Find hotels in Cutthroat Harbor Estates, Summerland Key from $111

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Discover 1,379 Cutthroat Harbor Estates hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (257)
"River boat houses, pool, kayak rentals. "
$217 nightly
The price is $245
Sep 7 - Sep 8
Total with taxes and fees
Old Wooden Bridge Resort and Marina
Parmer's Resort
Suite, 1 Bedroom, Kitchen, Sea Facing | Beach/ocean view

Parmer's Resort

2.5 star property
9.0 out of 10, Wonderful, (1005)
"Great place all around, will be going back in the future!"
$130 nightly
The price is $146
Sep 8 - Sep 9
Total with taxes and fees
Parmer's Resort
Barnacle Resort
Flat-screen TV

Barnacle Resort

3.0 star property
8.2 out of 10, Very Good, (40)
"Perfect place for a quiet getaway."
$251 nightly
The price is $283
Sep 3 - Sep 4
Total with taxes and fees
Barnacle Resort
Looe Key Reef Resort
Exterior

Looe Key Reef Resort

2.5 star property
7.4 out of 10, Good, (1001)
"We only stayed one night but it was nice and we enjoyed ourselves."
$107 nightly
The price is $120
Sep 26 - Sep 27
Total with taxes and fees
Looe Key Reef Resort
Little Torch Cottages
Exterior

Little Torch Cottages

2.0 star property
9.2 out of 10, Wonderful, (9)
"Felt like home. We'd stay here again!"
$551 nightly
The price is $620
Sep 7 - Sep 8
Total with taxes and fees
Little Torch Cottages
Sugar Loaf Lodge
Restaurant

Sugar Loaf Lodge

2.5 star property
8.2 out of 10, Very Good, (1001)
"Great sleep"
$99 nightly
The price is $111
Sep 3 - Sep 4
Total with taxes and fees
Sugar Loaf Lodge
Atlantic View Luxury Villa with Pool
Swim-up bar

Atlantic View Luxury Villa with Pool

3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
$874 nightly
The price is $983
Sep 13 - Sep 14
Total with taxes and fees
Atlantic View Luxury Villa with Pool
Hampton Inn Key West FL
Outdoor pool, pool umbrellas, sun loungers

Hampton Inn Key West FL

2.5 star property
9.0 out of 10, Wonderful, (1235)
"Excellent accommodations, clean and friendly staff . I would definitely stay here again. "
$147 nightly
The price is $165
Sep 4 - Sep 5
Total with taxes and fees
Hampton Inn Key West FL
The Laureate Key West
Indoor pool, outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas

The Laureate Key West

3.5 star property
9.0 out of 10, Wonderful, (1007)
"Great hotel and service "
$204 nightly
The price is $230
Sep 3 - Sep 4
Total with taxes and fees
The Laureate Key West
Hyatt Vacation Club at Windward Pointe, Key West
Outdoor pool

Hyatt Vacation Club at Windward Pointe, Key West

3.5 star property
9.6 out of 10, Exceptional, (1027)
"Love this place "
$241 nightly
The price is $272
Sep 16 - Sep 17
Total with taxes and fees
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Beach House, Key West
Outdoor pool

Hyatt Vacation Club at Beach House, Key West

3.5 star property
9.4 out of 10, Exceptional, (1025)
"Nice resort, great location. "
$206 nightly
The price is $232
Sep 3 - Sep 4
Total with taxes and fees
Hyatt Vacation Club at Beach House, Key West
Hilton Garden Inn Key West / The Keys Collection
Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)

Hilton Garden Inn Key West / The Keys Collection

3.5 star property
7.8 out of 10, Good, (1082)
"Great property and excellent staff. Very clean and enjoyable stay."
$126 nightly
The price is $142
Sep 8 - Sep 9
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
The Perry Hotel & Marina Key West
2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers

The Perry Hotel & Marina Key West

4.0 star property
9.4 out of 10, Exceptional, (1083)
"Great rooms awesome service beautiful pool!"
$174 nightly
The price is $195
Sep 3 - Sep 4
Total with taxes and fees
The Perry Hotel & Marina Key West
Blue Flamingo Resort Key West
2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)

Blue Flamingo Resort Key West

4.0 star property
7.8 out of 10, Good, (1580)
"I would love to stay there again! "
$168 nightly
The price is $189
Sep 3 - Sep 4
Total with taxes and fees
Blue Flamingo Resort Key West
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Reception

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

3.5 star property
8.4 out of 10, Very Good, (1013)
"Would stay again for sure"
$136 nightly
The price is $153
Sep 14 - Sep 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Oceans Edge Key West Resort, Hotel & Marina
Daily cooked-to-order breakfast for a fee

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
9.0 out of 10, Wonderful, (1735)
"Amazing place to stay! "
$219 nightly
The price is $247
Sep 3 - Sep 4
Total with taxes and fees
Oceans Edge Key West Resort, Hotel & Marina
DoubleTree Resort by Hilton Grand Key - Key West
Outdoor pool, open 7:00 AM to 11:00 PM, free cabanas, sun loungers

DoubleTree Resort by Hilton Grand Key - Key West

4.0 star property
8.0 out of 10, Very Good, (1005)
"Staff was great and property was extremely clean at all times. Very well maintained"
$141 nightly
The price is $159
Sep 8 - Sep 9
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
Havana Cabana at Key West
Outdoor pool, sun loungers

Havana Cabana at Key West

4.0 star property
8.8 out of 10, Excellent, (1766)
"Best hotel in Key West super affordable and great hotel. The pool and the bar are the best "
$156 nightly
The price is $175
Sep 4 - Sep 5
Total with taxes and fees
Havana Cabana at Key West
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
$230 nightly
The price is $259
Sep 3 - Sep 4
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Beachside Resort & Residences
Outdoor pool, pool umbrellas, sun loungers

Beachside Resort & Residences

3.5 star property
8.6 out of 10, Excellent, (1512)
"Was a wonderful place to stay "
$184 nightly
The price is $207
Sep 3 - Sep 4
Total with taxes and fees
Beachside Resort & Residences
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.

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Newfound Harbor Keys and Cook Island 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
"Clean and courteous. Only bad thing is they require a 10:00 am check out"
Lisa 2-night trip
Posted 10 hours ago
Hyatt Vacation Club at Beach House, Key West

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 from $111 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.