Cutthroat Harbor Estates, FL
Summerland Key
Visit Cutthroat Harbor Estates
Cutthroat Harbor Estates Hotel Deals

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cudjoe Key
The price is $539 total per night from Oct 31 to Nov 1
$539 total
per night
Oct 31 - Nov 1
Stay at this vacation home in Summerland Key. Enjoy laundry facilities, patios, and cable/satellite TV service. Our guests praise the property condition in our ...
8.4/10 Very Good! (117 reviews)
Property was clean and comfortable. Location was ideal for our visit and the host gave hreat instructions on locating our unit. Its not a 5 star hotel- if thats what you want, this isnt the place. But if you want a clean, comfortable, affordavlble and convenient location. This is it. Cant wait to ...
Reviewed on Aug 19, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
The price is $232 total per night from Nov 16 to Nov 17
$232 total
per night
Nov 16 - Nov 17
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
8.8/10 Excellent! (1,730 reviews)
This was my 4th year in a row staying at this property. Great views and a great location.
Reviewed on Oct 28, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
The price is $170 total per night from Nov 17 to Nov 18
$170 total
per night
Nov 17 - Nov 18
Stay at this 4-star family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
7.8/10 Good! (1,636 reviews)
Nice Hotel
Reviewed on Oct 26, 2025

Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
The price is $142 total per night from Nov 19 to Nov 20
$142 total
per night
Nov 19 - Nov 20
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
7.8/10 Good! (1,103 reviews)
Great room
Reviewed on Oct 26, 2025

DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd, Key West, FL
The price is $203 total per night from Nov 2 to Nov 3
$203 total
per night
Nov 2 - Nov 3
Stay at this 4-star business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8/10 Very Good! (1,010 reviews)
Some staff are rude but other wise it was a good stay
Reviewed on Oct 27, 2025

Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
The price is $226 total per night from Nov 18 to Nov 19
$226 total
per night
Nov 18 - Nov 19
Stay at this 3.5-star beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,635 reviews)
A real nice hotel away from the crowds and real nice room decor .. Tavern n Town is an A+ restaurant
Reviewed on Oct 27, 2025
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.
Check Cutthroat Harbor Estates hotel availability
Other neighborhoods around Cutthroat Harbor Estates

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.

Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Newfound Harbor Keys and Cook Island are some notable places to visit nearby.

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.

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.
Cutthroat Harbor Estates, FL
Explore a world of travel with Expedia
- Cudjoe Key Hotels
- RV Parks in Cudjoe Key
- Cottages in Cudjoe Key
- Resorts in Cudjoe Key
- Beach Hotels in Cudjoe Key
- Hotels with Restaurants in Cudjoe Key
- Villas in Cudjoe Key
- Pet-friendly Hotels in Cudjoe Key
- Cheap Hotels in Cudjoe Key
- Vacation Homes in Cudjoe Key
- 4 Star Hotels in Cudjoe Key
- Hilton Hotels in Cudjoe Key
- Fishing Resorts & in Cudjoe Key
- Motels in Cudjoe Key
- Condo Rentals in Cudjoe Key
- Houseboats in Cudjoe Key
- Historic Hotels in Cudjoe Key
- Hotels with a Pool in Cudjoe Key
- Summerland Key Hotels
- RV Parks in Summerland Key
- B&B in Summerland Key
- Cottages in Summerland Key
- Condo Rentals in Summerland Key
- Apartments in Summerland Key
- Vacation Homes in Summerland Key
- Villas in Summerland Key
- Resorts in Summerland Key
- Houseboats in Summerland Key
- Motels in Summerland Key
- 4 Star Hotels in Summerland Key
- 5 Star Hotels in Summerland Key
- Lower Keys Hotels
- Fishing Resorts & in Lower Keys
- Cheap Hotels in Lower Keys
- Pet-friendly Hotels in Lower Keys
- Beach Hotels in Lower Keys
- Cottages in Lower Keys
- 5 Star Hotels in Lower Keys
- Resorts in Lower Keys
- Motels in Lower Keys
- Extended Stay Hotels in Lower Keys
- 4 Star Hotels in Lower Keys
- RV Parks in Lower Keys
- Apartments in Lower Keys
- Hotels with Hot Tubs in Lower Keys
- Ski Hotels in Lower Keys
- Ramrod Key Hotels
- RV Parks in Ramrod Key
- Pet-friendly Hotels in Ramrod Key
- Motels in Ramrod Key
- Hotels with Bars in Ramrod Key
- B&B in Ramrod Key
- Condo Rentals in Ramrod Key
- Historic Hotels in Ramrod Key
- 4 Star Hotels in Ramrod Key
- Vacation Homes in Ramrod Key
- Beach Hotels in Ramrod Key
- Apartments in Ramrod Key
- Luxury Hotels in Ramrod Key
- Cottages in Ramrod Key
- Family Hotels in Ramrod Key
- Flights to Cudjoe Key
- Flights from Cudjoe Key
- Flights from Minneapolis - St. Paul to Cudjoe Key
- Flights from Boston to Cudjoe Key
- Flights from Orlando to Cudjoe Key
- Flights from Raleigh to Cudjoe Key
- Flights from Tampa to Cudjoe Key
- Flights to Summerland Key
- Flights from Summerland Key
- Flights from Melody Key
- Flights to Lower Keys
- Flights to Ramrod Key
- Car rentals near Cudjoe Key
- Budget Rental Cars in Cudjoe Key
- Enterprise Rental Cars in Cudjoe Key
- Sixt Rental Cars in Cudjoe Key
- Alamo Rent A Car Rental Cars in Cudjoe Key
- Fox Rental Cars Rental Cars in Cudjoe Key
- Thrifty Car Rental Rental Cars in Cudjoe Key
- Car rentals near Summerland Key
- Enterprise Rental Cars in Summerland Key
- Car rentals near Ramrod Key