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 ฿3,162 per night from 13 Sept to 14 Sept
฿3,162
฿6,705 total
13 Sept - 14 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! (2,488 reviews)
"Clean, friendly staff, awesome views, awesome shuttles. Great dinner. Only thing is breakfast was underwhelming"
Reviewed on 4 Sept 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is ฿3,609 per night from 7 Sept to 8 Sept
฿3,609
฿5,912 total
7 Sept - 8 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! (2,653 reviews)
"Todo estuvo espectacular"
Reviewed on 5 Sept 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿3,358 per night from 20 Sept to 21 Sept
฿3,358
฿5,852 total
20 Sept - 21 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 ...
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is ฿6,257 per night from 22 Sept to 23 Sept
฿6,257
฿8,520 total
22 Sept - 23 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! (1,262 reviews)
"The room was very spacious and had a beautiful view. Everything was very clean and the grounds were well maintained. 10/10"
Reviewed on 4 Sept 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is ฿3,617 per night from 15 Sept to 16 Sept
฿3,617
฿5,180 total
15 Sept - 16 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
Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
The price is ฿4,562 per night from 20 Sept to 21 Sept
฿4,562
฿5,132 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! (1,486 reviews)
"Great location right by the airport. Nice rooms but there's no reason to be in the rooms because Key West is absolutely beautiful and you want to be outside all day."
Reviewed on 5 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.
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 Munson Island.
