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Situated near the sea, this vacation home accommodates 20 guests across 11 bedrooms and 4 bathrooms. It features 1 outdoor pool, 1 hot tub, 5 bicycles, and 4 separate living rooms. Enjoy adventure activities like sailing and tubing, while nearby attractions include We Cycle Key West and Duval Street.
Highlights
Dive under the open sky
Relax and unwind in the top-rated outdoor pool, offering a refreshing retreat under the sun.
Beach equipment
A rare find — beach equipment ready to go for your days by the sea.
Centrally-located
You're never far from where you need to be with this convenient location.
Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests
This private four (4) house compound accommodates (20) guests and is has a private 10′ x 25′ heated pool including a 5’ x 10’ heated Jacuzzi. In addition, there is a private 8′ x 10′ heated Jacuzzi, Starlink high speed wi-fi network, and CCTV in the common elements (garden (2), pools (2), and property perimeters (3). There are brick walkways, and a 10′ x 40′ sun deck, including a stainless steel propane barbecue, chaise lounges for sunbathing and relaxing; and tables and chairs for dining. The design of the property lends itself perfectly for large gatherings with friends and family. This is a very unique Key West property for guests looking for a private,, authentic Key West experience.
1. MAIN HOUSE
Overview The Main House is a two (2) story 100+ year old, recently completely renovated “Conch” house. The house has an open downstairs floor plan, and four (4) private bedrooms upstairs. There is a downstairs wraparound porch, and a complimenting upstairs wrap around balcony, both of which overlook the pool, sundeck and Thomas Street. All window, door and floor trim is turn of the century style, and all windows are 6 / 6 double-hung sash.
The house has a Starlink high speed wi-fi network, streaming internet TV, and four (4) SMART HDTVs ((2) 40" Samsung SMART HDTVs, (1) 40" Sony SMART HDTV, and (1) 32" Samsung SMART HDTV). The house has five (5) tons of central air conditioning, and six (6) 52″ Hunter ceiling fans; there is a full size Whirlpool washer and dryer located at the rear of the house. There is a propane barbecue located on the pool deck.
The house can comfortably accommodate a maximum of eight (8) guests.
All linens and towels are furnished.
There are two (2) off-street parking spaces on the property.
First Floor The kitchen, dining room, living room are located on the first floor. Located off the living room is a half bathroom, which has a pedestal sink. The downstairs floor is a Golden Oak Pergo, and the downstairs ceiling is 9’ high.
Kitchen The contemporary galley kitchen is new with maple cabinets, Corian countertops, and a double compartment, integrated Corian sink. Kitchen equipment includes a GE range, GE microwave, GE dishwasher, garbage disposal, Samsung side-by-side refrigerator with icemaker and serve through ice and water dispenser, coffee maker, toaster, dishes, flatware, glasses (service for 8), pots, pans, and all basic cooking utensils. There is a set of two (2) French doors providing access from the kitchen to side porch, pool, and sundeck.
Dining Room The dining room has a wood Parson's dining room table with seating for eight (8). There is a ceiling fan in the dining room.
Living Room The living room has a sectional sofa with a queen sleeper and a lounge seat, a reading chair, an entertainment center, and a 40" Samsung SMART HDTV. The living room has recessed lighting, and a 52" Hunter ceiling fan.
Second Floor The second floor has four (4) private bedrooms – (2) queen beds and two (2) full beds. Each bedroom has a ceiling fan, and there is a 40" Samsung SMART HDTV in one bedroom, a 40" Sony SMART HDTV in another bedroom, and a 32" Samsung SMART HDTV in another bedroom. One bedroom provides access to the 275 square foot wrap around balcony, which overlooks the pool and sundeck, and Thomas Street. The second floor is carpeted, and there is a new full bathroom located on the second floor.
2. TURTLE HOUSE
Overview The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as having “an open, crisp, private space”. The house has two (2) gabled ceilings, which creates a contemporary, spacious living environment. The downstairs floor is Golden Oak Pergo. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double-hung sash. All linens and towels are furnished.
The house has a Starlink highspeed Wi-Fi network, a 43" Samsung SMART HDTV, and two (2) 26" Samsung 26″ SMART HDTVs. The house has central air conditioning, a ceiling fan, and access to a stacked washer and dryer. There is a stainless steel propane barbecue located on the pool deck.
The house can comfortably accommodate a maximum of five (5) guests – who are comfortable sharing an open living environment.
First Floor The kitchen, dining, living, and bathroom are located on the first floor. An architectural beam containing halogen lighting extends the entire length of the house. The bathroom, located off the living room, is completely new and has recessed LED lighting, a full shower, and sink. There are two (2) sets of French doors providing access to the rear courtyard where the 8’x10′ heated Jacuzzi is located.
Kitchen The contemporary galley kitchen is new with maple cabinets, black Zimbabwe granite countertops, stainless steel single compartment sink, and the ceiling has recessed LED lighting. Kitchen equipment includes an under the counter GE refrigerator, an under the counter Sub-Zero freezer with icemaker, a stainless steel electric range, garbage disposal, Quasar microwave, and Braun coffee maker, Krupps toaster, dishes, flatware, glasses (service for 6), pots, pans, and basic cooking utensils.
Dining Room The dining room has a wood Parson's dining room table with seating for six (6), and a maple with black Zimbabwe granite service credenza – complete with wine rack.
Living Room The living room has one (1) queen sleeper sofa, a queen bed, a relaxing chair, a 43" Samsung SMART HDTV, and an Onkyo receiver.
Master Loft Sleeping Area A staircase is used to access the master loft sleeping area. The loft has a queen size bed and a 26" Samsung SMART HDTV.
Guest Loft Sleeping Area A staircase is used to access the guest loft sleeping area. The loft has a full size bed and a 26" Samsung SMART HDTV.
3. CIGAR HOUSE
Overview The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, spacious, secluded and private. The cottage has a raised vaulted wood ceiling, creating a rustic, Caribbean ambiance. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double-hung sash. All linens and towels are furnished.
The house has a Starlink high speed wi-fi network, a 32" Sony SMART HDTV, and a 26" Sony SMART HDTV. The house has central air conditioning, a ceiling fan, and a stacked LP washer and dryer. There is a stainless steel propane barbecue located on the pool deck.
The cottage can comfortably accommodate a maximum of four (4) guests – who are comfortable sharing an open social living environment.
First Floor The kitchen, living, dining, sitting, and bathroom are located on the first floor. The living room has a queen sleeper sofa/daybed, a 32" Sony SMART HDTV. The bathroom, located off the living room, has been recently completely renovated and has a vaulted ceiling and full sized marble walk-in shower.
Kitchen The kitchen is new and contemporary with mahogany cabinets, white Corian countertops, and integrated Corian sink, and serve thru access to the dining room. The ceiling is vaulted with architectural beams and LED lighting. The kitchen has a pantry, refrigerator, electric range, garbage disposal, microwave, and Braun coffee maker, Krupps toaster, dishes, flatware, glasses (service for 6), pots, pans, and all the basic cooking utensils. There is a French door providing access to the rear deck where the washer and dryer are located.
Loft Sleeping Area A ladder is used to access the loft sleeping area. The loft has a full size bed, and a 26" Sony SMART HDTV.
4. CONCH HOUSE
Overview The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded and private. The raised vaulted ceiling creates an open living environment. The downstairs floor is the original Dade County Pine. All window, door, and floor trim is turn of the century style, and all windows are 6/6 double hung sash. All linens and towels are furnished.
The house has a secured Starlink wi-fi network, a 32" Sony SMART HDTV, and a 26" Samsung SMART HDTV. The house has central air conditioning, a ceiling fan, and a stacked LP washer and dryer. There is a stainless steel propane barbecue located on the pool deck.
The house can comfortably accommodate a maximum of five (5) guests – who are comfortable sharing an open sociable living environment.
First Floor The kitchen, living/dining room, a small bedroom, and a full bathroom. There is a queen sleeper sofa/day bed and a 32" Sony SMART HDTV in the living room. There is a full bed in the small bedroom located between the kitchen and the living room. The bathroom, located off the small bedroom, has been recently completely renovated – it has a vaulted ceiling, recessed lighting, oak cabinets, and black granite vanity top.
Kitchen The kitchen has serve thru access to the dining/living room. The kitchen ceiling is vaulted with recessed LED lighting. There is a stainless steel gas range, a stainless steel refrigerator, microwave, Braun coffee maker, garbage disposal, Krupps toaster, pots & pans, all basic cooking utensils; and dishes, flatware, glasses (service for 6). There are (2) French doors providing access to the rear deck where the washer and dryer are located.
Loft Sleeping Area A ship's ladder is used to access the loft sleeping area. The loft has a full size bed, and a Samsung 26″ HDTV.
CHICKENS & ROOSTERS The City of Key West protects chickens and roosters, and considers them as part of the history and charm of Key West. As a result, Key West and many of the islands throughout the Florida Keys have free-range chickens and roosters. You will definitely see and hear chickens and roosters during your stay in Key West. Some visitors to Key West love them, and some visitors hate them - personally, I enjoy them best roasted, with plantains, and black beans and rice!
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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 by the sea, this holiday home is in Old Town Key West, a neighbourhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Florida Keys National Marine Sanctuary - 6 min walk - 0.6 km
Ernest Hemingway Home and Museum - 6 min walk - 0.6 km
Key West Lighthouse and Keeper's Quarters Museum - 6 min walk - 0.6 km
Fort Zachary Taylor Historic State Park - 9 min walk - 0.8 km
Getting around
Key West, FL (EYW-Key West Intl.) - 14 min drive
Restaurants
Green Parrot Bar - 3 min walk
Blue Heaven - 5 min walk
Moondog Cafe & Bakery - 5 min walk
801 Bourbon Bar - 5 min walk
Mangoes Restaurant - 3 min walk
Frequently asked questions
Does Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests?
As of 1 Sept, 2026, prices found for a 1-night stay for 2 adults at Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests on 14 Dec, 2026 start from S$31,769, 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 Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests pet-friendly?
No, pets are not allowed at this property.
How much is parking at Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests?
On-site parking is available at the property.
What time is check-in at Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests?
Check-in begins at 4:00 PM.
What time is check-out at Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests?
Checkout is at 10:00 AM.
Where is Historic Old Town Key West Rental Compound - 11 Beds, 4 Sleeper Sofas, 20 Guests located?
Located in Old Town Key West, this holiday home is within a 5-minute walk of We Cycle Key West and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 10 minutes.
About the host
Hosted by Steven Justi
I travel as often as possible, with my beautiful partner - we always seem to gravitate to water and interesting places off the beaten path. We enjoy historic settings, renovating old buildings, good people, and a nice bottle of wine (...or two).
Why they chose this property
The neighborhood is alive, dynamic, and surrounded by Key West History - unquestionably the most intact Old Town Key West neighborhood on the island. There are excellent restaurants within walking distance, and Duval Street is only two blocks from the property - close enough, yet far enough away! Ft. Zachary Taylor, located only two blocks to the west of the property, is a National Historic Park and boasts the nicest beach with the best sunsets on the island.
What makes this property unique
Local Key West character is preserved. Authentic Key West experience. Perfect when accommodating large family reunions, weddings, corporate retreat, or just a large group of friends getting together. Four (4) individual, independent houses on a single Old Town Key West property; (11) full and queen beds and (4) sleeper sofas.