Entire home

~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.

Photo gallery for ~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.

A covered porch with wicker chairs and a small table, surrounded by lush tropical plants.
A swimming pool with a waterfall feature, surrounded by lush greenery and a covered deck with seating.
A white house with turquoise shutters, surrounded by lush greenery and palm trees.
A kitchen with a central island, bar stools, a refrigerator, a stove, and shelves with dishes.
A staircase with wooden steps and white balusters, leading to a dining area with a heart-shaped wall decoration.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • At the center of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Near Duval Street

Popular amenities

  • Patio
  • Private pool
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Washer

Explore the area

View in a map
Key West, FL
  • Place, Key West Naval Station
    ‪1 min walk‬
  • Place, Key West Cemetery
    ‪6 min walk‬
  • Place, Duval Street
    ‪12 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Spaces

Deck or patio
Kitchen
Separate dining area
Garden
Dining area

Add dates for prices

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About the neighborhood

Key West

Located in Key West, this vacation home is in the city center. 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. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
View more Vacation Homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Studios of Key West - 1 min walk - 0.0 km
  • Key West Theater - 1 min walk - 0.0 km
  • Key West Naval Station - 1 min walk - 0.1 km
  • Key West Cemetery - 6 min walk - 0.6 km
  • Duval Street - 12 min walk - 1.1 km

Getting around

  • Key West Intl. Airport (EYW) - 11 min drive

Restaurants

  • ‪Cuban Coffee Queen Waterfront - ‬10 min walk
  • ‪Schooner Wharf Bar - ‬13 min walk
  • ‪Half Shell Raw Bar - ‬11 min walk
  • ‪Square Grouper Key West - ‬9 min walk
  • ‪Harpoon Harry's Restaurant and Bar - ‬10 min walk

Frequently asked questions

Is ~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool. pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at ~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.?

As of Nov 12, 2026, prices found for a 1-night stay for 2 adults at ~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool. on Nov 29, 2026 start from $912, 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.

How much is parking?

Onsite parking is available at the property.

What time is check-in at ~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.?

Check-in begins at 4:00 PM.

What time is check-out at ~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.?

Check-out is at 10:00 AM.

Where is ~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool. located?

Located in Old Town Key West, this vacation home is within a 15-minute walk of Key West Theater and Duval Street. Florida Keys Beaches and Mallory Square are also within 1 mi (2 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 178 out of 197 reviews
Rating 8 - Good. 16 out of 197 reviews
Rating 6 - Okay. 3 out of 197 reviews
Rating 4 - Poor. 0 out of 197 reviews
Rating 2 - Terrible. 0 out of 197 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Great place

Rating Details: The property manager was more than 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: Very happy with the rental
Response from VrboOwner on Oct 20, 2026
Thank you for the kind words about Southard Comfort! We hope you'll come and stay with us again soon~ The Team @ HKWVR
From a partner site

10/10 Excellent

Southard Comfort Key West 2026

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: Fantastic home, location, and property management company! Couldn't ask for better!!!!
Response from VrboOwner on Sep 30, 2026
Why thank you kindly for the lovely review! We hope you'll choose to stay with us again, and soon! ~ The Team @ HKWVR
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property!! We were able to check in early and depart late to accommodate our flight! House and pool were beyond clean. Location was perfect. We could not ask for more!!!!!!! I lived in Key West for years and would send everyone I know to the Southern Comfort!!!
Stayed 5 nights in Aug 2026
Response from VrboOwner on Sep 12, 2026
What a nice review of Southard Comfort ~ we appreciate your taking the time to do so. ~ The Team @ Historic Key West Vacation Rentals
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
A Pleasant Stay in Key West!We enjoyed our time at this property during our visit to Key West. The property has a lot of charm, and the location was wonderful for enjoying everything Old Town has to offer.There were a few issues we encountered during our stay that we hadn’t anticipated based on the listing. However, we especially appreciated how kind, gracious, and responsive the property manager was whenever we reached out. She was genuinely lovely to work with and made us feel that our concerns were heard and taken seriously.While there are a few things that could be improved to make the overall experience even better, we appreciated the hospitality and the opportunity to enjoy this charming property. We would certainly consider staying with this management company again on a future visit to Key West.
Stayed 8 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was perfect and just as described. We will look forward to staying here again in the future!
Stayed 7 nights in Jun 2026
Response from VrboOwner on Jul 19, 2026
Thank you for choosing Southard Comfort and we are already looking forward to your next stay! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great property in a great location. We were able to easily bike to all of Old Town but didn't have any noise from traffic, etc. The pool was great to relax in and perfectly shaded. Will definitely try to stay here again next time I'm in Keys West.
Stayed 4 nights in Jun 2026
Response from VrboOwner on Aug 9, 2026
Thank you for taking the time to review us ~ and so nicely! We hope we'll see you at Southard Comfort again in the future! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was excellent!
Stayed 4 nights in Feb 2026
Response from VrboOwner on Mar 9, 2026
That is so nice to hear! We hope you'll come and stay with us again! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House and pool were perfect!!!!! Exactly what we needed
Stayed 8 nights in Feb 2026
From a partner site

10/10 Excellent

Couples Getaway

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 had a great stay at Southard Comfort. It was a perfect location, We walked everywhere. The pool was so refreshing after a day of fishing for our men and shopping for our women. The kitchen and dining room were ideal for our cooking and dining experience. We highly recommend this rental for all future couple getaways.
Response from VrboOwner on Jun 13, 2026
Thank you for the nice review of Southard Comfort! We hope you'll bring everyone back to stay with us again! ~ The Team @ HKWVR
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our trip wouldn’t have been the same if not for this lovely home we got to use as our hub. We loved the walkability, of course, but the layout, charm, and perks of this house really made this a great vacation.
Stayed 3 nights in Dec 2025
Response from VrboOwner on Jan 10, 2026
Thank you for the kind review of Southard Comfort! We're thrilled you enjoyed your time ~ we hope you'll come back again, soon! ~ The Team @ Historic Key West Vacation Rentals
From a partner site

10/10 Excellent

Total Comfort and Relaxation

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: Southard Comfort offers all the best things that KW has to offer and then some. Location is absolutely perfect, just slightly removed from the bustle of Duval St but close enough to walk everywhere. The pool was the absolute best thing to come home to to relax at the end of the day. The home felt like home and was setup up perfectly.
Response from VrboOwner on Jun 13, 2026
Thank you for the kind and lovely review of Southard Comfort! We hope you'll come and spend some more time in your Key West vacation home, especially in the pool. ~ The Team @ HKWVR
Verified review

10/10 Excellent

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

Great location

Wonderful house to stay in. Very good location to all things in Key West. Definitely would stay again.
Stayed 6 nights in Jun 2023
Response from VrboOwner on Jun 23, 2023
Thank you so much for the kind words about Southard Comfort. We hope you're already making plans to come and see us again, and soon! ~ Jennifer @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

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

Family vacation

We had a very enjoyable stay. The pool was very nice to cool off in at the end of the day. Beautiful home!
Stayed 5 nights in May 2025
Response from VrboOwner on Jun 4, 2025
Thank you for taking the time to give us such a nice review! We hope we'll see you again in the near future! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

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

The house was perfect! Clean, Great location with great features!

Amazing stay! From the warm greeting of the agents who helped us check in to the pool and maint staff who kept pool clean and plants looking great!
Stayed 6 nights in May 2022
Response from VrboOwner on Jun 5, 2022
You make Southard Comfort sound amazing ~ which it is! So glad you enjoyed your time with us and can't wait to see you again. ~ Jennifer & Team Historic Key West Vacation Rentals
Verified review

10/10 Excellent

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

Wonderful stay

We enjoyed our stay and loved the hospitality feel we got from Historic Keys. Next time we come, we will book directly through them.
Stayed 4 nights in Dec 2022
Response from VrboOwner on Dec 12, 2022
Michelle, thank you for the nice review. The rental is in a great location as well as having parking and the provate pool! We hope to see you again so you can enjoy more of Key West and all it has to offer! Cindy & the HKWVR team
Verified review

10/10 Excellent

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

Beautiful place

We had a wonderful time the house was close to all walked to most places it was very clean and was well equipped with everything we need since we stayed thanksgiving week and cooked definitely would recommend!!
Stayed 5 nights in Nov 2023
Response from VrboOwner on Dec 6, 2023
Thank you so much for the kind words about Southard Comfort! We are so happy to hear that you enjoyed your time here and hope you'll make it a plan to come for all the holidays. ~ Jennifer & Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

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

Our stay was as sweet as Key Lime Pie!

Thank you for an amazing stay. We came to Key West to celebrate 25+ years of military
Stayed 4 nights in Dec 2020
Response from VrboOwner on Dec 20, 2020
Shari, Thank you for your review of Southard Comfort. Thank you for your service to our country as well! We are so happy you had a good time and hope you will visit again soon. Stay well! Cindy & the HKWVR team
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome property! Exactly what we expected as per the ad. Had an amazing time. Would definitely stay here again and everyone in our party (6 adults) would highly recommend!
Stayed 4 nights in Aug 2025
Response from VrboOwner on Sep 4, 2025
We hope you're all making your way back to Key West to stay with us again at Southard Comfort! ~ The Team @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

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

Perfect house for our needs

Perfect home for a quick getaway.
Stayed 4 nights in Oct 2023
Response from VrboOwner on Oct 28, 2023
We are so happy you enjoyed your time at Southard Comfort! We hope you'll come and stay with us again ~ quick or longer. ~ Jennifer @ Historic Key West Vacation Rentals
Verified review

10/10 Excellent

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

Great Property

Clean, well maintained, nice pool
Stayed 2 nights in Mar 2023
Response from VrboOwner on Mar 16, 2023
Thank you for the kind words about Southard Comfort! We hope you'll come and see us again, and soon! ~ Jennifer & the Historic Key West Vacation Rentals team
Verified review

8/10 Good

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

Wonderful stay at Southard Comfort

We had a party of six stay the week of Thanksgiving and we loved staying at Southard Comfort. It was very spacious and comfortable. The small personal pool was very nice. Would definitely stay here again.
Stayed 4 nights in Nov 2021
Response from VrboOwner on Nov 29, 2021
We are so happy you had a good time for Thanksgiving and hope you're already making plans to come and see us again ~ maybe for another holiday? :) ~ Jennifer & Team Historic Key West Vacation Rentals
Verified review

10/10 Excellent

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

Great Hideaway but Close Enough to Fun

Our family loved this property. Perfect size and location for family of 4 with teens (boy and girl). Property management was great (Historic Key West Rentals) and local concierge (Dwell) was super helpful.
Stayed 5 nights in Jul 2022
Response from VrboOwner on Aug 11, 2022
We are so happy you and the family enjoyed your time at Southard Comfort ~ and to hear that we were helpful! :) Come and see us again, and soon! You have a family vacation home here with us! ~ Jennifer & Team Historic Key West Vacation Rentals
From a partner site

10/10 Excellent

A great place for a family to gather,

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: Our family came to Key West to celebrate a birthday. It was the perfect spot and the perfect house. Plenty of space in the home to be together but not crammed in. Key West offered something for everyone to enjoy as well. We would definitely visit here and stay in this home again.
Response from VrboOwner on Jan 20, 2026
Thank you, Nancy, for taking the time to review your stay at Southard Comfort! We are so happy that you enjoyed the home and location. We can't wait to welcome you back to Key West again! The Team at HKWVR
Verified review

10/10 Excellent

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

Everything was perfect - great location, the cocktail pool was very refreshing in the afternoon.

The house was very charming and perfectly decorated with Key West charm. House was clean and kitchen was well stocked. Beds were comfortable. Would definitely recommend this property.
Stayed 6 nights in Oct 2021
Response from VrboOwner on Oct 17, 2021
Kathy, thank you so much for reviewing Southard Comfort. We are happy you were pleased with everything. It is in a great location and the pool and parking are a great addition to it. Please come back and visit this Key West again. Always fun to be had! Cindy & the HKWVR team
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My family and I came to Key Eest for my mom’s 60th birthday. We had 6 guests and felt the house had plenty of space but was still cozy. Felt like we were at home, not like we were staying in a stuffy rental. The decor is really neat. The neighborhood was great, so close to anything we needed but far enough away from too much noise. Pool area was great. Heated to the perfect temperature, clean, and private. There was enough parking for a car and golf cart which was a pleasant surprise. Highly recommend!
Stayed 4 nights in Dec 2025
Response from VrboOwner on Dec 27, 2025
Glad to hear you enjoyed your time at Southard Comfort ~ we hope you'll come and stay with us again, and soon! ~ The Team @ Historic Key West Vacation Rentals
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