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

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

A spacious living room with a wooden floor, a ceiling fan, a large window with curtains, a pool view, and a 'Hay West' sign on the wall.
A living room with a wooden floor, a ceiling fan, a sofa, a coffee table, and a large mirror.
A wooden hallway with a rug, a chandelier, and a door with frosted glass panels.
A pool area with a wooden deck, lounge chairs, and a small gazebo.
A hallway with wooden floors and walls, a bed with pink pillows, a nightstand with a lamp, and framed artwork on the walls.

Reviews

9.6 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Duval Street

Popular amenities

  • Balcony
  • Private pool
  • Gas barbecue
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View in a map
Key West, FL
  • Place, Ernest Hemingway Home and Museum
    ‪15 min walk‬
  • Place, South Beach
    ‪15 min walk‬
  • Place, Southernmost Point
    ‪17 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪8 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Other Space 1

1 Double Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden

Add dates for prices

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About the area

Key West

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. The Kite House and Key West Butterfly and Nature Conservatory are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 12 min walk - 1.1 km
  • Clarence S. Higgs Memorial Beach Park - 14 min walk - 1.2 km
  • Ernest Hemingway Home and Museum - 15 min walk - 1.3 km
  • South Beach - 15 min walk - 1.3 km
  • Southernmost Point - 17 min walk - 1.5 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 10 min drive

Restaurants

  • ‪Sandy's Café - ‬2 min walk
  • ‪El Siboney Restaurant - ‬6 min walk
  • ‪Better Than Sex - ‬11 min walk
  • ‪Miami Subs - ‬13 min walk
  • ‪Dairy Queen - ‬5 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.

How much does it cost to stay at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!?

As of 25 Oct 2026, prices found for a 1-night stay for 2 adults at CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! on 1 Nov 2026 start from £686, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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!!?

Checkout 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 holiday 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 mile (2 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 180 out of 216 reviews
Rating 8 - Good. 27 out of 216 reviews
Rating 6 - Okay. 7 out of 216 reviews
Rating 4 - Poor. 0 out of 216 reviews
Rating 2 - Terrible. 2 out of 216 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was perfect for our family of 4 and enjoyed the pool every afternoon and early evenings after the long hot days in Key West! Love the layout and that all rooms have big beds
Stayed 4 nights in Jul 2026
Response from VrboOwner on 18 Aug 2026
Your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a fantastic place to stay and enjoy Key West
Stayed 3 nights in May 2026
Response from VrboOwner on 2 Jun 2026
Thank you for the kind words Melissa! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.
From a partner site

10/10 Excellent

Great Location!

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: We loved this place! The location was great, we walked to almost everything we did. The pool was awesome! It was very hot during our stay and the pool the perfect release from the heat! Rooms were clean and well maintained. I would highly recommend this place!
Response from VrboOwner on 21 Aug 2026
We’re so glad you had a great time with us. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
From a partner site

10/10 Excellent

Captain's Quarters - No Notes (except great ones!)

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: Wonderful experience from start to finish. Communication with the property management company was on point. House was as advertised. Rooms were great and the pool was a major highlight of the trip for our group. Very quiet neighborhood and close to amenities that we needed for provisioning.
Response from VrboOwner on 18 Aug 2026
We truly appreciate your review! It makes us happy to know you loved this property, and we’d be delighted to host you again anytime.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a beautiful home located in a quiet neighborhood in the north central section of Key West. The pool area is spacious and amazing. We had a party of 8 and had plenty of room. The kitchen floor was being renovated with wood on the floor which made it difficult to clean and a few minor issues with the fridge upon arrival which the property manager quickly resolved. Short distance to close by supermarkets and quiet enough to relax and enjoy quiet night. Overall, it was a great stay!
Stayed 7 nights in Jun 2026
Response from VrboOwner on 20 Aug 2026
Your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.
From a partner site

10/10 Excellent

Beautiful Historic 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: This is a wonderful home in a fantastic location. It’s close to everything, but is a tucked away, quiet gem! The house’s pool is large with a great deck. A must rental!
Response from VrboOwner on 18 Jul 2026
Thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Dinner on the beach at Latitudes to cap off a great weekend!
Stayed 4 nights in Mar 2026
Response from VrboOwner on 25 Mar 2026
We’re so glad you had a great time with us Warren. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great quiet location!
Stayed 5 nights in Oct 2025
Response from VrboOwner on 28 Nov 2025
We truly appreciate your review! It makes us happy to know you loved this home, and we’d be delighted to host you again anytime.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
Plenty of room for 3 couples and 1 single. Pool was great. Secluded and bigger than we expected based on the pictures. We had a small issue with insects in one of the bedrooms, but host quickly addressed. Front gate and porch area are ready for an update; but house was spacious and perfect for our party of 7.
Stayed 4 nights in Apr 2026
Response from VrboOwner on 11 May 2026
Your kind words mean the world to us Michael! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Feb 2026
Response from VrboOwner on 30 Mar 2026
We’re grateful for your glowing review Alexandra! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 6 nights in Mar 2026
Response from VrboOwner on 20 Apr 2026
Thanks so much for the lovely feedback Anita! We’re happy to hear you enjoyed the property and would love to host you again in the future.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Jan 2026
Response from VrboOwner on 22 Jan 2026
We’re grateful for your glowing review Kristan! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host Whitney was extremely accommodating and accessible. The pool area was lovely but not cleaned as we would have liked.
Stayed 6 nights in Jan 2026
Response from VrboOwner on 24 Feb 2026
Thank you for your review. We are delighted to hear that your property manager was so responsive. We are sorry that the pool was not as clean as you would have liked. We will relay your comments back to our team for review. Please come back again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay, enjoyed our time. The pool is bigger than the pictures give it credit for!
Stayed 3 nights in Jul 2025
Response from VrboOwner on 19 Sept 2025
Riley, thank you for the kind words! We’re so happy you enjoyed your stay in Key West, and we’d be thrilled to welcome you back for another unforgettable visit.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect stay, awesome communication with the property manager at all times 5
Stayed 3 nights in Aug 2025
Response from VrboOwner on 8 Sept 2025
Thank you for your kind review! We are delighted that you enjoyed the home and your stay!
From a partner site

10/10 Excellent

Carptains Quarters

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.
Response from VrboOwner on 27 Feb 2026
Thank you so much for your stellar review Mark! We really appreciate your kind words and suggestions. We hope you'll return again soon as our welcome guest!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location
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.
Stayed 4 nights in Jan 2026
Response from VrboOwner on 10 Feb 2026
We truly appreciate your review Karen! It makes us happy to know you loved this home, and we’d be delighted to host you again anytime.
Verified review

10/10 Excellent

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

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.
Stayed 4 nights in Jul 2025
Response from VrboOwner on 19 Nov 2025
Brittany, your kind words mean the world to us! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.
Verified review

10/10 Excellent

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

Great place

Great place. well located. Will be returning.
Stayed 6 nights in Apr 2025
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Great place

I would recommend this place to anyone! Very nice and great location.
Stayed 4 nights in May 2022
Response from VrboOwner on 15 Jul 2022
Thank you for your fantastic review Michael. It was a pleasure hosting you and we look forward to welcoming you again next time you visit the island!
Verified review

10/10 Excellent

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
Verified review

8/10 Good

Liked: Cleanliness, communication, location, listing accuracy
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.
Stayed 4 nights in Dec 2025
Response from VrboOwner on 5 Jan 2026
Thank you for your feedback on your recent stay William. We are so glad that you enjoyed your time spent at this home. We appreciate your feedback that we will relay back to the owners for consideration. Thank you again and please reach out to us for your next Key West vacation!
Verified review

10/10 Excellent

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

Perfect place for a family stay!

We loved this property- the house is beautiful and perfect size for all 10 of us. The backyard and pool were amazing! Will definitely be staying here again!
Stayed 5 nights in Feb 2023
Response from VrboOwner on 7 Nov 2023
We are so happy you found this property and its location ideal for your get away in Key West. We hope you'll stay with us again next time you visit!
From a partner site

10/10 Excellent

Fabulous Time in Key West

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.
Response from VrboOwner on 21 Feb 2026
Thanks for the great review Tammy! It’s always wonderful to hear when guests plan to return, and we can’t wait to welcome you again to our southernmost slice of paradise!
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