Hotels in Cutthroat Harbor Estates, Summerland Key

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Filter by

Guest rating
Guest rating
Star rating

Top 10 Hotels in Cutthroat Harbor Estates, Summerland Key

2 outdoor pools, open 8:00 AM to 10:00 PM, pool loungers
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, (1165)
"Will be staying here every single time we visit! "
United States
Rebecca
The price is RM2,584
RM3,178 total
includes taxes & fees
26 Dec - 27 Dec
The Perry Hotel & Marina Key West
Outdoor pool, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
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
8.0 out of 10, Very good, (1032)
"Very very nice stay! "
United States
Chloe
The price is RM512
RM716 total
includes taxes & fees
15 Dec - 16 Dec
DoubleTree Resort by Hilton Grand Key - Key West
Outdoor pool, open 6:00 AM to 10:00 PM, pool cabanas (surcharge)
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
8.0 out of 10, Very good, (1144)
" Dry friendly and good breakfast and excellent value for money "
United States
Meenakshi
The price is RM488
RM666 total
includes taxes & fees
15 Dec - 16 Dec
Hilton Garden Inn Key West / The Keys Collection
Outdoor pool, pool loungers
Havana Cabana at Key West

Havana Cabana at Key West

4.0 star property
30.3 km 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
The price is RM490
RM821 total
includes taxes & fees
8 Dec - 9 Dec
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
30.1 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1018)
"Our favorite place to stay in Key West!"
United States
Kevin
The price is RM657
RM855 total
includes taxes & fees
3 Dec - 4 Dec
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
29.2 km from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1025)
"Yes Nice room great service and nice property"
United States
Soham
The price is RM1,261
RM1,605 total
includes taxes & fees
18 Dec - 19 Dec
Hyatt Vacation Club at Beach House, Key West
Restaurant
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 star property
9 km 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
The price is RM409
RM460 total
includes taxes & fees
14 Dec - 15 Dec
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
29.5 km 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
The price is RM488
RM665 total
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Outdoor pool, pool umbrellas, pool loungers
Beachside Resort & Residences

Beachside Resort & Residences

3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1733)
"Great location with great bars and restaurants. "
United States
Pam
The price is RM632
RM920 total
includes taxes & fees
15 Dec - 16 Dec
Beachside Resort & Residences
Beach/ocean view
Parmer's Resort

Parmer's Resort

2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1012)
"Breakfast options, a heated pool"
United States
Ricardo
The price is RM474
RM669 total
includes taxes & fees
14 Dec - 15 Dec
Parmer's Resort
6 outdoor pools, free pool cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
27.4 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1760)
"Clean room..nice restaurant..friendly staff, convenient shuttle to and from downtown Key West. Well kept property !"
United States
Gary
The price is RM582
RM903 total
includes taxes & fees
3 Dec - 4 Dec
Oceans Edge Key West Resort, Hotel & Marina
Living area
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, (274)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina
Exterior
Looe Key Reef Resort

Looe Key Reef Resort

2.5 star property
7.2 km 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
Looe Key Reef Resort
Outdoor pool, pool umbrellas, pool loungers
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, (1286)
"Nice hotel , good location and amenities."
United States
Rahul
The price is RM889
RM1,000 total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn Key West FL
2 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4.0 star property
29.6 km 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
The price is RM493
RM788 total
includes taxes & fees
15 Dec - 16 Dec
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
30 km from Cutthroat Harbor Estates
9.6 out of 10, Exceptional, (1031)
"Rooms were great, grounds everywhere were fantastic!"
United States
Raymond
The price is RM1,137
RM1,465 total
includes taxes & fees
9 Dec - 10 Dec
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
28.9 km from Cutthroat Harbor Estates
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is RM480
RM1,232 total
includes taxes & fees
3 Dec - 4 Dec
Aqua Lodges at Hurricane Hole Marina
Exterior
Little Torch Cottages

Little Torch Cottages

2.0 star property
9.2 km from Cutthroat Harbor Estates
9.2 out of 10, Wonderful, (9)
"Felt like home. We'd stay here again!"
United States
William
Little Torch Cottages
Kayaking
Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina

2.0 star property
23.4 km from Cutthroat Harbor Estates
8.8 out of 10, Excellent, (158)
"Todo perfect"
Mexico
Rachel
The price is RM1,591
RM1,790 total
includes taxes & fees
12 Dec - 13 Dec
Sunshine Key RV Resort & Marina
Flat-screen TV
Barnacle Resort

Barnacle Resort

3.0 star property
13.3 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (40)
"Perfect place for a quiet getaway."
United States
David
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.
View all properties

Where to stay in Cutthroat Harbor Estates

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

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

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 Venture Out Keys.

Bay Point

While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Saddlebunch Keys.

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 Venture Out Keys.

Top Cutthroat Harbor Estates Hotel Reviews

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

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

10/10 Excellent
"Excellent "
Lusilda 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Key West at the Keys Collection

Explore a world of travel with Expedia

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 74 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.