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
฿1,824
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
฿1,607
per adult
82% of travellers recommend
Key West Mangrove Kayak Eco Tour
฿2,624
per adult
100% of travellers recommend
Key West Dolphin & Snorkeling Tour - Small Group
฿4,196
per adult
100% of travellers recommend
Top hotels in Cutthroat Harbor Estates
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is ฿3,649 per night from 20 Sept to 21 Sept
฿3,649
฿5,977 total
20 Sept - 21 Sept
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! (2,679 reviews)
"Room was not to clean and the resort fee is way to much for the place not to be as fun or lit."
Reviewed on 19 Sept 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿3,960 per night from 21 Sept to 22 Sept
฿3,960
฿6,559 total
21 Sept - 22 Sept
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! (1,856 reviews)
"Lana at the poolside bar was Awesome & so was Tosha in the cigar lounge as well the stay was very good Team Fenner will be back!!"
Reviewed on 19 Sept 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is ฿2,909 per night from 20 Sept to 21 Sept
฿2,909
฿6,458 total
20 Sept - 21 Sept
includes taxes & fees
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! (2,536 reviews)
"El hotel es muy lindo, el único problema que vimos fueron los elevadores pues el del edificio 2 está fuera de servicio y mi madre tuvo que caminar más y ella es impedida y el elevador del edificio 1 había que bajar a subirlo pues no funcionaba eventualmente desde el piso. Por lo demás todo ..."
Reviewed on 19 Sept 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is ฿3,514 per night from 4 Oct to 5 Oct
฿3,514
฿4,890 total
4 Oct - 5 Oct
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge) and a free local area shuttle. Our guests praise the pool and the ...
8.2/10 Very good! (1,329 reviews)
"The room was clean and exceptional. The staff was very friendly. The buffet was delicious 😋. Recommend it."
Reviewed on 18 Sept 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is ฿3,434 per night from 28 Sept to 29 Sept
฿3,434
฿4,987 total
28 Sept - 29 Sept
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 ...
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
The price is ฿6,094 per night from 4 Oct to 5 Oct
฿6,094
฿8,355 total
4 Oct - 5 Oct
includes taxes & fees
Stay at this hotel in Key West. Enjoy free Wi-Fi, free parking and a snack bar/deli. Our guests praise the pool and the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (1,282 reviews)
"The staff was very rude. Upon checkin we were not greeted. We chose this hotel for"
Reviewed on 19 Sept 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.
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.
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.
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 Pye Key.
