SIMONTON COURT HISTORIC INN & COTTAGES | Stay downtown in Key West

75 photos

Book direct

and save up to 10%

compared to Booking.com

Key details

Hotel Overview

320 Simonton Street, Key West, Florida, United States, 33040

Steps from Mallory Square

Perfect

9.2

/10

4.7

Loved by guests

Friendly staff
Spacious rooms
Heated pools
Comfortable beds
Delicious breakfast
Beautiful grounds

Simonton Court Historic Inn & Cottages - Adult-only historic inn near Southernmost Point

Simonton Court Historic Inn & Cottages is an adult-only property located in Old Town Key West, a 5-minute drive from the Southernmost Point of the continental United States. The property features four outdoor pools, lush gardens with restored Victorian and Conch architecture, and historic cottages originally built in 1880 for cigar factory workers. Guests have access to a complimentary continental breakfast, free Wi-Fi, and a 24-hour front desk. The property includes a tropical pathway known as Hurricane Alley, leading to cottages with exposed Dade County pine and private porches. Nearby attractions include Duval Street, Mallory Square, and the Key West Shipwreck Treasure Museum.

Additional perks of the hotel

Complimentary drink ticket per guest (Breakfast Cocktail or Happy Hour Cocktail)

Breakfast to-go option available

One complimentary active day pass (gym or bicycle rental)

Happy Hour with $5 drinks and snacks (Friday to Sunday, 3-5 PM)

Welcome Hour with $5 cocktails (Monday & Thursday, 3-4 PM)

On-site bike rentals ($20/day, one day complimentary with direct booking)

Key West Fitness Center access ($15/day, one complimentary pass with direct booking)

Yoga & meditation space by the Mansion pool

Rooms & Cottages

The property offers 30 unique rooms across five buildings, including historic cottages, a Victorian mansion, and an 1880s cigar factory. Cottages feature exposed Dade County pine, wood floors, and private porches, accommodating up to four guests with king or queen beds and loft sleeping areas. The Mansion includes a Bahamian-style residence with a poolside breakfast bar. The Historic Inn retains original cigar factory details with tropical Florida décor and a black-bottom pool. Manor House is a restored Conch-style shotgun house. Room types include Petite Queen, Deluxe Queen, Standard King, Deluxe King, King Suite (Poolside), Standard Cottage, and Deluxe Cottage.

Other conveniences

Air conditioning and ceiling fans

Mini-bar and tea/coffee maker

Safe deposit box and TV

Ironing facilities and garden furniture

Wet bar in select cottages and suites

Private porches, sundecks, or balconies

Poolside service and honor bar

Room service for beverages and snacks

Complimentary Keurig coffee in rooms

Complimentary local brew, iced/hot tea, and filtered water at the pool bar

Must-do experiences

Catch a sunset at Mallory Square for vibrant street performances.
Savor the Key Lime Pie at Kermit's for a delicious local treat.
Visit the Ernest Hemingway Home for literary history and cats.
Explore the art at the Key West Art & Historical Society's museum.
Try snorkeling at Dry Tortugas National Park for breathtaking views.

View all

Choose Your Room

Our listed hotels offer a variety of room types—double rooms, family suites, or deluxe options—all with features like breakfast, flexible cancellation policies, and exclusive deals.

Cottage

2 persons

1 King-size bed

Air conditioning

room details

Deluxe King Room

2 persons

1 King-size bed

Air conditioning

room details

King Suite Pool View

2 persons

1 King-size bed

Air conditioning

room details

Queen Room

2 persons

1 King-size bed

Air conditioning

room details

Click button to see more rooms

Show all rooms

Show all roomsLess

Room Rates & Availability Tracker

Find Deals for Your Travel Dates

Amenities

Thoughtful hotel amenities for a comfortable stay

General

Non-smoking rooms
Free Wi-Fi
Parking
Safe deposit box
24-hour reception
No pets allowed
Security
Adults only
Luggage storage
Vending machines
Smoke detectors
Fire extinguishers

Sports & Fitness

Diving
Snorkelling
Canoeing
Cycling
Golf course
Fishing

Services

Housekeeping
Laundry
Dry cleaning
Tours/Ticket assistance
Grocery shopping service

Business

Fax/Photocopying

Spa & Leisure

Outdoor swimming pool
Sun loungers
Garden area

Room features

Air conditioning
Mini-bar
Terrace
Garden furniture
Tea and coffee facilities
Ironing facilities

Hotel Location

320 Simonton Street, Key West, Florida, United States, 33040

Map view

320 Simonton Street, Key West, Florida, United States, 33040

City landmarks

Square

Mallory Square

700 m

Museum

The Ernest Hemingway Home and Museum

1.1 km

Museum

Truman Little White House

620 m

Landmark

Southernmost Point

1.5 km

Nature reserve

Key West Butterfly and Nature Conservatory

1.5 km

Cemetery

Key West Cemetery

970 m

Landmark

USCGC Ingham Maritime Museum

2.3 km

Aquarium

Key West Aquarium

640 m

Museum

Key West Shipwreck Treasure Museum

640 m

Monument

Southernmost Point of the Continental US

1.7 km

Museum

Florida Keys Eco-Discovery Center

1.3 km

Church

Saint Mary Star of the Sea

1.2 km

Nearby

Duval Street

510 m

511 Caroline St

Curry Mansion

210 m

Event hall

San Carlos Institute Casa Cuba

500 m

Garden

Nancy Forrester's Secret Garden

410 m

Museum

Ripley's Believe It or Not

510 m

Gallery

The Studios of Key West

50 m

Museum

Mel Fisher Maritime Heritage Museum

520 m

Garden

Audubon House and Tropical Gardens

510 m

Mallory Square between Whitehead and Wall sts.

Memorial Sculpture Garden

640 m

Church

Saint Paul's Episcopal Church of Key West

160 m

322 Duval St

The Oldest House

170 m

Square

Key West-Florida Keys Historical Military Memorial

510 m

Gallery

7 Artists & Friends Gallery

180 m

490 Whitehead St

US 1 Mile Marker 0

460 m

534 Fleming St

KEPart Studio-Gallery

210 m

Gallery

Gallery on Greene

230 m

410 Caroline St Between Duval and Whitehead Streets

Key West Pirates Well

250 m

519 Duval St

Peter Lik Gallery Key West

300 m

Restaurants

Hard Rock Cafe

230 m

313 Duval St

Fogarty's

280 m

227 Duval St

Fat Tuesday

200 m

305 Duval St

Faustos Food Palace

230 m

522 Fleming St

Explore Key West

Local Insights

Mallory Square

9 minutes' walk

Famous for sunset celebrations, this lively square offers street performances and local artistry amidst stunning waterfront views.

The Ernest Hemingway Home and Museum

13 minutes' walk

The former residence of the iconic author features beautiful gardens and a fascinating glimpse into Hemingway's life and work.

Truman Little White House

8 minutes' walk

The winter White House of President Truman offers historical tours showcasing its significance in American politics and history.

Key West Aquarium

8 minutes' walk

This interactive aquarium features marine exhibits and feeding sessions, great for families to learn about local sea life.

Snorkeling Tours

5 minutes' drive

Exciting snorkeling excursions available at nearby reefs, with rentals and guided tours offered for all skill levels.

Yoga on the Beach

5 minutes' drive

Relaxing yoga classes available on local beaches, perfect for unwinding. Check schedules for reservations and seasonal offerings.

Fogarty's

4 minutes' walk

Casual dining with a vibrant atmosphere. Known for seafood specialties and signature cocktails; reservations recommended.

Hard Rock Cafe

3 minutes' walk

Rock-themed dining spot famous for burgers and steaks. Family-friendly with a lively ambiance and memorabilia decorating the walls.

Fat Tuesday

3 minutes' walk

Famous for frozen drinks and vibrant atmosphere. Casual spot, ideal for quick bites and enjoying Key West's nightlife.

Sloppy Joe's

7 minutes' walk

Iconic bar known for live music and vibrant nightlife. Hosts weekly events and offers a lively atmosphere for all ages.

Key West Theater

10 minutes' drive

Showcases concerts and performances in a cozy venue. Family-friendly with local acts and well-known entertainment variety.

Transportation Tips

City Centre

Key West26 min · 2.1 km

Airports

Key West International Airport (EYW)10 min · 6.3 km

Unlock Early Booking Discounts

Grab Your Special Rates Today!

Check Rates

Property information and rules

Check-in

from 15:00-23:59

Check-out

until 11 am

Guest Parking

Private parking is possible on site (reservation might be needed) at USD 30 per day.

Internet

is available in public areas for free.

Breakfast

At the hotel Simonton Court Historic Inn & Cottages guests are invited to a full breakfast served for free.

Children & extra beds

There are no cots provided in a room.

Pets

Pets are not allowed.

Number of rooms:

Former name

simonton court historic inn & guesthouse

Questions of the users

About Simonton Court Historic Inn & Cottages

Is a light continental breakfast included with every room booking?

12 February 2024

Yes, each room comes with a complimentary light breakfast that features bagels, waffles, muffins, toast, yogurt, cereals, fresh fruit, juice, coffee, and tea. Enjoy your meal!

What is the total number of guest rooms available at the property?

27 March 2024

There are 30 unique rooms at this property, accommodating up to 85 guests in total. The atmosphere is more suited for individual travelers or couples rather than large group events.

What features make Simonton Court unique compared to other locations?

05 April 2024

Simonton Court Historic Inn & Cottages offers a tropical adult-only oasis with beautiful gardens and Victorian architecture. It's a living design property where every detail has been carefully crafted to enhance the unique Key West experience.

Are there any special promotions for booking directly through the website?

15 May 2024

Yes, booking directly comes with several benefits, including rate matching, late checkout, complimentary drinks, and breakfast options. Guests also receive perks like complimentary gym passes and personalized room recommendations.

Can I rent bikes onsite during my stay?

20 June 2024

Yes, bike rentals are available on-site for $20 per day, with one day complimentary when booking directly through the website. It's a great way to explore the beautiful surroundings of Key West.

Is there a designated space for yoga or meditation at the property?

22 July 2024

Yes, there is a dedicated yoga and meditation space available next to the Mansion pool, allowing guests to unwind and connect with their inner peace amidst a tranquil setting.

What time does housekeeping service the rooms?

19 August 2024

Housekeeping services are provided daily between 8 AM and 1 PM, ensuring rooms are well-maintained for a comfortable stay.

What are the options for socializing with other guests at the hotel?

11 September 2024

The hotel offers a Welcome Hour every Monday and Thursday, where guests can enjoy $5 cocktails and meet fellow travelers. Additionally, there is a Happy Hour weekend event featuring affordable drinks and snacks.

Is there a fitness center available nearby for guests?

03 October 2024

Yes, a popular local gym is located just a block away, where guests can access various fitness classes for $15 per day, a discounted rate when booked directly through the property.

What age group is welcomed at Simonton Court?

28 November 2024

The property is designated as adults only, welcoming guests aged 18 and older to ensure a peaceful and relaxing atmosphere.