Located in Key West, this holiday home is in the city centre. 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. The Kite House and Key West Butterfly and Nature Conservatory are also worth visiting. Looking to get your feet wet? Jet skiing, scuba diving and snorkelling adventures can be found near the property.
Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
South Beach - 9 min walk - 0.8 km
Key West Butterfly and Nature Conservatory - 9 min walk - 0.8 km
Southernmost Point - 11 min walk - 1.0 km
Getting around
Key West, FL (EYW-Key West Intl.) - 11 min drive
Restaurants
Dions Truman & White - 8 min walk
Ocean Grill & Bar - 7 min walk
Viva Argentinian Steakhouse - 7 min walk
Better Than Sex - 5 min walk
Sushi Song - 6 min walk
About this property
Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval
Welcome to 921 Windsor Lane, a newly built coastal-modern retreat in the heart of Old Town Key West. Located just half a block from Truman Avenue and about an 8-minute walk to Duval Street, this stand-alone home offers the perfect blend of comfort, style, privacy, and walkable island living. Designed for families, couples, and friends traveling together, the home sleeps up to 8 guests and has a layout that feels both open and inviting. Upstairs, you’ll find two large king bedrooms, each with its own private en-suite bathroom. Downstairs, the home offers additional sleeping space with two queen foam-mattress sleeper sofas, making it easy to accommodate extra guests comfortably. The main living area was designed for gathering and relaxing. A spacious open kitchen flows into the Florida Room/family room and dining area, while a separate living room offers even more space to spread out. The kitchen is fully equipped with a full-size refrigerator, 36-inch stove with oven, drawer microwave, ice maker, wine cooler, large island with seating for 4, and a double farmhouse-style sink. A dedicated coffee and tea station makes mornings easy before heading out to explore Key West. Upstairs, the home continues to impress with a convenient wet bar with sink & small fridge and washer and dryer. The primary suite features a king bed, walk-in closet, a spacious en-suite bathroom with walk-in shower, soaking tub, and a his & hers vanity, plus a private balcony overlooking the pool. The guest suite also has a king bed and a private en-suite bath with a walk-in shower and single vanity. Outside, the private backyard is built for lounging and enjoying the island atmosphere. The heated and chilled pool can be enjoyed year-round, and the pool deck includes two chaise lounges, additional easy seating, and side tables for laid-back afternoons and evenings at home. Rear doors from the house open directly to the pool area, creating an easy indoor-outdoor flow. One of the rare advantages of this Old Town location is the private gated parking. The property includes space for 1 car and 1 golf cart, an automatic sliding entry gate, an EV charging station, and a separate golf cart charging stationfor guests who choose to explore the island that way. The home also includes high-speed Wi-Fi, smart TVs with streaming capability in the bedrooms, family room, and pool area, plus beach gear for guest use including 4 beach chairs, 2 umbrellas, beach towels, and a small cooler. Whether you’re spending your days walking Old Town, dining on Duval, relaxing by the pool, or heading to the beach, 921 Windsor Lane is designed to make your Key West stay feel easy, stylish, and memorable.
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children
Children allowed: ages 0–17
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Events
No events allowed
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Pets
No pets allowed, service animals permitted
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Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Load the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
Secure/Close the gate upon leaving the property.
SURVEILLANCE ON PROPERTY!! For added security the front entry, side entry and back area of the house are equipped with surveillance.
Failure to complete these may result in a negative review from the host.
-Families/Responsible groups only
-No bachelor or bachelorette parties
-No Student Groups
-No Construction Workers
-Early Check-In and Late Check-Out, NOT guaranteed
-Quiet hours are usually 10PM to 8AM
-No illegal activities
-No unregistered overnight guests
Important information
You need to know
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
This property uses eco-friendly cleaning products
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, a first aid kit 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
Frequently asked questions
Does Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval?
As of 16 April 2026, prices found for a 1-night stay for 2 adults at Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval on 31 January 2027 start from NZ$2,709, 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 Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval pet-friendly?
No, only service animals are welcome at the property.
How much is parking at Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval?
On-site parking is available at the property.
What time is check-in at Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval?
Check-in begins at 4:00 PM.
What time is check-out at Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval?
Checkout is at 11:00 AM.
Where is Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval located?
Located in Old Town Key West, this holiday home is within a 10-minute walk of Saint Mary Star of the Sea, Duval Street and Ernest Hemingway Home and Museum. Florida Keys Beaches and South Beach are also within 15 minutes.
Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval Reviews
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