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 ฿2,885 per night from 20 Sept to 21 Sept
฿2,885
฿6,406 total
20 Sept - 21 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! (2,508 reviews)
"It was beautiful, not so crowded, relaxing, an peaceful"
Reviewed on 11 Sept 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is ฿3,624 per night from 14 Sept to 15 Sept
฿3,624
฿5,936 total
14 Sept - 15 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 ...
8.6/10 Excellent! (2,664 reviews)
"The only gripe I would give is I think our air in our room was not adjustable or maybe it was broken. Also shower was slippery! The staff were super super friendly. Love all the activities and games they offer. The best staff member was Irena at the pool bar! Give that girl a Raise! Would stay here ..."
Reviewed on 11 Sept 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿3,636 per night from 27 Sept to 28 Sept
฿3,636
฿6,176 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! (1,856 reviews)
"Staff very friendly and helpful. Really enjoyed our stay. Very clean and up to date. Great vibe.. amazing pool. Not as close as we thought to Duvall but not a problem with renting golf cart. Would stay here again in a heart beat"
Reviewed on 11 Sept 2026
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
The price is ฿6,044 per night from 4 Oct to 5 Oct
฿6,044
฿8,287 total
4 Oct - 5 Oct
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 ฿3,411 per night from 27 Sept to 28 Sept
฿3,411
฿4,953 total
27 Sept - 28 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 ฿3,461 per night from 22 Sept to 23 Sept
฿3,461
฿4,823 total
22 Sept - 23 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.
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.
