Cutthroat Harbor Estates
Summerland Key
Visit Cutthroat Harbor Estates
Things to do
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $78
per adult
88% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
CA $54
per adult
88% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
CA $98
per adult
76% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
CA $182
per adult
98% of travellers recommend
Cutthroat Harbor Estates Hotel Deals
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is CA $168 per night from Oct 5 to Oct 6
CA $168
CA $270 total
Oct 5 - Oct 6
includes taxes & fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.6/10 Excellent! (2,712 reviews)
"Registration staff very personable. Constant text to check if all is good or need anything."
Reviewed on Oct 3, 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is CA $124 per night from Oct 5 to Oct 6
CA $124
CA $276 total
Oct 5 - Oct 6
includes taxes & fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is CA $182 per night from Nov 2 to Nov 3
CA $182
CA $295 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
The price is CA $176 per night from Oct 11 to Oct 12
CA $176
CA $246 total
Oct 11 - Oct 12
includes taxes & fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is CA $156 per night from Oct 27 to Oct 28
CA $156
CA $216 total
Oct 27 - Oct 28
includes taxes & fees
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Oct 12 to Oct 13
CA $180
CA $286 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,802 reviews)
"This was our second time to stay here and this place never disappoints. Staff is wonderful too"
Reviewed on Oct 3, 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 and neighborhoods for the activities you enjoy most.
Sugarloaf Shores
While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.
Cudjoe Gardens
When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.
Bay Point
Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Big Pine Key Flea Market are some notable places to visit nearby.
