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

Key West, Florida
$1 avg/night
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

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...

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1650 Sq Ft (153 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Garden Gas Grill
  • POOL/SPA

    Heated Pool Private Pool
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Cycling Nearby Ecotours Nearby Fishing Nearby Fitness Facilities Nearby Marina Nearby Scuba Diving Nearby Swimming Nearby Water Skiing Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Games TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The City Center Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Concierge Services Housekeeping (on Request) Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Anita G.

    Submitted Apr 5, 2026

    Stayed Mar 19, 2026

    The house was beautiful and I was pleased to see that some basic items were at house coffee filter and laundry detergent simply but nice to not have to purchase. There were 5 adults and one child in our group and were very comfortable in family and dining room and the area around pool was large and roomy compared to others.

  • Alexandra S.

    Submitted Mar 13, 2026

    Stayed Feb 27, 2026

    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.

  • Warren B.

    Submitted Mar 10, 2026

    Stayed Mar 5, 2026

    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!

  • Rhonda C.

    Submitted Feb 24, 2026

    Stayed Feb 18, 2026

    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.

  • Tammy M.

    Submitted Feb 18, 2026

    Stayed Feb 12, 2026

    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.

  • Gwen R.

    Submitted Feb 6, 2026

    Stayed Jan 30, 2026

    The host Whitney was extremely accommodating and accessible. The pool area was lovely but not cleaned as we would have liked.

  • Karen E.

    Submitted Jan 22, 2026

    Stayed Jan 15, 2026

    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.

  • Kristan R.

    Submitted Jan 6, 2026

    Stayed Jan 1, 2026

    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!

  • William F.

    Submitted Dec 22, 2025

    Stayed Dec 17, 2025

    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.

  • Edward C.

    Submitted Nov 5, 2025

    Stayed Oct 31, 2025

    Great quiet location!

  • Devotion808 g.

    Submitted Aug 19, 2025

    Stayed Aug 14, 2025

    Perfect stay, awesome communication with the property manager at all times 5

  • Riley N.

    Submitted Aug 8, 2025

    Stayed Jul 24, 2025

    Great stay, enjoyed our time. The pool is bigger than the pictures give it credit for!

  • Megan B.

    Submitted Jul 28, 2025

    Stayed Jul 20, 2025

    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.

  • Britt N.

    Submitted Jul 18, 2025

    Stayed Jul 14, 2025

    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.

  • Tracy S.

    Submitted Jun 19, 2025

    Stayed May 31, 2025

    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

  • James G.

    Submitted May 4, 2025

    Stayed Apr 28, 2025

    Great place. well located. Will be returning.

  • A guest from Ral....

    Submitted Apr 21, 2025

    Stayed Apr 1, 2025

    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: Beautiful and serene property. Very clean and well stocked. Excellent location with lots of walkability. Generally quiet neighborhood, with some over head plane noise (near impossible to avoid that in KW though). Only issue was that the master bathroom toilet had issues flushing without opening the tank lid. So we opted to use other bathrooms during our stay.

  • Matt D.

    Submitted Apr 17, 2025

    Stayed Apr 12, 2025

    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!!

  • Christine P.

    Submitted Apr 14, 2025

    Stayed Apr 10, 2025

    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!

  • Emily D.

    Submitted Mar 31, 2025

    Stayed Mar 16, 2025

    House was great. Pool, amazing. Will stay here again!

  • Cathy K.

    Submitted Mar 31, 2025

    Stayed Mar 23, 2025

    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.

  • Pam A.

    Submitted Mar 11, 2025

    Stayed Feb 13, 2025

    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.

  • Submitted Mar 8, 2025

    Stayed Mar 4, 2025

    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.

  • Jennifer G.

    Submitted Feb 3, 2025

    Stayed Jan 31, 2025

    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

  • S C.

    Submitted Jan 29, 2025

    Stayed Jan 22, 2025

    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.

  • Terri A.

    Submitted Dec 29, 2024

    Stayed Dec 25, 2024

    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

  • Tara G.

    Submitted Dec 15, 2024

    Stayed Dec 7, 2024

    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.

  • Debbie W.

    Submitted Dec 2, 2024

    Stayed Nov 23, 2024

    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.

  • Kerrie B.

    Submitted Dec 1, 2024

    Stayed Nov 27, 2024

    Spent family vacation hanksgiving there, had great time. The beautiful home made us all feel like we were on a 5 star vaca

  • Teresa A.

    Submitted Nov 13, 2024

    Stayed Nov 8, 2024

    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!

  • Linda T.

    Submitted Nov 5, 2024

    Stayed Oct 8, 2024

    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.

  • kim n.

    Submitted Oct 23, 2024

    Stayed Dec 31, 1969

    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: This house was amazing! Extremely clean and had everything we needed! The pool was way bigger than we thought and Melanie was more than happy to heat it for us which was Awesome! We felt very secure and there was plenty of room for eight adults. All of our activities were easy to get to, but our location was quiet and peaceful. Melanie answered the phone, no matter what time I called her. She could not have been more attentive than she was. We enjoyed the separate dining room area, the washer and dryer were appreciated and the kitchen was amazing.Bathrooms were pretty and everything worked great. We were within walking distance of a grocery store, liquor store, other small restaurants, and Duval Street was easily walkable. We did have a golf cart for getting around and it was always easy to find parking close to the house. We would definitely stay here again!

  • kim n.

    Submitted Oct 22, 2024

    Stayed Oct 15, 2024

    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: This house was amazing! Extremely clean and had everything we needed! The pool was way bigger than we thought and Melanie was more than happy to heat it for us which was Awesome! We felt very secure and there was plenty of room for eight adults. All of our activities were easy to get to, but our location was quiet and peaceful. Melanie answered the phone, no matter what time I called her. She could not have been more attentive than she was. We enjoyed the separate dining room area, the washer and dryer were appreciated and the kitchen was amazing.Bathrooms were pretty and everything worked great. We were within walking distance of a grocery store, liquor store, other small restaurants, and Duval Street was easily walkable. We did have a golf cart for getting around and it was always easy to find parking close to the house. We would definitely stay here again!

  • Kelly M.

    Submitted Sep 9, 2024

    Stayed Sep 6, 2024

    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.

  • Karen S.

    Submitted Sep 8, 2024

    Stayed Aug 29, 2024

    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 home is beautiful and clean. It is locatedin a quite area with a lovely swimming pool in the back. The home is well equipped with anything you may need such as hair dryers, ironing board and iron. Restaurants are close by as well as a grocery and liquor store within walking distance. We were lucky to be able to check in at 12:00 instead of waiting until 4:00. I would consider renting this property in the future.

  • Brian Z.

    Submitted Aug 22, 2024

    Stayed Aug 8, 2024

    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.

  • Gina P.

    Submitted Aug 7, 2024

    Stayed Jul 31, 2024

    What a find!! I would definitely book again!

  • Lisa W.

    Submitted Jul 30, 2024

    Stayed Jul 11, 2024

    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

Your dates are Available!

Total

Includes taxes and fees
$920+
View details