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
฿1,840
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
฿1,622
per adult
86% of travellers recommend
Key West Mangrove Kayak Eco Tour
฿2,647
per adult
100% of travellers recommend
Key West Dolphin & Snorkeling Tour - Small Group
฿4,233
per adult
100% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
฿2,315
per adult
76% of travellers recommend
Top hotels in Cutthroat Harbor Estates
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is ฿3,532 per night from 2 Sept to 3 Sept
฿3,532
฿7,140 total
2 Sept - 3 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. ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is ฿3,631 per night from 3 Sept to 4 Sept
฿3,631
฿5,947 total
3 Sept - 4 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 ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿3,642 per night from 21 Sept to 22 Sept
฿3,642
฿6,187 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 ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is ฿3,774 per night from 7 Sept to 8 Sept
฿3,774
฿5,363 total
7 Sept - 8 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 ...
8.4/10 Very good! (1,083 reviews)
"My husband and I joined the hotel. I would definitely recommend this place. I felt like I was in a mini resort."
Reviewed on 31 Aug 2026
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
The price is ฿6,294 per night from 15 Sept to 16 Sept
฿6,294
฿8,570 total
15 Sept - 16 Sept
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! (1,257 reviews)
"This was my first time at an Hyatt and it was great.. loved the stay all around. No complaints about anything. Looking forward to next time."
Reviewed on 31 Aug 2026
Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
Fully refundable
The price is ฿4,589 per night from 20 Sept to 21 Sept
฿4,589
฿5,162 total
20 Sept - 21 Sept
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,487 reviews)
"Nice clean"
Reviewed on 31 Aug 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.
Check Cutthroat Harbor Estates hotel availability
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 Venture Out Keys.
