Hotels Near
Cutthroat Harbor Estates

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Featured Cutthroat Harbor Estates Hotels

Beachside Resort & Residences
Beachside Resort & Residences
3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
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! (1,287 reviews)
"Pretty solid. Room was a little small. Great pool"

Reviewed on Jul 4, 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West
Blue Flamingo Resort Key West
4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
7.6/10 Good! (1,448 reviews)
"Clean, comfortable well kept property and grounds. Friendly staff."

Reviewed on Jul 1, 2025

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
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! (1,667 reviews)
"The Staff at this resort are very nice. Ana was very accommodating and made sure we had a wonderful stay. The rooms were super clean and nice. The amenities were very fun. Overall oceans edge is the best Hotel in Key west!"

Reviewed on Jun 30, 2025

Oceans Edge Key West Resort, Hotel & Marina
Havana Cabana at Key West
Havana Cabana at Key West
4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in ...
8.8/10 Excellent! (1,742 reviews)
"The bartenders were wonderful."

Reviewed on Jul 2, 2025

Havana Cabana at Key West
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection
3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
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 ...
7.6/10 Good! (1,041 reviews)
"love it"

Reviewed on Jul 2, 2025

Hilton Garden Inn Key West / The Keys Collection
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West
4 out of 5
7001 Shrimp Road, Key West, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
9.4/10 Exceptional! (1,016 reviews)
"Lovely spot w great pool, a bit removed from downtown KW but very accessible"

Reviewed on Jul 4, 2025

The Perry Hotel & Marina Key West
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
3.5 out of 5
3852 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
Book a stay at this eco-certified hotel in Key West. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in ...
8.4/10 Very Good! (1,000 reviews)
"A but far from the center but very comfortable"

Reviewed on Jun 29, 2025

Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Hampton Inn Key West FL
Hampton Inn Key West FL
2.5 out of 5
3755 S Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.8/10 Excellent! (1,176 reviews)
"Would definitely recommend. Clean, great staff, complimentary breakfast and water bottles. We enjoyed exploring the city on a golf cart we rented from the concierge."

Reviewed on Jun 30, 2025

Hampton Inn Key West FL
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key West
3.5 out of 5
3675 South Roosevelt Boulevard, Key West, FL
Fully refundable
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff ...
9.4/10 Exceptional! (1,004 reviews)
"The check in is to late at 4pm and the check out to early at 10 am, basically you lost a whole day. It’s not fear for customers."

Reviewed on Jul 1, 2025

Hyatt Vacation Club at Windward Pointe, Key West
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West
4 out of 5
3990 S Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
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 ...
7.8/10 Good! (1,000 reviews)
"No comment"

Reviewed on Jun 25, 2025

DoubleTree Resort by Hilton Grand Key - Key West
Hyatt Vacation Club at Beach House, Key West
Hyatt Vacation Club at Beach House, Key West
3.5 out of 5
5051 Overseas Highway, Key West, FL
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and concierge services. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,000 reviews)
"We have stayed at several properties in Key West and this is one of our new favorites!! The pool and outdoor space is gorgeous!"

Reviewed on Jul 3, 2025

Hyatt Vacation Club at Beach House, Key West
Parmer's Resort
Parmer's Resort
2.5 out of 5
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,002 reviews)
Great stay with excellent staff, service, rooms!
"A wonderful stay! Great staff, service, and rooms! Very comfy bed with lamps on both sides for reading. Great shower and kitchen! Breakfast was much more than “Grab and Go. We held a large family event here and Parmer’s couldn’t be more accommodating."

Reviewed on Jun 22, 2025

Parmer's 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.

Hotels in Cutthroat Harbor Estates

Summerland Key is a city that has a lot going on, but you have your sights set on Cutthroat Harbor Estates. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Cutthroat Harbor Estates has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Cutthroat Harbor Estates hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Summerland Key so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Cutthroat Harbor Estates underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Cutthroat Harbor Estates city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Cutthroat Harbor Estates cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Cutthroat Harbor Estates at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $153
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Cutthroat Harbor Estates hotel you want, book it, and never look back. Because your great escape is ahead of you.