Skip to main content

Simonton Court Historic Inn & Cottages

2.5 star property
Four outdoor pools await at this charming Key West retreat, where guests can rent bikes to explore the historic streets and nearby Hemingway Home

Choose dates to view prices

Simonton Court Historic Inn & Cottages in Key West is a perfect base for island exploration. Guests enjoy a continental breakfast, sun-drenched pools, and rented bikes for town cycling. An area shuttle service makes visiting local attractions easy.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Free WiFi
  • Parking available
  • Laundry

Room options

Available filters for rooms
Showing 7 of 7 rooms

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
(25 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

View all photos for Deluxe Room, 1 Queen Bed

A hotel room with a bed, a desk, a chair, a lamp, and a television.

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
(38 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Deluxe Room, 1 King Bed

Minibar, in-room safe, iron/ironing board, WiFi (free)

Deluxe Room, 1 King Bed

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

View all photos for Luxury Suite

A spacious room with a large window overlooking a swimming pool, wicker furniture, and a table with a lamp.

Luxury Suite

9.0 out of 10
Wonderful
(12 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

Minibar, in-room safe, iron/ironing board, WiFi (free)

Luxury Cottage

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

You may also like

Ad
Exterior

La Concha Key West, Autograph Collection

Key West Historic District
  • Pool
  • Pet friendly
  • Free WiFi
  • Restaurant
9.0 out of 10, Wonderful, 441 reviews
$225 nightly
The price is $253
Aug 4 - Aug 5
Total with taxes and fees
La Concha Key West, Autograph Collection
Mod logo
Earn OneKeyCash on thousands of hotels when you sign in and book. More rewards for more adventures!
Sign inSign up, it's free

About the neighborhood

Located near the beach, Simonton Court Historic Inn & Cottages is in Key West Historic District, a neighborhood in Key West. 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. Sails To Rails Museum at Flagler Station and Mel Fisher Maritime Museum are also worth visiting. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with hiking/biking trails and skydiving. Visit our Key West travel guide
Map
320 Simonton St, Key West, FL, 33040

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    1 min walk - 0.0 miles
  • A cozy living room with a wooden floor, a sofa, a table with chairs, a lamp, and a ship model on top of a cabinet.
    Oldest House Museum and Garden
    3 min walk - 0.2 miles
  • A historical marker for The Little White House, built in 1890, used by American Navy officers, and listed on the National Register of Historic Places in 1974.
    Harry S. Truman Little White House
    6 min walk - 0.4 miles
  • A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.
    Mallory Square
    7 min walk - 0.4 miles
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    14 min walk - 0.8 miles

Getting around

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

Restaurants

  • Irish Kevin's
    4 min walk
  • The Bull & Whistle Bar
    3 min walk
  • Fogarty's and Flying Monkey's
    3 min walk
  • Wendy's
    3 min walk
  • Stinkin Crawfish Key West
    4 min walk

About this property

Simonton Court Historic Inn & Cottages

  • Hotel near Duval Street
  • Located close to Mallory Square and Ernest Hemingway Home and Museum, Simonton Court Historic Inn & Cottages provides free continental breakfast, a terrace, and a garden. Adventurous travelers may like the cycling at this hotel. Free in-room WiFi, with speed of 25+ Mbps, and dry cleaning/laundry services are available to all guests.
  • You'll also enjoy the following perks during your stay:
    • 4 outdoor pools along with sun loungers
    • Bike rentals, self parking (surcharge), and an area shuttle
    • A 24-hour front desk, luggage storage, and beach towels
    • Smoke-free premises, a front-desk safe, and a water dispenser
    • Guest reviews speak highly of the breakfast, pool, and helpful staff
  • Room features
  • All guestrooms are individually furnished, and boast comforts such as laptop-compatible safes and air conditioning, as well as perks like free WiFi and minibars. Guest reviews highly rate the clean rooms at the property.
  • More conveniences in all rooms include:
    • Free toiletries and hair dryers
    • 36-inch flat-screen TVs with cable channels
    • Coffee/tea makers, ceiling fans, and daily housekeeping

Similar properties

Exterior
Douglas House - Adults Only
Old Town Key West
  • Pool
  • Free WiFi
  • Air conditioning
  • Housekeeping
9.6 out of 10, Exceptional, 458 reviews
$147 nightly
The price is $166
Jul 27 - Jul 28
Total with taxes and fees
Douglas House - Adults Only
Compare similar properties

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

  • Area shuttle
  • 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

  • 4 outdoor pools
  • Bicycle rentals

Conveniences

  • 24-hour front desk
  • Guidebooks
  • Laundry facilities
  • Luggage storage
  • Safe at front desk
  • Vending machine
  • 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 30.00 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

Frequently asked questions

Does Simonton Court Historic Inn & Cottages have a pool?

Yes, this property has 4 outdoor pools.

How much does it cost to stay at Simonton Court Historic Inn & Cottages?

As of Jul 21, 2026, prices found for a 1-night stay for 2 adults at Simonton Court Historic Inn & Cottages on Jul 22, 2026 start from $168, 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 Simonton Court Historic Inn & Cottages pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Self parking is available for USD 30.00 per night. Limited spots are available.

What time is check-in at Simonton Court Historic Inn & Cottages?

Check-in start time: 3:00 PM; Check-in end time: 3:00 AM. Late check-in is available during limited hours.

What time is check-out at Simonton Court Historic Inn & Cottages?

Check-out is at 11:00 AM.

Where is Simonton Court Historic Inn & Cottages located?

Located in Key West Historic District, this hotel is within a 5-minute walk of Donkey Milk House and Duval Street. Florida Keys Beaches and Mallory Square are also within 10 minutes.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

Simonton Court Historic Inn & Cottages Reviews

9.8

Exceptional

9.8

Cleanliness

9.6

Amenities

9.8

Staff & service

9.6

Property conditions & facilities
Rating 10 - Excellent. 887 out of 1004 reviews
Rating 8 - Good. 85 out of 1004 reviews
Rating 6 - Okay. 20 out of 1004 reviews
Rating 4 - Poor. 5 out of 1004 reviews
Rating 2 - Terrible. 7 out of 1004 reviews

Reviews

Verified

8/10 Good

Rita

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Perfcet location and walk to everything , we very much enjoyed our stay!
Stayed 7 nights in Jun 2026
Verified

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

10/10 Excellent

Francis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very convenient location to the Old Town area. Easy walk to every place
Stayed 2 nights in Jun 2026
Verified

10/10 Excellent

Magdalena

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
my stay was excellent the staff was the best. I will sure return to this hotel
Stayed 1 night in May 2026
Verified

10/10 Excellent

Steven

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Without question a classic, convenient and beautiful Key West inn. The rooms were spacious, modern and tastefully decorated. Many small pools throughout the property with lush grounds. Nice breakfast served by such caring staff. Since my stay was in the summer, rates were unbelievably low which was the reason I booked Key West. If the price were right other times of the year I’d be back without question.
Stayed 2 nights in Jun 2026
Verified

10/10 Excellent

Doug

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property with a number of different pools. The breakfast was excellent along with all of the staff.
Stayed 1 night in May 2026
Verified

10/10 Excellent

Ian

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

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

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

10/10 Excellent

Elaine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place is a gem! This place is beautiful! They treat you as their personal guest, even a hand written welcome card. The staff, rooms, service from employees there was the best and better than any hotel. Kudos to Violet and the the front desk Gentleman and Karmala. Thank you for a wonderful stay.
Stayed 1 night in Jun 2026
Verified

10/10 Excellent

Kerline

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was very spacious and clean. The staff were extremely friendly and helpful. I love the way you choose your breakfast and they bring it to you at our table. The water pressure in the shower was awesome. Without a doubt I will return.
Stayed 1 night in Jun 2026
Verified

8/10 Good

Shawna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was wonderful, Johnathan checked us in and since we were early he kept out bags securely in the lobby we could eat lunch while we waited for iur room to be ready. The shower was a little to be desired, while big, there was not much water pressure and the water took a long time to get hot, but it wasnt a deal breaker by any means. There were also very few electrical outlets so my husband had to run his cord under the bed to be able to plug in his CPAP machine.
Stayed 4 nights in Jul 2026
Verified

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I really noticed all the little touches around the facility like the men’s bathroom had a mustache and the women’s had red lips! The flower petals on the walkway, the beautiful postcard, the towels wrapped nicely and in a wicker basket near the pool, the pool chair covers!! Not to mention the wonderful breakfast every morning! Violet was the absolute BEST! So special and welcoming. Had a fabulous stay and will be back again. Thank you so much!!!
Stayed 7 nights in Jun 2026
Verified

10/10 Excellent

Timothy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I can't believe how much we enjoyed staying here! So nice! The property is beautiful. The staff was excellent. The room was very quiet and comfortable. The location is perfect! One block from Duval Street. 5 minute walk to Mallory Square. We can't wait to go back!
Stayed 3 nights in May 2026
Verified

8/10 Good

Michelle

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place was warm and welcoming. Everyone we came into contact with was fabulously nice and pleasant. The breakfast was good. Air conditioning worked. The bed however was a little lumpy and difficult for decent sleep.
Stayed 4 nights in May 2026
Verified

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

10/10 Excellent

Annemarie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property is a quiet jewel in Key West, we had a last minute booking and the staff upgraded us! Awesome cottage suite with virtually private pool in a tropical oasis. Yet steps away from all the action on Duval. Breakfast was great, and the pools were so relaxing! No noisy roosters getting you up at crack of dawn courtesy of two cats on property. Only down side was our shower struggled to heat up, but a small price to pay for such a beautiful historic place!
Stayed 1 night in Jun 2026
Verified

10/10 Excellent

Evan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Simonton was amazing! It felt like you were in another world while on property. Mature foliage, cute cottages, and amazingly helpful and courteous staff. The rooms were on the older side but everything was well maintained and very comfortable. It was close to EVERYTHING as well we parked our car in their lot and didn’t use it once the entire time since everything was within walking distance. 10/10 recommend.
Stayed 2 nights in Jun 2026
Verified

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

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

10/10 Excellent

Hiram

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

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

10/10 Excellent

Jennifer

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

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

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