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

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

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms

Popular amenities

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

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...

Property manager

Wendy Zintsmaster & Team

Languages

English

Add dates for prices

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

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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

Pets not allowed

Children and extra beds

Children are welcome

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

About the neighborhood

Map
Key West, Florida

What's nearby

  • Duval Street - 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
  • Smathers Beach - 4 min drive - 2.0 km
  • Mallory Square - 4 min drive - 2.4 km

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

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.

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!!?

Check-out 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 vacation home is within a 15-minute walk of Key West Firehouse Museum, Duval Street, and Florida Keys Beaches. Ernest Hemingway Home and Museum and South Beach are also within 1 mi (2 km).

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

Reviews

9.6

Exceptional

Rating 10 - Excellent. 156 out of 188 reviews
Rating 8 - Good. 23 out of 188 reviews
Rating 6 - Okay. 7 out of 188 reviews
Rating 4 - Poor. 0 out of 188 reviews
Rating 2 - Terrible. 2 out of 188 reviews

9.8/10

Cleanliness

Reviews

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

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

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

10/10 Excellent

Jennifer G.

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

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

Tara G.

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

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

8/10 Good

Verified traveler

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy

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

Teresa A.

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

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

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

10/10 Excellent

Brian Z.

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

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

Donna W.

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

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

10/10 Excellent

Gina P.

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

Amazing!!

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

10/10 Excellent

Brian M.

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

Awesome

Great Home and location
Stayed 3 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Lisa W.

Amazing house !!!

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: everything you need while staying in Key West
Stayed 3 nights in Jul 2024

10/10 Excellent

Theresa Ann N.

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

Best kept secret

The house was lovely
Stayed 4 nights in Nov 2023

10/10 Excellent

tracy b.

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

Great house

What a great property in key west! Pool and back yard area were perfect!
Stayed 3 nights in Sep 2023

10/10 Excellent

John W.

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

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

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

10/10 Excellent

Brenda A.

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

Great time

Great place, did echo lots but not a real bother. Great location and close to good food and needs in walking distance!
Stayed 5 nights in Nov 2023

10/10 Excellent

Kelly M.

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

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
This review comes from a trusted partner site and has not been verified.

6/10 Okay

Pam A.

Nice home in need of some love

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very unhappy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This home is in need of some attention. It was dusty and looks nothing like the picture. It is quite along walk to the major Key West attractions. Planes fly over so much, and a lot on the weekends. It seems to never stop. It is extremely loud and the planes are very low. We had an issue with the shower drain and they sent someone out very quickly. The kitchen is in need of attention and the front gate was hanging off to one side because the latch is broken. The pool area was the best part. It’s very warm and we really enjoyed that. The shared bathroom is odd and the shower is a bit hard to navigate. It’s a big step in and difficult to get out of. Cute but not very functional.

8/10 Good

Terri A.

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

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

Lisa F.

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

Great rental for large group

Outstanding house accommodating 12 of us. The pool was absolutely wonderful!
Stayed 6 nights in May 2022

10/10 Excellent

Shawna G., Glendale

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

Such a great place!

Had such a great time! Perfect location. Easy access. Best family vacation spot!
Stayed 3 nights in Aug 2019

10/10 Excellent

Irina S.

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

Vacation with family friends

Stayed for a week and had a great time. Lovely house, amazing pool, great location. Highly recommend.
Stayed 6 nights in Apr 2021
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Larry C.

Captain's Quarter 2 Day 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: Awesome
Stayed 2 nights in Mar 2024