Title: Monthly historic old town rental Key West quaint 1 block to Duval - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=34145992&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire apartment # Monthly historic old town rental Key West quaint 1 block to Duval ## Photo gallery for Monthly historic old town rental Key West quaint 1 block to Duval ![Beach - Monthly historic old town rental Key West quaint 1 block to Duval (Key West)](https://images.trvl-media.com/lodging/35000000/34150000/34146000/34145992/e1369158.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Exterior detail - Monthly historic old town rental Key West quaint 1 block to Duval (Key West)](https://images.trvl-media.com/lodging/35000000/34150000/34146000/34145992/8798aebd.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining - Monthly historic old town rental Key West quaint 1 block to Duval (Key West)](https://images.trvl-media.com/lodging/35000000/34150000/34146000/34145992/e70e7963.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV, DVD player - Monthly historic old town rental Key West quaint 1 block to Duval (Key West)](https://images.trvl-media.com/lodging/35000000/34150000/34146000/34145992/a0232ff4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Monthly historic old town rental Key West quaint 1 block to Duval (Key West)](https://images.trvl-media.com/lodging/35000000/34150000/34146000/34145992/145362ea.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies In the heart of Key West, 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead offers a charming retreat. Take in the view of the iconic Lighthouse from your front porch or unwind on your private deck surrounded by tropical beauty. This historic home features original local art, a cozy living room with TV/DVD player and fully-equipped kitchen perfect for BBQs. ## Reviews 8.0 Very good ### Entire apartment 2 bedrooms1 bathroomSleeps 4 ## Popular amenities - Kitchen - Washer - Dryer - Free WiFi - Air conditioning - Outdoor Space ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire apartment to yourself and will only share it with other guests in your party. ### Monthly historic old town rental Key West quaint 1 block to Duval Historic 2-Bedroom Cigar Maker’s Cottage – A Key West Gem! Step back in time and experience Old Key West charm in this delightful 2-bedroom Cigar Maker's Cottage, built in the 1880s. Nestled at 1008 Whitehead Street, the cottage sits just across from where a bustling cigar factory once stood on Truman Avenue. The home's rich history includes ownership by David Kaufelt, a beloved Key West author and literary figure. From the front porch, enjoy views of the iconic Key West Lighthouse, a perfect spot for relaxing and people-watching. Just a half block from the Hemingway House and one block from vibrant Duval Street, the location offers both tranquility and easy access to the heart of Key West’s culture and nightlife. Inside, the home offers: 2 cozy bedrooms: one with a full-size bed and the second with two twins (which can be converted into a king upon request) A bright, art-filled living room featuring works by local Key West artists and equipped with a TV and DVD player A fully equipped kitchen with French doors that open to a lush tropical deck—ideal for indoor-outdoor living Step outside to your private deck oasis—perfect for grilling on the large gas BBQ, dining al fresco, or unwinding with a cold drink under swaying palms. Whether you’re looking to write the next great novel, reconnect with island life, or simply relax in comfort and history, this lovingly maintained cottage is your perfect piece of paradise. Good to Know Minimum stay: 28 nights Ideal for month-long getaways, writers’ retreats, or snowbird escapes Pet-friendly on approval (inquire first) Prime Location 1/2 block to Hemingway House 1 block to Duval Street Short walk to beaches, galleries, bars, and restaurants Located on Whitehead Street, full of local history and charm Outdoor Living Enjoy lush tropical landscaping and Key West breezes Sip coffee on the front porch with views of the Key West Lighthouse Amenities Fully equipped kitchen with French doors opening to the deck Smart TV & DVD player High-speed WiFi Air conditioning & ceiling fans Private tropical deck with: Dining area Lounge seating Large gas BBQ grill The Space 2 Bedrooms, 1 Bath Bedroom 1: Full-size bed Bedroom 2: Two twin beds (can be converted to a king upon request) Sleeps up to 4 guests Tastefully decorated with original Key West artwork Historic touches meet modern comfort ## Property amenities ### Internet - Available in the apartment: Free WiFi ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Ice maker - Microwave - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 1 bathroom - Bathtub or shower - Hair dryer - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - DVD player - TV with cable/satellite channels ### Outdoor areas - Balcony - Barbecue grill ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - In the city center - Near a hospital - Near the marina - Near the sea ### Things to do - Bicycles - Boat - Golf - Kayak - Tennis - Birdwatching nearby - Cycling nearby - Ecotours nearby - Fishing nearby - Golfing nearby - Jet skiing nearby - Sailing nearby - Snorkeling nearby - Surfing/bodyboarding nearby - Swimming nearby - Water skiing nearby - Windsurfing nearby ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector not reported (host has not indicated whether there is a smoke detector on the property) ### General - Bicycles ## Similar properties ![Sundeck](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/580edbc7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pegasus International Hotel Old Town Key West - Pool - Hot tub - Breakfast included - Parking included 8.2 Very good 1,003 reviews CA $492 CA $623 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04&selected=977303&PinnedHotelID=977303&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cd9b522f.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### DoubleTree Resort by Hilton Grand Key - Key West Key West - Pool - Free airport shuttle - Pet friendly - Free WiFi 8.2 Very good 1,005 reviews CA $539 CA $652 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-24&endDate=2026-03-25&selected=470834&PinnedHotelID=470834&HadPinnedHotel=true®ionId=-1&adults=2) ![Private beach, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pier House Resort & Spa Key West Historic District - On private beach - Pool - Hot tub - Spa 9.0 Wonderful 1,049 reviews CA $916 CA $1,122 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-22&endDate=2026-03-23&selected=19307&PinnedHotelID=19307&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Hilton Garden Inn Key West / The Keys Collection New Town - Pool - Hot tub - Pet friendly - Free WiFi 8.0 Very good 1,207 reviews CA $419 CA $510 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09&selected=1376&PinnedHotelID=1376&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/21900/21871/ca442072.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Fairfield by Marriott Inn & Suites Key West at The Keys Collection New Town - Pool - Breakfast included - Parking included - Free WiFi 8.6 Excellent 1,007 reviews CA $441 CA $534 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13&selected=21871&PinnedHotelID=21871&HadPinnedHotel=true®ionId=-1&adults=2) ![Oceanfront Walkout Suite - King | View from room](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Casa Marina Key West, Curio Collection by Hilton Old Town Key West - On private beach - Pool - Spa - Pet friendly 8.4 Very good 560 reviews CA $694 CA $873 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-04&endDate=2026-03-05&selected=12346&PinnedHotelID=12346&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/889900/889862/d2b2f582.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Marquesa Hotel Old Town Key West - Pool - Restaurant - Air conditioning - Parking available 9.8 Exceptional 1,000 reviews CA $776 CA $950 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-31&endDate=2026-04-01&selected=889862&PinnedHotelID=889862&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/113000000/112580000/112580000/112579922/c3bf2d26.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Ricky's Retreat - Truman @ Duval | Ideal Getaway! 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as 1680-71533 ## About the area Located by the sea, this apartment is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Fort Zachary Taylor Historic State Park and Florida Keys Beaches. MLK Community Pool & Community Center and Key West Butterfly and Nature Conservatory are also worth visiting. Discover the area's water adventures with jet skiing and snorkeling nearby, or enjoy the great outdoors with ecotours and cycling. [Visit our Key West travel guide](https://www.expedia.ca/Key-West.dx1187) [View more Apartments in Key West](https://www.expedia.ca/Key-West-Apartments.d1187-aaApartments.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.55006%2C-81.80028&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=-jRpRG9kwQHqlzq0G-I9jQ_FWSo=) Key West, Florida ### What's nearby - ![Duval Street featuring signage](https://images.trvl-media.com/place/6068616/5997ee0c-eca4-415b-b051-99f4d38fbc11.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Duval Street 2 min walk \- 0.2 km - ![Ernest Hemingway Home and Museum featuring heritage elements and a house](https://images.trvl-media.com/place/501376/3b4c31fa-338d-424b-aa0f-482ad359d16a.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Ernest Hemingway Home and Museum 2 min walk \- 0.2 km - ![South Beach featuring a sandy beach and general coastal views as well as a small group of people](https://images.trvl-media.com/place/6246827/42d13a3e-a933-4e9f-b857-cde9f4314a24.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) South Beach 6 min walk \- 0.5 km - ![Key West Butterfly and Nature Conservatory showing flowers, animals and zoo animals](https://images.trvl-media.com/place/6068597/8af8294e-5c8c-4043-8818-b037bf02c028.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Key West Butterfly and Nature Conservatory 6 min walk \- 0.5 km - ![Southernmost Point showing signage](https://images.trvl-media.com/place/501380/6b10fd25-a167-4157-b127-b099a5ff5ea1.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Southernmost Point 8 min walk \- 0.7 km ### Getting around - Key West Intl. Airport (EYW) 10 min drive ### Restaurants - 801 Bourbon Bar 5 min walk - Old Town Tavern 3 min walk - Circle K 3 min walk - Rams Head Southernmost 4 min walk - Moondog Cafe & Bakery 2 min walk ## Frequently asked questions ### Is Monthly historic old town rental Key West quaint 1 block to Duval pet-friendly? ### What time is check-in at Monthly historic old town rental Key West quaint 1 block to Duval? ### What time is check-out at Monthly historic old town rental Key West quaint 1 block to Duval? ### Where is Monthly historic old town rental Key West quaint 1 block to Duval located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Monthly historic old town rental Key West quaint 1 block to Duval Reviews ## Reviews ### Very good All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 3 8 - Good 1 6 - Okay 1 4 - Poor 1 2 - Terrible 0 ## Reviews This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### A guest from Pennsboro, WV Apr 3, 2024 #### Busy Heart of Key West Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We greatly enjoyed our stay. The apartment is located steps away from the lighthouse, Hemingway House, Buoy, and Duval. We look forward to next winter at 1008 Whitehead. ##### A guest from Pennsboro, WV This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Scott J. Dec 15, 2019 #### Great Stay Rating Details: The property manager was very helpful. The vacation rental was very clean. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved the location, the cute little two bedroom. the house was well equipped with kitchen utensils. we really enjoyed being in the quieter section of town at night but during the day sitting on the porch and all the people watching was just great. Love the property and we will be back for sure in a year. ##### Scott J. This review comes from a trusted partner site and has not been verified. ### 8/10 Good Oct 18, 2019 #### A month of fun in Key West Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We enjoyed staying at the Cigar Makers Apartment. Interesting how it is A part of history. We were there a month visiting friends and attending 3 big week long events. Bicycling and the Duval loop bus stop being close by made for easy transportation to everywhere we wanted to go. We had friends visit us during the month. Everyone was pleased. This review was submitted before 2018 and has not been verified. ### 6/10 Okay #### robin L. Dec 3, 2017 #### Good basic housing Rating Details: The property manager was very helpful. The vacation rental was clean. I was more than happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Nothing special but the price was right. We gave up our usually required pool to save $50 a day. Cottage is tiny and kitchen has no range, just a small convection oven and 2 burner top. Old and quaint it does have a slight mildew problem. Location, near southernmost point, good for beach access, but quite a walk from Mallory Sq. and all the action. ##### robin L. Stayed 30 nights in Nov 2017 This review was submitted before 2018 and has not been verified. ### 4/10 Poor #### Tony A. Oct 1, 2016 #### Cigar Makers Cottage 1008 Whitehead St. KW Rating Details: The property manager was more than helpful. The vacation rental was very dirty. I was very happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The cottage is old and has character. There are several areas of the building that needs to be repaired and or replaced. We only stayed in the first floor 2 bedroom section which was large enough for 2 couples. The second bedroom with twin beds did not have good A/C since it is located in the living room and the windows cannot be opened. Several bugs were able to get into the room due to the window not being sealed properly and it has mold around the edges. The WiFi was great and so was the kitchen. The TV only had 14 workable channels and looks like an oversized monitor. The bathroom shower works good, but there are several tiles that have mold and the caulking is cracked or broken off. The bathroom does not have a fan so you have to use the window to vent the room and it has a missing piece of glass. We liked sitting on the back deck, but we had to sweep the deck at least twice a day from all of the trees dropping leaves and sticks. The outside steeps leading to the second floor deck are not safe to use since it is to small to walk up and it is wrapped around a tree that you have to lean under to use the steps. The stairs need to be fixed for safety reasons. There is no on or off street automobile parking within 50 feet of the cottage. The management and maintenance staff are very nice and respond to requests. The location of the cottage is great, but there is a lot of street noise that start at 7am with trucks and street sweepers. If you are looking for a quite location this is not where you want, but it is a good location to DuVall and KW historical places. ##### Tony A. This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### Stan E. Oct 21, 2014 #### Cigar Makers cottage Oct-Nov 2014 Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very pleasant stay--ideal for 2 people--great location very near Hemingway House--interior as pictured--very cozy--tree-shaded deck great for outdoor living--parking was not a problem even though you have to park on street--only drawback was no closet in cottage and might be a little tight for 2 couples to stay--good value for the price compared to other small houses in KWest. ##### Stan E. ## Expedia's Latest Trends ### Hotels > [Park Central South Beach](https://www.expedia.ca/Miami-Hotels-The-Celino-South-Beach.h1168.Hotel-Information) > > [The Grayson Miami Downtown](https://www.expedia.ca/Miami-Hotels-The-Grayson-Miami-Downtown.h6535.Hotel-Information) > > [Private Parking, Heated Pool - Banana Split](https://www.expedia.ca/Key-West-Hotels-Banana-Split-Popular-Suite-In-Heart-Of-Downtown-Key-West.h74054073.Hotel-Information) > > [Hampton Inn Ft. 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