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Frequently Asked Questions (FAQ'S)

Rates & Minimum Stays

Our Key West rental home in-season rates are generally December 15(ish) – Mid-April. Off-season rates are Mid-April – December 14(ish). These dates are moved a bit depending on the year so please be sure to check each property’s rate table for specifics. Holidays and special events may have higher rates and special minimum stays; the rate tables will reflect that too.

We have two types of rentals: Monthly/Seasonal and Nightly/Weekly. Most Nightly or Weekly rentals have a 5 - 7 night minimum in season, 2 - 4 nights in off season. (Truman Annex properties have a 7 night minimum year round.) The Monthly/Seasonal rentals always have a 29 night minimum. Discounts are often available for the monthlies; especially in off season…so please ask! Sometimes we can do less than minumims (at select Nightly/Weekly properties) if we can fit you in between two other rentals, so again, please ask!

Monthly/Seasonal rentals have a cap on utilities such as electric, water, and propane.

There are no additional cleaning fees (unless staying at a pet-approved property). A check-in and check-out cleaning is included in your rental price, provided you keep up with it and leave the home in good condition. Please see our Rules and Procedures for details. Excessive cleaning charges will be charged back to you.

There is a $30 Reservation Fee and a $49 Damage Waiver (see below) on all rentals plus the applicable sales tax (currently 12.5%).

For Weekly Rentals only – Published rates are based on a 7 night stay and a maximum of 2 people per bedroom. Stays of less than 7 nights for homes that allow such will incur surcharges to help cover the cost of cleaning, supplies, etc. since the quote you receive either online, via e-mail or by phone includes the cleaning cost. These surcharges can range from 5% for 6 nights up to 20% for 3 night rentals. For example, if a unit Rate Table shows that a unit is $1,400 + tax for the week (which is $200 per night) and you choose to book just 3 nights; the effective nightly rate will end up being $260 + Tax (20% surcharge.) A 6 night rental at this same property would be $210 + Tax per night, etc. Extra person charges of $30 per day, per person (up to the maximum allowed in a property) will apply. For example, if you are looking at anything on the 2 Bedroom page for Weeklys and it says Sleep 5 or Sleeps 6 (as opposed to just Sleeps 4) then you would pay the Extra Person charge for that 5th or 6th person. The $30 Extra Person Fee(s) per person, per night, are not surcharged for stays of less than 7 nights.

Making a Reservation and Payments

  • A 50% deposit is required to make a reservation. This may be done over the phone. We accept AMEX, MC, VISA and Discover.
  • We also accept checks and money orders and will hold your reservation for five days while you send it.
  • Please review the weekly and monthly/seasonal rental contracts so you know what the contract will be before you reserve, not after.  Please call us if you have questions about it.
  • Once you make your deposit, we will send you a contract, the credit card slip (if applicable) and other informational paperwork. Please sign the contract and return a copy to us along with our copy of the signed credit card slip (again if applicable.)
  • Your remaining balance is due 60 days prior to arrival (90 days for Monthly/Seasonal homes). If you are paying by credit card you must call us to do so.
  • Reservations made less than 60 days prior to arrival must be paid in full at the time of the reservation.
  • A Damage Wavier is required for all rentals. The cost is $49.00. The Damage Waiver is designed to cover unintentional damages to the rental unit interior that occur during Guest’s stay, up to a maximum of $1,000. Terms and conditions apply and will be set forth in your rental contract.

Cancellation Policies

All notices of cancellation must be received in writing to Historic Hideaways.

  • For Nightly/Weekly Rental homes, cancellations 60 days or more from your scheduled arrival date will incur a $250 cancellation fee.  If cancellation is within 60 days of scheduled arrival, no refund is available and Historic Hideaways shall retain any amounts previously paid by Guest as liquidated damages. 
  • For Monthly/Seasonal Rental homes, cancellations 90 days or more from your scheduled arrival date will incur a $500 cancellation fee.  If cancellation is within 90 days of scheduled arrival, no refund is available, and Historic Hideaways shall retain any amounts previously paid by Guest as liquidated damages. 

If you wish to change the arrival/departure date of your initial reservation to less time, it falls under the terms of the cancellation policy. Travel Insurance fees are non-refundable after the 10 day ‘free look’ period.  Reservation Fees are always non-refundable regardless of cancellation date. Hurricanes: There is not a separate cancellation policy in effect that pertains to hurricanes. Hurricane Season is June 1 – November 30. Most Travel Insurance Companies cover Hurricanes as part of their polices. Please check with your Travel Insurance Agent.

Travel Insurance

Red Sky Travel Insurance provides optional Sun Trip Preserver® travel insurance coverage for our guests. Sun Trip Preserver provides cancellation and interruption services as well as emergency assistance and travel services. Protect yourself in the event of hurricane evacuations and family emergencies such as illness or death in the family. The insurance protects your vacation investment in the case of any unforeseen covered events. The travel insurance is optional and the cost is 6.95% of your total reservation stay. Click HERE for information about how best to insure your trip

Damage Waiver 

As part of your stay, your Damage Waiver is designed to cover unintentional damages to the rental unit interior that occur during your stay, provided that the damages are disclosed to management prior to check-out. The fee for this is $49.00 and is nonrefundable. The plan will pay a maximum benefit of $1,000. Any damages that exceed $1,000 will be charged to the credit card on file. The Damage Waiver is subject to the conditions, terms, and administrative procedures set forth in your rental agreement.

The Damage Waiver will not apply if damage results from the following: intentional acts of a Guest or invitee; negligence or willful or wanton conduct of a Guest or invitee; damages not promptly reported to Historic Hideaways consistent with the Damage Waiver agreement; theft or damage to any property owned or brought into the unit by the Guest or an invitee; theft of items belonging to the unit without a valid police report; and damage or theft of any kind if the number of persons occupying the unit exceeds the unit’s occupancy limit. 

The Guest must report any loss or damage to the unit or its contents immediately to Historic Hideaways management staff at 305.294.3064. In addition, you will be provided a form upon check-in. This form should be filled out and dropped off to our office prior to, or no later than, your check-out. The Damage Waiver is void if damage is not reported promptly. Representatives of Historic Hideaways have administrative authority of the Damage Waiver.

Check In / Check Out

Check-in is accomplished at our office,1109 Duval Street, Key West. Check-in time is between 3 pm and 5 pm. If you are arriving later than 5 pm or on a Sunday or holiday where the office might be closed, we have to arrange a late check-in for you, so you must contact this office no later than 48 hours prior to arrival to make those check-in arrangements. We cannot guarantee early check-ins, but it never hurts to ask us and we’ll see what we can do.

Check-out time is 11 am. Late check-outs may or may not be available. Again, please ask us. If it is during the week you can sometimes leave your bags with us if you have to be out of the unit at 11 am but have a later flight. Please follow the checkout procedures on the Rules and Procedures sheet you received with your contract.

Additional Items of Interest

  • Read our Rules and Procedures.
  • Historic Hideaways is unable to rent to persons under 25 years of age. Any student group arriving will be denied access to the property and will forfeit their deposit.
  • All homes are equipped with linens, kitchenware and cleaning supplies/items.
  • For Nightly/Weekly Rental Homes – If the property has a private pool that can be heated, the cost to heat the pool (86 degrees or less) is included in the Rental Fee for Season Rentals only (December 15th – April 30th.) Heaters are kept on during this time frame, so Guest does not need to request pool heat prior to arrival. For all other times of the year for these properties, pool heat is an option but must be requested three (3) days in advance for an additional fee of $150.
  • Shared Pool Homes - Shared pools are not under the control of Owner, Historic Hideaways or Guest, and therefore no changes or requests for heat are permitted. (The HOA/COA regulates the pool temperature throughout the year.)
  • No smoking is allowed inside our units. This is for fire safety purposes for guests and units. However, most of our units have lovely outdoor areas, porches, patios, etc. for smoking purposes.
  • Unless approved by us, NO PETS are allowed. We do have some units that are Dog Friendly so please ask. For pet friendly homes there are restrictions that include, but may not be limited to, the following: pet friendly means dogs, no other animal is permitted. Dogs are restricted to one (1) large dog or two (2) small dogs. Due to Homeowner Insurance restrictions we are unable to accommodate the following breeds: Pit Bull Terriers, Staffordshire Terriers, Rottweilers, German Shepherds, Presa Canarios, Chows Chows, Doberman Pinschers, Akitas, Wolf-hybrids, Mastiffs, Cane Corsos, Great Danes, Alaskan Malamutes, Siberian Huskies nor any mixed breed that contain one of the preceding as part of that mix.
  • If you are going to have a car/vehicle, please be sure to ask us about parking.
  • All of our vacation rentals are properly licensed by the City of Key West and any other required goverment agency.
  • Fraud Prevention: Historic Hideaways LLC never authorizes or allows any of our properties to be placed, nor advertised, on any third party sites other than FlipKey and TripAdvisor. So if you see any of our listings on a third party site other than one of these 2, it is unauthorized and could be a scam. (Unfortunately, all of us vacation rental companies down here have to deal with this ongoing issue.)
  • Third Party/OTA Listings (i.e FlipKey and Trip Advisor) don’t do a very good job of pulling the proper data from our site to theirs, especially the amenities. Since we cannot guarantee that the information any OTA pulls from our site is accurate, if you came to us through them be sure to look at all the information on our site related to your particular rental to be sure you have the most accurate, up to date, information!