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 ฿4,208 per night from 15 Oct to 16 Oct
฿4,208
฿6,627 total
15 Oct - 16 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 ฿3,692 per night from 11 Oct to 12 Oct
฿3,692
฿7,371 total
11 Oct - 12 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. ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿4,744 per night from 25 Oct to 26 Oct
฿4,744
฿7,472 total
25 Oct - 26 Oct
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 ฿4,280 per night from 27 Oct to 28 Oct
฿4,280
฿5,950 total
27 Oct - 28 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! (1,111 reviews)
"Don’t use this hotel their unethical & have horrible customer service. They refused to be helpful when I was in a terrible situation. Book another hotel"
Reviewed on 7 Oct 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is ฿3,996 per night from 11 Oct to 12 Oct
฿3,996
฿5,442 total
11 Oct - 12 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 ฿4,390 per night from 15 Oct to 16 Oct
฿4,390
฿5,885 total
15 Oct - 16 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! (1,159 reviews)
"This is an excellent property i every way. Staff are outstanding. The free shuttle to downtown every hour is a huge plus!"
Reviewed on 8 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.
