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Simonton Court Historic Inn & Cottages

Property class: 2.5

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Photo gallery for Simonton Court Historic Inn & Cottages

A modern interior with a staircase, a sofa set, a wooden table, and a television.
A pathway flanked by lush green foliage leading to a gated entrance.
A spacious room with a large bed, a sofa, a chair, a small table, and a television.
A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Pool
  • Free WiFi
  • Parking available
  • Laundry
The current price is $168
$149 nightly
$168 total
Total with taxes and fees
Aug 30 - Aug 31

Explore the area

View in a map
523 Eaton Street, Key West, FL, 33040
  • Place, Duval Street
    ‪1 min walk‬
  • Place, Harry S. Truman Little White House
    ‪6 min walk‬
  • Place, Mallory Square
    ‪7 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪12 min drive‬

Room options

View all photos for Room, 1 Queen Bed

A four-poster bed with white linens, two orange pillows, and a wooden headboard. A painting of a tropical scene hangs above the bed.

Room, 1 Queen Bed

9.4 out of 10
Exceptional
(28 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Deluxe Room, 1 Queen Bed

A white staircase leading to an upper level, a white sofa with pink and white pillows, a black coffee table, and a framed picture on the wall.

Deluxe Room, 1 Queen Bed

9.8 out of 10
Exceptional
(15 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Room, 1 King Bed

A bedroom with a bed, a sofa, a small table, and two paintings on the wall.

Room, 1 King Bed

9.4 out of 10
Exceptional
(39 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Deluxe Room, 1 King Bed

A bedroom with a large bed, two bedside tables with lamps, a ceiling fan, a wooden wall with a painting, and a door with shutters.

Deluxe Room, 1 King Bed

9.6 out of 10
Exceptional
(30 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Luxury Suite

A room with a white sofa, a red chair, a glass coffee table, and a ceiling fan.

Luxury Suite

9.2 out of 10
Wonderful
(13 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Basic Cottage

A spacious living area with a staircase, a flat-screen TV, a round table, and a sofa with orange cushions.

Basic Cottage

10.0 out of 10
Exceptional
(1 review)
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Bed
  • Free WiFi

View all photos for Luxury Cottage

A living room with a white sofa, a round coffee table, and a ceiling fan.

Luxury Cottage

10.0 out of 10
Exceptional
(3 reviews)
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Queen Bed
  • Free WiFi

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  • Pool
  • Pet friendly
  • Free WiFi
  • Restaurant
4.6 out of 5, Wonderful, 1,398 reviews
$250 nightly
The price is $281
Aug 30 - Aug 31
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns

About the neighborhood

Key West

With a stay at Simonton Court Historic Inn & Cottages in Key West (Key West Historic District), you'll be a 3-minute walk from Duval Street and 6 minutes by foot from Florida Keys Beaches. .This hotel is 0.4 mi (0.7 km) from Mallory Square and 0.7 mi (1.1 km) from Ernest Hemingway Home and Museum.

What's nearby

  • Duval Street - 1 min walk - 0.0 miles
  • Oldest House Museum and Garden - 3 min walk - 0.2 miles
  • Harry S. Truman Little White House - 6 min walk - 0.4 miles
  • Mallory Square - 7 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 14 min walk - 0.8 miles

Getting around

  • Key West Intl. Airport (EYW) - 12 min drive

Restaurants

  • ‪Sloppy Joe's Bar - ‬5 min walk
  • ‪Conch Republic Seafood Company - ‬6 min walk
  • ‪Kermit's Key West Key Lime Shoppe - ‬5 min walk
  • ‪Cuban Coffee Queen Waterfront - ‬7 min walk
  • ‪Schooner Wharf Bar - ‬5 min walk

About this property

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages offers 18 air-conditioned accommodations with minibars and laptop-compatible safes. Each accommodation is individually furnished and decorated. 36-inch flat-screen televisions come with cable channels.

Bathrooms include complimentary toiletries and hair dryers. This Key West hotel provides complimentary wireless Internet access, with a speed of 25+ Mbps. Additionally, rooms include coffee/tea makers and irons/ironing boards. Housekeeping is provided daily.

2 outdoor swimming pools are on site.

The recreational activities listed below are available either on site or nearby; fees may apply.

Make yourself at home in one of the 18 individually decorated guestrooms, featuring minibars and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have complimentary toiletries and hair dryers. Conveniences include phones, as well as laptop-compatible safes and coffee/tea makers.
Dip into one of the 2 outdoor pools or enjoy other recreational amenities, which include bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and discounted use of a nearby fitness facility.
A complimentary continental breakfast is served daily from 8:30 AM to 10:30 AM.
Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and luggage storage. Self parking (subject to charges) is available onsite.
A complimentary continental breakfast is served each morning between 8:30 AM and 10:30 AM.

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • In-room WiFi speed: 25+ Mbps
  • Available in some public areas: Free WiFi

Parking and transportation

  • Onsite parking available only on request
  • Self parking on site (USD 35 per night; includes in/out privileges)
  • Limited onsite self parking

Food and drink

  • Free continental breakfast available daily 8:30 AM to 10:30 AM

Things to do

  • 2 outdoor pools
  • Bicycle rentals

Conveniences

  • 24-hour front desk
  • Guidebooks
  • Luggage storage
  • Safe at front desk
  • Water dispenser

Guest services

  • Concierge services
  • Dry cleaning/laundry service
  • Housekeeping (daily)
  • Tour and ticket assistance

Outdoors

  • Beach towels
  • Garden
  • Pool loungers
  • Terrace

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Upper floors accessible by stairs only

More

  • Smoking not allowed

Room amenities

Bedroom

  • Bedsheets provided

Bathroom

  • Free toiletries
  • Hair dryer
  • Towels provided

Entertainment

  • 36-inch flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Minibar

More

  • Air conditioning
  • Ceiling fan
  • Electrical adapters
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Laptop-compatible safe
  • Phone

Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: 3:00 AM
Early check-in subject to availability
Late check-in subject to availability
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

Guests must contact the property in advance for check-in instructions; front desk staff will greet guests on arrival at the property
To make arrangements for check-in please contact the property ahead of time using the information on the booking confirmation
If you are planning to arrive after 11:30 PM please contact the property in advance using the information on the booking confirmation
Guests driving to the property should contact this property in advance (e.g., directions)
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets not allowed

Children and extra beds

Children 18 and younger are not allowed at this property; All guests older than 18 are welcome

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Deposit: USD 00.01 per stay

We have included all charges provided to us by the property.

Optional extras

  • Self parking fee: USD 35.00 per night (in/out privileges)

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

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
Guests must contact this property in advance to reserve onsite parking
This property accepts credit cards, debit cards, and cash
Safety features at this property include a fire extinguisher and a smoke detector
Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property

We should mention

This property does not have elevators
Children 18 years old and younger are not permitted at this property

Property is also known as

Simonton Court Historic Inn Guesthouse
Simonton Court Historic Inn & Cottages Hotel
Simonton Court Historic Inn & Cottages Key West
Simonton Court Historic Inn & Cottages Hotel Key West

Simonton Court Historic Inn & Cottages Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 888 out of 1007 reviews
Rating 8 - Good. 86 out of 1007 reviews
Rating 6 - Okay. 20 out of 1007 reviews
Rating 4 - Poor. 6 out of 1007 reviews
Rating 2 - Terrible. 7 out of 1007 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.6/10

Amenities

9.6/10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Olha

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay overall! Friendly staff, clean rooms, and a perfect location for exploring the Keys and relaxing in this little paradise 🌴
Stayed 1 night in May 2026
Verified review

10/10 Excellent

kelly

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Defiantly would stay again and so close to everything
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Joe

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent place to stay! Convenient for walking to anywhere close to Duvall Street.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Ian

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was delicious.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Samantha

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Room was big, clean, and had amazing AC. Many pools and complimentary breakfast. The location was super convenient as well. We loved it and would love to stay again
Stayed 3 nights in May 2026
Verified review

8/10 Good

Jason

Liked: Staff & service, amenities, property conditions & facilities
Very unique, great staff, and great location
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Rebekah

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful property and extremely comfortable bed.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Greg

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff really stood out at this place! Very impressive!! Rooms were very clean.
Stayed 2 nights in May 2026
Verified review

8/10 Good

Christoph

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Easy breakfast, great for on the go. Beautiful pools. Room A/C was great.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Adam

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property is our favorite in Key West. I gives you that old time Key West feel. The grounds are gorgeous and well kept. This property offers easy access to everything(beach, food, sights, and bars). The staff are amazing. They are very helpful and friendly. This is the best stay on the island.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Kimberly

Liked: Cleanliness, staff & service, property conditions & facilities
Great experience! Multiple pools and very charming setting. Great spot to relax yet close to Duval
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Don

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent environment, nice property very comfortable. I will return on my next visit.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Jennifer

Liked: Cleanliness, amenities, property conditions & facilities
Great stay, clean room, and amazing staff!
Stayed 2 nights in Jan 2026
Verified review

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, property conditions & facilities
Loved our stay here. The staff is so friendly and helpful. The property so quaint and well taken care of. Would recommend to anyone. We will be back for sure!!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Hiram

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Clean room
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Nathan R

Liked: Cleanliness, property conditions & facilities
Our favorite place in Key West.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Thomas

Liked: Cleanliness, amenities, property conditions & facilities
Room was very clean,well furnished and staff were all very friendly. This was our 6th time staying here and it never disappoints.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Becky

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location. Cool vibe.
Stayed 1 night in Feb 2026
Verified review

10/10 Excellent

Mike

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The courtyard was beautiful and relaxing especially at night. Staff was very accommodating and helpful. Bed was comfortable. Being able to have breakfast on site was a nice way to start the morning at a slower pace. It was a bit noisy but that is to be expected based on the location.
Stayed 1 night in Apr 2026
Verified review

8/10 Good

Ric

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was the best part of the experience. Jonathan and Violet were outstanding with their welcoming attitude and were very helpful whenever we needed something. Other members of the front desk staff and housekeeping were also very helpful and friendly.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Patrick

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff is super friendly. The room was smaller than I was expecting, but very clean and unique. I had some problems with the mattress in the room, but the manager did his best to fix it. Excellent location. Within walking distance of pretty much everything. We are planning to stay here again next year.
Stayed 3 nights in Apr 2026
Verified review

8/10 Good

Tina

Clean room. Very comfortable bed! Quaint atmosphere. Friendly staff. Outstanding location for walking to Duvall Street and historic sites.
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Tiffany

Liked: Cleanliness, amenities, property conditions & facilities
I loved staying here! The room was great and the staff was awesome!
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

Meghan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff is always the best. Jonathan is amazing and always so attentive and appreciative. He remembers us every time we come there and makes sure we are taken care of. He needs a raise!
Stayed 1 night in May 2026
Verified review

10/10 Excellent

RICHARD

Liked: Cleanliness, amenities, property conditions & facilities
Excellent staff!
Stayed 7 nights in Feb 2026

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