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Charming Old Town Bungalow | Cottage in Key West

9.6 (7 Reviews) |   Pet Friendly   3 Bedrooms  3 Bathrooms  6 Guests
Key West Historic District Cottage | Charming Old Town Bungalow

3 Bedroom Cottage in Key West Historic District, Key West

Welcome to Charming Old Town Bungalow, where over a century of Key West history meets the laid-back island lifestyle you've been dreaming about.
Originally built in 1908 as a tobacco barn, this beautifully restored home invites you to experience authentic Old Town living surrounded by tropical beauty, timeless architecture, and modern comforts. Rich in character and thoughtfully updated, Charming Old Town Bungalow offers the perfect blend of historic charm and modern convenience, creating an unforgettable setting for your Key West vacation.
Surrounded by lush island landscaping and filled with authentic Key West character, you'll immediately fall in love with the soaring 9-foot ceilings, beautiful Dade County Pine walls, elegant crown molding, and inviting porches that make this home feel like a true island escape.
The Perfect Old Town Location
Leave your car behind and experience Key West the way the locals do. Located in the heart of the Historic Old Town neighborhood, you'll be just four blocks from world-famous Duval Street, where you'll discover lively restaurants, local shops, art galleries, live music, and endless island charm. Spend your days exploring picturesque streets lined with colorful conch homes, then take a leisurely 15-minute walk to the beach or enjoy one of Key West's spectacular sunsets.
Wake up to the sound of island birds, grab a coffee from a nearby café, and spend your days strolling Old Town, discovering hidden gardens, local galleries, and waterfront restaurants. Whether you're biking through town, enjoying fresh seafood at a neighborhood café, or wandering home after an evening on Duval Street, everything you want to experience is just moments away.
Relax in Your Own Private Island Retreat
After a day of adventure, come home and unwind in your own peaceful oasis. Sip your morning coffee on the welcoming front porch, enjoy afternoon cocktails on the cozy side porch, or step into the intimate private outdoor space surrounded by tropical landscaping. As the sun begins to set, make your way to the private upstairs observation deck, where you can relax with your favorite drink and soak in the warm island breeze that makes Key West so unforgettable.
Comfortable Spaces for Gathering
The spacious open-concept living area creates the perfect place for family and friends to gather after a day of exploring. High ceilings and abundant natural light make the home feel bright and airy, while comfortable seating and a large television provide the perfect setting for relaxing evenings together. The dining table comfortably seats six, making it easy to enjoy meals, games, and conversations that become lasting vacation memories.
The fully equipped kitchen features a gas stove and everything needed to prepare everything from a quick island breakfast to a delicious dinner after a day on the water.
Peaceful Accommodations
Designed with comfort in mind, the home offers three inviting bedrooms and three full bathrooms, providing plenty of space for everyone to spread out and relax.
* One bedroom is conveniently located on the first floor.
* Two additional bedrooms are located upstairs for added privacy.
* Every bedroom features a ceiling fan to keep you cool and comfortable after a day in the Florida sunshine.
Why You'll Love Staying Here
* Historic 1908 Key West home full of authentic character
* Originally a tobacco barn with beautifully preserved architecture
* Prime Old Town location just four blocks from Duval Street
* Approximately a 15-minute walk to the beach
* Spacious open-concept living areas with 9-foot ceilings
* Beautiful Dade County Pine and crown molding throughout
* Multiple porches plus a private upstairs observation deck
* Lush tropical landscaping and fenced yard
* Off-street parking for one vehicle
* Walk or bike to restaurants, shopping, galleries, attractions, and nightlife
Whether you're planning a family vacation, a getaway with friends, or simply looking to experience the authentic charm of Key West, Charming Old Town Bungalow offers the perfect blend of historic character, tropical relaxation, and an unbeatable Old Town location.
If you're here for an adventure or simply a chance to slow down and unwind, we hope you'll fall in love with Key West just as we have. From sunrise coffee on the porch to unforgettable island sunsets, your perfect getaway begins here.
We don't just offer places to stay—we help create unforgettable Key West memories. We look forward to welcoming you to paradise.
Warm island regards,
Your Island Hosts
Key West Luxury Vacation Rentals, Inc.
Luxury accommodations. Genuine island hospitality.

Charming Old Town Bungalow is located in Key West Historic District. Charming Old Town Bungalow provides accommodation, featuring Air Conditioner, Barbecue/Outdoor Cooking, Kitchen, among other amenities. This Cottage features Air Conditioner, Parking and Pet Friendly to make your stay a comfortable one.

Charming Old Town Bungalow has 3 Bedrooms , 3 Bathrooms, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Key West Historic District has interesting places to visit. If you want to learn more about the Cottage in Key West Historic District, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pet Friendly
TV
Balcony/Terrace
Security/Safety
Bedding/Linens
Wellness Facilities
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Heating
Internet
Kitchen
Laundry

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 25
Check-out
Check-out before 10:00 am contactless check-out available
Child Policy
Children are welcome. note from host: stairs on property, no baby gate provided.
Pet Policy
Pets allowed service animals are welcome, and are exempt from fees welcoming dogs only 2 total (up to 20 lbs per pet) restrictions apply; for more information contact the property at the number on the booking confirmation

Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed onsite parties or group events are strictly prohibited host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

Victoria C.
Mar 27, 2026 06:20:00 AM
Review Score:   10
Summary: Great location, Great Hosts
See All Reviews

FAQ's

Is this property pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the property have a swimming pool?

No, this Charming Old Town Bungalow does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in property?

Best-rates for the Charming Old Town Bungalow starts from $609 per night with includes Heating, Internet, Laundry, Air Conditioner, Barbecue/Outdoor Cooking, Kitchen, Entertainment, Parking, TV, Security/Safety, Bedding/Linens, Wellness Facilities, Child Friendly, Pet Friendly, Balcony/Terrace with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is property a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cottage Good or guests have recommended them suitable for families. As reported by the owner or manager, the cottage has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the property wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Charming Old Town Bungalow has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the property?

Based on the information reported by the owner or manager, the Charming Old Town Bungalow indicates 1 day stay policy at this cottage. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for property?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.