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

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TV - CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! (Key West)
Interior - CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! (Key West)
4 bedrooms, iron/ironing board, free WiFi, bed sheets - CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!! (Key West)
Step into this historic Old Town home, and you'll feel the charm of vintage Key West. Rich Dade County wood surfaces, nautical accents, and comfortable decor create a warm atmosphere. Relax in the living room with a flat-screen TV or unwind by the lagoon-style pool surrounded by lush tropical landscaping.

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms3 bathrooms153 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

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 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

  • Smoke-free property

Services and conveniences

  • Concierge services
  • Housekeeping on request
  • Iron/ironing board

Location highlights

  • In the city centre
  • 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
  • Snorkelling 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 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
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
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 area

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 Fort Zachary Taylor Historic State Park and Florida Keys Beaches. 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. Visit our Key West travel guide
View more Holiday homes in Key West
Map
Key West, FL

What's nearby

  • Duval Street featuring signage
    Duval Street
    12 min walk - 1.1 km
  • South Beach featuring a sandy beach and general coastal views as well as a small group of people
    South Beach
    12 min walk - 1.1 km
  • Key West Butterfly and Nature Conservatory featuring animals, flowers and zoo animals
    Key West Butterfly and Nature Conservatory
    12 min walk - 1.1 km
  • Southernmost Point featuring signage
    Southernmost Point
    14 min walk - 1.2 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    15 min walk - 1.3 km

Getting around

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

Restaurants

  • Dions Truman & White
    2 min walk
  • Sandy's Café
    1 min walk
  • El Siboney Restaurant
    6 min walk
  • Moose Lodge
    11 min walk
  • Mangia Mangia
    11 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!!?

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).

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

Reviews

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.
More informationOpens in a new window
Rating 10 - Excellent. 166 out of 200 reviews
Rating 8 - Good. 25 out of 200 reviews
Rating 6 - Okay. 7 out of 200 reviews
Rating 4 - Poor. 0 out of 200 reviews
Rating 2 - Terrible. 2 out of 200 reviews

9.8

Cleanliness

9.6

Location

Reviews

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

Emily D.

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

10ac duke

House was great. Pool, amazing. Will stay here again!
Stayed 4 nights in Mar 2025

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

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 M.

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

Awesome

Great Home and location
Stayed 3 nights in Jun 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

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

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

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

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

Bridget S.

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

Beautiful backyard oasis

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.
Stayed 4 nights in Apr 2024

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

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

8/10 Good

A guest from Raleigh, NC

A quick trip

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.
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

Kaylee F., United States

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

Great house with a great location

Very spacious house for a large group, with a nice size pool. Easy check in and check out. They accommodated early check in and out. Quiet neighborhood with plenty of places to walk to and not far from duval!
Stayed 5 nights in Jul 2023
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

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

10/10 Excellent

Krisi C.

ahhhmazing

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 really enjoyed our stay. The house was very clean and comfortable. We had a larger group and the home had everything we needed.

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.

10/10 Excellent

Tania G.

Celebration of life

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 got together as a family to celebrate my father-in-law‘s life. A third generation conch that has lived his life in Key West. Captain’s Quarters was perfect.
Stayed 2 nights in Apr 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jaclyn H.

Fantastic 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: The house was absolutely beautiful! Favorite part was the pool and the front porch for sure! Management company was wonderful to work with! They were extremely responsive and informative!
Stayed 4 nights in Mar 2024

8/10 Good

Deanna P.

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

Anniversary celebration!

Anniversary celebration! Over all it was great! The tables and counter tops needed wiping down. Otherthanthatitwasgreat
Stayed 4 nights in Jul 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Terri K.

A lovely and comfortable stay

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: We had a great weekend stay at the Captain's Quarters. The house and pool were lovely. We had everything we needed and were close to a bike rental which is a great way to travel around Key West. Check in and out were easy. Thank you
Stayed 2 nights in Oct 2023

10/10 Excellent

Lacey R.

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

Best in stay 2023

Our stay at the Captain’s Quarters was a perfect setting for a birthday trip! The house is uniquely decorated, and the wood paneling keeps the house cool during the sticky days. All the amenities were spot on, and the pool was a perfect spot to sit and enjoy the day. What made our stay perfect was the quick response from Melaine. Her response time was short, and she offered to go above and beyond for each of our asks! We would not only recommend staying with our family and friends but will be returning!!
Stayed 4 nights in Sep 2023