Like no other place on this remarkable island, the gated and secluded rooftop community above Duval Square is the perfect place to vacation. Quaint townhomes cluster a story above a charming bricked-in square featuring restaurants, shops, an art gallery, and more. Best of all, the enclave is adjacent to and overlooks the world-famous Duval Street. Enjoy the sights of Key West’s main artery from the spectacular rooftop pool. Maybe do a little sunning or people watch. And when you’ve had enough, enter the air-conditioned comfort and tranquility of this townhome with its generous two-level living space, private deck with a hot tub, 2 bedrooms with a balcony off the master suite, and 2.5 baths.
NOTICE: The COA that oversees this complex imposes a $50 per rental fee. This additional fee will be added to your rental agreement when booking and appears as a Reimburse Owner charge.
The townhouse door opens into a front foyer with windows on two sides inviting the sunshine in. Or pull the shades for seamless privacy. Here there’s a bench, hooks for hanging items, a bookcase, baskets, in other words plenty of surfaces for sun lotion, pool towels, your keys and a guidebook, so they’ll be handy to grab when you venture out.
Next in the floor plan is the kitchen, done in cloud white cabinets and white Whirlpool appliances against ocean blue walls and coordinating area rug below. One side of the U-shaped countertop also serves double duty as a convenient breakfast bar complete with chairs. All the kitchen amenities you’d expect are at your fingertips. This is an ideal kitchen for preparing a four-course meal or for warming leftovers from some fabulous meal you ate out the night before. A window over the double sink provides plenty of ambient light or later, as the day turns to evening, use the contemporary track lighting. Next to the kitchen is a laundry closet with washer and dryer, a catch-all closet for a broom and the like, and an ever-so-convenient guest half bath.
The home’s dining space features a crafted wooden table and chairs and a handsome and functional hutch with drawers and cabinets. The track lighting mirroring that in the kitchen carries through to the dining and living areas. The dining area features an eye-catching rope chandelier which provides illumination and an artistic focal point for the area.
To the front is the living room space outfitted with a couch that pulls out into queen bed and a matching love sea. Both invite lounging. The seating is dotted with colorful pillows that take their fabric cue from a nearby swivel chair while the ottoman that doubles as a coffee table blends with the fabric of the couches. Below is an area rug that cushions the natural tile floor beneath while a Florida ceiling fan whirrs above. Across the room is a cabinet with shelves and drawers and space for the large flat screen TV which is in perfect position for viewing from the seating area. Of course, there’s cable and wireless high-speed internet. This is the perfect space for reading, watching a movie, or enjoying family and friends.
From the living area, through glass doors is the private deck with a bubbly hot tub. Or maybe you’re in the mood for a mid-morning meal or starlight dinner in which case there’s a perfect table and four chairs out here to accommodate.
If you don’t already wish you could move in permanently, you’ll probably feel that way once you see the upstairs. A staircase leads to the second floor with its two bedrooms and two full baths. Each bedroom is professionally decorated with lamps, end tables, a TV, spacious closet space for hanging items and chest of drawers for foldable items. The first room offers a comfy queen bed and en-suite full bath. The second, the Master bedroom, offers a just-as-comfy king bed, en-suite full bath, and, through glass doors, a private fresh air balcony with four chairs. If you feel inclined to enjoy a morning latte or nightcap, this is the perfect spot.
After you’ve checked out this exceptional living space, wander down to the temperature-controlled pool reserved for the exclusive use of Duval Square townhouse residents. The pool and chaise loungers are very inviting. Sit here under the canopied roof for shade or out in the sun to work on a tan. If other bathers are enjoying the pool at the same time, you can strike up a conversation, share vacation stories, and get tips about great places to go in Key West. Although the townhome comes with covered parking for a car, you can walk or bike almost anywhere you want to go from this ideal location.
When adventure calls, wander down to the shops, boutiques, a full-service salon, and restaurants that comprise the charming Duval Square. The Square has the feel of a courtyard garden with the convenience of services and food added in. Down a few steps from here brings you to Duval Street itself, which has been officially designated a Great Street by the American Planning Association. A left turn will head you toward the shores of the Atlantic and a right turn will head you toward the Gulf.
In between are all the things that make the Conch Republic so famous: beaches, tours, museums, shopping, over two hundred restaurants, bars, and the Key West Aquarium where you can pet a shark if you dare. Or maybe you’d prefer to have butterflies land on your shoulder at the Butterfly Conservatory. Perhaps have your picture taken at the Southernmost Point buoy or pose with a parrot perched on your head. If the arts are of interest, you’ve come to the right place for music, movies, plays, art galleries, lectures, artists in residence open studios, and more.
Check your phone for sunset times so you don’t miss the world-famous celebration at Mallory Square. Be there as locals and visitors alike gather seven days a week, 365 days a year, to witness the sun sinking into the horizon. Be sure to applaud as the last round edge of fiery orange disappears. If you’re lucky, maybe you’ll see the elusive “green flash” and claim the bragging rights for years to come. Then stick around as artists and street performers entertain the enthusiastic crowd with performing cats, fire eaters, musicians, fortune tellers, and more
Find opportunities for all kinds of water sports along the Historic Seaport boardwalk. Maybe sign up for a sunset sail, a fishing charter, or try water sport opportunities like diving, parasailing, snorkeling, jet-skiing, and more. Maybe take a Conch Train or Trolly ride to preview the island. If this is your first trip to the Conch Republic, a guidebook from Books & Books on Eaton Street or a stop at the Chamber of Commerce Information Center on Greene Street will help make sure you don’t miss anything. Other info on the current music scene, movies, plays, gallery openings, and charitable events can be found at milezerokeywest.com (calendar section). Historic Hideaways' informative Area Guide/Events page located on our website also has a Calendar of Events. We DO NOT guarantee that the information VRBO (and affiliated sites) scrapes from our site to display on theirs is 100% accurate, particularly the amenities. If you come to us through them, be sure to look at all the information on our site related to your rental once you book to be sure you have accurate and up to date information.
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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 indicated that there is a carbon monoxide detector on the property
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 has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Key West
Located near the beach, this holiday home is in Old Town Key West, a neighbourhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
Ernest Hemingway Home and Museum - 3 min walk - 0.3 km
South Beach - 6 min walk - 0.6 km
Key West Butterfly and Nature Conservatory - 6 min walk - 0.6 km
Southernmost Point - 8 min walk - 0.7 km
Getting around
Key West, FL (EYW-Key West Intl.) - 9 min drive
Restaurants
Circle K - 1 min walk
Old Town Tavern - 2 min walk
Cuban Coffee Queen (Duval) - 2 min walk
Rum Bar at the Speakeasy Inn - 1 min walk
Banana Cafe - 3 min walk
Frequently asked questions
Does Duval Square - Downtown Key West! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Duval Square - Downtown Key West!?
As of 31 May, 2026, prices found for a 1-night stay for 2 adults at Duval Square - Downtown Key West! on 1 Sept, 2026 start from S$633, 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 Duval Square - Downtown Key West! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Duval Square - Downtown Key West!?
On-site parking is available at the property.
What time is check-in at Duval Square - Downtown Key West!?
Check-in begins at 4:00 PM.
What time is check-out at Duval Square - Downtown Key West!?
Checkout is at 11:00 AM.
Where is Duval Square - Downtown Key West! located?
Located in Old Town Key West, this holiday home is steps away from City Zoo Gallery and Duval Street. Florida Keys Beaches and Southernmost Point are also within 10 minutes.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Perfect place to stay. The house was clean, the pool was so nice to relax and cool off in. Good location we could walk to lots of place and Lyft was very reasonable for one we did not want to walk to.
We had a very pleasant stay at this property. Everything is as described, the decor and artwork were well done (love the artwork!) It would be helpful to know that there is a closet which provides hammock floats for pool as well as a couple coolers and chairs and even a fishing pole! I would recommend looking through the closets and drawers before buying items to see what may have been provided or left behind by other tenants. The appliances are all pretty dated, except for the washer and dryer, but they got the job done! A beautiful, well-maintained place to stay - located closer to the south end of Duval St.
This property was perfectly located, close to eveything, peaceful, and beautiful! We loved being able to relax on the patio and the rooms were lovely. We would definitely stay here again.
Jamie Z.
Stayed 5 nights in Feb 2025
Response from VrboOwner on 4 Apr, 2025
HI Jamie,
Glad you enjoyed yourself. We look forward to you visiting us soon.
We stayed here over the Thanksgiving holiday. It was a great location right on Duval but set back so it was quiet. The condo was very clean and had all of the supplies we needed. Would definitely stay again!
Margaret R.
Stayed 3 nights in Nov 2023
Response from VrboOwner on 22 Dec, 2023
Hi Margaret,
I am glad you enjoyed your Thanksgiving holiday. I see that you have already booked again with us next year. We look forward to having you back.
The place was perfect for three adults - spacious living area and primary bedroom and bath (looks just like the pics). The secondary bedroom is great for 1 adult. Terrific location surrounded by great restaurants, galleries, and bike rentals places. Would definitely stay again.
Loved it! Great proximity to everything & at the same time quiet for Duval st!
Caroline H.
Stayed 14 nights in Feb 2025
Response from VrboOwner on 10 Mar, 2025
Hi Caroline,
Glad you enjoyed your time at the property. This property is special, because it is on the quieter side of Duval, but just a quick walk away to everything. We look forward to you coming back to visit.
We stayed just a few days at this property and really enjoyed our stay. Everything was very clean. We didn't use the washer/dryer or dishwasher so I can't comment on those. The place is decorated to keep you in the vacation mood. Very easy to get to everything since it's right off Duval. Definitely would stay here again.
Danika F.
Stayed 4 nights in Apr 2023
Response from VrboOwner on 30 May, 2023
Hi Danika,
Thank you for staying with us. I am glad you enjoyed the property. Come back and see us soon.
Sabrina was very helpful getting us checked in a little bit early. Location, location, location!!! This property is right off Duval on the quiet end and close to restaurants/shops. We had a great time and will be back.
My daughter and I stayed for three nights for my 70th birthday and we loved the accommodations and decor !! My Husband and I would love to stay in the future !! 😄
Dave L.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 20 Sept, 2024
Hi Dave,
Nice to hear y'all had a wonderful time. It's a beautiful property and an amazing location. I look forward to y'all coming back to visit.
The Condo was located right in the middle of Duval Street.Very nice and quiet and within walking distance of restaurants and shopping. The kitchen was stocked with everything you would find in your own kitchen. There was lots of hot water for showers and plenty of linens.All and all a good place to stay.
Fern C.
Stayed 7 nights in Jan 2025
Response from VrboOwner on 27 Feb, 2025
Hi Fern,
Glad y'all had a great trip. It's nice to be on the quieter side of Duval. You can still walk to everything. Come back and visit us soon.
This property is beautiful and in a great location. Questions to the property manager were answered quickly. The only negative (not necessarily a negative, just a comparison to other rentals) was no welcoming basket/package. We would stay here again! A plus is parking accommodations!
Jessie Z.
Stayed 4 nights in Apr 2023
Response from VrboOwner on 11 May, 2023
Hi Jessie,
I am glad you enjoyed your stay. The property is in a great location and has an awesome porch to spend time on. The parking really helps in Old Town. Come back and stay with us anytime.
Duval Street is the place to be! The condo was nicely laid out but older, tired & overly decorated. Disappointed in size of second bedroom & shower( which leaked). Great access to pool which had covered area & lots of lounging chairs. Location allowed for easy walking to all activities. Felt a bit pricey for older accommodations.
Anne and Ralph C.
Stayed 7 nights in Mar 2025
Response from VrboOwner on 7 Apr, 2025
HI Anne and Ralph,
I am glad you enjoyed your trip and the great location of Duval Square. We will take a look at that shower. Thank you for bringing this to our attention. The great news is we will be installing hardwood floors on the stairs and upstairs bedrooms later this year. Come back and visit us again.
About the host
Hosted by Historic Hideaways
Languages:
English
Premier Host
They consistently provide great experiences for their guests