Close to Ernest Hemingway Home and Museum and Duval Street, Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval provides amenities such as laundry facilities. Stay connected with free in-room WiFi.
Entire home
2 bedrooms3 bathrooms186 sq m
Popular amenities
Pool
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
Add dates for prices
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.
Property amenities
Beach
Beach loungers
Beach towels
Pool/Spa
Heated pool
Outdoor pool
Private pool
Internet
Available in the house: Free WiFi
Parking and transport
Electric car charging station on site
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Ice maker
Kitchen island
Kitchenette
Lobster/crab pot
Microwave
Oven
Paper towels
Refrigerator
Toaster
Dining
Dining table
Bedrooms
2 bedrooms
Bedsheets provided
Bathroom
2.5 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Living room
Separate dining area
Entertainment
Smart TV
Outdoor areas
Balcony
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Service animals only (pets not allowed)
Suitability/Accessibility
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
7 steps to reach entrance
Area rugs in public areas
Gravel flooring in public areas
Handrails in stairways (76 centimetre high)
Tile flooring in public areas
Upper floors accessible by stairs only
Smoke-free property
Services and conveniences
Housekeeping on request
Iron/ironing board
Safe
Location highlights
In the city centre
Near a health/beauty spa
Near a hospital
Near the marina
Things to do
Heated pool
Cycling nearby
Golfing nearby
Jet skiing nearby
Motor boating nearby
Parasailing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Swimming nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Check-out instructions
The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Return all furniture to original locations.
Put all beach towels if used in Master Bathroom.
Remove all food from kitchen and refrigerator.
Empty all trash into outside trash bin
Put all remotes, speakers, and house items back to their original locations.
Set the thermostats to 78 degrees.
Leave beach cooler, empty, dry and open if used,
Turn off all lights, TVs, close windows
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.
Rules
-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 10PM to 8AM
-No illegal activities
-No unregistered overnight guests
Pets
Pets not allowed (service animals are welcome, and are exempt from fees)
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
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
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
This property does not have any lifts
About the area
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. Discover the area's water adventures with jet skiing, scuba diving and snorkelling nearby, or enjoy the great outdoors with cycling. Visit our Key West travel guide
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.
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.
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Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval Reviews