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  • Historic Hideaways
  • Historic Hideaways
    • 800.654.5131
    • 305.294.3064
    • (0) My Favorites
    • Don't Miss Out on Specials & News
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Bay's Hideaway
Admiral's Lane
Admiral's Lane
Conch in Training
Kemp House
Kemp House
Poinciana House
Bella Vita
Noah Lane
Noah Lane

View Properties by Bedrooms

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View Properties by Island Area

  • New Town
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Key West map
New TownMidtownThe MeadowsCasa MarinaOld TownTruman Annex

Beautiful Key West
Vacation Rentals

Our Featured Properties

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Azure Daydream
4 Bedrooms
3 Bathrooms
Monthly and Seasonal Rentals

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Campbell Eyebrow House
1 Bedroom
2 Bathrooms
Monthly and Seasonal Rentals

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Coral Condo
1 Bedroom
1 Bathrooms
Nightly and Weekly Rentals

Managing & Renting The Finest Vacation Rental Homes in Key West

Through Historic Hideaways, you can rent and enjoy a Key West Vacation Rental for the same amount of money...or less...than it costs to rent a hotel room! Choose from private and historic Key West Vacation Rental homes with private pools, a cozy cottage, vacation houses, condominiums or townhomes with a shared pool. Each of the unique and charming Key West Vacation Rentals on our website has a detailed description, along with great interior and exterior photos, a list of amenities, and a map location. Whether you're looking for an oceanfront rental, an Old Town vacation rental or a house in one of the residential areas of the island like Casa Marina, we have you covered.

In addition to the convenience of our Online Booking and Real Time availability check, our website can answer your most Frequently Asked Questions. You can also get information on our Rental Rules and Procedures, see copies of our Rental Contracts, and even get some information on the benefits of the Travel Insurance we offer. We think you'll enjoy looking through some of the beautiful Vacation Rentals in Key West that Historic Hideaways is proud to represent. Once you've vound your perfect vacation home, book securely online with us.

Neighborhoods that we have rentals in:

  • Old Town
  • Truman Annex
  • Casa Marina
  • Mid Town
  • The Meadows
  • New Town 
Rated excellent on TripAdvisor and FlipKey

Historic Hideaways

Key West

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Concierge Services

Concierge Services Key West Florida
Additional Services

If you have a dining question or want an activity that isn't listed here, please contact us and we'll answer...

All Day Tours
All Day Adventures

This is the package for those who want to experience multiple activities like snorkeling, kayaking, jet skiing, water trampolines, and...

Events

2022 Herman Lucerne Memorial Backcountry Fishing Championship
Event Starts
09/16/2022 - 4:30pm

The 2022 Herman Lucerne Memorial is a two-day tournament

...
Fantasy Fest 2022!
Event Starts
10/21/2022 - 12:00am

2022 THEME: Cult Classics & Cartoon Chaos

Fantasy Fest is

...
RWO
Key West 2022 Boat Races
Event Starts
11/06/2022 - 12:00am

Key West 2022 Boat Races

...
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Contact Us

Historic Hideaways
1109 Duval StreetKey West, Florida 33040USA

Phone: 305.294.3064Fax: 305.294.8632

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Proud Members of

  • Better Business Bureau
  • Florida Vacation Rental Managers Association
  • Vacation Rental Managers Association
  • Key West Chamber of Commerce
  • Key West Business Guild
  • Trustwave PCI Compliance

© 2022 Historic Hideaways All rights reserved. Photos by Rob O’Neal. This information, though deemed accurate, is not guaranteed and may be subject to errors, omissions, change of price, or withdrawal without notice.

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