Entire home

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

Choose dates to view prices

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.
Property video
A modern kitchen with a central island, stainless steel appliances, and a decorative backsplash.
A swimming pool with lounge chairs and a TV screen, surrounded by a house with a balcony.
A spacious living room with a flat-screen TV, comfortable seating, a ceiling fan, and large windows offering a view of the outdoors.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms3 bathrooms186 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

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

Room options

Similar properties

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.
During your stay at this vacation home, you're just a quick walk from Duval Street. Features include an outdoor pool and laundry facilities. Free WiFi and a private pool are available in the vacation home.
  • Air-conditioned home with private pool, kitchen, and washing machine
  • Free WiFi (speed: 500+ Mbps (good for 6+ people or 10+ devices))
  • Take a swim in the outdoor pool
  • Amenities include laundry facilities, a car charging station, and a living plant wall
  • Within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum
As a guest of this vacation home, you'll find an outdoor pool, laundry facilities, and a living plant wall. The front desk is open around the clock.

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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Double-glazed windows
  • Eco-friendly cleaning products used
  • Electric car charging station
  • Housekeeping (on request)
  • Living plant wall
  • Local artist showcase
  • Recycling
  • Reusable coffee/tea filters
  • Reusable cups
  • Reusable tableware
  • Some LED lighting used
  • Unit size: 2,000 square feet
  • Water-efficient showers
  • Water-efficient toilets

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

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 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 trash
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

  • No pets allowed, but service animals are welcome

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

873534

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

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Chasen G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place was great. Location was perfect without being too close to Duval. Beautiful, new property with a high quality finishout. Very close to CVS, groceries, and all the good stuff.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Joseph X.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Key West Stay!Beautiful, immaculate home in an amazing location near Duval Street and the Southernmost Point! Very close to all the fun and good restaurants!The house was spotless, beautifully decorated, and had the perfect Key West vibe. We loved the private pool and outdoor space, and having private on-site parking with room for a large truck or potentially two cars was a huge plus. The complimentary concierge service was another fantastic touch that made our stay even more enjoyable. Highly recommended—we would absolutely stay here again!
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Beth W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home and the staff we absolutely amazing. When we asked for things or extras the staff were like ninjas and appeared out of thin air to accommodate our every needs. We very much enjoyed our girls trip and we all plan to book again! Thank you so much for the wonderful stay in the keys!
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

John W.

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 5 nights in Jul 2026