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.
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
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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
Pets
No pets 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
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 14-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
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 158 out of 190 reviews
10 - Excellent
158
Rating 8 - Good. 23 out of 190 reviews
8 - Good
23
Rating 6 - Okay. 7 out of 190 reviews
6 - Okay
7
Rating 4 - Poor. 0 out of 190 reviews
4 - Poor
0
Rating 2 - Terrible. 2 out of 190 reviews
2 - Terrible
2
9.8/10
Cleanliness
Reviews
10/10 Excellent
Britt N., Pasadena, MD
18 Jul 2025
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.
Britt N.
Stayed 4 nights in Jul 2025
8/10 Good
Jeramie K.
17 Jun 2025
Liked: Cleanliness
Jeramie K.
Stayed 5 nights in May 2025
10/10 Excellent
Jonard B.
30 May 2025
Liked: Cleanliness
Amazing Place
Jonard B.
Stayed 3 nights in May 2025
10/10 Excellent
James G.
4 May 2025
Liked: Cleanliness
Great place
Great place. well located. Will be returning.
James G.
Stayed 6 nights in Apr 2025
10/10 Excellent
Matt D.
17 Apr 2025
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!!
Matt D.
Stayed 5 nights in Apr 2025
10/10 Excellent
Christine P.
14 Apr 2025
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!
Christine P.
Stayed 2 nights in Apr 2025
10/10 Excellent
Emily D.
31 Mar 2025
Liked: Cleanliness
10ac duke
House was great. Pool, amazing. Will stay here again!
Emily D.
Stayed 4 nights in Mar 2025
10/10 Excellent
Cathy K.
31 Mar 2025
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.
Cathy K.
Stayed 5 nights in Mar 2025
8/10 Good
Verified traveller
8 Mar 2025
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.
Verified traveller
Stayed 2 nights in Mar 2025
10/10 Excellent
Jennifer G.
3 Feb 2025
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
Jennifer G.
Stayed 3 nights in Jan 2025
10/10 Excellent
S C.
29 Jan 2025
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.
S C.
Stayed 3 nights in Jan 2025
8/10 Good
Terri A., Fairhope AL
29 Dec 2024
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
Terri A.
Stayed 4 nights in Dec 2024
10/10 Excellent
Tara G.
15 Dec 2024
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.
Tara G.
Stayed 7 nights in Dec 2024
10/10 Excellent
Debbie W.
2 Dec 2024
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.
Debbie W.
Stayed 4 nights in Nov 2024
10/10 Excellent
Kerrie B.
1 Dec 2024
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
Kerrie B.
Stayed 4 nights in Nov 2024
10/10 Excellent
Teresa A.
13 Nov 2024
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!
Teresa A.
Stayed 4 nights in Nov 2024
8/10 Good
Linda T.
5 Nov 2024
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.
Linda T.
Stayed 7 nights in Oct 2024
10/10 Excellent
Kelly M.
9 Sept 2024
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.
Kelly M.
Stayed 2 nights in Sep 2024
10/10 Excellent
Brian Z.
22 Aug 2024
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.
Brian Z.
Stayed 3 nights in Aug 2024
10/10 Excellent
Gina P.
7 Aug 2024
Liked: Cleanliness
Amazing!!
What a find!! I would definitely book again!
Gina P.
Stayed 3 nights in Jul 2024
10/10 Excellent
Adriana A.
31 Jul 2024
Liked: Cleanliness
Adriana A.
Stayed 3 nights in May 2024
10/10 Excellent
Donna W.
30 Jun 2024
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.
Donna W.
Stayed 4 nights in Jun 2024
2/10 Terrible
Ashley R.
22 Jun 2024
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.
Ashley R.
Stayed 6 nights in May 2024
10/10 Excellent
Brian O.
15 Jun 2024
Liked: Cleanliness
Awesome
We loved the home! The decor, the pool, and the location were all perfect