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

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A heated pool
Interior
Terrace/patio
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Fridge, microwave, oven, dishwasher

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms1650 sq ft

Popular amenities

  • Dryer
  • Washer
  • Kitchen
  • Pool
  • Barbecue grill
  • Outdoor Space

Explore the area

Map
Key West, Florida
  • Duval Street
    ‪12 min walk‬
  • Southernmost Point
    ‪14 min walk‬
  • Mallory Square
    ‪4 min drive‬
  • Key West, FL (EYW-Key West Intl.)
    ‪7 min drive‬

Room options

About the neighborhood

Key West

Located in Old Town Key West, this vacation home is a leisurely stroll from popular sights such as Duval Street and Florida Keys Beaches. The vacation home includes a private pool, a kitchen, and a balcony.

What's nearby

  • Duval Street - 12 min walk - 0.7 miles
  • Southernmost Point - 14 min walk - 0.8 miles
  • Ernest Hemingway Home and Museum - 15 min walk - 0.8 miles
  • Smathers Beach - 4 min drive - 1.3 miles
  • Mallory Square - 4 min drive - 1.5 miles

Getting around

  • Key West Intl. Airport (EYW) - 8 min drive

Restaurants

  • ‪Sandy's Cafe - ‬2 min walk
  • ‪El Siboney Restaurant - ‬6 min walk
  • ‪Dairy Queen - ‬5 min walk
  • ‪Thai Island Restaurant - ‬19 min walk
  • ‪Miami Subs - ‬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”. Guests may also park at the Old Town Parking Garage which allows daily and monthly rates.

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...
The vacation home is air-conditioned and features a kitchen, 2.5 bathrooms, and a balcony. There's space to spread out with 4 bedrooms and a dining area. Guests can enjoy a TV and stay connected with free WiFi. Other standard amenities include a private pool, a washing machine, and a coffee maker. Housekeeping is available on request.

Property manager

Wendy Zintsmaster & Team

Languages

English

Similar properties

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 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

Pets

  • This property doesn't allow pets

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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25
Property Registration Number 25230-28078

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, and a deadbolt lock.

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

What can I see close to this vacation home?

This vacation home is situated in Old Town Key West within a short 13-minute walk of Duval Street and also 14 minutes on foot from Florida Keys Beaches. You'll also find Ernest Hemingway Home and Museum and South Beach less than a mile away.

Will I be able to park at this vacation home?

No, this vacation home doesn't offer parking.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home; however, the accommodation features a private pool.

Is CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! a good place to stay for couples?

Amenities that appeal to couples at this historic vacation home include a private pool and a kitchen along with a heated pool.

Are there hot tubs at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

No, but this vacation home does have a heated pool.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Does this vacation home have connecting rooms?

No, this vacation home doesn't feature connecting guestrooms.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 3.1 mi away (8 minutes by car).

Are there rooms with balconies that I can book at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

Yes, every accommodation at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! comes with a balcony.

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 154 out of 186 reviews
Rating 8 - Good. 23 out of 186 reviews
Rating 6 - Okay. 7 out of 186 reviews
Rating 4 - Poor. 0 out of 186 reviews
Rating 2 - Terrible. 2 out of 186 reviews

9.8/10

Cleanliness

Reviews

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

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

10/10 Excellent

Brian Z.

Liked: Cleanliness

Spearfishing Trip to Key West

House was great. Have stayed many places in Key West - this may be one of the nicer properties. Has a grill, very nice sleeping arrangements. Close to all the places you want to get to. Nice Quiet street.
Stayed 3 nights in Aug 2024

10/10 Excellent

Gina P.

Liked: Cleanliness

Amazing!!

What a find!! I would definitely book again!
Stayed 3 nights in Jul 2024

10/10 Excellent

Adriana A.

Liked: Cleanliness
Stayed 3 nights in May 2024

10/10 Excellent

Donna W.

Liked: Cleanliness

Captain's Quarters

The location and condition of the property, ease of check-in, communication with the property representatives, and entire vacation experience with friends were unforgettable.
Stayed 4 nights in Jun 2024

2/10 Terrible

Ashley R.

Disliked: Cleanliness

DON’T DO IT

The rental management company ruined our stay and it’s just standard practice. During our stay, the separate cottage bedroom was not usable because it was infested with huge ants. Literally, ANTS WERE EVERYWHERE. The cottage accounts for a separate bedroom by the pool, connected to the outdoor shower. They knew about ants before we arrived but waited until we got there so we could let the exterminator in with the key. So they finally spray toxic chemicals all over the bedroom and tell us we shouldn’t go in for 48 hours. So…we don’t have enough bedrooms. Dead ants covered the bedroom. Next, you’ll be interrupted by the pool cleaners who demand you leave the pool area for 2 hours, followed by the landscapers who came AFTER the pool was cleaned and spent 3 hours cutting, mowing, trimming bushes, and then blowing all the debris (back into the pool) I contacted management who was “out for the day” and she never called me back. I complained about not getting a call back and this woman actually created a fake screen shot of her fake attempt at trying to call me….or someone programmed in her phone as “tenant blah blah blah” she claimed she tried to call back and the call was “cancelled” so she is just dumb. She called a number, pressed cancel, and then took a screen shot and this was her proof of trying to contact me. I own property and would fire my team if they acted this way. Don’t rent from this company.
Stayed 6 nights in May 2024

10/10 Excellent

Brian O.

Liked: Cleanliness

Awesome

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

10/10 Excellent

Brian M., Napa, CA

Liked: Cleanliness

Awesome

Great Home and location
Stayed 3 nights in Jun 2024

10/10 Excellent

Linda C.

Liked: Cleanliness

Perfect for our family celebration

We had 3 adults varying ages celebrating a 30th birthday. The house couldn't have been more perfect. Charm alongside the perfect layout for personal space as well as areas to be together at the pool family room or dining room. The pool amazing. House immaculate with all amenities needed. Bikes to rent are just a couple blocks away (walking) we had no issue parking for one car. Easy bike ride or nice walk to Duvall. And our host Melanie was a star! Quick to respond but really everything was laid out clearly from start to finish, there wasn't much to ask other than what kind of coffee maker was available (both drip and keurig btw which was great) We would love to stay at this property again. Easy. Beautiful. Thanks Melanie!
Stayed 4 nights in May 2024

10/10 Excellent

Bridget S.

Liked: Cleanliness

Beautiful backyard oasis

The house was clean and well stocked with essentials, had lots of character and nicely decorated. The backyard was beautiful with an amazing pool and lots of lounge chairs and outdoor seating. Wonderful stay for our group of 6 adults.
Stayed 4 nights in Apr 2024

10/10 Excellent

John W.

Liked: Cleanliness

KW Group

Had 9 people stay, accommodated everyone well. Good location, bit of a walk to things, Uber quick. Pool was awesome, great areas to relax between excursions.
Stayed 5 nights in Feb 2024