Cutthroat Harbor Estates
Summerland Key
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Top hotels in Cutthroat Harbor Estates
Amazing waterfront home with private beach, dock, pool, WiFi & outdoor kitchen
Cudjoe Key FL
Stay at this beach holiday home in Summerland Key. Enjoy private pools, a beach locale and patios. Popular attractions Florida Keys Beaches and Venture Out Keys ...
10/10 Exceptional! (5 reviews)
Great location on the water!
This home was fantastic! Aside from the trouble we had with getting a response from the management company on a couple of issues upon arrival(the owner quickly took care of the issues after a couple of weeks waiting for Vacasa), our stay was great! The house was clean and decorated beautifully. Location ...
Reviewed on 23 Mar 2024
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is €301 per night from 19 Apr to 20 Apr
€301
per night
19 Apr - 20 Apr
Stay at this family-friendly hotel in Key West. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
8.2/10 Very Good! (1,997 reviews)
From front desk staff, management to security, everyone was fantastic. There was a Navy event causing one of the amenities to be reserved and inaccessible for the duration of our stay which was a bummer since we booked this resort for the amenities. The pool with a DJ and backyard games were an absolute ...
Reviewed on 23 Mar 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is €346 per night from 13 Apr to 14 Apr
€346
per night
13 Apr - 14 Apr
Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 2 restaurants and a private beach. Our guests praise the pool and the helpful staff in their reviews. ...
8.6/10 Excellent! (2,089 reviews)
Shuttle times are extremely accurate. Beautfil place with friendly staff. Only wish checkout time was a bit later. Elevators were out our entire stay. We were on third floor. The staff did offer to help carry our luggage up.
Reviewed on 22 Mar 2026
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
The price is €352 per night from 12 Apr to 13 Apr
€352
per night
12 Apr - 13 Apr
Stay at this luxury hotel in Key West. Enjoy free Wi-Fi, 6 outdoor pools and a marina. Our guests praise the pool and the restaurant in their reviews. Popular ...
9/10 Wonderful! (1,837 reviews)
Nice place. Came for our 25th wedding anniversary. We had a couple issues that were rectified immediately. I would say it's more of a family type rather than a couple/adult oriented atmosphere!
Reviewed on 23 Mar 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is €309 per night from 30 Mar to 31 Mar
€309
per night
30 Mar - 31 Mar
Stay at this business-friendly hotel in Key West. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,706 reviews)
So much fun!
Reviewed on 22 Mar 2026
The Laureate Key West
3444 N Roosevelt Boulevard Key West FL
The price is €315 per night from 15 Apr to 16 Apr
€315
per night
15 Apr - 16 Apr
Stay at this beach hotel in Key West. Enjoy a 24-hour front desk, a 24-hour business centre and daily housekeeping. Our guests praise the pool and the helpful ...
9.2/10 Wonderful! (1,007 reviews)
Very well equipped
Reviewed on 22 Mar 2026
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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Other neighbourhoods around Cutthroat Harbor Estates
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.
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 Munson Island.
Sugarloaf Shores
Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.
