Find hotels in Cutthroat Harbor Estates, Summerland Key from ￥17,213

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Discover 1,400 Cutthroat Harbor Estates hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

2 outdoor pools, open 8:00 AM to 10:00 PM, sun 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, (1151)
"Will be staying here every single time we visit! "
United States
Rebecca
The price is ￥22,131
￥33,839 total
includes taxes & fees
Nov 30 - Dec 1
The Perry Hotel & Marina Key West
Outdoor pool, open 7:00 AM to 11:00 PM, 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, (1002)
"Very very nice stay! "
United States
Chloe
The price is ￥20,895
￥28,723 total
includes taxes & fees
Dec 1 - Dec 2
DoubleTree Resort by Hilton Grand Key - Key West
Outdoor pool, open 6:00 AM to 10:00 PM, 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, (1125)
"Awesome room, soft bed, hot shower! "
United States
Leia
The price is ￥13,477
￥19,508 total
includes taxes & fees
Dec 1 - Dec 2
Hilton Garden Inn Key West / The Keys Collection
Outdoor pool, sun 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, (1749)
"Great place to stay!"
United States
Maria
The price is ￥19,457
￥31,991 total
includes taxes & fees
Dec 15 - Dec 16
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, (1003)
"Our favorite place to stay in Key West!"
United States
Kevin
The price is ￥24,573
￥31,992 total
includes taxes & fees
Nov 17 - Nov 18
The Laureate Key West
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, (1007)
"Very nice. !"
United States
Kerry J
The price is ￥16,537
￥22,942 total
includes taxes & fees
Dec 1 - Dec 2
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
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, (1002)
"Nice resort, great location. "
United States
Joey Max
The price is ￥37,958
￥49,657 total
includes taxes & fees
Dec 16 - Dec 17
Hyatt Vacation Club at Beach House, Key West
6 outdoor pools, free 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, (1738)
"Staff was wonderful, helpful, happy to help!"
United States
Billy Osburn
The price is ￥20,748
￥32,616 total
includes taxes & fees
Dec 7 - Dec 8
Oceans Edge Key West Resort, Hotel & Marina
Suite, 1 Bedroom, Kitchen, Sea Facing | 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, (1001)
"Wonderful spot…loved it!!!"
Canada
Christopher
The price is ￥16,812
￥23,956 total
includes taxes & fees
Nov 20 - Nov 21
Parmer's Resort
Restaurant
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 star property
9 km from Cutthroat Harbor Estates
8.2 out of 10, Very Good, (1001)
"Tiki hit closed, wish I had known Staff very nice, rooms fine"
United States
James
The price is ￥15,300
￥17,213 total
includes taxes & fees
Nov 30 - Dec 1
Sugar Loaf Lodge
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV
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, (271)
"We will definitely stay here again. Perfect spot to relax. Clean Rooms "
United States
Gregory
Old Wooden Bridge Resort and Marina
Outdoor pool, pool umbrellas, sun 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, (1260)
"Great property and location."
United States
Indraneel
The price is ￥30,289
￥34,075 total
includes taxes & fees
Nov 30 - Dec 1
Hampton Inn Key West FL
Outdoor pool, pool umbrellas, sun loungers
Beachside Resort & Residences

Beachside Resort & Residences

3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1688)
"Very cool place to vacation "
United States
Gabriel
The price is ￥19,908
￥30,220 total
includes taxes & fees
Nov 17 - Nov 18
Beachside Resort & Residences
2 outdoor pools, open 7:00 AM to 11:00 PM, 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, (1700)
"The resort was clean & staff was great!"
United States
Adam
The price is ￥13,889
￥24,318 total
includes taxes & fees
Nov 17 - Nov 18
Blue Flamingo Resort Key West
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, (1002)
"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
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, (1002)
"Clean room great staff beautiful hotel and very spacious rooms. "
United States
German
The price is ￥37,965
￥49,665 total
includes taxes & fees
Dec 1 - Dec 2
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 ￥17,391
￥45,471 total
includes taxes & fees
Nov 17 - Nov 18
Aqua Lodges at Hurricane Hole Marina
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 ￥59,502
￥66,940 total
includes taxes & fees
Dec 12 - Dec 13
Sunshine Key RV Resort & 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)
"Will return "
United States
Vanessa
Little Torch Cottages
Apartment | 1 bedroom
Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony

2.0 star property
29.3 km from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
The price is ￥40,047
￥58,197 total
includes taxes & fees
Dec 1 - Dec 2
Island View 1BR Residence With Balcony
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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Hotels in Cutthroat Harbor Estates with a pool

Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
  • Pool
8.4 out of 10, Very Good, (117)
The price is ￥34,774
￥83,323 total
includes taxes & fees
Nov 18 - Nov 19
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
See more properties

Top guest rated hotels in Cutthroat Harbor Estates

Restaurant
Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole Marina
2.0 star property
    8.8 out of 10, Excellent, (168)
    The price is ￥17,391
    ￥45,471 total
    includes taxes & fees
    Nov 17 - Nov 18
    Aqua Lodges at Hurricane Hole Marina
    See more properties

    Where to stay in Cutthroat Harbor Estates

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

    Bay Point

    Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches 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 Venture Out Keys are some notable places to visit nearby.

    Top Cutthroat Harbor Estates Hotel Reviews

    Hilton Garden Inn Key West / The Keys Collection

    Hilton Garden Inn Key West / The Keys Collection

    10/10 Excellent
    "Excellent staff. Only problem was that the shuttle did not stop at the circle but drove right by the side street and we had to take a taxi back after having waited for 30 minutes."
    Rebeca 1-night trip
    Posted 13 hours ago
    Hilton Garden Inn Key West / The Keys Collection

    Explore a world of travel with Expedia

    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.
    What's the best accommodation 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 traveler data.
    How many hotels will I find in Cutthroat Harbor Estates?
    Expedia has 73 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.