Old Town Rentals USA Florida Key West Old Town

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

9.6 (192 Reviews) |   4 Bedrooms  2 Bathrooms  10 Guests  Stay&Play
Old Town House | CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!

4 Bedroom House in Old Town, Key West

HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL....
Once you step through the threshold ofthis Old Town home you feel enveloped in vintage Key West.Dade County wood surfaces, nauticalaccents plus appealing and comfortable decormake 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 apedestalsink. 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 hadupdates completed in the spacioushomes 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...

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm! is located in Old Town. CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm! provides accommodation, featuring Security/Safety, Kitchen, Entertainment, among other amenities. This House features Security/Safety, Kitchen, Entertainment, to make your stay a comfortable one.

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm! has 4 Bedrooms , 2 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Old Town has interesting places to visit. If you want to learn more about the House in Old Town, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Pool
  • TV
  • View
  • Private Pool
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Guest Services
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets not allowed
Smoking Policy Smoking is not permitted
Other Policy 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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited property registration number 25230-28078 safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Key West, 33040, USA

What Our Guests say 500 + Reviews

Jun 19, 2025 03:46:00 PM
Summary: 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
Tracy S. Tracy S.
May 5, 2025 04:45:02 AM
Summary: Great place. well located. Will be returning.
James G. James G.
Apr 21, 2025 05:17:00 PM
Summary: 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.
A guest from Raleigh, NC A guest from Raleigh, NC
Apr 18, 2025 12:39:49 AM
Summary: 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. Matt D.
Apr 14, 2025 07:05:01 AM
Summary: 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. Christine P.
Apr 1, 2025 01:22:08 AM
Summary: House was great. Pool, amazing. Will stay here again!
Emily D. Emily D.
Mar 31, 2025 11:35:24 PM
Summary: 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. Cathy K.
Mar 11, 2025 12:05:00 PM
Summary: 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.
Pam A. Pam A.
Mar 8, 2025 11:59:42 PM
Summary: 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.
Feb 4, 2025 02:27:25 AM
Summary: 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. Jennifer G.

FAQ's

Is this Old Town house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Old Town house have a swimming pool?

Yes, this Old Town house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Old Town house?

Best-rates for the Old Town house starts from $1,239 per night with includes Internet, Security/Safety, Kitchen, Entertainment, View, Balcony/Terrace, Sports/Activities, Barbecue/Outdoor Cooking, Child Friendly, Private Pool, Ocean View, Bedding/Linens, Guest Services, Laundry, Air Conditioner, Pool, TV, Oceanfront, Wellness Facilities StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Old Town house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Old Town house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Old Town house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Old Town house?

Based on the information reported by the owner or manager, the Old Town house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Old Town house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Old Town house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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