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1000 sq. ft. Welcome to Key West Getaway in Old Town!
In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying here is what an elegant, tropical condo stay in downtown Key West is all about.
This three-story Southard Square condo has been recently renovated and offers a great layout to enjoy your monthly stay. Enter the ground level just steps away from your dedicated off-street parking spot to a den with a convenient workstation and television. The couch in the den pulls out to a queen sleeper. Level one also includes the master bedroom featuring a king bed, ceiling fan, and a newly renovated bathroom with a walk-in shower. A full-size washer and dryer are also included on this level for your convenience.
The main living area is located on the second floor, including a well-equipped kitchen that is the perfect setting for preparing meals and easy clean up with the dishwasher and disposal. This level also includes the main dining & living area with vaulted ceilings and a full bath.
Glass slider doors off the living area opens to a balcony offering a relaxing spot to enjoy morning coffee as the sun comes up over Old Town Key West.
The stairway from the second level leads to a third-floor open loft bedroom. This is where you will find the queen bed, armoire, and skylights on either side of the ceiling providing good daytime light and a ceiling fan.
Unique Benefits
Location, location, location. This is truly in the heart of Key West where you can walk to Duval Street, Ernest Hemingway House, the waterfront, Sunset at Mallory Square, the Southernmost Point and dozens of great restaurants. Also, this is one of the largest pools in Old Town Key West. They just don't make pools this big anymore in Old Town.
Southard Square Condominium in Old Town Key West! Close to everything: restaurants, bars, water sport activities, galleries, and world-famous Duval Street. Five Brothers Coffee Shop, a local and visitors' favorite is on the same block. That's where you will get your morning cafe con leche. World-famous Duval Street is just a stroll or bike ride away.
This lovely townhome community is nestled in the heart of Old Town Key West and a short stroll to Duval Street and the Historic Seaport. And Mangia Mangia on the same block to the west. That's where you'll find great Italian dinners.
The unit itself sits near the far end of Griffin Lane on the east side of building. Other houses on the lane are historic Conch houses.
When you arrive, park your car in your dedicated parking space located right in front of the unit entrance.
Mangia Mangia, Sarabeths, Two Friends (for breakfast), Garbo's Grill, Louie's Backyard and Cafe Sole.
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Jun 01 - Jun 30 2026 | $9,000 | 28 nights | |||
Jul 01 - Jul 31 2026 | $9,000 | 28 nights | |||
Sep 01 - Sep 30 2026 | $9,000 | 30 nights | |||
Oct 01 - Oct 31 2026 | $9,000 | 30 nights |
Fees:
Last updated on November 29, 2025
RobertOld Town Getaway
Excellent property; highly recommended. Holly is an amazing host: very responsive and accommodating. She provided detailed check in/out instructions, descriptions of the property amenities, and a tour guide for the area. When we arrived the coffee maker was on the fritz so she had it replaced immediately. The property is clean, comfortable, and a short walk to just about anything on the island. We very much enjoyed our stay and look forward to returning in the future; thank you Holly!
Stayed: April 2024 Submitted: May 09, 2024
Eric T.Fantastic location and unit!
We stayed at Holly's Key West Getaway from October 2022 through May 2023, and it was absolutely fantastic. The unit is in a complex perfectly located in Key West, within blocks of great restaurants, attractions, and Key West sights & sounds.The unit itself is spacious and well-designed, with three floors offering plenty of room to spread out. The lower level had a comfortable primary bedroom, full (recently renovated) bathroom, and office/sitting area. The second floor featured a generous living room, a full bath, and a functional kitchen. The third floor has another full bedroom, perfect for guests.The complex was always well-maintained, and the shared swimming pool was a huge bonus. Overall, our stay was a great experience, and we would highly recommend it to anyone looking for a comfortable, convenient place to stay in Key West.Also: Holly (the landlord) is amazing!!
Stayed: October 2022 Submitted: February 21, 2024
Host response
"Thank you Eric for the review! You are always welcome back anytime!"
Bill H.Key West Getaway
Our stay at Holly's condo was fantastic. The unit is well kept, clean and nicely furnished. It has two full bathrooms with an nicely updated shower. The unit is in the best complex in Old Town.....well kept grounds with a wonderful pool area. Holly was easy to communicate with and very responsive. We look forward to our next trip.
Stayed: October 2023 Submitted: January 27, 2024
Host response
"Thank you Bill for the review. We loved having you stay and hope to see you again next year."
Lynn G.Fabulous Condo!
We rented this condo for four months. It is super clean and very comfortable. The pool is awesome. Having a parking space four steps from your door is unheard of in KW. The location couldn’t be better. Right in the middle of Old Town. Lots of restaurants, shops, and attractions are within a short walking distance. The owner is very responsive and takes excellent care of the property.
Stayed: January 2024 Submitted: January 27, 2024
Host response
"Thank you Lynn for the wonderful review. Looking forward to seeing you next year!"
Yes, the townhouse has one dedicated space right in front of the unit.
Yes, pets under 50 lbs are allowed upon approval by the owner and with a small pet fee.
Member since 2023
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