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

Vacation home near Duval Street in Key West

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

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

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
    ‪12 min walk‬
  • Place, Southernmost Point
    ‪14 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

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About the neighborhood

Key West

Seaside stay .Within a 15-minute walk of this Old Town Key West vacation home, you'll find Duval Street and Florida Keys Beaches. Key West Firehouse Museum and The Unitarian Universalist Fellowship of Key West are also within half a mile (1 km).
View more Vacation Homes in Key WestOpens in a new window

What's nearby

  • Duval Street - 12 min walk - 0.7 miles
  • Clarence S. Higgs Memorial Beach Park - 12 min walk - 0.7 miles
  • South Beach - 12 min walk - 0.7 miles
  • Key West Butterfly and Nature Conservatory - 12 min walk - 0.7 miles
  • Southernmost Point - 14 min walk - 0.8 miles

Getting around

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

Restaurants

  • ‪Dions Truman & White - ‬2 min walk
  • ‪Sandy's Café - ‬1 min walk
  • ‪Moose Lodge - ‬11 min walk
  • ‪Better Than Sex - ‬11 min walk
  • ‪El Siboney Restaurant - ‬6 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...

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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
  • Golfing 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

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

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

Frequently asked questions

How close is CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! to the airport?

This vacation home is 3 mi (10-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! to the beach?

This vacation home is a short 13-minute walk from Florida Keys Beaches and 14-minute walk from Clarence S. Higgs Memorial Beach Park. Don't forget your sunscreen!

Does CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

No, there is no casino at this vacation home.

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.

Is there free parking at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

Free parking is not available at this vacation home.

Does CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! have a pool?

Yes, there's a private pool.

Does CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! have a spa?

There are no spa services available at this vacation home.

How close is CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! to downtown Key West?

This vacation home is 0.7 mi away from Key West.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 171 out of 205 reviews
Rating 8 - Good. 25 out of 205 reviews
Rating 6 - Okay. 7 out of 205 reviews
Rating 4 - Poor. 0 out of 205 reviews
Rating 2 - Terrible. 2 out of 205 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Alexandra S.

Liked: Cleanliness
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

10/10 Excellent

Warren B., Westport, CT USA

Liked: Cleanliness
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

10/10 Excellent

Melanie W.

Stayed 4 nights in Jan 2026

10/10 Excellent

sarah h.

Stayed 2 nights in Jan 2026

8/10 Good

Gwen R.

Liked: Cleanliness
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

10/10 Excellent

Karen E.

Liked: Cleanliness
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

10/10 Excellent

Kristan R.

Liked: Cleanliness
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

8/10 Good

William F.

Liked: Cleanliness
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

10/10 Excellent

Brandon M.

Stayed 4 nights in Nov 2025

10/10 Excellent

Sam S.

Stayed 2 nights in Oct 2025

10/10 Excellent

Edward C.

Liked: Cleanliness
Great quiet location!
Stayed 5 nights in Oct 2025

10/10 Excellent

Devotion808 g.

Liked: Cleanliness
Perfect stay, awesome communication with the property manager at all times 5
Stayed 3 nights in Aug 2025

10/10 Excellent

Riley N.

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

10/10 Excellent

Britt N., Pasadena, MD

Liked: Cleanliness

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

8/10 Good

Jeramie K.

Liked: Cleanliness
Stayed 5 nights in May 2025

10/10 Excellent

Jonard B.

Liked: Cleanliness

Amazing Place

Stayed 3 nights in May 2025

10/10 Excellent

James G.

Liked: Cleanliness

Great place

Great place. well located. Will be returning.
Stayed 6 nights in Apr 2025

10/10 Excellent

Matt D.

Liked: Cleanliness

Perfect

The house is equipped with everything you need. Plenty of room to spread out for 8 people. Pool was plenty warm. Grill was helpful. Being a landlord, I was impressed from start to finish! Whitney our Conseirge was so attentive and super helpful with any amenities that we needed. Al the vendors of KW added to a great vacation!!
Stayed 5 nights in Apr 2025

10/10 Excellent

Christine P.

Liked: Cleanliness

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

10/10 Excellent

Emily D.

Liked: Cleanliness

10ac duke

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

10/10 Excellent

Cathy K.

Liked: Cleanliness

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

8/10 Good

Verified traveler

Liked: Cleanliness

Parking not available even though it was listed

Listing on VRBO said there was parking with this property. Upon arrival there did not appear to be any. Contacted property manager and she said that parking was not available. Sent her a screenshot of listing saying parking is available. She informed her marketing department which said it was checked that parking was not available. However on the VRBO site it said it was. This was a huge disappointment as we had people with mobility issues.
Stayed 2 nights in Mar 2025

10/10 Excellent

Jennifer G.

Liked: Cleanliness

A Gem!

This property was perfect. The house itself is lovely and has a great set up. 4 bedrooms (one is in a little attached cottage outside). The pool is a very nice addition. The home is located a little bit off the beaten track, so it is quiet. It is in walking distance of everything. We would definitely stay here again!walkingof
Stayed 3 nights in Jan 2025

10/10 Excellent

S C.

Liked: Cleanliness

Must Stay Location!

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 spent 4 days and 3 nights. Captains Quarters was wonderful. Great location with avg transportation cost of 8. Loved the front porch and the neighborhood. Keep in mind there is an early noise ordinances at 8pm so you need to be mindful at the pool if night swimming. Woke up with the chickens every morning and relaxed in this home. The bathtub is high and for older folk would be difficult but there are two other showers one outdoors which was great under the stars! The beds and pillows were top notch and we all slept very well. Biggest issue was the deck door to the pool was very difficult to open. It stuck a lot. Thank you to the host for the great communication and I highly recommend using their free concierge service. We had food waiting for us after a very stressful travel day. They really aided in our decompression. I will be back and will stay here again.
Stayed 3 nights in Jan 2025

8/10 Good

Terri A., Fairhope AL

Liked: Cleanliness

A Good Find on Key West

My family enjoyed our stay at Captain’s Quarters. The children especially enjoyed the heated pool and there was adequate room for the seven of us. The bedding was comfortable and it was handy that all of the bedrooms had TVs. There is normally places to park out front if one happens to have a golf cart. There are some issues that need to be addressed and we had many electrical plugs that were very old and wouldn’t work so charging phones became an issue. … It could use a freshen up as window treatments are falling down off the French doors and it just looks like there needs to be a redo by the owners to justify the cost. We are used to staying in nicer places, but I understand that KW is not like staying at The Four Seasons. It’s
Stayed 4 nights in Dec 2024