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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. - Simonton Court Historic Inn & Cottages (Key West)
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery. - Simonton Court Historic Inn & Cottages (Key West)
A spacious room with a large bed, a sofa, a chair, a small table, and a television. - Simonton Court Historic Inn & Cottages (Key West)
A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design. - Simonton Court Historic Inn & Cottages (Key West)
A pathway flanked by lush green foliage leading to a gated entrance. - Simonton Court Historic Inn & Cottages (Key West)
A short walk from Duval Street and Mallory Square, Simonton Court Historic Inn & Cottages provides free continental breakfast, a terrace, and a garden. Adventurous travelers may like the cycling at this hotel. Stay connected with free in-room WiFi, with speed of 25+ Mbps, and guests can find other amenities such as dry cleaning/laundry services.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Free WiFi
  • Parking available
  • Laundry

Off-peak, on budget: 30% or more off select hotels in our fall sale

Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

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
(28 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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

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

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

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

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

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

About the neighborhood

Located near the beach, Simonton Court Historic Inn & Cottages is in Key West Historic District, a neighborhood in Key West. 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 Smathers Beach. 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 ecotours. Visit our Key West travel guide
Map
523 Eaton Street, 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 white house with red and white flags, surrounded by lush greenery and palm trees.
    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 vintage typewriter on a wooden table with a notebook and pen beside it.
    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
  • Irish Kevin's
    4 min walk
  • Margaritaville
    5 min walk
  • The Bull & Whistle Bar
    3 min walk
  • Rick's Bar
    5 min walk

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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

American ExpressDiners ClubDiscoverMastercardVisa

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

Frequently asked questions

Does Simonton Court Historic Inn & Cottages have a pool?

Yes, this property has 2 outdoor pools.

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 35.00 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.

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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. 879 out of 1001 reviews
Rating 8 - Good. 89 out of 1001 reviews
Rating 6 - Okay. 20 out of 1001 reviews
Rating 4 - Poor. 6 out of 1001 reviews
Rating 2 - Terrible. 7 out of 1001 reviews

Reviews

Verified review

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 review

10/10 Excellent

SARAH

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Cute historic spot with various small pools for relaxing and it’s a quiet escape from the noise of the bars etc. Really great breakfast and lovely staff. So comfortable with beautiful grounds!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Cindy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The STAFF is AMAZING. Truly, the best amenity of this, my favorite place to stay in Key West, is the delightful, friendly, helpful, amazing staff!
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Mari

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property, wonderful staff. We hope to visit again soon.
Stayed 1 night in Jun 2026
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

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 review

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 review

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 review

10/10 Excellent

Ian

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was delicious.
Stayed 2 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

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

10/10 Excellent

Kim

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Simonton Historical Inn was everything we expect of a Key West B & B. Beautiful lush landscape and gardens, historically significant buildings (think 1880's). The wood floor of our room had a noticeable slant to the left ( to be expected of a historical building and charming.). The staff could not have been friendlier and they were very helpful with every question answered. The room was quaint and clean, a bit of mold in the shower but we were there in August and the humidity of the sub-tropics is brutal. Bed was comfortable but the bedding could use an update. Continental breakfast was very good. Overall we liked the accommodations and would return.
Stayed 1 night in Aug 2026
Verified review

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 review

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 review

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 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

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 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

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 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

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 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

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 review

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