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 Rp2.538.173 per night from 16 Jul to 17 Jul
Rp2.538.173
Rp4.578.078 total
16 Jul - 17 Jul
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! (2,336 reviews)
"Perfect place to stay. We would have had so much fun if we had known about that place last year. We definitely will come back"

Reviewed on 9 Jul 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 Rp2.253.551 per night from 12 Jul to 13 Jul
Rp2.253.551
Rp3.548.534 total
12 Jul - 13 Jul
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 ...
8.4/10 Very good! (2,510 reviews)
"My favorite place I’ve stayed ever. My wife and I spent the first 3 nights of our honeymoon at the Blue Flamingo Resort. We spent most of one our days at the resort. Honestly, we could have stayed there the whole time but we booked a lot. We had the Oceanview King room. We loved the pool. We enjoyed ..."

Reviewed on 8 Jul 2026

Blue Flamingo Resort Key West
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
The price is Rp2.802.978 per night from 9 Aug to 10 Aug
Rp2.802.978
Rp3.660.084 total
9 Aug - 10 Aug
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 ...
8/10 Very good! (1,272 reviews)
"Staff super friendly, and overall it’s a nice hotel. The traffic was loud if you stayed in the front building. It was also difficult to make a left turn out of the parking lot onto Rosevelt Dr."

Reviewed on 8 Jul 2026

Hilton Garden Inn Key West / The Keys Collection
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
The price is Rp2.334.614 per night from 26 Jul to 27 Jul
Rp2.334.614
Rp3.767.448 total
26 Jul - 27 Jul
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! (1,825 reviews)
"What an amazing experience. Can't wait to visit again soon."

Reviewed on 9 Jul 2026

Havana Cabana at 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 Rp6.120.905 per night from 9 Aug to 10 Aug
Rp6.120.905
Rp7.696.648 total
9 Aug - 10 Aug
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 ...
9.4/10 Exceptional! (1,181 reviews)
"I highly recommend this property! The place was beautiful and the pool and grounds really lovely. Can't wait to go back."

Reviewed on 8 Jul 2026

Hyatt Vacation Club at Windward Pointe, Key West
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
The price is Rp2.760.285 per night from 26 Jul to 27 Jul
Rp2.760.285
Rp4.190.124 total
26 Jul - 27 Jul
includes taxes & fees
Stay at this business-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 ...
9.4/10 Exceptional! (1,292 reviews)
"This hotel is amazing! The view, the location, the cleanliness, the staff, everything was perfect! We enjoyed a week long stay for my 40th birthday and didn’t want to leave! The shower was HUGE in the king bed room we stayed in. The bed itself was comfortable and had a pull out sofa bed for the kids. ..."

Reviewed on 8 Jul 2026

The Perry Hotel & Marina Key West
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.

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.

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.

Breezeswept Beach Estates

While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Big Pine Key Flea Market and Cook Island.



Cutthroat Harbor Estates Travel Guide