Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
Highlights
Arcade/game room
A rare find - fun for all ages with on-site arcade and game room.
Walkable and wonderful
Guests love the walkable location for its easy access on foot.
Discover nearby landmarks
Near Duval Street
11 bedrooms11 bathroomsSleeps 22
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue grill
Explore the area
Key West, FL
Duval Street
Place, Duval Street
2 min walk
Ernest Hemingway Home and Museum
Place, Ernest Hemingway Home and Museum
9 min walk
Southernmost Point
Place, Southernmost Point
15 min walk
Key West, FL (EYW-Key West Intl.)
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
About this property
WATSON HOUSE GRAND ESTATE on Simonton St
The Grand Estate is comprised of the Mansion and the Villa offering 11 bedrooms and baths. It is ideal for family gatherings or intimate corporate getaways. It is steps away from Duval ST, the seaport and everything old town has to offer.
The 1840's Mansion is a lovingly restored and renovated 3 story Victorian home with 7 bedrooms and bathrooms. Interior painting and some additional redecorating projects were recently completed and new furnishing were added.
Upon entering, notice the beautiful, 12’ high original ceilings. There is a front living room, a family game room, dining room, and a kitchen featuring granite counter tops and stainless-steel appliances. There are also 2 bedrooms and baths on the first floor.
The New Orleans themed bedroom has a four poster queen bed. The bathroom is ensuite and has a tub/ shower combo with a dramatic high tiled archway above. The original solarium is home to a unique bedroom with Cuban tile floors and an ample king bed. The bathroom is nearby and has a tiled walk-in shower.
The banister from the 1890’s and beautiful chandelier guide you up the staircase to the 4 bedrooms and 4 bathrooms on the 2nd floor. The front bedroom has a queen bed and French doors leading to the balcony that spans the width of the house and offers a view of the historic streetscape below. The ensuite bathroom is finished in tile and has a walk-in shower. The west bedroom offers a pencil-style four poster queen bed. The room has original Dade County Pine wood planked floors and large windows. The bathroom is ensuite with a tiled walk-in shower. The east bedroom contains a king bed and features island style wicker furnishings. The ensuite bathroom has a tiled walk-in shower. The back bedroom has a modern aesthetic with a king bed and two sets of French doors leading to the balcony overlooking the outdoor living space and pool. The ensuite bathroom has double sinks and a tiled walk-in shower.
The third floor offers a unique, private, split-level suite with its own media area, small kitchen, bedroom with a king bed, and a full bathroom. The suite has beautiful hardwood floors and offers a private balcony with a view of the pool area. The bathroom’s two skylights are a unique feature bringing in the natural light and one is actually above the walk-in tiled shower. A bonus privacy and safety feature of this house is an exterior back staircase to the second and third floors.
Between the Mansion and the Villa lies a large sun deck and the first of 2 pools. This area is perfect for lounging, grilling and poolside dining. The pool may be heated in the cooler months and delightfully refreshing during the rest of the year.
The Villa is located at the rear corner of the pool area. Those staying here may also park and enter and exit through the villa's front entrance. The Villa’s soothing color palate welcomes you with warm sand tones and relaxing hues of blue. The design is a balance of modern furnishings with some leather and wood. The beautiful travertine marble floors are laid throughout the house. The open concept living, dining and cooking offers a kitchen with sleek wooden cabinets, granite counter tops, top-of-the-line appliances and fixtures.
All of the bedrooms are ensuite; 3 have king beds and 1 has 2 twins which can be made into a king. The bathrooms in the king rooms have walk-in, tiled showers and the bedroom with the twins offers a bathtub with in-tub tiled shower.
The L shaped pool with jacuzzi jets curves around to a covered deck with a long granite bar-top with seating which also provides the perfect place for arranging a poolside buffet.
Villa Bedding 2 King, 1 CA King, 2 Twin beds (which can be made into a King)
Parking: Three off-street parking spaces; 2 at the mansion and 1 at the villa.
There may be times when scheduling allows for the rental of the Mansion or the Villa individually. The gate between the properties is closed and locked making each home separate and private.
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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
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Key West
Located in Key West, this holiday home is in the city centre. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. 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 cycling and hiking/biking trails.
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
Mangoes Restaurant - 4 min walk
DJ's Clam Shack - 4 min walk
Jack Flats - 4 min walk
Bearded Lady - 3 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 17 Jul, 2026, prices found for a 1-night stay for 2 adults at WATSON HOUSE GRAND ESTATE on Simonton St on 14 Dec, 2026 start from S$26,887, 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. Southernmost Point and Mallory Square 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.
Great property. Great location had groceries delivered with concierge service and so helpful. Golf carts were delivered for the group. No problems at all.
Deanna J.
Stayed 8 nights in Jun 2026
Response from VrboOwner on 11 Jul, 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!
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.
Kevin V.
Stayed 5 nights in Mar 2026
Response from VrboOwner on 28 Mar, 2026
Thank you so much for your wonderful review! We’d love to welcome you all back again!
Great property, very convenient to a lot of stores, restaurants, nightlife, etc. Would definitely go back.
Stan W.
Stayed 5 nights in Aug 2025
Response from VrboOwner on 28 Aug, 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!
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
Elizabeth F.
Stayed 7 nights in Jun 2024
Response from VrboOwner on 26 Jun, 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.
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.
Brian T.
Stayed 5 nights in Mar 2024
Response from VrboOwner on 19 Mar, 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!
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.
Melainie M.
Stayed 8 nights in Mar 2024
Verified
8/10 Good
Meri G.
7 Aug, 2024
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.
Meri G.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 13 Aug, 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.
About the host
Hosted by Rent Key West Vacations
Languages:
English, Spanish
Premier Host
They consistently provide great experiences for their guests