Cutthroat Harbor Estates Travel Guide

Summerland Key

A calm lake with several white birds, including herons and pelicans, on the water's edge.
A beach with dead trees and a calm sea at sunset.

Things to do


Top hotels in Cutthroat Harbor Estates

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is Rp1.887.440 per night from 1 Sept to 2 Sept
Rp1.887.440
Rp3.815.263 total
1 Sept - 2 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! (2,485 reviews)
"Room was clean, exactly what we had hoped for. Staff was friendly and helpful!"

Reviewed on 30 Aug 2026

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is Rp2.054.157 per night from 1 Sept to 2 Sept
Rp2.054.157
Rp3.306.158 total
1 Sept - 2 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! (2,651 reviews)
"My room did not have a secondary lock; it was broken. And there was not enough outlets in the room."

Reviewed on 31 Aug 2026

Blue Flamingo Resort Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
The price is Rp2.459.327 per night from 2 Sept to 3 Sept
Rp2.459.327
Rp3.889.187 total
2 Sept - 3 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! (1,855 reviews)
"Rooms were clean and well kept, the only complaint is the water in the shower took approximately 5 min to warm up. Had to turn water on and let it run. Pool was spacious and DJ played a variety of music. We would stay here again."

Reviewed on 30 Aug 2026

Havana Cabana at Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
The price is Rp2.016.648 per night from 7 Sept to 8 Sept
Rp2.016.648
Rp2.865.868 total
7 Sept - 8 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 ...
8.4/10 Very good! (1,082 reviews)
"Check-in was easy, and the front desk staff were extremely kind and accommodating. We thought they were wonderful. Our only complaint was an unfortunate incident with another staff member. A middle-aged woman in a green shirt, wearing earbuds/headphones, was riding a motorized mobility scooter through ..."

Reviewed on 30 Aug 2026

DoubleTree Resort by Hilton Grand Key - Key West
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
The price is Rp3.363.086 per night from 15 Sept to 16 Sept
Rp3.363.086
Rp4.579.657 total
15 Sept - 16 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 ...
Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
The price is Rp2.459.327 per night from 1 Sept to 2 Sept
Rp2.459.327
Rp2.766.743 total
1 Sept - 2 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)
"not clean at all"

Reviewed on 31 Aug 2026

Hampton Inn Key West FL
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 Venture Out Keys.



Cutthroat Harbor Estates Travel Guide