Hotels near Jackson Square, Key West

The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

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Our top choices for Jackson Square hotels

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.

A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

A swimming pool with lounge chairs, surrounded by palm trees and greenery.

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 0.6 km from Jackson Square

John

S$300

includes taxes & fees

6 Oct - 7 Oct

A tropical outdoor area with palm trees, hanging plants, and string lights.

An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.

A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.

A large, two-story building with a balcony, surrounded by dense tropical foliage.

2. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

Maricela

S$161

includes taxes & fees

6 Oct - 7 Oct

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

A colonial-style building with a porch, surrounded by lush tropical vegetation.

A couple walking along a poolside pathway surrounded by lush greenery.

A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.

3. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Forrest

S$322

includes taxes & fees

6 Oct - 7 Oct

A porch with a white railing, a bench, and a flag.

A pool area with lounge chairs and a dining table, surrounded by palm trees and a house with a porch.

A living room with a sofa, a glass coffee table, a TV, and a painting on the wall.

A spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.

4. The Conch House Heritage Inn

Old Town Key West, 0.7 km from Jackson Square

John

S$273

includes taxes & fees

6 Oct - 7 Oct

A pool area with lounge chairs and a table, surrounded by palm trees.

A hotel room with a large bed, a nightstand, a desk, a bathroom with a shower, and a painting of a pier over water on the wall.

A building with a neon sign that reads "Orchid Key Inn."

A neon sign for Orchid Key Inn with a 'VACANCY' sign below it.

5. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

Nicholas

S$312

includes taxes & fees

12 Oct - 13 Oct

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.

A narrow room with a bed, a potted plant, and a window with blinds.

A spacious living room with a sofa, chairs, and a dining table. There are large windows with blinds, a door leading to a patio, and a ceiling with exposed beams.

6. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.1 km from Jackson Square

Nestor

S$364

includes taxes & fees

6 Oct - 7 Oct

A two-story house with a covered porch, a brick pathway, and a large tree.

A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.

A covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.

A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

7. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Darrell

S$559

includes taxes & fees

12 Oct - 13 Oct

A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

A pool area with lounge chairs and a wooden building with balconies.

A garden with a pond, rocks, and various plants.

A compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.

8. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Osvaldo

S$261

includes taxes & fees

11 Oct - 12 Oct

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

A lush garden with a variety of tropical plants and a paved walkway.

A two-story building with a white picket fence, a mailbox, and a small tree in front.

9. Duval House

Downtown Key West, 0.4 km from Jackson Square

Christopher

S$200

includes taxes & fees

6 Oct - 7 Oct

A pool area with lounge chairs and palm trees.

A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.

10. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

Anthony

S$491

includes taxes & fees

27 Oct - 28 Oct

A room with a bed, a ceiling fan, and a window with blinds.

A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.

A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

A cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.

11. The Mermaid & Alligator

Old Town Key West, 0.8 km from Jackson Square

Adam

S$330

includes taxes & fees

8 Oct - 9 Oct

A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

A cozy living room with a wooden ceiling, a sofa set, two side tables with lamps, and framed artwork on the wall.

A wicker outdoor seating area with two chairs and a table, surrounded by lush tropical foliage.

A spacious living room with a high ceiling, a ceiling fan, a large painting, a sofa, a coffee table, and a dining area with a table and chairs.

12. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Tricia

S$210

includes taxes & fees

6 Oct - 7 Oct

A large, ornate hotel with a pool, palm trees, and a view of the ocean.

A grand staircase with ornate railings and a chandelier.

A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.

A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

13. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

yessy

S$362

includes taxes & fees

26 Oct - 27 Oct

A gated entrance with lush green foliage and a white picket fence.

A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.

A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

A covered outdoor dining area with white chairs and tables, surrounded by lush greenery and a wooden deck.

14. Coco Plum Inn

Downtown Key West, 0.1 km from Jackson Square

Riley

S$204

includes taxes & fees

12 Oct - 13 Oct

A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.

A breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.

A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.

A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.

15. Westwinds Inn

Historic Seaport, 0.8 km from Jackson Square

Anthony

S$233

includes taxes & fees

6 Oct - 7 Oct

A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.

A room with a bed, a desk, a chair, a lamp, a painting of a boat on water, and a view of the sea.

A garden with a stone pathway, a wooden fence, and various tropical plants.

A pool area with a circular pool, lounge chairs, and a gazebo.

16. Alexander Palms Court

Casa Marina, 1.2 km from Jackson Square

Andrew

S$171

includes taxes & fees

6 Oct - 7 Oct

A poolside area with lounge chairs, umbrellas, and a pergola.

A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.

An open door leading to a pool area with a wicker chair and a sofa inside a room with a view of the pool.

A wooden bench with a cushion and a small table, surrounded by bamboo plants and a wooden deck.

17. Ella's Cottages - Key West Historic Inns

Old Town Key West, 0.5 km from Jackson Square

tracy

S$395

includes taxes & fees

6 Oct - 7 Oct

A covered porch with white railings, wooden benches, and a hanging light fixture.

A pool area with lounge chairs and a small palm tree.

A sign for Marrero's Guest Mansion in Key West, FL, by Verdigris Hotels.

A bedroom with a four-poster bed, a wicker chair, a wooden dresser, and a television.

18. Marrero's Guest Mansion

Downtown Key West, < 0.1 km from Jackson Square

Michael

S$451

includes taxes & fees

7 Oct - 8 Oct

A hotel with a covered entrance, multiple balconies, and palm trees.

A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.

A room with a stone wall, a wooden bench, a cactus, and a framed painting.

19. Opal Key Resort & Marina, Key West

Old Town Key West, 0.5 km from Jackson Square

Susan

S$423

includes taxes & fees

6 Oct - 7 Oct

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

A hotel with a pool, bicycles, and lush greenery.

The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.

The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

20. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

sam

S$214

includes taxes & fees

6 Oct - 7 Oct

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Compare popular hotels close to Jackson Square

Property	Property class	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,001 reviews	View
Douglas House - Adults Only	9.8 Exceptional 548 reviews	View
The Gardens Hotel	9.8 Exceptional 1,006 reviews	View
The Conch House Heritage Inn	9.8 Exceptional 191 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,002 reviews	View

Top Jackson Square Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"This was a great property! Not expensive but with all the amenities. Close to Duvall. The only drawback were the roosters! But I think that’s everywhere in Key West."

The Cabana Inn Key West - Adults Only

10/10 Excellent

"Near Duvall street but still quiet."

Pier House Resort & Spa

10/10 Excellent

"Love pier house resort"

The Gardens Hotel

10/10 Excellent

"Very homey and luxurious at the same time"

Amsterdam's Curry Mansion Inn

8/10 Good

"Good value compared to other locations we have stayed at the past 25 years. Great location and in easy walking distance of most bars, restaurants and points of interest on the island. Room was clean and well supplied with everything you need. There is no on site host, so if you have questions or concerns you must call the guest experience manager. Everything is self service from gaining access to your room, obtaining extra towels, removing trash, etc.. Our room was upstairs in the main mansion. The only issue we had with our stay was that the stairway was not well lit at night. Somewhat dangerous!"

The Southernmost Inn - Adults Only

10/10 Excellent

"This place was great quiet and close to everything"

Tranquility Guest House

10/10 Excellent

"Great, calm space. I loved the pool and grabbing a cup of coffee and sitting in this tropical sanctuary while slowly waking up. The location is amazing. Most everything in the main part of Key West for visitors is within easy walk. Soledad and Karina kept the whole property nice and tidy. And the manager Federico was incredibly responsive. Once I arrived I received a text making sure I didn't need anything. It was a perfect way to spend a peaceful week away from my weird life."

La Concha Key West, Autograph Collection

10/10 Excellent

"The location on Duval is perfect, the hotel is top notch, and the staff can't do enough for you. Everyone from the GM to the housekeeping staff always wish you a good day and ask if there is anything they can do for you no matter how many times they see you. Perfect place to stay in Key West and we will be returning for sure!"

Heron House - Adult Only

10/10 Excellent

"I’ve been to Key West many times, the Heron House is by far the best property we have stayed at. Perfect location to walk to Duval, Mallory Square. Great pool, friendly staff."

Other attractions near Jackson Square

A historic building with ornate architecture, a balcony, and a coat of arms.

San Carlos Institute - Casa Cuba

8.6/10 (34 reviews)

You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's beautiful beaches or experience its lively festivals.

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A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

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We Cycle Key West

You can do some window-shopping at We Cycle Key West during your stay in Key West.

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St. Paul's Episcopal Church

9.0/10 (73 reviews)

St. Paul's Episcopal Church is just one of the places to see in Key West, so why not enjoy the other things to explore during your travels? Discover the area's lively bars and its lively festivals.

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Key West Film Society

7.6/10 (9 reviews)

You can get tickets for a performance at Key West Film Society during your trip to Key West. In the area, take in the lively festivals and beautiful sunsets.

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The Key West Theater

You can make plans for a show at The Key West Theater on your trip to Key West. Discover the area's great live music or seek out its cycling trails.

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Red Barn Theater

8.0/10 (10 reviews)

You can get tickets for a performance at Red Barn Theater on your trip to Key West. Wander the seaside and beautiful beaches in the area.

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Hellings House Museum

You can spend an afternoon exploring the galleries in Hellings House Museum during your travels in Key West. Experience the area's entertainment choices and great live music.

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Frequently asked questions

What's the area like around Jackson Square?

Jackson Square is located in an area of Key West known for its beautiful ocean views, bar scene and cycling. If you're looking for a convenient place to stay, take a look at the 1672 hotels and other accommodation options you'll find within a mile.

What's the best hotel to stay close to Jackson Square?

Adjacent to Jackson Square, La Concha Key West, Autograph Collection is one of the top choices for your stay based on our traveller data, and this hotel offers 3 restaurants and 2 bars. Other good options close by include Southernmost Beach Resort and Guesthouses and Pier House Resort & Spa.

How many hotels can I expect to find close to Jackson Square?

Expedia has 1672 hotels and other accommodation options within a mile from Jackson Square.

If I need to cancel the hotel reservation for my stay near Jackson Square, will I receive a refund?

Yes, you'll find most hotel bookings are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Add your dates and click on "Search", then you can filter by "fully refundable" to get the top deals on offer near Jackson Square.

What can I see and do near Jackson Square?

Harry S. Truman Little White House, Ernest Hemingway Home and Museum and Florida Keys Eco - Discovery Center feature a variety of fascinating exhibits to see while you're in town. Key West Lighthouse and Keeper's Quarters Museum, Fort Zachary Taylor Historic State Park and Fort East Martello Museum and Gallery are some of the local landmarks to explore. You can check out the local talent at Red Barn Theater, Key West Film Society and The Key West Theater.

Hotels near Jackson Square

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

2. Douglas House - Adults Only

3. The Gardens Hotel

4. The Conch House Heritage Inn

5. Orchid Key Inn - Adults Only

6. Alexander's Guesthouse - Adult Exclusive

7. The Marquesa Hotel

8. Island City House Hotel

9. Duval House

10. Santa Maria Suites

11. The Mermaid & Alligator

12. Ambrosia Key West

13. Southernmost House - Adult Exclusive

14. Coco Plum Inn

15. Westwinds Inn

16. Alexander Palms Court

17. Ella's Cottages - Key West Historic Inns

18. Marrero's Guest Mansion

19. Opal Key Resort & Marina, Key West

20. Silver Palms Inn & Historic Homes

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

The Cabana Inn Key West - Adults Only

Pier House Resort & Spa

The Gardens Hotel

Amsterdam's Curry Mansion Inn

The Southernmost Inn - Adults Only

Tranquility Guest House

La Concha Key West, Autograph Collection

Heron House - Adult Only

Other attractions near Jackson Square

San Carlos Institute - Casa Cuba

Duval Street

We Cycle Key West

St. Paul's Episcopal Church

Key West Film Society

The Key West Theater

Red Barn Theater

Hellings House Museum

Frequently asked questions