The Best Hotels Closest to Jackson Square in Key West - 2026 Updated Prices

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 building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.

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, 0.4 mi from Jackson Square

John

£126

includes taxes & fees

30 Sept - 1 Oct

A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.

A pool with a lion head sculpture in the center.

A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

2. Artist House Key West

Historic Seaport, 0.2 mi from Jackson Square

NATHAN

£86

includes taxes & fees

11 Oct - 12 Oct

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

A bar area with a counter, chairs, and a clock.

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

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

3. The Gardens Hotel

Downtown Key West, 0.2 mi from Jackson Square

Forrest

£238

includes taxes & fees

28 Sept - 29 Sept

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

A spacious living room with a wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.

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.

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

4. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 0.7 mi from Jackson Square

Nestor

£215

includes taxes & fees

28 Sept - 29 Sept

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

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.

A two-story white house with green shutters, a wooden door, and a white picket fence.

5. The Conch House Heritage Inn

Old Town Key West, 0.4 mi from Jackson Square

John

£161

includes taxes & fees

28 Sept - 29 Sept

A modern outdoor area with a pool, lounge chairs, and a bar area.

An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

A modern hotel room with a bed, sofa, coffee table, and artwork.

A modern hotel with a prominent glass facade, palm trees, and a clear sky.

6. H2O Suites - Adults Only

Uptown - Upper Duval, 0.6 mi from Jackson Square

Corey

£264

includes taxes & fees

28 Sept - 29 Sept

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 restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.

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, 0.2 mi from Jackson Square

Darrell

£271

includes taxes & fees

28 Sept - 29 Sept

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 wooden deck with lush greenery and a pool area.

8. Douglas House - Adults Only

Uptown - Upper Duval, 0.5 mi from Jackson Square

michael

£97

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.

A wooden door with glass panels, leading to an interior space with furniture and plants.

A cozy room with a wicker chair, a small table with a bottle and glasses, and a view of a yellow room through an open door.

A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

9. Tropical Inn

Downtown Key West, 0.3 mi from Jackson Square

Molly

£101

includes taxes & fees

28 Sept - 29 Sept

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

A row of blue bicycles parked under a tree, with a white fence and a building in the background.

A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.

A covered outdoor area with a wooden staircase, seating, and potted plants.

10. The Grand Guesthouse

Old Town Key West, 0.7 mi from Jackson Square

Alissa

£115

includes taxes & fees

30 Sept - 1 Oct

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

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

A covered walkway with a wooden ceiling, white railings, and a brick path.

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

11. Island City House Hotel

Historic Seaport, 0.4 mi from Jackson Square

Osvaldo

£131

includes taxes & fees

28 Sept - 29 Sept

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

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.

A poolside area with lounge chairs, a covered seating area, and a small pool.

12. The Mermaid & Alligator

Old Town Key West, 0.5 mi from Jackson Square

Brian

£153

includes taxes & fees

28 Sept - 29 Sept

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

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

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

A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

13. Duval House

Downtown Key West, 0.3 mi from Jackson Square

Christopher

£106

includes taxes & fees

5 Oct - 6 Oct

A pool area with lounge chairs and palm trees.

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

A sign for Santa Maria Resort surrounded by lush greenery 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.

14. Santa Maria Suites

Uptown - Upper Duval, 0.7 mi from Jackson Square

Anthony

£262

includes taxes & fees

28 Sept - 29 Sept

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

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.

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.

15. Ambrosia Key West

Old Town Key West, 0.3 mi from Jackson Square

Tricia

£114

includes taxes & fees

28 Sept - 29 Sept

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

A pool area with a covered seating area, palm trees, and a small pavilion.

A yellow building with a door marked '7'.

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

16. Alexander Palms Court

Casa Marina, 0.8 mi from Jackson Square

Andrew

£101

includes taxes & fees

28 Sept - 29 Sept

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.

17. Coco Plum Inn

Downtown Key West, < 0.1 mi from Jackson Square

Riley

£114

includes taxes & fees

29 Sept - 30 Sept

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

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.

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

A two-story yellow house with a porch, white railings, and green shutters.

18. Silver Palms Inn & Historic Homes

Old Town Key West, 0.6 mi from Jackson Square

sam

£119

includes taxes & fees

28 Sept - 29 Sept

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

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

A two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.

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

19. Westwinds Inn

Historic Seaport, 0.5 mi from Jackson Square

Anthony

£118

includes taxes & fees

28 Sept - 29 Sept

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 living room with a large mirror, a wicker chair, a television on a wooden cabinet, and a window with a view of palm trees.

20. Marrero's Guest Mansion

Downtown Key West, < 0.1 mi from Jackson Square

Michael

£224

includes taxes & fees

28 Sept - 29 Sept

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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 1,006 reviews	View
Artist House Key West	9.8 Exceptional 456 reviews	View
The Gardens Hotel	9.8 Exceptional 1,003 reviews	View
Alexander's Guesthouse - Adult Exclusive	9.8 Exceptional 169 reviews	View
The Conch House Heritage Inn	9.8 Exceptional 190 reviews	View

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

8/10 Good

"Nice place, but over priced"

The Gardens Hotel

10/10 Excellent

"Excellent Hotel, staff very helpful and room was excellent. Breakfast was included which was delicious. Beautiful surrounding gardens. Highly recommend"

Coco Plum Inn

10/10 Excellent

"Great stay! Great location"

Pegasus International Hotel

8/10 Good

"I like this property. it was clean, comfortable and the pool was great. The only reason I gave it a 4 instead of a 5 is the check in was very odd as the lobby closed at 6pm and no one answered the phone # posted on the door. We started to panic after about 10 to 15 minutes standing at the door waiting and not knowing if we were going to have a hotel. Luckly right about the time I started to reach out to Expedia to complain my phone rang and it was the hotel lady who then came and got us checked in from there. I would stay here again."

La Concha Key West, Autograph Collection

10/10 Excellent

"Great location"

Douglas House - Adults Only

10/10 Excellent

"Everything about Douglas‘s house was exceptional. Especially the staff. We stayed well over a week and it was so worth it top-notch. Cannot wait to go back. Who was beautiful and well kept little kitchenette for coffee in our room. And the refrigerator just perfect."

Tranquility Guest House

8/10 Good

"I was completely unaware that this is a not your usual guest house that has a lobby or check-in. There is not one. I wanted to check my bags early, but that was a chore. All of the gates are locked with keypads, and I don't have the combination. Finally I see a cleaning lady, and despite a language barrier, we figure things out and I she tells me to gate entry codes as well as the code to pickup my luggage from the cleaning closet. Finally, I was text messaged all of the information for my room and the door codes, etc. Pretty much, room service, towels, and amenities are upon request, and they send you test messages asking if you need anything. It was an interesting stay in that regard. And I checked out by text message too."

Duval House

10/10 Excellent

"Fly in, Uber to and from the Duvall, fly home! Great place to have a fun time!"

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"From before we arrived we already knew we chose the right place to stay! We had questions about parking our motorcycle on property and there was no hesitation to share information and also connect with us. The staff is great. We are recommending this location and properties to friends and family. Next time we’re in town, 100% this will be the place we stay. Location is great and the property is fun to explore. Thank you all for making our stay memorable!"

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, Mel Fisher Maritime Museum and Ernest Hemingway Home and Museum 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, Waterfront Playhouse and Key West Film Society.

Search Hotels Near Jackson Square, Key West

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

2. Artist House Key West

3. The Gardens Hotel

4. Alexander's Guesthouse - Adult Exclusive

5. The Conch House Heritage Inn

6. H2O Suites - Adults Only

7. The Marquesa Hotel

8. Douglas House - Adults Only

9. Tropical Inn

10. The Grand Guesthouse

11. Island City House Hotel

12. The Mermaid & Alligator

13. Duval House

14. Santa Maria Suites

15. Ambrosia Key West

16. Alexander Palms Court

17. Coco Plum Inn

18. Silver Palms Inn & Historic Homes

19. Westwinds Inn

20. Marrero's Guest Mansion

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

The Gardens Hotel

Coco Plum Inn

Pegasus International Hotel

La Concha Key West, Autograph Collection

Douglas House - Adults Only

Tranquility Guest House

Duval House

Winslow's Bungalows - Key West Historic Inns

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