Facade/entrance in Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

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Hotel Highlights

Discover your tropical paradise at Simonton Court Historic Inn & Cottages, a four-star gem tucked away in the vibrant heart of Key West. Located at 320 Simonton Street, just a breezy 1.3mi from the lively city center, this adults-only retreat beautifully marries historic charm with modern comforts. With prices starting as low as $269, guests can revel in the serene ambiance while enjoying all the perks that this delightful inn has to offer.

Bed in Simonton Court Historic Inn & Cottages
Bed in Simonton Court Historic Inn & Cottages

Rooms

King Suite with Pool View in Simonton Court Historic Inn & Cottages

Show 8 photos

1 King Size Bed

Suite, Pool View

Minibar

Refrigerator

Air conditioning

Tea/Coffee maker

Experience luxury and tranquility in our King Suite with Pool View. This elegant suite features a spacious king size bed, a minibar, and a refrigerator. Relax and enjoy the stunning pool view while sipping a cup of coffee or tea, and make use of our other amenities such as an iron, TV, telephone, and a safe. This room is perfect for couples seeking a peaceful and indulgent escape.

Queen Room in Simonton Court Historic Inn & Cottages

Show 6 photos

1 Queen Size Bed

Queen Room

Minibar

Refrigerator

Air conditioning

Tea/Coffee maker

Experience a comfortable stay in our cozy Queen Room, specially designed for couples. Enjoy the convenience of a minibar, refrigerator, and air conditioning, as well as additional amenities like an iron, TV, telephone, and safe for a perfect retreat.

King Room in Simonton Court Historic Inn & Cottages

Show 7 photos

1 King Size Bed

King Room

Minibar

Refrigerator

Air conditioning

Tea/Coffee maker

Welcome to our King Room, a luxurious and spacious double room perfect for couples. Relax in the comfort of our king-size bed, and enjoy amenities like a minibar, refrigerator, and air conditioning for a truly enjoyable stay.

Discover More

Dive into a world of relaxation with a splash in the inviting outdoor swimming pool or bask on the sun-kissed terrace with complimentary beach chairs and loungers waiting just for you. For the more adventurous souls, snorkeling and golf options are available at extra charges to add a splash of excitement to your stay. Not to mention, the cozy, air-conditioned non-smoking rooms promise restful nights and rejuvenating mornings. Plus, with free Wi-Fi and a 24-hour front desk at your service, your every need is just a stone's throw away.

Property building in Simonton Court Historic Inn & Cottages
Pool view in Simonton Court Historic Inn & Cottages

Experience the Best

With an impressive 1073 reviews under its belt, Simonton Court boasts delighted guests raving about their unforgettable experiences. From the picturesque garden that greets you upon entry to the thoughtfully curated amenities, this enchanting inn serves as your perfect home base for immersing yourself in the magic of Key West. So come and discover a tropical haven where charming history meets contemporary delight—your island getaway awaits!

Bed in Simonton Court Historic Inn & Cottages
Bed in Simonton Court Historic Inn & Cottages

Plan Your Stay

Immerse yourself in the delightful atmosphere at Simonton Court Historic Inn & Cottages, where every corner is adorned with tropical beauty and welcoming charm. Picture yourself strolling through the breathtaking gardens, a kaleidoscope of vibrant flowers swaying in the balmy breeze. The multiple sparkling outdoor pools are the perfect spots to unwind or make a splash with friends; there’s no better way to embrace your vacation than soaking up the sun or enjoying a refreshing dip with a poolside cocktail in hand. Whether you're lounging under a palm tree or diving into the refreshing waters, the laid-back ambiance is sure to leave you blissfully relaxed.

Food and drinks in Simonton Court Historic Inn & Cottages
Restaurant/places to eat in Simonton Court Historic Inn & Cottages

Amenities

Outdoor swimming pool

Adults only

Free wifi

Air conditioning

Terrace

24-hour front desk

Non-smoking rooms

Beach chairs/Loungers

Bathroom in Simonton Court Historic Inn & Cottages
Bathroom in Simonton Court Historic Inn & Cottages

Pools

Outdoor, All ages

All season,

Outdoor

All season,

Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & Cottages
Restaurant/places to eat in Simonton Court Historic Inn & Cottages
The staff was very good from the welcome to our final goodbye. Everyone was extremely helpful, rooms and all aspects were very clean, and any request was always taken care of. Our stay with Simonton Cottages was way above anything that we were expecting. We were welcomed by Johnathan and Violet, they are married, they are the nicest couple, always trying their best to make sure you have the best stay possible. Then there's Eric, he's the food and beverage tour leader and it was the best food tour ever. All stops were excellent and more food than we could eat, got it to go. Then there was the coconut and shell painting, with cocktails, Eric did a great job of entertain us, coaching the painting and pouring drinks. Wonderful bonus to our Key West stay at Simonton Court.

Peter

Everything about the property is nice, the vegetation is so beautiful you feel like in a little jungle I love that. Every single staff member is soooo nice and helpful always in a good mood. We stayed here in July 2024 and then loved it so much we came back in September 2024.. so close to Duval st you can walk anywhere but also just far enough you don’t hear any loud music. Siminton beach is also just a walk away but We usually rent the onsite bikes and can literally bike anywhere on the island. It is a quaint and quiet place they have four pools and it’s never crowded. Rooms are so beautiful and spacious beds comfortable.

Rachael

The walkway just past the front gate is magical. Full of lush trees, plants, and orchids. At night it is lit with beautiful lighting. The heated black bottom pool was our favorite and seemed secluded as there are not a ton of guests and there are 4 pools to choose from. The staff was very friendly and helpful. Lots of complimentary breakfast options, you put in an order, and they deliver it to your outdoor table by the pool or on the mansion porch. This was really the getaway my husband and I needed to decompress, recharge, and soak up the tropics.

Anna

Great location just one street away from Duval St so yet away from the late night noise. Beautiful gardens and grounds like an oasis that could be anywhere else in the Caribbean. Unit being in historic buildings was rustic with lots of charm with modernised bathroom and modernised kitchenette bench/sink. Lovely fluffy white towels. Choice of 4 swimming pool areas. Staff were all very helpful and friendly. Good continental breakfast including boiled eggs. Iced tea, water and ice to help yourself at anytime. Carparking on site for extra charge.

Angie

Room was very nice - property was very pretty, nice outdoor space, multiple pools, parking was extra but reserved off- street just around the corner, location is very close to the key west theater which is why we came there, very close to Duval street, the main tourist street, staff was excellent from pre-check in all the way to check out, we had a very early check out which we informed the desk of and they had an order sheet for us to have a to-go breakfast ready for us. Lovely property all the way around.

Keith

The staff was very good from the welcome to our final goodbye. Everyone was extremely helpful, rooms and all aspects were very clean, and any request was always taken care of. Our stay with Simonton Cottages was way above anything that we were expecting. We were welcomed by Johnathan and Violet, they are married, they are the nicest couple, always trying their best to make sure you have the best stay possible. Then there's Eric, he's the food and beverage tour leader and it was the best food tour ever. All stops were excellent and more food than we could eat, got it to go. Then there was the coconut and shell painting, with cocktails, Eric did a great job of entertain us, coaching the painting and pouring drinks. Wonderful bonus to our Key West stay at Simonton Court.

Peter

Everything about the property is nice, the vegetation is so beautiful you feel like in a little jungle I love that. Every single staff member is soooo nice and helpful always in a good mood. We stayed here in July 2024 and then loved it so much we came back in September 2024.. so close to Duval st you can walk anywhere but also just far enough you don’t hear any loud music. Siminton beach is also just a walk away but We usually rent the onsite bikes and can literally bike anywhere on the island. It is a quaint and quiet place they have four pools and it’s never crowded. Rooms are so beautiful and spacious beds comfortable.

Rachael

The walkway just past the front gate is magical. Full of lush trees, plants, and orchids. At night it is lit with beautiful lighting. The heated black bottom pool was our favorite and seemed secluded as there are not a ton of guests and there are 4 pools to choose from. The staff was very friendly and helpful. Lots of complimentary breakfast options, you put in an order, and they deliver it to your outdoor table by the pool or on the mansion porch. This was really the getaway my husband and I needed to decompress, recharge, and soak up the tropics.

Anna

Great location just one street away from Duval St so yet away from the late night noise. Beautiful gardens and grounds like an oasis that could be anywhere else in the Caribbean. Unit being in historic buildings was rustic with lots of charm with modernised bathroom and modernised kitchenette bench/sink. Lovely fluffy white towels. Choice of 4 swimming pool areas. Staff were all very helpful and friendly. Good continental breakfast including boiled eggs. Iced tea, water and ice to help yourself at anytime. Carparking on site for extra charge.

Angie

Room was very nice - property was very pretty, nice outdoor space, multiple pools, parking was extra but reserved off- street just around the corner, location is very close to the key west theater which is why we came there, very close to Duval street, the main tourist street, staff was excellent from pre-check in all the way to check out, we had a very early check out which we informed the desk of and they had an order sheet for us to have a to-go breakfast ready for us. Lovely property all the way around.

Keith

The staff was very good from the welcome to our final goodbye. Everyone was extremely helpful, rooms and all aspects were very clean, and any request was always taken care of. Our stay with Simonton Cottages was way above anything that we were expecting. We were welcomed by Johnathan and Violet, they are married, they are the nicest couple, always trying their best to make sure you have the best stay possible. Then there's Eric, he's the food and beverage tour leader and it was the best food tour ever. All stops were excellent and more food than we could eat, got it to go. Then there was the coconut and shell painting, with cocktails, Eric did a great job of entertain us, coaching the painting and pouring drinks. Wonderful bonus to our Key West stay at Simonton Court.

Peter

Everything about the property is nice, the vegetation is so beautiful you feel like in a little jungle I love that. Every single staff member is soooo nice and helpful always in a good mood. We stayed here in July 2024 and then loved it so much we came back in September 2024.. so close to Duval st you can walk anywhere but also just far enough you don’t hear any loud music. Siminton beach is also just a walk away but We usually rent the onsite bikes and can literally bike anywhere on the island. It is a quaint and quiet place they have four pools and it’s never crowded. Rooms are so beautiful and spacious beds comfortable.

Rachael

The walkway just past the front gate is magical. Full of lush trees, plants, and orchids. At night it is lit with beautiful lighting. The heated black bottom pool was our favorite and seemed secluded as there are not a ton of guests and there are 4 pools to choose from. The staff was very friendly and helpful. Lots of complimentary breakfast options, you put in an order, and they deliver it to your outdoor table by the pool or on the mansion porch. This was really the getaway my husband and I needed to decompress, recharge, and soak up the tropics.

Anna

Great location just one street away from Duval St so yet away from the late night noise. Beautiful gardens and grounds like an oasis that could be anywhere else in the Caribbean. Unit being in historic buildings was rustic with lots of charm with modernised bathroom and modernised kitchenette bench/sink. Lovely fluffy white towels. Choice of 4 swimming pool areas. Staff were all very helpful and friendly. Good continental breakfast including boiled eggs. Iced tea, water and ice to help yourself at anytime. Carparking on site for extra charge.

Angie

Room was very nice - property was very pretty, nice outdoor space, multiple pools, parking was extra but reserved off- street just around the corner, location is very close to the key west theater which is why we came there, very close to Duval street, the main tourist street, staff was excellent from pre-check in all the way to check out, we had a very early check out which we informed the desk of and they had an order sheet for us to have a to-go breakfast ready for us. Lovely property all the way around.

Keith

Location

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

Reservations:

+1 (888) 385-8465

or
Simonton Court Historic Inn & Cottages

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