Cutthroat Harbor Estates, FL

Summerland Key



Cutthroat Harbor Estates Hotel Deals

Just 20 miles from Key West!  Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy laundry facilities, patios, and cable/satellite TV service. Our guests praise the property condition in our ...
8.2/10 Very Good! (115 reviews)
"Great experience"

Reviewed on 6 August 2025

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
The price is SAR 469 per night from Aug 25 to Aug 26
SAR 469
SAR 718 total
25 Aug - 26 Aug
includes taxes & fees
Stay at this 3.5-star 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. ...
8.4/10 Very Good! (1,471 reviews)
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"

Reviewed on 20 August 2025

Beachside Resort & Residences
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 SAR 380 per night from Sep 1 to Sep 2
SAR 380
SAR 533 total
1 Sep - 2 Sep
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 ...
7.8/10 Good! (1,069 reviews)
"Most excellent facility with very accommodating staff."

Reviewed on 18 August 2025

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

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
The price is SAR 445 per night from Sep 21 to Sep 22
SAR 445
SAR 712 total
21 Sep - 22 Sep
includes taxes & fees
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
7.8/10 Good! (1,548 reviews)
"Good for the price! Cleanliness can improve, when we complained about the cleaning our room we were promptly moved rooms and were very satisfied. Breakfast situation is a bit off, way overpriced for the portion, prepaid breakfast for the room but only offered one complimentary plate? Literally the ..."

Reviewed on 19 August 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 SAR 629 per night from Sep 2 to Sep 3
SAR 629
SAR 926 total
2 Sep - 3 Sep
includes taxes & fees
Stay at this 4-star 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 ...
8.8/10 Excellent! (1,716 reviews)
"I loved everything about this resort. So clean and easy to navigate our way around. Transportation offered worked well for us."

Reviewed on 18 August 2025

Oceans Edge Key West Resort, Hotel & Marina
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 SAR 784 per night from Sep 1 to Sep 2
SAR 784
SAR 1,051 total
1 Sep - 2 Sep
includes taxes & fees
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff ...
9.4/10 Exceptional! (1,014 reviews)
A great weekend trip
"We found the room well appointed and clean, plenty of space for relaxing and spreading out. We really appreciated the large balcony/deck with table and ocean views. The decor/design was a little dated but it is clean and in good shape overall. The pool/bar area is excellent and has good views of ..."

Reviewed on 19 August 2025

Hyatt Vacation Club at Windward Pointe, 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.

Other neighborhoods around Cutthroat Harbor Estates

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Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Venture Out Keys, some noteworthy sights in the nearby area.

Cudjoe Gardens
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Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Newfound Harbor Keys and Cook Island are some notable places to visit nearby.

Breezeswept Beach Estates
Sugarloaf Shores featuring a bay or harbor

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.

Sugarloaf Shores

Cutthroat Harbor Estates, FL

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