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

Holiday home with private pool, near Duval Street

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

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

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms153 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Key West, FL
  • Place, South Beach
    ‪12 min walk‬
  • Place, Southernmost Point
    ‪14 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪15 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪6 min drive‬

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About the area

Key West

This holiday home places you in the centre of Key West, within just a 15-minute stroll of popular places like Duval Street and Florida Keys Beaches. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 2.5 bathrooms and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a dishwasher. A living room, a dining area and a TV are also available. Housekeeping is available on request. .This smoke-free holiday home offers concierge services, a garden and gas grills. Plus you'll find laundry facilities. .Attractions within a 20-minute walk of this Old Town Key West holiday home include Ernest Hemingway Home and Museum and South Beach.
View more Holiday homes in Key WestOpens in a new window

What's nearby

  • Clarence S. Higgs Memorial Beach Park - 12 min walk - 1.1 km
  • South Beach - 12 min walk - 1.1 km
  • Key West Butterfly and Nature Conservatory - 12 min walk - 1.1 km
  • Southernmost Point - 14 min walk - 1.2 km
  • Ernest Hemingway Home and Museum - 15 min walk - 1.3 km

Getting around

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

Restaurants

  • ‪Dions Truman & White - ‬2 min walk
  • ‪Sandy's Café - ‬1 min walk
  • ‪El Siboney Restaurant - ‬6 min walk
  • ‪Mangia Mangia - ‬11 min walk
  • ‪Bobby's Monkey Bar - ‬12 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

  • Smoke-free property

Services and conveniences

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

Location highlights

  • In the city centre
  • 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
  • Snorkelling 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 and check-out are 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
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
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. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector and a deadbolt lock in all 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

Are there any beaches close to CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

Yep, CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! is a short 13-minute walk from Florida Keys Beaches. Fun beach activities include jet skiing, snorkelling and scuba diving.

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

Yep, and guests love it! CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! has a heated pool and a pool.

What luxury perks are available at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

This property features a heated pool, as well as a private pool and a living room.

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

No, but there is a private pool.

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

No, CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! does not offer an airport shuttle service.

What time are check-in & check-out at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

No, pets are not allowed.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 164 out of 197 reviews
Rating 8 - Good. 24 out of 197 reviews
Rating 6 - Okay. 7 out of 197 reviews
Rating 4 - Poor. 0 out of 197 reviews
Rating 2 - Terrible. 2 out of 197 reviews

9.8/10

Cleanliness

Reviews

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 traveller

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

10/10 Excellent

Tara G.

Liked: Cleanliness

Antique dreamy Key West gem🩵

We really love this place. The pool is excellent and well heated! We swam even on the one cold day we had. Really great customer service and response from the management. Everything was clean and well maintained and worked! Definitely a Key West dream house with the old timey historic feel that we all love about the island…and a great pool.
Stayed 7 nights in Dec 2024

10/10 Excellent

Debbie W.

Liked: Cleanliness

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

10/10 Excellent

Kerrie B.

Liked: Cleanliness

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

10/10 Excellent

Teresa A.

Liked: Cleanliness

Great House, Great Host

Our family of eight really enjoyed our time in Key West. This was a first-time visit for all of us. The Captain's Quarters is a beautiful and comfortable home, in a quiet neighborhood, with a welcoming patio & pool, and an attentive & caring property manager. We were made to feel welcome and valued. I will be sharing this listing with family and friends, and would not hesitate to stay at this property again. Thank you!
Stayed 4 nights in Nov 2024

8/10 Good

Linda T.

Liked: Cleanliness
Dead growth in yard created a mess constantly on the pool. Out door furniture shows wear and some are broken. Need throw blankets. Blackout curtains would be appreciated in the bedrooms. Some doors do not latch and/or lock.
Stayed 7 nights in Oct 2024

10/10 Excellent

Kelly M.

Liked: Cleanliness

Amazing Stay at Captain's Quarters

I absolutely loved this property. It was beautiful and impeccably decorated in true Key West fashion. The house is full of beautiful antiques and nautical art. The management team was very communicative and accommodating. The pool was amazing for a midday break because it was so deep and the perfect temperature. This house was definitely a splurge for us but we made up for it by cooking at home. The kitchen and the house had everything we needed and a working grill so we were able to have amazing meals at home. I absolutely love this property I would definitely stay here again.
Stayed 2 nights in Sep 2024