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

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Exterior
Pool
Dining
Room
Living area
2 bedrooms2+ bathroomsSleeps 8185.8 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
NZ$2,709
avg per night

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Place, Southernmost Point
    ‪11 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Rooms & beds

2 bedrooms (sleeps 8)

Bedroom 1- Master Bedroom

1 King Bed

Bedroom 2- Guest Bedroom

1 King Bed

Living Room 1

1 Queen Sofa Bed

Living Room 2

1 Queen Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1 - Master Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2- Guest Bathroom

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3 - Half bathroom

Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Number of living rooms
Garden
Dining area
The current price is NZ$2,709
avg per night

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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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