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
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿4,836 per night from 3 Nov to 4 Nov
฿4,836
฿7,573 total
3 Nov - 4 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! (1,888 reviews)
"Enjoyed my stay. Staff was nice and friendly. Bartender at Flama Cabana was awesome."
Reviewed on 19 Oct 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is ฿4,181 per night from 25 Oct to 26 Oct
฿4,181
฿6,585 total
25 Oct - 26 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! (2,741 reviews)
"Very nice place to stay they even offer a shuttle bus to duval"
Reviewed on 19 Oct 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is ฿3,910 per night from 27 Oct to 28 Oct
฿3,910
฿7,595 total
27 Oct - 28 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! (2,630 reviews)
"Friendly clean facilities!!!"
Reviewed on 19 Oct 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is ฿3,869 per night from 28 Oct to 29 Oct
฿3,869
฿5,486 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! (1,123 reviews)
"I didn’t like the front desk clerk who check us in, not friendly AT ALL!!! Did not feel welcome."
Reviewed on 20 Oct 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is ฿3,551 per night from 28 Oct to 29 Oct
฿3,551
฿4,940 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 ...
8.2/10 Very good! (1,347 reviews)
"Pros: great location, nice pool area, clean room, price good for the area, friendly staff. Cons: ice machine near our room broken, one of the elevators was out of order, bed uncomfortably firm, despite the website saying they had dinner inside the only food choices were from the poolside bar. Still ..."
Reviewed on 19 Oct 2026
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3852 North Roosevelt Boulevard Key West FL
The price is ฿3,899 per night from 26 Oct to 27 Oct
฿3,899
฿5,331 total
26 Oct - 27 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! (1,173 reviews)
"For me 10 of 100 great hotel very clean and very good room omg super nice , breakfast very good ."
Reviewed on 20 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.
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 Big Pine Key Flea Market.
