Cutthroat Harbor Estates Travel Guide
Summerland Key
Visit Cutthroat Harbor Estates
Top hotels in Cutthroat Harbor Estates
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is 2.504.984 ₫ per night from 13 Sept to 14 Sept
2.504.984 ₫
5.311.974 ₫ total
13 Sept - 14 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. ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is 2.859.672 ₫ per night from 7 Sept to 8 Sept
2.859.672 ₫
4.684.131 ₫ total
7 Sept - 8 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! (2,656 reviews)
"Saw good reviews of hotel but needed to stay there myself. I must say I was pleasantly surprised. Please note the hotel is about a minute from the entrance into Key West which is OK for us. The lobby from the moment you enter has an amazing smell due to a scent they put out. We loved it. The lobby ..."
Reviewed on 5 Sept 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is 2.660.160 ₫ per night from 20 Sept to 21 Sept
2.660.160 ₫
4.636.243 ₫ total
20 Sept - 21 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! (1,849 reviews)
"Very unique location and the staff was amazing (I think the pool bartender is now a member of the family!). Enjoyed time around the pool. The shuttle and concierge made things very simple on to do and transportation around Key West. We will be back guaranteed!"
Reviewed on 5 Sept 2026
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is 4.957.286 ₫ per night from 22 Sept to 23 Sept
4.957.286 ₫
6.750.546 ₫ total
22 Sept - 23 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 2.865.670 ₫ per night from 15 Sept to 16 Sept
2.865.670 ₫
4.104.078 ₫ total
15 Sept - 16 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 ...
Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
The price is 3.614.166 ₫ per night from 20 Sept to 21 Sept
3.614.166 ₫
4.065.937 ₫ total
20 Sept - 21 Sept
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,486 reviews)
"Great location right by the airport. Nice rooms but there's no reason to be in the rooms because Key West is absolutely beautiful and you want to be outside all day."
Reviewed on 5 Sept 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 Munson Island.
