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 Express Day Trip from Miami
฿2,375
per adult
88% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
฿1,276
per adult
88% of travellers recommend
Key West Mangrove Kayak Eco Tour
฿2,624
per adult
100% of travellers recommend
Top hotels in Cutthroat Harbor Estates
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is ฿2,973 per night from 17 Sept to 18 Sept
฿2,973
฿6,492 total
17 Sept - 18 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! (2,503 reviews)
"Our stay was excellent! Everyone was super nice"
Reviewed on 9 Sept 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is ฿3,608 per night from 13 Sept to 14 Sept
฿3,608
฿5,910 total
13 Sept - 14 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 ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿3,620 per night from 27 Sept to 28 Sept
฿3,620
฿6,149 total
27 Sept - 28 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 ...
9/10 Wonderful! (1,853 reviews)
"Almost everything was perfect. Food and drinks were excellent. Staff was all friendly and helpful. The place was clean and well maintained. The pool, gorgeous. The whole place is so cute. My only complaint was the shower. The water pressure was not great and I would have loved a shower head that ..."
Reviewed on 9 Sept 2026
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
The price is ฿5,899 per night from 23 Sept to 24 Sept
฿5,899
฿8,117 total
23 Sept - 24 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 ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is ฿3,396 per night from 29 Sept to 30 Sept
฿3,396
฿4,931 total
29 Sept - 30 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 ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is ฿3,735 per night from 16 Sept to 17 Sept
฿3,735
฿5,128 total
16 Sept - 17 Sept
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 ...
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 Munson Island.
