dec 3 - Dec 4
Total with taxes and fees
Sugar Loaf Lodge
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, (1015)
"It was a good stay for the price and near to the old town"
United States
sushma
$143 nightly
The price is $161
Dec 16 - Dec 17
Total with taxes and fees
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
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, (1733)
"Great location with great bars and restaurants. "
United States
Pam
$202 nightly
The price is $228
Dec 16 - Dec 17
Total with taxes and fees
Beachside Resort & Residences
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, (1012)
"Breakfast options, a heated pool"
United States
Ricardo
$144 nightly
The price is $162
Dec 14 - Dec 15
Total with taxes and fees
Parmer's Resort
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, (1761)
"Clean room..nice restaurant..friendly staff, convenient shuttle to and from downtown Key West. Well kept property !"
United States
Gary
$194 nightly
The price is $218
Dec 3 - Dec 4
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, (274)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
$259 nightly
The price is $292
Dec 3 - Dec 4
Total with taxes and fees
Old Wooden Bridge Resort and Marina
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, (1005)
"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
$164 nightly
The price is $184
Dec 8 - Dec 9
Total with taxes and fees
Looe Key Reef Resort
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, (1286)
"Nice hotel , good location and amenities."
United States
Rahul
$215 nightly
The price is $242
Dec 14 - Dec 15
Total with taxes and fees
Hampton Inn Key West FL
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, (1751)
"Loved staying here and would again next time we are in Key West!!"
Canada
David
$169 nightly
The price is $191
Dec 4 - Dec 5
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, (1031)
"Rooms were great, grounds everywhere were fantastic!"
United States
Raymond
$315 nightly
The price is $354
Dec 9 - Dec 10
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
$265 nightly
The price is $298
Dec 3 - Dec 4
Total with taxes and fees
Aqua Lodges at Hurricane Hole 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 9 - Dec 10
Total with taxes and fees
Little Torch Cottages
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
Flat-screen TV
Barnacle Resort

Barnacle Resort

3.0 star property
8.3 mi from Cutthroat Harbor Estates
8.2 out of 10, Very Good, (40)
"Perfect place for a quiet getaway."
United States
David
$251 nightly
The price is $283
Dec 3 - Dec 4
Total with taxes and fees
Barnacle Resort
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 Saddlebunch Keys 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

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

10/10 Excellent
"My stay at this hotel was absolutely outstanding! From the moment I arrived, I felt welcomed and well taken care of. The staff were incredibly professional, friendly, and always ready to help with anything I needed."
Lubna Bahjat 3-night trip
Posted 1 day ago
Oceans Edge Key West Resort, Hotel & Marina

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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