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Simonton Court Historic Inn & Cottages

2.5 star property

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your current months are December, 2024 and January, 2025.
December 2024
January 2025

Photo gallery for Simonton Court Historic Inn & Cottages

King Room D | Balcony
Luxury Suite | Living area | 36-inch flat-screen TV with cable channels, TV
Deluxe Cottage B | View from room
Room, 1 Queen Bed | Minibar, in-room safe, individually decorated, individually furnished
Deluxe King Suite A | Terrace/patio

Reviews

9.8 out of 10

Exceptional

Popular amenities

  • Pool
  • Breakfast included
  • Air conditioning
  • 24/7 front desk
    24/7 front desk
  • Parking available
    Parking available
  • Laundry
    Laundry

Explore the area

Map
320 Simonton St, Key West, FL, 33040
  • Duval Street
    3 min walk
  • Audubon House and Tropical Gardens
    6 min walk
  • Harry S. Truman Little White House
    7 min walk
  • Key West, FL (EYW-Key West Intl.)
    12 min drive

Room options

View all photos for Room, 1 Queen Bed

Room, 1 Queen Bed | Minibar, in-room safe, individually decorated, individually furnished

Room, 1 Queen Bed

  • Sleeps 2
  • 1 Queen Bed

View all photos for Deluxe Room, 1 Queen Bed

Deluxe Room, 1 Queen Bed | Minibar, in-room safe, individually decorated, individually furnished

Deluxe Room, 1 Queen Bed

  • Sleeps 2
  • 1 Queen Bed

View all photos for Room, 1 King Bed

Room, 1 King Bed | Minibar, in-room safe, individually decorated, individually furnished

Room, 1 King Bed

  • Sleeps 2
  • 1 King Bed

View all photos for Deluxe Room, 1 King Bed

Minibar, in-room safe, individually decorated, individually furnished

Deluxe Room, 1 King Bed

  • Sleeps 2
  • 1 King Bed

View all photos for Luxury Suite

Luxury Suite | Living area | 36-inch flat-screen TV with cable channels, TV

Luxury Suite

  • Sleeps 2
  • 1 King Bed

View all photos for Basic Cottage

36-inch flat-screen TV with cable channels, TV

Basic Cottage

  • Sleeps 4
  • 1 King Bed and 1 Queen Bed

View all photos for Luxury Cottage

Minibar, in-room safe, individually decorated, individually furnished

Luxury Cottage

  • Sleeps 4
  • 1 King Bed and 1 Queen Bed
Room
Winslow's Bungalows - Key West Historic Inns
Pool
Breakfast included
Pet friendly
Free WiFi
4.5 out of 5, Wonderful, (949)
The price is $419
per night
$513 total
includes taxes & fees
Dec 5 - Dec 6
Winslow's Bungalows - Key West Historic Inns

Reviews

9.8

Exceptional

Rating 10 - Excellent. 591 out of 665 reviews" "
Rating 8 - Good. 49 out of 665 reviews" "
Rating 6 - Okay. 15 out of 665 reviews" "
Rating 4 - Poor. 3 out of 665 reviews" "
Rating 2 - Terrible. 7 out of 665 reviews" "

9.8/10

Cleanliness

9.8/10

Staff & service

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.6/10

Eco-friendliness

Reviews

10/10 Excellent

Sebastian, Hollywood

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property, nice amenities, professional and courteous staff.
Stayed 1 night in Aug 2024

10/10 Excellent

RADANA

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was clean and neat, everyone is very friendly and helpful. So glad we booked this place last minute. The best time we've ever had in Key west. You will not get anything more authentic than this place. Loved it!
Stayed 2 nights in Aug 2024

10/10 Excellent

Scott Steven

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Staff was amazing!
Stayed 3 nights in Aug 2024

10/10 Excellent

Nick

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Perfect couples retreat
Amazing boutique hotel. Clean comfortable and great rates. Staff were great
Stayed 2 nights in Aug 2024

10/10 Excellent

Joshua

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The perfect place to spend a weekend getaway!
Stayed 2 nights in Jun 2024

10/10 Excellent

RIchard

Traveled with group
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
12 out of 10! And that is not a misprint!
Wow! This will be our go-to for future KW stays. Perfect location. Beautiful grounds and room. Super comfortable. But really, it’s the people. From our first interactions over the phone setting up scooter rental, to the personal texts we got as our arrival neared to the front desk help radiating genuine happiness and helpfulness to the young lady helping us with breakfast: 12 out of 10. This is the kind of environment and friendly service that the world needs more of. Thank you, all of you. Can’t wait to get back!
Stayed 1 night in Aug 2024

10/10 Excellent

James

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Aug 2024

10/10 Excellent

Diana, Chicago

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent stay. Beautiful and conveniently located. Jonathan and Eric very helpful and friendly. Note: parking on site is limited and costs $30 per night. Would stay again!
Stayed 1 night in Aug 2024

8/10 Good

Paul, Chicago

Liked: Cleanliness, staff & service
Stayed 3 nights in Aug 2024

10/10 Excellent

David

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities
Jonathan and staff was excellent! We enjoyed the balcony view to the pool area!
Stayed 4 nights in Aug 2024

10/10 Excellent

Rita

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was friendly. We were upgraded to a deluxe room which was beautiful. There was no parking available onsite due to them being fully booked; however, they gave us a map to a parking lot that was about a 10 min walk and was $15 a night. Easy walk to Mallory Square.
Stayed 1 night in Aug 2024

10/10 Excellent

Veronica

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff is amazing and so personable especially Jonathan!! Recommend this place to anyone who will listen.
Stayed 3 nights in Aug 2024

10/10 Excellent

Amy

Stayed 3 nights in Jul 2024

10/10 Excellent

Amy

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It was nice and clean so beautiful full of greenery. All staff we came in contact with were nice and helpful when we needed help. This is my second visit to this establishment and I highly recommend it to anyone who wants a peaceful place to rest their heads on vacation.
Stayed 3 nights in Jul 2024

6/10 Okay

Shon

Liked: Cleanliness, staff & service
Stayed 3 nights in Jul 2024

10/10 Excellent

Richard

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Location, Location, Location
Exceptional location. We were able to walk or bike everywhere! Lots of trees on the property made it extremely lush. Room was on a high floor. No elevators. Room door was extremely sticky and difficult to close and open the door. Thus it was loud. The bed is a little hard. We loved the ability to rent a bike for 24 hours. Best part they pump cool water into the pools during the hottest summer days!!!!
Stayed 2 nights in Jul 2024

10/10 Excellent

Richard

Traveled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Location, Location, Location
Exceptional location. We were able to walk or bike everywhere! Lots of trees on the property made it extremely lush. Our room was on the 3rd floor. No elevators. Our door was extremely sticky and difficult to close and open the door. Thus it was loud. The bed is a little hard. We loved the ability to rent a bike for 24 hours. Best part they pump cool water into the pools during the hottest summer days!!!!
Stayed 2 nights in Jul 2024

10/10 Excellent

MERCY

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was immaculate. The staff was wonderful. Will definitely be back.
Stayed 1 night in Jul 2024

10/10 Excellent

Joseph

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Jul 2024

10/10 Excellent

Mark, Fort Myers

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great property with multiple pools, great breakfast and attentive staff. Only negative was smoke detector went of/malfunctioned and wasn't resolved quickly. Will stay here again hopefully......
Stayed 2 nights in Jul 2024

10/10 Excellent

Jeffery

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 5 nights in Jul 2024

10/10 Excellent

dennis

Stayed 2 nights in Jul 2024

6/10 Okay

Ande

Traveled with partner
Liked: Amenities, property conditions & facilities
Pros: Overall the property was very charming. Cute pools and cottages. Landscape was very pretty and lush. It was nice to have a breakfast option, but the options were slim, but enough. Location is good and very close to everything. They offer filtered cold water which is nice not to have to buy water bottles. They offer happy hour art classes and the teacher--Eric is fantastic! Very fun perk! Cons: At first glance it looks clean, but when you start to look closer, not very clean. Could use a good deep clean. There are a lot of things falling apart or in disrepair. Many projects that could really make this place shine and feel more upscale and fresh. Some staff seemed kinda putout and a bit cynical-- not as service friendly as we hoped--especially for the price - others were fantastic. Parking is a hike if you don't buy on site - but I guess that is Key West for you.
Stayed 3 nights in Jul 2024

10/10 Excellent

Thomas

Stayed 1 night in Jul 2024

10/10 Excellent

adam

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful historic location. Very quiet with a friendly staff and clean rooms. Would definitely stay again.
Stayed 1 night in Mar 2024