Cutthroat Harbor Estates Travel Guide

Tourist Guide

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.

Activities


Our pick of the best 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 FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and patios. Our guests praise the property condition in their reviews. Popular ...
8.4/10 Very good! (133 reviews)
"Ramp is a dirt ramp but was just fine with 17’ flats boats. Also the pool was great after being on the water each day"

Reviewed on 18 Oct 2026

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

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundable
The price is NZ$379 per night from 2 Dec to 3 Dec
NZ$379
2 Dec - 3 Dec
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! (1,902 reviews)
"The shuttle service is extremely helpful if you don’t have a car given it is quietly away from the heavy tourist area. The pool was wonderful with an array of floats. Nice temperature! Bar service and breakfast were great. Staff was very nice and informative about places to go and eat. They could ..."

Reviewed on 11 Nov 2026

Havana Cabana at Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is NZ$333 per night from 16 Nov to 17 Nov
NZ$333
16 Nov - 17 Nov
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 ...
Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
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. ...
Beachside Resort & Residences
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 NZ$323 per night from 18 Nov to 19 Nov
NZ$323
18 Nov - 19 Nov
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 ...
DoubleTree Resort by Hilton Grand Key - Key West
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

3.5 out of 5
3852 North Roosevelt Boulevard Key West FL
The price is NZ$319 per night from 29 Nov to 30 Nov
NZ$319
29 Nov - 30 Nov
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the breakfast and the pool in their ...
8.8/10 Excellent! (1,200 reviews)
"Great place to stay, 15min from downtown."

Reviewed on 11 Nov 2026

Fairfield by Marriott Inn & Suites Key West at 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.

Our guide on 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 Big Pine Key Flea Market.



Cutthroat Harbor Estates Travel Guide

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