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

Top rated by guests

9.6Outstanding

(198 Ratings)

"Great quiet location!"

Edward C.

Don't miss out! Price and availability may change

9.6 / 10.0

Outstanding(198 Ratings)

House in Key West, FL

10 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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...

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

Non-smoking

No pets allowed

Family friendly

Map of Key West, FL

Nearby attractions

The Key West Butterfly and Nature Conservatory

0.6 mi

Mallory Square

1.1 mi

Southernmost Point of the Continental U.S.A.

0.7 mi

The Hemingway Home and Museum

0.7 mi

$$$$

Top rated by guests

9.6Outstanding

(198 Ratings)

"Great quiet location!"

Edward C.

Don't miss out! Price and availability may change

$$$$

9.6 / 10.0

Outstanding(198 Ratings)

House in Key West, FL

10 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Top-tier experienceA high end property in this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Map of Key West, FL

Nearby attractions

The Key West Butterfly and Nature Conservatory

0.6 mi

Mallory Square

1.1 mi

Southernmost Point of the Continental U.S.A.

0.7 mi

The Hemingway Home and Museum

0.7 mi

About this house rental

Amenities

Non-smoking

No pets allowed

Family friendly

Ratings and reviews

9.6 / 10.0

Outstanding(198 Ratings)

10.0 / 10.0

Great quiet location!

10.0 / 10.0

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

10.0 / 10.0

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

10.0 / 10.0

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.

10.0 / 10.0

Great place. well located. Will be returning.

8.0 / 10.0

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.

10.0 / 10.0

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!!

10.0 / 10.0

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!

10.0 / 10.0

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

10.0 / 10.0

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.

6.0 / 10.0

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.

8.0 / 10.0

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.

10.0 / 10.0

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

10.0 / 10.0

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.

8.0 / 10.0

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

10.0 / 10.0

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.

10.0 / 10.0

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.

10.0 / 10.0

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

10.0 / 10.0

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!

8.0 / 10.0

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.

10.0 / 10.0

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!

10.0 / 10.0

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.

10.0 / 10.0

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.

10.0 / 10.0

What a find!! I would definitely book again!

10.0 / 10.0

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

2.0 / 10.0

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.

10.0 / 10.0

We loved the home! The decor, the pool, and the location were all perfect

10.0 / 10.0

Great Home and location

10.0 / 10.0

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!

10.0 / 10.0

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.

10.0 / 10.0

6.0 / 10.0

Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: I will start by saying that while we had a nice stay and appreciated the historic detail of the home and the great pool area, we would not choose this home again. Our group of 7 felt it was very overpriced compared to other options and past stays in Key West. The pros of this house are that it has great historic detail, is nicely decorated, has a lovely pool, and comfortable beds. But there were a bunch of functional issues. We are a group that cooks and had to go out to buy things like a second cutting board and a knife that worked.There were also a lot of little things that did not work in the house, and little things that most places at this expensive of a price include were not. Also, the 4th bedroom is literally just a bed and sink.The highlight of the house is definitely the pool, which was very clean and kept pleasantly warm and had lots of deck furniture. It made our stay. The property manager was very helpful and responsive and with a little maintenance and added amenities, those could be improved, but generally we did not feel this house was worth the price and fees.

10.0 / 10.0

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.

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

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

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.

Explore similar stays in Key West

Explore all rentals in Key West

10.0 / 10.0

Outstanding

The Southernmost Comfort House

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

House in Key West, FL

Reasons to book

About this house rental

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

Map of Key West, FL

Nearby attractions

House in Key West, FL

Reasons to book

Map of Key West, FL

Nearby attractions

About this house rental

Amenities

Ratings and reviews

FAQs

Is parking included with this house?

Is there a pool at this house?

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

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

Explore similar stays in Key West

Related destinations