Summerland Key Hotel Guide. Hotels in Cutthroat Harbor Estates, Summerland Key, United States of America

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Our top choices for Cutthroat Harbor Estates hotels

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, (281)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina

Barnacle Resort

Barnacle Resort
3.0 star property
13.3 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (42)
"I booked on the day of arriving (weekday) within a hour I had all the information needed for entry. Rooms were clean. BBQ grill, cooking utensils, kayaks, rowboat and bicycles are there to enjoy. Property is on a private road so there is very little traffic and noise was non-existent. The lady on property was so sweet and made my stay that much more enjoyable. If you enjoy being outside, you will see deer, they are everywhere and will walk up to you. Nature at its finest, so pleasant. Sign on...
United States
Lawrence
Barnacle Resort

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, (1001)
"Staff very polite and accommodating. "
United States
Gregory Mark
Looe Key Reef Resort

Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1005)
"Beautiful and relaxing "
United States
Michael
The price is €213
includes taxes & fees
5 Jan - 6 Jan 2026
Parmer's Resort

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
9 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (1006)
"Great place to stary. Staff was very nice."
United States
norka
The price is €190
includes taxes & fees
22 Jan - 23 Jan 2026
Sugar Loaf Lodge

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
2.5 km from Cutthroat Harbor Estates
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. "
United States
Preetam
The price is €877
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool

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
8.8 out of 10, Excellent, (1758)
"The place is great!"
United States
Anna
The price is €287
includes taxes & fees
4 Jan - 5 Jan 2026
Oceans Edge Key West Resort, Hotel & Marina

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, (1797)
"Great, friendly staff, nice amenities, easy parking and convenient location "
Canada
Caitlyn
The price is €279
includes taxes & fees
6 Jan - 7 Jan 2026
Blue Flamingo Resort Key West

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
6.1 km from Cutthroat Harbor Estates
The price is €706
includes taxes & fees
6 Jan - 7 Jan 2026
Starlight Serenity - Hideaway w Stunning Views

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
8.2 out of 10, Very good, (1009)
"Nice property, comfortable stay - cookies and staff are great!"
United States
David
The price is €259
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree Resort by Hilton Grand Key - Key West

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, (1295)
"Wonderful stay"
United States
Lindsey
The price is €267
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Key West FL

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, (1007)
"Nice place to stay!"
Canada
Baohua
The price is €269
includes taxes & fees
6 Jan - 7 Jan 2026
The Laureate Key West

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, (1170)
"Great location, clean rooms, and great pools!"
United States
Robin
The price is €324
includes taxes & fees
14 Jan - 15 Jan 2026
Hilton Garden Inn Key West / The Keys Collection

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3.5 star property
29.5 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1013)
"Staff is friendly and knowledgeable in local attractions."
United States
Sheng
The price is €248
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1817)
"Great stay"
United States
james
The price is €273
includes taxes & fees
4 Jan - 5 Jan 2026
Beachside Resort & Residences

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, (1008)
"Great staff, hotel and pool."
United States
Lilly
The price is €421
includes taxes & fees
7 Jan - 8 Jan 2026
Hyatt Vacation Club at Windward Pointe, Key West

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, (1179)
"great place to stay "
United States
michael
The price is €302
includes taxes & fees
8 Jan - 9 Jan 2026
The Perry Hotel & Marina Key West

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, (1006)
"The room was clean and property was so nice and relaxing. "
United States
Kristen
The price is €421
includes taxes & fees
7 Jan - 8 Jan 2026
Hyatt Vacation Club at Beach House, Key West

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, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is €367
includes taxes & fees
5 Jan - 6 Jan 2026
Aqua Lodges at Hurricane Hole Marina
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

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

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 Upper Sugarloaf Sound.

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 Sugarloaf Beach.

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 Crab Key.

Top Cutthroat Harbor Estates Hotel Reviews

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.
What's a favourite hotel to stay in Cutthroat Harbor Estates?
For your stay in Cutthroat Harbor Estates, Just 20 miles from Key West! Oceanfront, dockage, swimming pool is one of the top choices based on our traveller data.
How many hotels are there in Cutthroat Harbor Estates?
Expedia has 75 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.