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Frequently Asked Questions (FAQ'S)

Rates & Minimum Stays

Our Key West rental home in-season rates are generally December 15 – April 30. Off-season rates are from May 1 – December 14. These dates are moved a bit sometimes so 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 weekly. Most weekly rentals have a 7-night minimum in season, 3 nights in off season. The monthly/seasonal rentals always have a 30-night minimum. Discounts are often available for the monthlies; especially in off season…so please ask!

Sometimes we can do less than 7 nights during season (at select properties) if we can fit you in between two other weekly rentals, so again, please ask!

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

There are no separate, 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 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 the “nightly” rate 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 (provided you keep up with it.) 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 Weeklies 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. 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 Security Deposit Plan is required. The cost is $39.00. The Security Deposit plan is designed to cover unintentional damages to the rental unit interior that occur during Guest’s stay, provided that the damages are disclosed to Historic Hideaways prior to Check Out. The policy will pay a maximum benefit of $500. Guest is still required to present a Credit Card to take an imprint, and for Guest to sign, for any items not covered by the plan, but Historic Hideaways will not charge any amount to Guest’s credit card unless authorized pursuant to the terms of the Rental Contract. Any damages that exceed $500 will be charged to the credit card on file. Full details of the Security Deposit plan coverage are contained below.

Cancellation Policies

All notices of cancellation must be received in writing to Historic Hideaways. If you cancel 60 days or more from your scheduled arrival date, the following cancellation fees apply:

  • Weekly Rental Homes: $250
  • Monthly/Seasonal Rental Homes: $500

If you cancel within the 60-day window prior to arrival, no refund is available.

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.

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

Click HERE for information about how best to insure your trip

Security Deposit Plan 

As part of your stay, your Security Deposit plan 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 $39.00 and is non-refundable. The plan will pay a maximum benefit of $500. Any damages that exceed $500 will be charged to the credit card on file.

If, during your stay at one of our Rental Properties, a named Guest causes any damage(s) to real or personal property of the unit as a result of inadvertent acts or omissions, Historic Hideaways will reimburse the Owner, on behalf of the Guest, for the cost of repair or replacement of such property up to a maximum benefit of $500. Certain terms and conditions apply.

Terms and Conditions of Protection plan

The Security Deposit Plan is subject to the conditions, terms, and the administrative procedures listed below. The maximum amount that the Plan will cover is $500 per stay.

General Exclusions

The Security Deposit Plan has certain conditions. The program will not pay a benefit for theft or damage resulting from:

  • Natural Disaster; Intentional acts of any named Guest; Gross negligence, willful and wanton conduct by a named Guest;
  • Any cause, if the Guest does not report the loss or damage to the staff of Historic Hideaways LLC by the Contract Termination Date;
  • Normal wear and tear of the Rental Property unit;
  • Loss of use of the Rental Property unit; Theft or damage to any property owned by or brought by any named Guest or unnamed person onto the Rental Property premises;
  • Theft or damage caused by anyone visiting other than a Guest;
  • Theft (of items belonging to the unit) without a valid police report; Damage or theft in a Rental Property unit if the number of persons occupying the unit exceeds that unit’s occupancy limit.

The Plan takes effect at check-in. All coverage shall terminate upon normal checkout time of the unit or the departure of the Covered Guest, whichever occurs first.

Administrative Procedures

The Guest must report any loss or damage to the unit or its contents immediately to Historic Hideaways LLC management staff at 305.294.3064. In addition, you were given 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. This limited damage protection is void if not reported promptly. Representatives of Historic Hideaways LLC have ultimate administrative authority. Arbitration is required before litigation. The prevailing party in any arbitration of litigation shall be entitled to recovery and/or reimbursement of all fees in connection with it.

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 Weekly Rental Homes – Private heated pools, if applicable, are only provided from December 16 to April 30. This can be an option out of season subject to an additional fee.
  • 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 Pet Friendly so please ask.
  • If you are going to have a car/vehicle, please be sure to ask us about parking.
  • Internet: the Amenities page of each unit will tell you if the unit has high-speed internet access.
  • All of our vacation rentals are licensed by the City of Key West.
  • 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.)
  • Speaking of FlipKey and Trip Advisor, while we love them and can’t live without them, they 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 FlipKey/TripAdvisor 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.