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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 this.

We have two types of rentals: Monthly/Seasonal and Nightly/Weekly. Most Nightly or Weekly rentals have a 2 - 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 30 DAY minimum. Discounts are often available for the monthlies; especially in off season…so please ask! Sometimes we can do less than published minimums (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 and water.

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 $95 Reservation Fee and a $59 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 and supplies 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.

Damage Waiver 

As part of your stay, the non-refundable Damage Waiver pays for unintentional damages to the rental unit that occur during your stay, provided that the damages are disclosed to management prior to check-out. The fee for this is $59.00 and is nonrefundable. Any damages that exceed $1,000 will be charged to the credit card on file. The Damage Waiver is not insurance nor an insurance product. 

Making a Reservation and Payments

  • A Minimum 50% deposit on the Rental Fee is required to make a reservation. This may be done over the phone or by booking online. 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 or 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 rental agreement, key log, and other paperwork. Please sign the contract, key log, and return executed copies of both, along with a copy of your driver's license or photo ID. (Please redact the ID number for security.)
  • Your remaining balance is due 60 days prior to arrival (90 days for Monthly/Seasonal homes) and will be automatically processed using the credit card on file.
  • Reservations made less than 60 days prior to arrival (90 days for Monthly/Seasonal homes) must be paid in full at the time of the reservation.

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 cancellation fee of $250 or 10% of the total Rental Fee, whichever is greater.  If cancellation is within 60 days of scheduled arrival, no refund is available. It is strongly advised to purchase Travel Insurance.
  • For Monthly/Seasonal Rental homes, cancellations 90 days or more from your scheduled arrival date will incur a cancellation fee of $500 or 10% of the total Rental Fee, whichever is greater.  If cancellation is within 90 days of scheduled arrival, no refund is available. It is strongly advised to purchase Travel Insurance.

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 is non-refundable after the 14 day ‘free look’ period.  Reservation Fees are also non-refundable, regardless of cancellation date. Hurricanes: Since there is not a separate cancellation policy in effect that pertains to hurricanes (Hurricane Season is June 1 – November 30) you are strongly advised to purchase Travel Insurance. 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. 

If you are interested in learning about 'Cancel for any reason' Travel Insurance polices Red Sky recommends checking out since Red Sky does not offer this type of policy.

Check In / Check Out

Check-in is accomplished at our office,1109 Duval Street, Key West. Check-in time is AFTER 4 P.M. Keys will not be available in the lockboxes on our front porch until Check In time. All required paperwork and documents MUST be in Historic Hideaways possession 72 BUSINESS HOURS prior to arrival or we will not leave keys out/allow check in. Once we have all required paperwork you will receive a final e-mail with the lockbox number and code for your check in, so please do not wait until the last minute to be sure you have all items returned to us and you have your lockbox Letter and Code or you risk being denied entry to your rental. 

Check-out time is 11 A.M. Please follow the checkout procedures on the Rules and Procedures sheet you received with your contract.

Additional Items of Interest & Importance

  • Read our Rules and Procedures webpage. A copy is also provided with your contract paperwork.
  • 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.
  • For Nightly/Weekly Rental Homes with Private Heated Pools – The cost to heat the pool (85 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.
  • Monthly/Seasonal Rental Homes with Private Heated Pools - The Guest is in control of the pool heat and may adjust it to their liking; keeping in mind Monthly/Seasonal Rentals have caps on utilites and you pay anything above said caps.
  • 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.)
  • Homeowners may have surveillance devices around the exterior of the home. Historic Hideaways is not in the care, custody, or control of their placement, use, or what they may, or may not, record.
  • No smoking is allowed inside our units. 
  • Unless approved by us, NO DOGS are allowed. We do have some units that are Dog Friendly. They are marked as such on our website. For Dog 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. Guest is responsible for an additional pet fee of $200. 
  • If you are going to have a car/vehicle, please be sure to ask us about parking.
  • What is Provided - To lessen the stress of preparing and packing for your trip, your vacation rental is stocked with a minimum of the following: All linen and towels. Kitchens have kitchenware, silverware, drinkware, blenders, pots and pans and drip coffee makers. There is an iron and ironing board and at least one handheld hairdryer. We ask Housekeeping to supply the properties with all necessary cleaning items one usually needs (mop/broom/vacuum). Housekeeping also provides 2 rolls of toilet paper per bathroom, one small bar of soap per shower, and enough paper towels, laundry soap (if applicable), dishwashing soap, and garbage bags to get you started. We always suggest that Guests get settled in first. This way you can see what the property does and doesn’t have before making your grocery list and going to the store.

  • Our vacation rentals are licensed.

  • Fraud Prevention: Historic Hideaways LLC never authorizes or allows any of our properties to be placed, nor advertised, on any third party site other than FindRentals and VRBO. (We never advertise on Craigslist.) If you see any of our listings on a third party site other than FindRentals or VRBO, it is unauthorized and a scam.
  • We cannot guarantee that the information an 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!