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.
Property video
A spacious living room with a flat-screen TV, comfortable seating, a ceiling fan, and large windows offering a view of the outdoors.
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.
A swimming pool with lounge chairs and a TV screen, surrounded by a house with a balcony.

Reviews

10 out of 10
Exceptional

Highlights

  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Discover nearby landmarks
    Walk to Duval Street

Popular amenities

  • Balcony
  • Private pool
  • Kitchenette
  • Air-conditioning
  • Electric vehicle charging point
  • Refrigerator

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, South Beach
    ‪11 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 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
Kitchenette
Balcony
Separate dining area
Number of living rooms
Dining area

Add dates for prices

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About the area

Key West

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.
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Map
Key West, FL

What's nearby

  • Duval Street - 6 min walk - 0.6 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • South Beach - 11 min walk - 0.9 km
  • Key West Butterfly and Nature Conservatory - 11 min walk - 0.9 km
  • Southernmost Point - 12 min walk - 1.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 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.

How much does it cost to stay at Luxury Windsor, Key West Retreat- Old Town ; Pool, Gated Parking, Walk to Duval?

As of 26 Oct 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 30 Oct 2026 start from £1,508, 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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

9.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent property - easy check in and check out; excellent communication; great location and off street parking! Would definitely stay again and highly recommend.
Stayed 4 nights in Sep 2026
Response from VrboOwner on 4 Oct 2026
Thank you for the wonderful review! It was truly a pleasure having you at The Windsor House. We’re so glad you had a great visit to Key West, and we hope we’ll have the opportunity to welcome you back again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house, loved sitting out by the pool. Easy walking to Duval Street.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

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
Response from VrboOwner on 29 Jul 2026
Thank you for your wonderful review and for making Windsor House part of your Key West getaway. We are thrilled to hear that you had a memorable stay and enjoyed your experience. Our goal is to create a refined and comfortable retreat where every detail is thoughtfully considered, allowing our guests to relax and fully enjoy all that Key West has to offer. We truly appreciate your kind words and hope to have the pleasure of hosting you again for another exceptional visit. Warm Regards, Tejas and The Windsor House Team Part of the Silver Palms Inn and Historic Homes
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and new house. Spacious and modern, the pool set up is amazing! Very nice host, and responsive to requests. We hope to return someday on a future Key West visit.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

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
Response from VrboOwner on 13 Aug 2026
Dear Beth, Thank you so much for your wonderful review! We're thrilled that you and your friends had such a memorable girls' trip and enjoyed the home and our team's hospitality. It was a pleasure hosting you, and we can't wait to welcome you all back to The Windsor House for your next Key West getaway! Krishna And The Windsor House Team Part Of Silver Palms Inn and Historic Homes.
Verified review

10/10 Excellent

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
Response from VrboOwner on 13 Aug 2026
Dear Joseph, Thank you for taking the time to share your experience and for choosing The Windsor House. We’re so pleased you had a wonderful stay and truly appreciate your kind words and recommendation. It was a pleasure hosting you, and we would love to welcome you back to Key West again soon! Warm Regards, Krishna & The Windsor House Team Part of Silver Palms Inn and Historic Homes.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 5 nights in Jul 2026
Response from VrboOwner on 6 Aug 2026
Dear John, Thank you for your 10/10 rating! We're delighted you chose The Windsor House for your stay and truly appreciate your support. It was a pleasure hosting you, and we hope to welcome you back to Key West again soon.
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