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.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

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

￥28,449

￥32,005 total

includes taxes & fees

Sep 10 - Sep 11

A covered porch with white railings, a ceiling fan, and a table with chairs.

A two-story house with a porch, a large tree, and a fire hydrant.

A bedroom with a wooden headboard, a bed with white bedding, a blue patterned throw, and a view through a window with blinds.

A room with a wooden floor, a sofa with patterned cushions, a table, a chair, a lamp, and a window with blinds.

2. The Porch on Frances Inn

Old Town Key West, 1 km from Jackson Square

Corrynne

￥17,742

￥24,642 total

includes taxes & fees

Sep 7 - Sep 8

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 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.

3. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Brian

￥26,195

￥29,470 total

includes taxes & fees

Sep 21 - Sep 22

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 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.

4. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

LISA

￥29,982

￥42,509 total

includes taxes & fees

Sep 21 - Sep 22

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

A patio with a white wicker lounge chair, a wooden table with a book and a potted plant, surrounded by lush tropical foliage and 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 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

￥27,981

￥31,479 total

includes taxes & fees

Sep 8 - Sep 9

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

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.

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

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

6. H2O Suites - Adults Only

Uptown - Upper Duval, 1 km from Jackson Square

Kourosh

￥39,632

￥55,124 total

includes taxes & fees

Sep 13 - Sep 14

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.

A wooden deck with lush greenery and a pool area.

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

7. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

savannah

￥15,926

￥19,708 total

includes taxes & fees

Sep 9 - Sep 10

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

8. The Mermaid & Alligator

Old Town Key West, 0.8 km from Jackson Square

Johnny

￥28,098

￥31,610 total

includes taxes & fees

Sep 7 - Sep 8

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

9. Duval House

Downtown Key West, 0.4 km from Jackson Square

Robert

￥14,990

￥20,220 total

includes taxes & fees

Sep 8 - Sep 9

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

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

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.

10. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Paul

￥24,001

￥27,001 total

includes taxes & fees

Sep 9 - Sep 10

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

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

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.

11. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Travis

￥24,072

￥30,984 total

includes taxes & fees

Sep 8 - Sep 9

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

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

12. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

June Young

￥43,552

￥59,534 total

includes taxes & fees

Sep 7 - Sep 8

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.

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

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.

13. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

Shawn

￥12,504

￥24,605 total

includes taxes & fees

Sep 8 - Sep 9

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

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

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

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

14. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

Mark

￥21,745

￥44,218 total

includes taxes & fees

Sep 20 - Sep 21

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

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

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

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

15. Coco Plum Inn

Downtown Key West, 0.1 km from Jackson Square

Jake

￥20,956

￥23,575 total

includes taxes & fees

Sep 14 - Sep 15

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 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.

16. Westwinds Inn

Historic Seaport, 0.8 km from Jackson Square

John

￥18,147

￥20,415 total

includes taxes & fees

Sep 27 - Sep 28

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

17. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Kate

￥20,957

￥23,577 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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.

18. Weatherstation Inn

Truman Annex, 0.3 km from Jackson Square

Svetlana

￥26,381

￥29,679 total

includes taxes & fees

Sep 8 - Sep 9

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.

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.

19. Ella's Cottages - Key West Historic Inns

Old Town Key West, 0.5 km from Jackson Square

Susannah

￥30,440

￥42,148 total

includes taxes & fees

Sep 10 - Sep 11

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

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

20. Marrero's Guest Mansion

Downtown Key West, < 0.1 km from Jackson Square

Michael

￥34,186

￥38,460 total

includes taxes & fees

Sep 14 - Sep 15

View all properties

Compare popular hotels close to Jackson Square

Property	Star rating	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,010 reviews	View
The Porch on Frances Inn	9.8 Exceptional 138 reviews	View
The Gardens Hotel	9.8 Exceptional 1,001 reviews	View
The Marquesa Hotel	9.8 Exceptional 1,002 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,006 reviews	View

Top Jackson Square Hotel Reviews

Duval House

10/10 Excellent

"Duval House is a beautiful historic Caribbean styled property. It is charming, lush, private and full of charm. The rooms are quaint, clean and updated. The grounds are lush and tropical. The staff is very nice and helpful. The continental breakfast is set in the beautiful garden. The Duval House is a wonderful place."

Tranquility Guest House

10/10 Excellent

"The room was clean and the staff was very friendly. Highly recommended"

Pier House Resort & Spa

10/10 Excellent

"Great location. Staff were very nice. Room clean. Food good."

Heron House - Adult Only

10/10 Excellent

"We love staying here. Other guests have always been friendly and it’s so relaxed it’s always a great time!"

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"The staff were outstanding, especially Anna at the front desk. They all were so warm and welcoming. The rooms were spacious and clean. The pool was clean and mostly quiet (which was nice and relaxing)."

The Cabana Inn Key West - Adults Only

10/10 Excellent

"Property was close to Duval and conveniently located with pool and hot tub access. Breakfast and happy hour offerings were an added bonus. We had booked the owner's suite and it exceeded our expecations."

The Gardens Hotel

10/10 Excellent

"I honestly can’t rave enough about this place. From the first phone call to check out, everyone was so pleasant and helpful. The grounds are immaculately maintained, the property is absolutely beautiful. Tastefully whimsical !!! The rooms are clean, the beds are comfy, all the way down to the linens. Everything is spot on. The location is just off Duval Street but you would never know it. It is so charming. Our waitress/bartender was the best! We met the owner and all I can say is she is the most delightful woman. You can see she has her heart in the establishment. There is even a wine gallery on site. I can’t wait to come back!"

Lighthouse Hotel - Key West Historic Inns

10/10 Excellent

"Great boutique hotel! The room was clean, the bed was very comfortable, and the location was perfect—just one block from Duval Street, with restaurants nearby. Breakfast was also better than I expected! Live music by the pool (afternoon and during breakfast) and at night was very quiet! Overall, a very pleasant stay!"

Duval Inn

10/10 Excellent

"Honestly, great location and loved our room! The only thing is I don’t think we got our VIP welcome gift. Not the end of the world!"

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.

See properties

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.

See properties

We Cycle Key West

You can search for that perfect souvenir at We Cycle Key West during your trip to Key West.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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 1681 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 1681 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 Waterfront Playhouse, Key West Film Society, and The Key West Theater.

Find hotels near Jackson Square, Key West from ￥19,708

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. The Porch on Frances Inn

3. The Gardens Hotel

4. The Marquesa Hotel

5. Orchid Key Inn - Adults Only

6. H2O Suites - Adults Only

7. Douglas House - Adults Only

8. The Mermaid & Alligator

9. Duval House

10. Island City House Hotel

11. The Grand Guesthouse

12. Santa Maria Suites

13. Silver Palms Inn & Historic Homes

14. Southernmost House - Adult Exclusive

15. Coco Plum Inn

16. Westwinds Inn

17. Ambrosia Key West

18. Weatherstation Inn

19. Ella's Cottages - Key West Historic Inns

20. Marrero's Guest Mansion

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Duval House

Tranquility Guest House

Pier House Resort & Spa

Heron House - Adult Only

Hyatt Centric Key West Resort and Spa

The Cabana Inn Key West - Adults Only

The Gardens Hotel

Lighthouse Hotel - Key West Historic Inns

Duval Inn

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