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 ฿4,195 per night from 13 Oct to 14 Oct
฿4,195
฿6,605 total
13 Oct - 14 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 ฿3,579 per night from 12 Oct to 13 Oct
฿3,579
฿7,233 total
12 Oct - 13 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! (2,599 reviews)
"The resort was nice. Room was clean. Shuttle to downtown was excellent. Would stay here again. The only comment would be that the resort was showing some wear. We stayed 2 nights and were happy with our stay for what we paid."
Reviewed on 10 Oct 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is ฿4,728 per night from 25 Oct to 26 Oct
฿4,728
฿7,447 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 ฿4,265 per night from 27 Oct to 28 Oct
฿4,265
฿5,930 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! (1,113 reviews)
"The rooms were nice. The staff were friendly, but the back yard lounge/pool area was my favourite. Beautiful place to longe day or night. The free shuttle to Duval street runs every hour and made it so easy to enjoy downtown!"
Reviewed on 10 Oct 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is ฿4,111 per night from 25 Oct to 26 Oct
฿4,111
฿5,568 total
25 Oct - 26 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 ฿4,676 per night from 12 Oct to 13 Oct
฿4,676
฿6,206 total
12 Oct - 13 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! (1,161 reviews)
"The staff was very helpful, the room was very spacious, very clean, and the king bed was very comfortable. The hotel was amazing and we enjoyed our staying. Highly recommend."
Reviewed on 9 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.
