Entire home

Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval

Photo gallery for Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval

A poolside area with wicker furniture, a blue umbrella, and potted plants. - Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval (Key West)
Property video
A dining area with a table set for four, surrounded by wicker chairs, a white sofa, and a large window with a view of greenery. - Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval (Key West)
A modern kitchen with a central island, stainless steel appliances, and a decorative backsplash. - Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval (Key West)
A spacious living room with a flat-screen TV, comfortable seating, a ceiling fan, and large windows offering a view of the outdoors. - Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval (Key West)
Close to Duval Street and Mallory Square, Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval provides amenities like laundry facilities. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • 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.

Similar properties

About the area

Located in Key West, this vacation home is in the city center. 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 snorkeling nearby, or enjoy the great outdoors with cycling. Visit our Key West travel guide
View more Vacation homes in Key West
Map
Key West, FL

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    6 min walk - 0.6 km
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    9 min walk - 0.8 km
  • A wooden sign with information about South Beach, Key West, Florida, including public beach status, restaurant hours, and beach chair rental.
    South Beach
    11 min walk - 0.9 km
  • A building with a sign reading "The Key West Butterfly & Nature Conservatory".
    Key West Butterfly and Nature Conservatory
    11 min walk - 0.9 km
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    12 min walk - 1.1 km

Getting around

  • Key West Intl. Airport (EYW)
    11 min drive

Restaurants

  • Circle K
    7 min walk
  • Sandy's Café
    8 min walk
  • Old Town Tavern
    7 min walk
  • El Siboney Restaurant
    5 min walk
  • Better Than Sex
    5 min walk

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.

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?

Onsite 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?

Check-out 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 vacation 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.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval Reviews

10

Exceptional

9.8

Cleanliness

9.6

Location
Rating 10 - Excellent. 8 out of 8 reviews
Rating 8 - Good. 0 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

Reviews

Verified review

10/10 Excellent

Stayed 2 nights in Oct 2026