Let us be your ticket to paradise. Historic Hideaways manages and rents the finest vacation homes in Key West — from private homes with their own pools, to cozy cottages, condominiums, and townhomes, most with pools, in Old Town, Truman Annex, The Meadows, Casa Marina, and Mid & New Town.
Homes run from one bedroom to four-plus, many are dog-friendly, and stays are available nightly, weekly, or monthly.
Each vacation rental on our site comes with a detailed description, interior and exterior photos, a full amenities list, and a map location, so you know exactly what you're booking and where it sits on the island. Real-time availability and online booking let you reserve in minutes, and our site also covers rental rules and procedures, frequently asked questions, and travel insurance. Our concierge team can help with the rest of the trip once you're booked.
1109 Duval Street, Key West. Call 305.294.3064 or browse and book at HistoricHideaways.com.
Beautiful cottage, perfect location, wonderful pool and patio area! VERY private yet close to all the action!!
KB
kirstie byrant
Jul 19, 2026
5.0
Brandy was amazing! Made me feel at home ❤️ thank you so much for welcoming us 😊
DP
David Presser
Jul 1, 2026
5.0
We have used your service many times and have always been thrilled with our stay!!!!
5 STARS
SW
Sandra Wilkins
Jun 30, 2026
5.0
This was a girls trip and the house was absolutely wonderful. We all approved and highly recommend. We did rent a car for our stay but could have Uber’s much cheaper. And parking can be a challenge. We used the car only twice. Most everything is within walking distance and definitely within scooter distance.
MB
Mike B.
Jun 23, 2026
5.0
We have stayed all over Old Town, and this property is one of our favorites. It is very quiet, clean, and perfect for two people. It had everything we needed to cook light meals, and we loved the great little pool that we had all to ourselves!"
Frequently Asked Questions About Historic Hideaways
What types of vacation rentals does Historic Hideaways offer in Key West?
Historic Hideaways offers private and historic Key West vacation rental homes with private pools, cozy cottages, condominiums, and townhomes with shared pools.
How do the rental prices at Historic Hideaways compare to hotel room rates?
You can rent and enjoy a Key West vacation rental through Historic Hideaways for the same amount of money or less than it costs to rent a hotel room.
What are the business hours for Historic Hideaways?
Historic Hideaways is open Monday through Friday from 9:00 AM to 5:00 PM, Saturday from 12:00 PM to 5:00 PM, and closed on Sundays.
Where is Historic Hideaways located?
Historic Hideaways is located at 1109 Duval St, Key West, FL 33040, United States.
What payment options does Historic Hideaways accept?
Historic Hideaways accepts American Express, Check, Discover, Mastercard, and Visa for payment.
How can I contact Historic Hideaways for rental inquiries?
You can contact Historic Hideaways via email at rentals@historichideaways.com or by phone at +1 305-294-3064.
Are there any art galleries near Historic Hideaways?
Yes, nearby you can visit art galleries such as Cocco & Salem Gallery and Cocco And Salem, perfect for exploring local art before or after your stay.
What bars or wine bars are located close to Historic Hideaways?
Nearby, you can enjoy drinks at Grand Vin Wine Bar, The Rum Bar, Rum Bar at the Speakeasy Inn, and Outer Space, offering a variety of atmospheres for visitors.
Is there a convenient ice cream or restaurant option near Historic Hideaways?
Yes, Flamingo Crossing Ice Cream offers ice cream, burgers, and restaurant dining just nearby for a casual meal or treat.
What shopping options are available near Historic Hideaways?
You can find unique shopping experiences nearby including Life is Good Key West (clothing and gifts), Happy Rooster Gifts & More (souvenirs and flowers), Island Cigar Factory, and Purely Paradise Natural Bath Products.
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