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
฿1,856
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
฿1,096
per adult
82% of travellers recommend
Key West Mangrove Kayak Eco Tour
฿2,671
per adult
100% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
฿2,335
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 ฿4,193 per night from 26 Oct to 27 Oct
฿4,193
฿6,602 total
26 Oct - 27 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 ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is ฿3,921 per night from 28 Oct to 29 Oct
฿3,921
฿7,615 total
28 Oct - 29 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! (2,617 reviews)
"We were very happy with how nice, clean and comfortable our 1 bedroom was. The staff was very helpful via text messages for anything we needed like coffee. The pool was clean and well kept. The shuttle bus to Duval street was a very pleasant surprise and the drivers were really prompt."
Reviewed on 15 Oct 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿4,927 per night from 2 Nov to 3 Nov
฿4,927
฿7,672 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 ...
9/10 Wonderful! (1,878 reviews)
"pool was the best with food and bar right next. shuttle service to town was excellent can't wait to go back!"
Reviewed on 15 Oct 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is ฿3,995 per night from 28 Oct to 29 Oct
฿3,995
฿5,625 total
28 Oct - 29 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 ...
8.4/10 Very good! (1,116 reviews)
"Beautiful resort. Very good restaurant on site. Shuttle bus to and from Old Town Key West every hour. The staff was exceptional. Highly recommend this resort."
Reviewed on 13 Oct 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is ฿3,905 per night from 28 Oct to 29 Oct
฿3,905
฿5,336 total
28 Oct - 29 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 ...
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3852 North Roosevelt Boulevard Key West FL
The price is ฿4,193 per night from 25 Oct to 26 Oct
฿4,193
฿5,659 total
25 Oct - 26 Oct
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 ...
8.6/10 Excellent! (1,168 reviews)
"Unable to understand with the staff on my arrival. It was so frustrating!! Other than that nice atmosphere."
Reviewed on 15 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.
