Sign up for our emails to get exclusive news, information and the best rates on your vacation!
No, HKWVR manages properties for various owners.
Please be advised that the Guest signing the Rental Contract must be 25 years of age and must occupy the property for the full duration of the reservation. Singles under 25 are prohibited unless accompanied by a parent or legal guardian for the full term of the reservation. No weddings, parties, large gatherings, commercial business, filming, or other similar activities are permitted at our properties.
All HKWVR Rentals include a microwave, coffee maker, toaster, cookware, dinnerware, utensils, glasses, iron/ironing board, linens, blankets, and towels. We also provide the following starter supplies for your convenience - salt/pepper set, coffee filters, trash bags, hand soap, dish detergent, dishwasher tabs (if home has dishwasher), laundry pods (if home has a washer/dryer), and sample-size toiletries. Once depleted, you can replenish what you need. We do NOT provide pantry items, spices/seasonings, or groceries.
Not all properties have designated parking unless noted in the description. Street parking may be available. Please avoid parking in any spots labeled “Residential Permit” or blocking any curbs/driveways.
Cancellation & refund for Nightly/Weekly Rentals: 60 days or less prior to arrival date - There will be no refund, entire amount collected is forfeited. 61 days or more outside of arrival date - Full refund, less $500 cancellation fee OR 10% + tax of reservation total, whichever is greater, regardless of reservation date. Cancellations & refunds for Monthly Rentals:90 days or less prior to arrival date - There will be no refund, entire amount collected is forfeited. 91 days or more outside of arrival date - Full refund, less $500 cancellation fee OR 10% + tax of reservation total, whichever is greater, regardless of reservation date. Notice of cancellation must be in writing or via email to [email protected]. We cannot return fees collected by third-party websites.
Due to strict guidelines to Key West cancellation policies, we strongly encourage you to purchase Red Sky travel insurance. Travel insurance may cover you up to the entire reservation cost, minus any travel insurance cost. You may purchase Travel Insurance through Historic Key West Vacation Rentals or through an agency of your choice. This insurance is available to U.S. residents and Red Sky can provide several international policies, with just a few exceptions depending on the country. Hurricanes: If you are traveling during Hurricane Season, which is June 1 through November 30, we strongly suggest you purchase Travel Insurance. There will be no refunds for weather (tropical disturbances, hurricane, etc.) or for early departure.
Check in is 4 PM EST and Check out is 10 AM EST. Housekeeping and maintenance professionals must have access to the properties between 10 AM and 4 PM, therefore early check-ins or late check-outs are not possible.
If you are staying in a keyless property, you will receive the door access code/gate code via text & you can go straight to the property @ 4 PM EST. If you are in a property with keys, you will need to go to our office first (1119 White Street, Key West, FL, 33040) and pick up your keys. You can then go to the home and check in at 4 PM EST.
Are there check-out procedures?Yes. When staying in one of our beautiful homes, you will receive a HKWVR Guide Link. This link provides you with check-out procedures along with any other information you may need for your stay.
You can call our office with any problems or concerns. We also have an after hours emergency line that is provided prior to check in.
We do not provide daily maid services. If this is something you wish to have, we can provide a quote from our professional housekeepers.
Most owners have mail forwarding in effect at their properties. You may have mail and small packages delivered to our office. Post as: ℅ Historic Key West Vacation Rentals, Attn: (the Rental Contract holder name), 1119 White Street, Key West, FL, 33040.
Our monthly property rates are available 16 months out and bookings are first come, first serve. We do not hold properties for the following year.
Call us! If you see one of our homes listed on a site that is not our own, it is most likely a scam. Please report this to us immediately.
Historic Key West Vacation Rentals offers luxury homes, historic conch cottages, monthly rentals, pet-friendly accommodations, family vacation homes, and private pool properties throughout Key West.
Many Historic Key West Vacation Rentals properties are located in the heart of Old Town Key West, near Duval Street, historic landmarks, restaurants, galleries, and nightlife.
Yes. Historic Key West Vacation Rentals offers nightly, weekly, monthly, and extended-stay rentals depending on the property and season.
For peak travel periods such as winter, spring break, Fantasy Fest, and holidays, booking 6–12 months in advance is recommended.
Amenities vary by property but often include fully equipped kitchens, private pools, outdoor patios, Wi-Fi, laundry facilities, parking, and gas grills.
Some properties offer off-street parking or designated parking spaces. Parking details are included in each rental listing.
All Historic Key West Vacation Rentals properties are smoke-free. Property-specific policies are outlined in each listing.
Properties are located throughout Old Town Key West, near Duval Street, Truman Annex, Casa Marina, Midtown, and surrounding neighborhoods.
Yes. Historic Key West Vacation Rentals specializes in monthly and multi-month vacation rentals for snowbirds, remote workers, and extended-stay travelers.
Monthly rentals typically require a 28- to 30-night minimum stay depending on city regulations and property guidelines.
Many monthly rentals include utilities such as water, internet, and basic electric usage. Specific details vary by property.
Yes. Most long-term rentals are fully furnished and move-in ready.
Old Town, Truman Annex, Casa Marina, and Midtown are popular for monthly and seasonal stays because of walkability and local amenities.
Snowbird season generally runs from November through April.
Yes. Many properties include high-speed Wi-Fi and work-friendly spaces for remote professionals and digital nomads.
Some properties offer reduced nightly rates for weekly or monthly reservations.
Yes. Historic Key West Vacation Rentals offers luxury accommodations featuring private pools, gourmet kitchens, tropical outdoor living spaces, and premium locations.
Luxury rentals may include heated pools, chef’s kitchens, outdoor lounges, concierge recommendations, and private courtyards.
Many luxury properties are located within walking distance of Duval Street while still offering privacy and quiet surroundings.
While concierge services vary, guests receive local recommendations and guidance to help create personalized Key West experiences.
Yes. Many luxury homes are ideal for romantic getaways, anniversaries, and honeymoon vacations.
Yes. Historic Key West Vacation Rentals offers homes with private pools throughout Key West.
Some pools are heated seasonally. Property listings specify pool details and heating availability.
Many private pool homes are ideal for families and include outdoor dining spaces and multiple bedrooms.
Some properties feature tropical landscaping, private courtyards, and fenced pool areas for additional privacy.
Select Historic Key West Vacation Rentals properties are pet-friendly.
There is an additional Fet Fee. Pet fees and policies vary by property.
Yes. Key West offers several pet-friendly parks, walking areas, and outdoor dining options, as well as Dog Beach on the island's south end.
Guests should review each property’s pet policy regarding breed restrictions, size limits, and additional fees.
Yes. Many properties are designed for families and groups with multiple bedrooms, kitchens, and outdoor gathering spaces.
Many homes are close to beaches, museums, the Key West Butterfly Conservatory, Mallory Square, and family-friendly restaurants.
Old Town and Casa Marina are popular with families because of walkability and beach access.
Yes. Historic Key West Vacation Rentals offers romantic cottages, private pool homes, and luxury retreats perfect for couples.
Popular romantic activities include sunset cruises, beach walks, fine dining, live music, and historic tours.
Yes. Some properties feature private courtyards, tropical gardens, and quiet Old Town locations.
Yes. Key West is one of the most welcoming LGBTQ+ destinations in Florida.
Many properties are within walking distance of Duval Street, LGBTQ+ bars, entertainment venues, and Pride events.
Key West Pride is typically held each June and attracts visitors from around the world.
Popular events include Key West Pride, Tropical Heat, Womenfest, and Fantasy Fest.
Historic Key West is known for colorful conch homes, walkable streets, tropical gardens, rich literary history, and vibrant culture.
A conch house is a traditional Key West-style home known for large porches, high ceilings, and island-inspired architecture.
Many Historic Key West Vacation Rentals properties are restored historic homes and cottages.
Guests enjoy access to the Hemingway Home, Southernmost Point, Duval Street, Mallory Square, museums, restaurants, and galleries.
Many properties are close to beaches including Smathers Beach, Higgs Beach, Fort Zachary Taylor Beach, and Sunset Key access points.
Guests enjoy snorkeling, fishing, boating, kayaking, paddleboarding, sunset cruises, and beach biking.
Fort Zachary Taylor Beach is often considered one of the best beaches for swimming and sunsets.
Yes. Key West offers easy access to fishing charters, snorkeling tours, sailing trips, and eco-adventures. Our Concierge can assist with securing your reservations.
Key West is a year-round destination, though winter and spring are especially popular.
Popular events include Fantasy Fest, Hemingway Days, Key West Pride, Songwriters Festival, and holiday celebrations.
Yes. Fantasy Fest is one of the island’s most popular annual events, and accommodations book quickly.
Winter reservations should ideally be booked several months in advance due to high demand.
Forgot password