The Best Hotels Closest to Jackson Square in Key West for 2026

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

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

₩238,872

₩268,731 total

includes taxes & fees

Sep 30 - Oct 1

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

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

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

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.

2. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

Nicholas

₩238,872

₩268,731 total

includes taxes & fees

Sep 30 - Oct 1

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

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.

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

3. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Forrest

₩307,806

₩346,282 total

includes taxes & fees

Sep 30 - Oct 1

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

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

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.

4. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Darrell

₩309,889

₩424,859 total

includes taxes & fees

Sep 24 - Sep 25

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

5. The Conch House Heritage Inn

Old Town Key West, 0.7 km from Jackson Square

John

₩224,438

₩252,493 total

includes taxes & fees

Sep 29 - Sep 30

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

6. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.1 km from Jackson Square

Nestor

₩120,961

₩186,910 total

includes taxes & fees

Sep 24 - Sep 25

A gated entrance to Villas Key West with a brick pathway leading to the gate.

A house with a porch, a table, and a door with a number '6'.

A covered porch with wicker furniture, a large potted plant, and a sign for Villas Key West.

A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

7. Key West Villas

Downtown Key West, 0.3 km from Jackson Square

Margaret

₩352,514

₩396,588 total

includes taxes & fees

Oct 15 - Oct 16

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

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.

A bar area with a modern design, featuring a flat-screen TV mounted on a textured wall, two stools, and a bar stocked with various bottles.

8. H2O Suites - Adults Only

Uptown - Upper Duval, 1 km from Jackson Square

Kourosh

₩378,129

₩516,878 total

includes taxes & fees

Sep 27 - Sep 28

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

A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden deck with a view of a lush garden and a pool.

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

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

9. Tropical Inn

Downtown Key West, 0.4 km from Jackson Square

Molly

₩130,746

₩180,974 total

includes taxes & fees

Sep 27 - Sep 28

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

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

10. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Osvaldo

₩208,378

₩234,424 total

includes taxes & fees

Sep 24 - Sep 25

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

A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.

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

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

11. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Alissa

₩152,898

₩205,894 total

includes taxes & fees

Sep 24 - Sep 25

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

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

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.

12. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

michael

₩138,274

₩171,114 total

includes taxes & fees

Sep 24 - Sep 25

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

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

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

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

13. The Mermaid & Alligator

Old Town Key West, 0.8 km from Jackson Square

Brian

₩243,954

₩274,449 total

includes taxes & fees

Sep 28 - Sep 29

A pool area with lounge chairs and palm trees.

A hotel named "Santa Maria" with a prominent illuminated sign, a glass entrance, and a view of the ocean.

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

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, 1.2 km from Jackson Square

Anthony

₩378,129

₩516,878 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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.

15. Duval House

Downtown Key West, 0.4 km from Jackson Square

Anne

₩148,365

₩196,447 total

includes taxes & fees

Oct 5 - Oct 6

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

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

16. Westwinds Inn

Historic Seaport, 0.8 km from Jackson Square

Tricia

₩157,554

₩177,249 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

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

17. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

sam

₩108,560

₩213,623 total

includes taxes & fees

Sep 28 - Sep 29

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

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

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

A yellow building with a door marked '7'.

18. Alexander Palms Court

Casa Marina, 1.2 km from Jackson Square

Andrew

₩163,820

₩184,303 total

includes taxes & fees

Sep 24 - Sep 25

A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.

A breakfast tray with croissants, orange juice, and coffee on a table by a window with a view of a pool and greenery.

A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.

A two-story building with a white picket fence, palm trees, and a clear blue sky.

19. Weatherstation Inn

Truman Annex, 0.3 km from Jackson Square

Svetlana

₩229,046

₩257,677 total

includes taxes & fees

Sep 24 - Sep 25

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.

20. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Tricia

₩184,426

₩207,479 total

includes taxes & fees

Sep 27 - Sep 28

View all properties

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
Orchid Key Inn - Adults Only	9.8 Exceptional 1,002 reviews	View
The Gardens Hotel	9.8 Exceptional 1,002 reviews	View
The Marquesa Hotel	9.8 Exceptional 1,001 reviews	View
The Conch House Heritage Inn	9.8 Exceptional 189 reviews	View

Top Jackson Square Hotel Reviews

Douglas House - Adults Only

10/10 Excellent

"We stay at The Douglas House often and it’s always perfect! This time was no exception - great staff, clean rooms and well kept property. Location is perfect for easily getting anywhere on the island! We will definitely be back, hopefully soon!"

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"The facility was beautiful and the amenities were great! just keep in mind it is a walk to the seaport and the main part of Duval, which became a little too far to walk back in forth, which we knew it would be a walk when we booked it."

Pier House Resort & Spa

10/10 Excellent

"The resort was well maintained, the staff very friendly, the beach, pool and restaurant made for an amazing vacation."

The Gardens Hotel

10/10 Excellent

"Beautiful place, very nice pool, nice spacious rooms. Wonderful staff."

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"This property was the perfect spot for seeing all of Key West. We had a brief problem with our door and the team was so responsive and apologetic and offered things to make it right. Have already recommended to friends and family in the 24hrs of being home."

Heron House - Adult Only

8/10 Good

"It was all about location for me"

Duval House

10/10 Excellent

"Loved the chilled pool!"

The Cabana Inn Key West - Adults Only

10/10 Excellent

"Great stay. Clean and well Maintained. Friendly staff."

Opal Key Resort & Marina, Key West

10/10 Excellent

"Always love staying at the Opal."

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 search for that perfect souvenir at We Cycle Key West during your trip to 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 stay in 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 biking trails.

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Red Barn Theater

8.0/10 (10 reviews)

You can enjoy a show 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 trip to 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 biking. If you're looking for a convenient place to stay, check out the 1672 hotels and other accommodations you'll find within a mile.

Where is the best place 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 traveler 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 will I be able to find close to Jackson Square?

Expedia has 1672 hotels and other accommodations 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! The majority of hotel bookings are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to review the best deals near Jackson Square.

Where can I learn more about changing or cancelling my trip in the area near Jackson Square?

For more information about updating your stay near Jackson Square or cancelling it, click here.

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.

Find hotels near Jackson Square, Key West from ₩171,114

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

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Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

2. Orchid Key Inn - Adults Only

3. The Gardens Hotel

4. The Marquesa Hotel

5. The Conch House Heritage Inn

6. Alexander's Guesthouse - Adult Exclusive

7. Key West Villas

8. H2O Suites - Adults Only

9. Tropical Inn

10. Island City House Hotel

11. The Grand Guesthouse

12. Douglas House - Adults Only

13. The Mermaid & Alligator

14. Santa Maria Suites

15. Duval House

16. Westwinds Inn

17. Silver Palms Inn & Historic Homes

18. Alexander Palms Court

19. Weatherstation Inn

20. Ambrosia Key West

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Douglas House - Adults Only

Southernmost Beach Resort and Guesthouses

Pier House Resort & Spa

The Gardens Hotel

Winslow's Bungalows - Key West Historic Inns

Heron House - Adult Only

Duval House

The Cabana Inn Key West - Adults Only

Opal Key Resort & Marina, Key West

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