A rare find — relax in the peaceful, private garden space.
Centrally-located
You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Walk to Duval Street
4 bedrooms2+ bathroomsSleeps 10
Popular amenities
Private pool
Kitchen
Washing machine
Air-conditioning
Barbecue
Balcony
Explore the area
Key West, FL
Clarence S. Higgs Memorial Beach Park
Place, Clarence S. Higgs Memorial Beach Park
14 min walk
Ernest Hemingway Home and Museum
Place, Ernest Hemingway Home and Museum
15 min walk
Southernmost Point
Place, Southernmost Point
17 min walk
Key West, FL (EYW-Key West Intl.)
Airport, Key West, FL (EYW-Key West Intl.)
8 min drive
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Queen Bed
Other Space 1
1 Double Sofa Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Toilet · Shower only
Bathroom 3
Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
About this property
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this Old Town home you feel enveloped in vintage Key West. Dade County wood surfaces, nautical accents plus appealing and comfortable decor make this a true "Captain's Quarters". Hang out in the living room with flat screen TV. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
SLEEPING ARRANGEMENTS... You will have many sleeping options while staying in this stunning home as it comfortably sleeps 8-10 guests. There are three bedrooms located in the main house and a one bedroom cottage off the rear deck by the pool. As you enter the main hallway, there are two queen guest bedrooms immediately to your left and right. They each have TVs, storage for clothing and the option of using the hall or rear bathrooms. The master bedroom is fitted with a king size bed, flat screen, closet and has an interior door that leads to a full bathroom. You will find a cast iron clawfoot tub with rain shower as well as a vintage pedestal sink. The rear bathroom off the family room has a tiled shower with glass door and a pedestal sink. There is a powder room off the kitchen that houses the washer and dryer. It has a door to the rear deck that can double for cottage use. The cottage is your fourth bedroom with a queen size bed, pedestal sink, dresser and flat screen with a view of the pool! If you have one or two more guests they can use the queen sized sleeper sofa in the family room.
AMENITIES... Captains' Quarters had updates completed in the spacious homes layout and decor in 2015. Impressively rich Dade County pine and high ceilings make this property a real stand out. The kitchen is fully equipped to meet your cooking needs and has a formal dining room steps away. Your family can dine together at the table for six or use the space to play games or cards.
OUTDOOR LIVING... Lush tropical landscaping greets you at the front gate and wraps around the property. Once inside, you will find a covered porch with a swing and seating area perfect for your morning coffee or to curl up with a book. A winding path will take you around the side yard to a real gem; the lagoon-style pool! The large private, heated pool is situated in the rear yard surrounded by a composite deck with plenty of seating. There is a gas grill and outdoor table covered with a large umbrella meant for six to dine al fresco and grill your fresh catch of the day. If you are a sun worshiper you can kick back and relax on one of the five lounge chairs that surround the pool. Enjoy an outdoor shower to rinse off and head into town!
PARKING... This home does not have designated parking but there is on street parking in the surrounding neighborhood. Please refrain from parking in spots marked “residential permit”.
DISTANCES TO BEACHES... Higgs Beach is 0.8 mi South Beach is 0.9 mi Smathers Beach is 1.7 mi Fort Zachary Taylor Beach is 1.7 m
CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!
CANCELLATION... Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.
ISLAND TIME AWAITS... Virtual Tour Url: https://my.matterport.com/show/?m=38pMuidYYdf
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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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Key West
Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. The Kite House and Key West Butterfly and Nature Conservatory are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
Clarence S. Higgs Memorial Beach Park - 14 min walk - 1.2 km
Ernest Hemingway Home and Museum - 15 min walk - 1.3 km
South Beach - 15 min walk - 1.3 km
Southernmost Point - 17 min walk - 1.5 km
Getting around
Key West, FL (EYW-Key West Intl.) - 10 min drive
Restaurants
Circle K - 13 min walk
Sandy's Café - 2 min walk
Circle K - 13 min walk
Dions Truman & White - 2 min walk
El Siboney Restaurant - 6 min walk
Frequently asked questions
Does CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?
As of 21 Aug 2026, prices found for a 1-night stay for 2 adults at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! on 28 Sept 2026 start from AU$3,791, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! pet-friendly?
No, pets are not allowed at this property.
What time is check-in at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?
Check-in begins at 4:00 PM.
What time is check-out at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?
Checkout is at 10:00 AM.
Where is CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! located?
Located in Old Town Key West, this holiday home is within a 15-minute walk of Key West Firehouse Museum, Duval Street and Florida Keys Beaches. Ernest Hemingway Home and Museum and Southernmost Point are also within 1 mile (2 km).
About the host
Hosted by Wendy Zintsmaster & Team
Languages:
English
Premier Host
They consistently provide great experiences for their guests