Historic Hideaways - The Finest Vacation Rental Homes in Key West!

Historic Hideaways

Historic Hideaways has been in the vacation home business in Key West for over 25 years. Local Knowledge from Local Owners in Key West Florida. We specialize in Weekly, Monthly, and Seasonal Key West Vacation Rentals.

All of our vacation home properties are located on the island of Key West itself...most in the Old Town Historic District. Our quality Key West vacation home rentals include villas, condos, townhomes, and private rental homes. Choose from these private and historic Key West Vacation Rentals with private pools, or a cozy cottage, or condominiums with a shared pool. Through Historic Hideaways, you can enjoy a Key West Vacation Rental with unique and charming details, features, amenities, and views.

Our Staff to Guest ratio is one of the best in Key West. This allows us to give you ( our guests ) the personal service we have come to be known for. Call or email us with any questions regarding your Key West destination, a property, our service, or to request a quote.


Company Overview

Historic Hideaways
In Business Since 1997
1109 Duval Street
Key West Florida 33040

* Trusted Find Rentals Member Since July 2018

Interested in Booking a Vacation Rental with Historic Hideaways?


Historic-Key-West-Property-Florida-Keys

Property Management from Historic Hideaways

We have been in the Key West rental business for over 25 years, and have a vast knowledge of, and appreciation for, the Key West rentals market. We hope to put this experience to work for you! We offer property management for monthly and weekly vacation rentals.  Please let us know how Historic Hideaways can service your Key West property management needs.

Review our Value Proposition for Property Owners of Key West

Historic-Key-West-Vacation-Rental-Management-Company

Property Specials from Historic Hideaways 

Historic Hideaways offer some last minute vacation Specials on our Weekly and Monthly Key West Vacation Rental Accommodations.

Visit Historic Hideaways Vacation Rental Specials

Historic-Key-West-Vacation-Rental-Management-Property


Vacation Rentals from Historic Hideaways

The Sanctuary
$6,000/month
Home in Key West Florida
5 Beds • 5 Full Baths • Sleeps 10
Historic Hideaways
Paradise Grand
$9,900/month
Home in Key West Florida
5 Beds • 4 Full Baths • Sleeps 10
Historic Hideaways
Truman House
$770/night
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 10
Historic Hideaways
Pool Area
$625/night
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 8
Historic Hideaways
Admiral's Lane
$4,200/week
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 8
Historic Hideaways
Key West vacation home with pool and 4 bedrooms close to the beach and Duval Street : Island Style
$695/night
Home in Key West Florida
4 Beds • 3 Full Baths • Sleeps 8
Historic Hideaways


Need a Company to Manage Your Vacation Property?

Get Vacation Property Managed

Looking to have your vacation property managed by a professional rental management company? You have come to the right place.

If you own a vacation property in Key West, Old Town Key West, Truman Annex of Key West or the surrounding areas and are interested in hiring a professional management company , you can contact Historic Hideaways to help you.


Historic Hideaways Reviews

Have you rented with Historic Hideaways?
Let other travelers know your experience by submitting a review!