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

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

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

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 0.6 km from Jackson Square

Teresa

￥37,924

￥42,664 total

includes taxes & fees

Oct 25 - Oct 26

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 wooden deck with lush greenery and a pool area.

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

￥24,948

￥30,874 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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.

3. H2O Suites - Adults Only

Uptown - Upper Duval, 1 km from Jackson Square

Kimberly

￥49,603

￥66,502 total

includes taxes & fees

Oct 28 - Oct 29

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 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."

4. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

ben

￥39,072

￥43,956 total

includes taxes & fees

Oct 26 - Oct 27

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

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

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

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

5. Key West Villas

Downtown Key West, 0.3 km from Jackson Square

Margaret

￥48,361

￥54,408 total

includes taxes & fees

Nov 18 - Nov 19

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

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.

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

6. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Gisele

￥42,620

￥47,947 total

includes taxes & fees

Oct 27 - Oct 28

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.

7. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.1 km from Jackson Square

Nestor

￥38,375

￥49,799 total

includes taxes & fees

Oct 28 - Oct 29

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

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

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

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

8. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Josh

￥68,001

￥85,418 total

includes taxes & fees

Oct 26 - Oct 27

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

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.

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

9. The Conch House Heritage Inn

Old Town Key West, 0.7 km from Jackson Square

Jennifer

￥45,270

￥50,929 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

10. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Elise

￥29,787

￥33,510 total

includes taxes & fees

Oct 26 - Oct 27

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.

11. Duval House

Downtown Key West, 0.4 km from Jackson Square

Cathrine

￥23,618

￥29,978 total

includes taxes & fees

Oct 25 - Oct 26

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

A sign for Santa Maria Resort surrounded by lush greenery and palm trees.

12. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

Anthony

￥47,394

￥64,017 total

includes taxes & fees

Oct 26 - Oct 27

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

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

13. Westwinds Inn

Historic Seaport, 0.8 km from Jackson Square

Anthony

￥25,679

￥28,889 total

includes taxes & fees

Oct 25 - Oct 26

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 hotel room with a bed, a nightstand, a chair, a small table, and a ceiling fan.

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

14. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

RICHARD

￥34,484

￥38,795 total

includes taxes & fees

Oct 25 - Oct 26

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 large, two-story house with a prominent tower and a covered porch.

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

15. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

Amy

￥28,389

￥52,000 total

includes taxes & fees

Oct 25 - Oct 26

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.

16. Coco Plum Inn

Downtown Key West, 0.1 km from Jackson Square

August

￥31,645

￥35,600 total

includes taxes & fees

Oct 28 - Oct 29

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

A bright kitchen with white cabinetry, a white island, wicker pendant lights, and geometric patterned backsplash.

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

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

17. Ella's Cottages - Key West Historic Inns

Old Town Key West, 0.5 km from Jackson Square

Henry

￥39,628

￥52,607 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

18. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

sam

￥14,123

￥26,589 total

includes taxes & fees

Oct 25 - Oct 26

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

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

19. Alexander Palms Court

Casa Marina, 1.2 km from Jackson Square

Brenda

￥28,301

￥31,841 total

includes taxes & fees

Oct 21 - Oct 22

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

A waterfront hotel with multiple balconies, a dock, and boats.

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

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

20. Opal Key Resort & Marina, Key West

Old Town Key West, 0.5 km from Jackson Square

Ann

￥40,927

￥52,267 total

includes taxes & fees

Nov 4 - Nov 5

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Compare popular hotels close to Jackson Square

Property	Star rating	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,002 reviews	View
Douglas House - Adults Only	9.8 Exceptional 563 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 669 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,001 reviews	View
Key West Villas	9.8 Exceptional 279 reviews	View

Top Jackson Square Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

8/10 Good

"had family emergency and had to leave 2 days early and reached out to Expedia for refund and they stated Winslow bungalows is DECLINING any refund"

Opal Key Resort & Marina, Key West

10/10 Excellent

"We had no issues. Room clean, restaurant good!"

Coco Plum Inn

10/10 Excellent

"My husband and i throughly enjoyed ourselves. The rooms were clean, good sized and the AC worked great! The property and pool are very well maintained. Every morning we had a fresh breakfast made for us which is completely and the staff was very friendly and accommodating. Lastly, location was key! No pun intended, lol. We would definitely stay at Coco Plum again."

The Southernmost Inn - Adults Only

10/10 Excellent

"Great place."

Duval House

10/10 Excellent

"Amazing location balcony was great to see gombay parade come by will be back"

The Gardens Hotel

10/10 Excellent

"Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto"

The Cabana Inn Key West - Adults Only

8/10 Good

"Everything was pretty good except couldn’t get tv to work properly to watch playoffs. Would stay again close to everything"

Paradise Inn Key West - Adults Only

10/10 Excellent

"Fantastic property! Quiet, clean and close to everything. Wonderful pool area and the landscaping and grounds make you feel secluded."

Tranquility Guest House

10/10 Excellent

"Tranquility is just that. Quiet except for local roosters, safe, peaceful and private. There’s no front desk but the manager was in touch and checked in frequently. Great neighborhood nestled between Duval and the state park with fabulous beach."

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, 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.

Find hotels near Jackson Square, Key West from ￥26,589

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

2. Douglas House - Adults Only

3. H2O Suites - Adults Only

4. Orchid Key Inn - Adults Only

5. Key West Villas

6. The Gardens Hotel

7. Alexander's Guesthouse - Adult Exclusive

8. The Marquesa Hotel

9. The Conch House Heritage Inn

10. Island City House Hotel

11. Duval House

12. Santa Maria Suites

13. Westwinds Inn

14. Ambrosia Key West

15. Southernmost House - Adult Exclusive

16. Coco Plum Inn

17. Ella's Cottages - Key West Historic Inns

18. Silver Palms Inn & Historic Homes

19. Alexander Palms Court

20. Opal Key Resort & Marina, Key West

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Opal Key Resort & Marina, Key West

Coco Plum Inn

The Southernmost Inn - Adults Only

Duval House

The Gardens Hotel

The Cabana Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

Tranquility Guest House

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