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CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

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TV
4 bedrooms, iron/ironing board, free WiFi, bed sheets
A heated pool
TV
Interior

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms1650 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪12 min walk‬
  • Place, South Beach
    ‪15 min walk‬
  • Place, Southernmost Point
    ‪17 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Room options

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About the neighborhood

Key West

A stay at this vacation home places you in the heart of Key West, within a 15-minute walk of Duval Street and Florida Keys Beaches. .This vacation home is 0.9 mi (1.5 km) from Southernmost Point and 1.5 mi (2.4 km) from Smathers Beach.

What's nearby

  • Duval Street - 12 min walk - 0.7 miles
  • Clarence S. Higgs Memorial Beach Park - 14 min walk - 0.8 miles
  • Ernest Hemingway Home and Museum - 15 min walk - 0.8 miles
  • South Beach - 15 min walk - 0.8 miles
  • Southernmost Point - 17 min walk - 0.9 miles

Getting around

  • Key West Intl. Airport (EYW) - 10 min drive

Restaurants

  • ‪Dions Truman & White - ‬2 min walk
  • ‪Sandy's Café - ‬2 min walk
  • ‪Rainbow Cafe (MARC) - ‬7 min walk
  • ‪Better Than Sex - ‬11 min walk
  • ‪Moose Lodge - ‬11 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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 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...
Make yourself comfortable in this air-conditioned vacation home, which features a private pool. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Complimentary wireless internet access is available to keep you connected.
Take in the views from a garden and make use of amenities such as concierge services and gas grills.
Guests will find features like internet access.

Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Living room
  • Separate dining area

Entertainment

  • Games
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Garden
  • Gas grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In the city center
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling 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 (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Housekeeping (on request)
  • Unit size: 1,650 square feet

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

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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
Property Registration Number 25230-28078

Property is also known as

"captain's Quarters" Vintage Retreat That is Full Charm House
"captain's Quarters" Vintage Key West Retreat That is Full Charm
"captain's Quarters" Vintage Retreat That is Full Charm
"captain's Quarters" Vintage Retreat That is Full Charm House
"captain's Quarters" Vintage Key West Retreat That is Full Charm
"captain's Quarters" Vintage Retreat That is Full Charm House
"captain's Quarters" Vintage Key West Retreat That is Full Charm
2450-154388
"captain's Quarters" Vintage Retreat That is Full Charm

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 173 out of 208 reviews
Rating 8 - Good. 26 out of 208 reviews
Rating 6 - Okay. 7 out of 208 reviews
Rating 4 - Poor. 0 out of 208 reviews
Rating 2 - Terrible. 2 out of 208 reviews

9.8/10

Cleanliness

Reviews

Verified

10/10 Excellent

Warren B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Captain's Quarters was exactly as advertised and so perfect for our stay in Key West! Great proximity to everything and the property manager was on point every step of the way. Thank you for a wonderful weekend to celebrate our family!
Dinner on the beach at Latitudes to cap off a great weekend!
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Alexandra S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was wonderful. We had a great time. Whitney was super easy to communicate with and the property was lovely. Backyard area was spacious and pool was warm and clean. Highly recommend.
Stayed 3 nights in Feb 2026
Verified

8/10 Good

Gwen R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host Whitney was extremely accommodating and accessible. The pool area was lovely but not cleaned as we would have liked.
Stayed 6 nights in Jan 2026
From a partner site

10/10 Excellent

Rhonda C.

Carptains Quarters

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The place was great for out whole Family. Cool Spot in Key West. Pool was nice could use more night time lighting. Clean nicely maintained. Great people to work with.
Verified

10/10 Excellent

Edward C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great quiet location!
Stayed 5 nights in Oct 2025
Verified

10/10 Excellent

Kristan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was spotlessly clean with comfortable bedrooms and shared spaces. The kitchen had everything we needed and the location was walkable to everything we wanted. Lived it!
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Karen E.

Liked: Cleanliness, check-in, communication, location
Very nice home. Beautiful pool. Great location. Lovely front porch. Close to perfect!It would have been very hard and uncomfortable if we had 10 adults in our group, though. It advertises… sleeps 10.. Dining table, seats 8 at the most.
Stayed 4 nights in Jan 2026
From a partner site

10/10 Excellent

Tammy M.

Fabulous Time in Key West

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Went with 4 couples. The house was a perfect set up and we had a fabulous time. We could not have asked for better service with the rental company. They were there at every turn if we needed anything. We would definitely rent from them again. The house is full of old world charm, heated pool was great! The deck was fun for our happy hours and social hours. I would recommend to anyone with large groups or families.
Verified

8/10 Good

William F.

Liked: Cleanliness, communication, location, listing accuracy
Great location, fairly quiet street. Great backyard with pool, very private. The separate bedroom was perfect for my son who wanted to sleep in. The mattress in the master sagged in the middle and was very soft, a new mattress is needed. Kitchen was well stocked with utensils, we cooked breakfast every morning. Host was accommodating with letting us leave luggage before and after stay due to flights.
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Devotion808 g.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect stay, awesome communication with the property manager at all times 5
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Riley N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, enjoyed our time. The pool is bigger than the pictures give it credit for!
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Britt N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

We loved this house. It was nice to be a little off the beaten path but a short walk/bike ride everywhere. Great pool, comfortable beds, well stocked kitchen (plates, utensils, cookware, some spices) and plenty of room for 6 adults.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

James G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Great place. well located. Will be returning.
Stayed 6 nights in Apr 2025
From a partner site

10/10 Excellent

Megan B.

Good location

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: It was perfect for my family of six and parents to join us. Nice to have the bedroom off the back for privacy.
Verified

10/10 Excellent

Debbie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Stay

Captains Quarters is a beautiful house, great location, walking distance to Duval, clean, heated pool and plenty of amenities to make your stay enjoyable. Would def stay there again.
Stayed 4 nights in Nov 2024
Verified

10/10 Excellent

Kerrie B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home

Spent family vacation hanksgiving there, had great time. The beautiful home made us all feel like we were on a 5 star vaca
Stayed 4 nights in Nov 2024
Verified

10/10 Excellent

Michael m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

I would recommend this place to anyone! Very nice and great location.
Stayed 4 nights in May 2022
Verified

10/10 Excellent

Lynn M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place for a family stay!

We loved this property- the house is beautiful and perfect size for all 10 of us. The backyard and pool were amazing! Will definitely be staying here again!
Stayed 5 nights in Feb 2023
Verified

10/10 Excellent

Emily D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

10ac duke

House was great. Pool, amazing. Will stay here again!
Stayed 4 nights in Mar 2025
Verified

10/10 Excellent

Christine P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay!

We loved the house. From the location, to ambiance and heated pool- it was all amazing! We didn’t cook at all and spent most of our time out and about, but we used the pool day and night. We had 2 couples and 2 additional friends and it was the perfect amount of space and privacy! Would highly recommend this spot and nearby is a cute little bike shop to easily rent a bike cruiser or golf cart for your time!
Stayed 2 nights in Apr 2025
From a partner site

10/10 Excellent

Tracy S.

Perfect Girls trip stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house has true key west character. So comfortable.Pool was great. Location is 1 block from a great cafe, liquor store and grocery store!20 minute walk to Duval St
Verified

10/10 Excellent

Michael T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and perfect pool

Couldn’t recommend this location more! We loved the pool and all that key west had to offer
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

Cathy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great gathering and memory making home away from home

We recently celebrated my sister in law’s 60th birthday with a trip to Key West. Our niece and nephew joined us along with their significant others. The home was large enough to accommodate us all, close to Duval and all Old Key West attractions and the backyard pool and deck were wonderful and relaxing.
Stayed 5 nights in Mar 2025
Verified

10/10 Excellent

Courtney W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

An Amazing Getaway Oasis

The property, house, location, and management were absolutely amazing! We highly recommend for any family and/or group of friends!
Stayed 4 nights in Jul 2022
Verified

10/10 Excellent

Brian O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome

We loved the home! The decor, the pool, and the location were all perfect
Stayed 6 nights in Jun 2024