Cutthroat Harbor Estates Travel Guide

Summerland Key



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 3.501.561 ₫ per night from 30 Nov to 1 Dec
3.501.561 ₫
5.273.376 ₫ total
30 Nov - 1 Dec
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! (1,680 reviews)
Staff was horrible on directions to room. We had to give directions to 4 different sets of new guests as well as getting lost ourselves. Place was great. Nice location.

Reviewed on 13 Nov 2025

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 2.830.312 ₫ per night from 2 Dec to 3 Dec
2.830.312 ₫
4.666.458 ₫ total
2 Dec - 3 Dec
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 ...
7.8/10 Good! (1,693 reviews)
What a fun little resort. The amenities are fabulous! They have live music. We heard Ike Kanakanaui. He was REALLY good!

Reviewed on 14 Nov 2025

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
The price is 4.295.803 ₫ per night from 2 Dec to 3 Dec
4.295.803 ₫
6.422.753 ₫ total
2 Dec - 3 Dec
includes taxes & fees
Stay at this luxury hotel in Key West. Enjoy free Wi-Fi, 6 outdoor pools and a marina. Our guests praise the pool and the restaurant in their reviews. Popular ...
8.8/10 Excellent! (1,739 reviews)
We thoroughly enjoyed our stay at Oceans Edge. It was a beautiful relaxing oasis for us to spend a few days. The weather was not great (windy & a little chilly) so we couldn't use the paddleboards or kayaks. The food at the restaurant was delicious and we ended up eating there for almost all our ...

Reviewed on 18 Nov 2025

Oceans Edge Key West Resort, Hotel & Marina
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
Fully refundableReserve now, pay when you stay
The price is 4.481.424 ₫ per night from 15 Dec to 16 Dec
4.481.424 ₫
6.575.805 ₫ total
15 Dec - 16 Dec
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! (1,147 reviews)
What a beautiful property! We had an amazing time. Plenty of amenities and the staff was top notch.

Reviewed on 13 Nov 2025

The Perry Hotel & Marina 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 3.482.028 ₫ per night from 30 Nov to 1 Dec
3.482.028 ₫
4.807.573 ₫ total
30 Nov - 1 Dec
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 ...
8/10 Very Good! (1,009 reviews)
We had a great time in Key West. The DoubleTree was clean, safe, and staff were friendly! The airport shuttle is on demand so they will take you to the airport whenever. The shuttle to downtown ran every hour until 11pm. Billy was the bartender while we were there and he was AWESOME! If you go, please ...

Reviewed on 17 Nov 2025

DoubleTree Resort by Hilton Grand Key - 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 2.297.982 ₫ per night from 2 Dec to 3 Dec
2.297.982 ₫
3.326.540 ₫ total
2 Dec - 3 Dec
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 ...
7.8/10 Good! (1,127 reviews)
Clean room

Reviewed on 16 Nov 2025

Hilton Garden Inn Key West / The Keys Collection
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.

Other neighbourhoods around Cutthroat Harbor Estates

Default Image

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 Venture Out Keys.

Cudjoe Gardens
Default Image

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.

Breezeswept Beach Estates
Default Image

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.

Sugarloaf Shores


Cutthroat Harbor Estates Travel Guide

Choose two or more items and save on your trip: