Hotels in Cutthroat Harbor Estates

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Jul - 19 Jul
Tomorrow
19 Jul - 20 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 Hotels in Cutthroat Harbor Estates

Old Wooden Bridge Resort and Marina
Relax in a cozy seating area with a sofa and small table, and enjoy a fully equipped kitchenette with microwave, coffee maker, and refrigerator.

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (249)
"Old Wooden Bridge was one of the coolest and most relaxing spots my family and I have ever stayed at! House Boat was clean and wonderful view of the beautiful waters in Big Pine Key! Also we were greeted by Key Deer every night which was an Amazing experience! "
Old Wooden Bridge Resort and Marina
Parmer's Resort
Relax in a serene outdoor space surrounded by a tranquil body of water and a distant shoreline.

Parmer's Resort

2.5 star property
9.0 out of 10, Wonderful, (1000)
"The private beach was incredible, staff was friendly. Didn't take advantage of the free breakfast but to even have the option was amazing. Bed was a little rickety but that if anything is my only critique. "
The price is S$225
includes taxes & fees
10 Aug - 11 Aug
Parmer's Resort
Looe Key Reef Resort
Relax amidst lush greenery and palm trees, surrounded by serene structures and a peaceful walkway.

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."
The price is S$262
includes taxes & fees
10 Aug - 11 Aug
Looe Key Reef Resort
Sugar Loaf Lodge
Enjoy meals and drinks in a relaxed setting by the calm water.

Sugar Loaf Lodge

2.5 star property
8.2 out of 10, Very good, (1000)
"Good to stay for a night ! "
The price is S$143
includes taxes & fees
10 Aug - 11 Aug
Sugar Loaf Lodge
Barnacle Resort
Relax in a serene outdoor space with ocean views, a round table, and two wicker chairs.

Barnacle Resort

3.0 star property
8.2 out of 10, Very good, (39)
"Perfect place for a quiet getaway."
The price is S$389
includes taxes & fees
19 Aug - 20 Aug
Barnacle Resort
Little Torch Cottages
Enjoy ocean views from the hotel's beachfront balconies, with access to the beach via the wooden pier.

Little Torch Cottages

2.0 star property
9.2 out of 10, Wonderful, (9)
"Felt like home. We'd stay here again!"
Little Torch Cottages
Atlantic View Luxury Villa with Pool
Relax by the serene pool surrounded by lush greenery and a white picket fence.

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. "
The price is S$1,311
includes taxes & fees
25 Jul - 26 Jul
Atlantic View Luxury Villa with Pool
Aqua Lodges at Hurricane Hole Marina
Relax by the marina with a casual meal or snack at this tranquil waterfront spot.

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (158)
"Such a unique stay and affordable!"
The price is S$305
includes taxes & fees
24 Jul - 25 Jul
Aqua Lodges at Hurricane Hole Marina
Hilton Garden Inn Key West / The Keys Collection
Relax by the serene pool surrounded by palm trees and lounge chairs.

Hilton Garden Inn Key West / The Keys Collection

3.5 star property
7.8 out of 10, Good, (1042)
"Good hotel and it includes breakfast!"
The price is S$197
includes taxes & fees
27 Jul - 28 Jul
Hilton Garden Inn Key West / The Keys Collection
Oceans Edge Key West Resort, Hotel & Marina
Enjoy dining with a view of the marina from our outdoor dining area.

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
8.8 out of 10, Excellent, (1688)
"This is a fantastic resort. "
The price is S$361
includes taxes & fees
21 Jul - 22 Jul
Oceans Edge Key West Resort, Hotel & Marina
Hampton Inn Key West FL
Relax by the pool surrounded by tall palm trees and enjoy a refreshing swim.

Hampton Inn Key West FL

2.5 star property
9.0 out of 10, Wonderful, (1194)
"Nice place to stay."
The price is S$356
includes taxes & fees
11 Aug - 12 Aug
Hampton Inn Key West FL
Hyatt Vacation Club at Windward Pointe, Key West
Relax by the resort pool, surrounded by palm trees and offering a clear view of the ocean.

Hyatt Vacation Club at Windward Pointe, Key West

3.5 star property
9.4 out of 10, Exceptional, (1001)
"Great hotel! Lot of amenities! "
The price is S$453
includes taxes & fees
4 Aug - 5 Aug
Hyatt Vacation Club at Windward Pointe, Key West
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Dine al fresco amidst lush greenery and a serene garden setting.

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

3.5 star property
8.4 out of 10, Very good, (1006)
"Good breakfast and quiet place."
The price is S$208
includes taxes & fees
12 Aug - 13 Aug
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Blue Flamingo Resort Key West
Relax by the serene pool surrounded by lush greenery and palm trees.

Blue Flamingo Resort Key West

4.0 star property
7.8 out of 10, Good, (1471)
"Clean, great accommodations."
The price is S$255
includes taxes & fees
22 Jul - 23 Jul
Blue Flamingo Resort Key West
DoubleTree Resort by Hilton Grand Key - Key West
Relax by the resort pool surrounded by palm trees and lounge chairs.

DoubleTree Resort by Hilton Grand Key - Key West

4.0 star property
7.8 out of 10, Good, (1003)
"Pool was great"
The price is S$230
includes taxes & fees
10 Aug - 11 Aug
DoubleTree Resort by Hilton Grand Key - Key West
The Perry Hotel & Marina Key West
Relax by the serene pool surrounded by palm trees and lounge chairs, with a marina in the background offering access to water activities.

The Perry Hotel & Marina Key West

4.0 star property
9.4 out of 10, Exceptional, (1029)
"Great view, restaurants on site, clean rooms. "
The price is S$315
includes taxes & fees
12 Aug - 13 Aug
The Perry Hotel & Marina Key West
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, (1000)
"We loved it there and are already planning next years trip!"
The price is S$295
includes taxes & fees
20 Jul - 21 Jul
The Laureate Key West
Hyatt Vacation Club at Beach House, Key West
Relax by the resort pool surrounded by lush greenery and lounge chairs.

Hyatt Vacation Club at Beach House, Key West

3.5 star property
9.2 out of 10, Wonderful, (1001)
"It was a wonderful stay! "
The price is S$386
includes taxes & fees
11 Aug - 12 Aug
Hyatt Vacation Club at Beach House, Key West
Beachside Resort & Residences
Relax by the pool surrounded by palm trees and take in the view of the ocean.

Beachside Resort & Residences

3.5 star property
8.6 out of 10, Excellent, (1351)
"Perfect get away with friends, family!"
The price is S$259
includes taxes & fees
20 Jul - 21 Jul
Beachside Resort & Residences
Havana Cabana at Key West
Relax by the pool surrounded by palm trees and thatched umbrellas, with lounge chairs and a fun flamingo float.

Havana Cabana at Key West

4.0 star property
8.8 out of 10, Excellent, (1753)
"We loved staying here "
The price is S$361
includes taxes & fees
10 Aug - 11 Aug
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.

Where to stay in Cutthroat Harbor Estates

Find the best Cutthroat Harbor Estates areas for the activities you enjoy most.
Sugarloaf Shores map

Sugarloaf Shores

Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.

Cudjoe Gardens map

Cudjoe Gardens

While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Florida Keys Beaches.

Breezeswept Beach Estates map

Breezeswept Beach Estates

While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Cook Island and Big Pine Key Flea Market.

Top Cutthroat Harbor Estates Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"The rooms are perfect. They have laundry inside the room. I found only one inconvenience, the air conditioning is not very cold, however, we survive. They have a fan in the room as well. Employees are very friendly, professional and helpful. I highly recommend this place. "
Grete 3-night trip
Posted 1 day ago
Sugarloaf Key Hotel at KOA Resort

Frequently asked questions

What's it like in Cutthroat Harbor Estates?

Travellers to Summerland Key's Cutthroat Harbor Estates neighbourhood will be sure to enjoy a stay here.

How many hotels are there in Cutthroat Harbor Estates?

Expedia has 77 hotels and other accommodation options in Cutthroat Harbor Estates to choose from, making this an ideal home base for exploring the greater Summerland Key area.

If I need to cancel my hotel reservation in Cutthroat Harbor Estates, will I receive a refund?

Yes! Most hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Add dates, click "Search", then use the filter option "fully refundable" to get the best options available in Cutthroat Harbor Estates.

What are the top things to see and do in Cutthroat Harbor Estates?

A few places to visit in the area around Cutthroat Harbor Estates include Venture Key, Out Key and Venture Out Keys. Crab Key and Pye Key are also worth a visit when you're out sightseeing in Summerland Key.