WATSON HOUSE GRAND ESTATE on Simonton St

Photo gallery for WATSON HOUSE GRAND ESTATE on Simonton St

A spacious room with a large bed, a seating area, and a television.
A modern living room with a sofa, coffee table, and chairs. There is a fireplace, a window with blinds, and artwork on the walls.
A spacious living room with a fireplace, white furniture, and a ceiling fan.
A covered outdoor area with a glass table and chairs, surrounded by white railings and lush greenery.
A two-story colonial-style building with a central entrance, a balcony on the upper floor, and a gated driveway.

Reviews

9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Duval Street

Popular amenities

  • Balcony
  • Private pool
  • Arcade/game room
  • Barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪2 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Place, South Beach
    ‪14 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 min drive‬

Rooms & beds

11 bedrooms (sleeps 22)

Bedroom 1

1 King Bed and 1 Single Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed

Bedroom 6

1 Queen Bed

Bedroom 7

1 King Bed

Bedroom 8

1 King Bed

Bedroom 9

1 King Bed

Bedroom 10

1 King Bed

Bedroom 11

2 Single Beds

11 bathrooms

Bath 1 Ensuite

Bath 2 Ensuite

Bath 3 Ensuite

Bath 4 Ensuite

Bath 5 Ensuite

Bath 6 Ensuite

Bath 7 Hall

Bath 8 Ensuite

Bath 9 Ensuite

Bath 10 Ensuite

Bath 11 Ensuite

Spaces

Deck or patio
Kitchen
Balcony
Garden

Add dates for prices

Similar properties

Welcome to TOP OF OLD TOWN...
**TOP OF OLD TOWN @ DUVAL SQUARE** Home + Last Key White Glove Service...
Uptown - Upper Duval
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (24 reviews)
**TOP OF OLD TOWN @ DUVAL SQUARE** Home + Last Key White Glove Service...

About the area

Key West

Located in Key West, this holiday home is in the city centre. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and The Kite House are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking and ecotours.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 2 min walk - 0.2 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Key West Lighthouse and Keeper's Quarters Museum - 9 min walk - 0.8 km
  • South Beach - 14 min walk - 1.2 km
  • Southernmost Point - 15 min walk - 1.3 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 13 min drive

Restaurants

  • ‪Margaritaville - ‬4 min walk
  • ‪Wendy's - ‬5 min walk
  • ‪Mangoes Restaurant - ‬4 min walk
  • ‪Jack Flats - ‬4 min walk
  • ‪DJ's Clam Shack - ‬4 min walk

Frequently asked questions

Does WATSON HOUSE GRAND ESTATE on Simonton St have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at WATSON HOUSE GRAND ESTATE on Simonton St?

As of 7 November 2026, prices found for a 1-night stay for 2 adults at WATSON HOUSE GRAND ESTATE on Simonton St on 15 December 2026 start from NZ$21,952, 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 WATSON HOUSE GRAND ESTATE on Simonton St pet-friendly?

No, pets are not allowed at this property.

How much is parking at WATSON HOUSE GRAND ESTATE on Simonton St?

On-site parking is available at the property.

What time is check-in at WATSON HOUSE GRAND ESTATE on Simonton St?

Check-in begins at 4:00 PM.

What time is check-out at WATSON HOUSE GRAND ESTATE on Simonton St?

Checkout is at 10:00 AM.

Where is WATSON HOUSE GRAND ESTATE on Simonton St located?

Located in Old Town Key West, this holiday home is within a 10-minute walk of Duval Street, Florida Keys Beaches and Ernest Hemingway Home and Museum. Mallory Square and South Beach are also within 1 mile (2 km).

Reviews

9.6

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. 6 out of 8 reviews
Rating 8 - Good. 2 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

9.4/10

Cleanliness

10/10

Check-in

9.4/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property. Great location had groceries delivered with concierge service and so helpful. Golf carts were delivered for the group. No problems at all.
Stayed 8 nights in Jun 2026
Response from VrboOwner on 11 July 2026
Thank you so much for the wonderful review! We're thrilled you had such a fantastic stay and that your experience was seamless! We love hearing that everything went smoothly for your group. Your kind words mean the world to us, and we'd be delighted to welcome you back anytime. Thank you for choosing us!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property, very convenient to a lot of stores, restaurants, nightlife, etc. Would definitely go back.
Stayed 5 nights in Aug 2025
Response from VrboOwner on 28 August 2025
That's fantastic to hear Stan! We are so glad you had such a great stay. We're very proud of the property's location and convenience, so your feedback means a lot to us. We look forward to welcoming you back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home is ideally located and absolutely charming. It was perfect for our party of 16. The villa was great for the younger families and mansion was wonderfully appointed for the parents and grandparents. The two pools were busy with the kids playing and sunbathing. Everything is just right outside the door. This is a great choice for a large group with diverse vacation expectations.
Stayed 5 nights in Mar 2026
Response from VrboOwner on 28 March 2026
Thank you so much for your wonderful review! We’d love to welcome you all back again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key West family birthday and graduation trip

This property worked very well for our large group of 20. We loved the fact that the rooms had their own bathrooms. The younger crowd had a great time in the villa. We all enjoyed the pool and grill area. One of the best things was the location. We did rent golf carts but we could easily walk many place too. We had a great trip and were a sad to leave. Thanks
Stayed 7 nights in Jun 2024
Response from VrboOwner on 26 June 2024
Dear Elizabeth, Thank you for you wonderful review and time. We glad you enjoyed your stay and will be happy to welcome you again.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great for large family and/or friends with great location

We really had a good time and it was amazing to find a house that support 11 couples. The location was excellent for walking to all locations in old town. The house is old and while modernized awhile ago, it still has a old house feel. The only negative feedback is it does need some maintenance. (i.e. pool deck has many warped boards, one refrigerator didn't get very cold, an exhaust fan didn't work). However, I recommend to anyone in a large group, as I'm not sure you can do much better on the island.
Stayed 5 nights in Mar 2024
Response from VrboOwner on 19 March 2024
Thank you for taking the time to review our property. We appreciate all feedback. We have addressed your maintenance issues and have already scheduled a contractor to work on the deck this summer. We hope to have you stay with us again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unbeatable location

This house was perfect for our group. We had all ages and the houses ability to sleep a group of 22 was fantastic. Beds were extremely comfortable and bathrooms were very nice. The house looks exactly as pictured—it is high end! But the location was by far the best: walking distance to nearly everything. We rarely used our cars other than to go to Hog Fish and instead relied on golf carts and bikes to go to the beach and Upper Duval. The only thing to keep in mind is that the kitchen is small by normal standards so you won’t want to make more than a quick breakfast or snacks at home. The grill is pretty small as well. However, given its location, you don’t need to cook anything! Overall great experience and vacation was had by all.
Stayed 8 nights in Mar 2024
Verified review

8/10 Good

Liked: Check-in, location, listing accuracy

Watson-7/20-27/2024

Had a nice stay, but would like to recommend for future renters: - Mop all floors; we left shoes outside, but feet were very dirty shortly after walking around. - Lots of knives, but none were sharp. - Any chance an outdoor shower could be put in one of the spaces where there were 3 each (?) of washers/dryers? - Need more dish towels as well as glassware, silverware and plates; the house is supposed to hold 22 people, but there were barely enough of those for our 16 guests. - Third floor door was broken when we arrived; couldn’t close it. - A fridge with an ice maker or a separate ice machine would be great. - Need manual on how to get dishwasher started; very difficult to operate. Also couldn’t read the temps on the stove very well. - There are many loose boards around the pool deck that made it hazardous to walk around the pools. We’ve rented through VRBO many times, and I don’t usually give negative reviews; but I feel the owner/Rent Key West need to know any issues for future renters.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 13 August 2024
Thank you for taking the time to review our property. We value our guests feedback. Our housekeepers are held to high standards. We expect our home to be thoroughly cleaned, including mopping the floors. We would have sent the housekeepers back if you had reported this to us while you were here. We have done an inventory of our kitchen supplies and have replenished some items at your suggestion. All the decking outside is currently being replaced. It is important to point out that each home on the estate is stocked and supplied to meet the needs of the maximum occupancy per home. The mansion has a max occupancy of 14 people and the villa has a max occupancy of 8 people.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in May 2026
Tell us how we can improve our siteShare feedback