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 Sunset Cruise & Glass Bottom Eco Tour
฿2,294
per adult
76% of travellers recommend
Top hotels in Cutthroat Harbor Estates
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is ฿3,965 per night from 5 Oct to 6 Oct
฿3,965
฿6,348 total
5 Oct - 6 Oct
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! (2,712 reviews)
"Registration staff very personable. Constant text to check if all is good or need anything."
Reviewed on 3 Oct 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is ฿2,929 per night from 6 Oct to 7 Oct
฿2,929
฿6,505 total
6 Oct - 7 Oct
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! (2,581 reviews)
"Clean and modern rooms, has covered parking, housekeeping does a good job. Pool was nice, plenty of towels outside. Shuttle to downtown every hour. Management is quick to remedy any issues. Restaurant on premises. I would definetly stay here again."
Reviewed on 4 Oct 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿4,296 per night from 2 Nov to 3 Nov
฿4,296
฿6,957 total
2 Nov - 3 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 ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is ฿4,134 per night from 11 Oct to 12 Oct
฿4,134
฿5,784 total
11 Oct - 12 Oct
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 ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is ฿3,751 per night from 8 Oct to 9 Oct
฿3,751
฿5,163 total
8 Oct - 9 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)
"I left several rings when I checked out. The staff called me and held them at the front desk. These rings were worth quite a lot of money. I am so thankful and grateful that they did this."
Reviewed on 3 Oct 2026
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
The price is ฿4,238 per night from 12 Oct to 13 Oct
฿4,238
฿6,731 total
12 Oct - 13 Oct
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! (1,802 reviews)
"This was our second time to stay here and this place never disappoints. Staff is wonderful too"
Reviewed on 3 Oct 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.
