Find hotels in Cutthroat Harbor Estates, Summerland Key

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Our top choices for Cutthroat Harbor Estates hotels

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, (160)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
The price is ₩450,634
₩506,971 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sunshine Key RV Resort & 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

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, (279)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina

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, (1000)
"Was nice roo.s and close to my charter boat captain "
United States
Nicholas
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, (1004)
"Beautiful and relaxing "
United States
Michael
The price is ₩284,565
₩368,346 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Parmer's Resort

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 ₩831,088
₩1,516,736 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Atlantic View Luxury Villa with 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, (1004)
"The room was clean and property was so nice and relaxing. "
United States
Kristen
The price is ₩589,002
₩729,114 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hyatt Vacation Club at Beach House, Key West

Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1806)
"Great stay"
United States
james
The price is ₩374,033
₩495,584 total
includes taxes & fees
Jan 4 - Jan 5, 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, (1004)
"Great staff, hotel and pool."
United States
Lilly
The price is ₩589,002
₩729,114 total
includes taxes & fees
Jan 7 - Jan 8, 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, (1178)
"great place to stay "
United States
michael
The price is ₩384,378
₩523,187 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Perry Hotel & Marina Key West

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, (1784)
"Great, friendly staff, nice amenities, easy parking and convenient location "
Canada
Caitlyn
The price is ₩357,700
₩485,533 total
includes taxes & fees
Jan 8 - Jan 9, 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 ₩636,542
₩1,209,777 total
includes taxes & fees
Dec 22 - Dec 23
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, (1003)
"Nice property, comfortable stay - cookies and staff are great!"
United States
David
The price is ₩353,416
₩447,458 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree Resort by Hilton Grand Key - Key West

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
9 km from Cutthroat Harbor Estates
8.2 out of 10, Very Good, (1005)
"Great place to stary. Staff was very nice."
United States
norka
The price is ₩205,371
₩231,050 total
includes taxes & fees
Dec 22 - Dec 23
Sugar Loaf Lodge

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, (1292)
"Wonderful stay"
United States
Lindsey
The price is ₩410,890
₩462,251 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn Key West FL

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, (1164)
"Great location, clean rooms, and great pools!"
United States
Robin
The price is ₩461,199
₩560,412 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Hilton Garden Inn Key West / The Keys Collection

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, (1005)
"Nice place to stay!"
Canada
Baohua
The price is ₩367,895
₩455,451 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Laureate Key West

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, (1009)
"Staff is friendly and knowledgeable in local attractions."
United States
Sheng
The price is ₩344,255
₩428,834 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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 ₩344,403
₩635,118 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Aqua Lodges at Hurricane Hole Marina

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, (1721)
"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 ₩438,531
₩596,950 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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 and neighborhoods for the activities you enjoy most.

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Upper Sugarloaf Sound and Florida Keys Beaches are some notable places to visit nearby.

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Upper Sugarloaf Sound, some noteworthy sights in the nearby area.

Bay Point

Bay Point might not have many top sights, but Lower Sugarloaf Sound and Sugarloaf Beach 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 Crab Key are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

Frequently asked questions

What's it like in Cutthroat Harbor Estates?
Travelers to Summerland Key's Cutthroat Harbor Estates neighborhood will be sure to enjoy a stay in this neighborhood.
How many hotels will I find in Cutthroat Harbor Estates?
Expedia has 74 hotels and other accommodations 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 reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of booking. Add dates, click "Search", then you can filter by "fully refundable" to view the best deals in Cutthroat Harbor Estates.
Where can I learn more about changing or cancelling my trip to Cutthroat Harbor Estates?
For more details about changing or cancelling your trip to Cutthroat Harbor Estates, click here.
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.