Cutthroat Harbor Estates Travel Guide
Summerland Key
Visit Cutthroat Harbor Estates
Things to do
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
฿1,876
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
฿1,108
per adult
82% of travellers recommend
Key West Mangrove Kayak Eco Tour
฿2,699
per adult
100% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
฿2,360
per adult
76% of travellers recommend
Top hotels in Cutthroat Harbor Estates
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿4,833 per night from 29 Nov to 30 Nov
฿4,833
฿7,569 total
29 Nov - 30 Nov
includes taxes & fees
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! (1,899 reviews)
"Clean comfortable room, helpful van drivers and van service. Great staff."
Reviewed on 6 Nov 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is ฿4,186 per night from 15 Nov to 16 Nov
฿4,186
฿6,593 total
15 Nov - 16 Nov
includes taxes & fees
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 ...
8.6/10 Excellent! (2,775 reviews)
"Really nice spot. Great for families and large groups"
Reviewed on 6 Nov 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
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! (2,669 reviews)
"Staff were helpful and approachable. The room was beautiful and well equipped to keep us satisfied. We enjoyed the pool and adjacent bar which offers excellent fried chicken. The grounds were well kept and the beach area was clean and relaxing. Peacefully quiet while offering fun activities like ..."
Reviewed on 6 Nov 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is ฿4,123 per night from 15 Nov to 16 Nov
฿4,123
฿5,768 total
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly resort in Key West. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the helpful staff and ...
8.4/10 Very good! (1,132 reviews)
"Everything clean and politely"
Reviewed on 6 Nov 2026
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3852 North Roosevelt Boulevard Key West FL
The price is ฿4,238 per night from 15 Nov to 16 Nov
฿4,238
฿5,709 total
15 Nov - 16 Nov
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the breakfast and the pool in their ...
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
The price is ฿3,952 per night from 15 Nov to 16 Nov
฿3,952
฿6,403 total
15 Nov - 16 Nov
includes taxes & fees
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! (1,795 reviews)
"Fire alarm went off at 3 AM on Novembe 5th, but the siren could not be heard at all inside room 2306 due to the front vestibule. I only realized what was happening when I looked out the window and saw a crowd outside. There was absolutely zero communication or direction from hotel staff and no fire ..."
Reviewed on 7 Nov 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.
Where to stay in Cutthroat Harbor Estates
Find the best Cutthroat Harbor Estates areas for the activities you enjoy most.
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.
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 Florida Keys Beaches.
Bay Point
While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.
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 Big Pine Key Flea Market.
