Key West Jackson Square Hotels: 2026 Limited-Time Hotel Deals @Expedia

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

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

John

HK$1,276

HK$1,436 total

includes taxes & fees

14 Sept - 15 Sept

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 couple walking along a poolside pathway surrounded by lush greenery.

2. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Jason

HK$1,316

HK$1,481 total

includes taxes & fees

21 Sept - 22 Sept

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 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.

3. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

LISA

HK$1,506

HK$2,135 total

includes taxes & fees

28 Sept - 29 Sept

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 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 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

Nicholas

HK$1,276

HK$1,436 total

includes taxes & fees

16 Sept - 17 Sept

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 room with a bed, sofa, coffee table, and artwork.

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

5. H2O Suites - Adults Only

Uptown - Upper Duval, 1 km from Jackson Square

Kourosh

HK$2,188

HK$2,991 total

includes taxes & fees

14 Sept - 15 Sept

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.

6. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Paul

HK$1,206

HK$1,356 total

includes taxes & fees

13 Sept - 14 Sept

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 wooden deck with lush greenery and a pool area.

7. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

michael

HK$924

HK$1,144 total

includes taxes & fees

29 Sept - 30 Sept

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 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.

8. Duval House

Downtown Key West, 0.4 km from Jackson Square

Robert

HK$776

HK$1,042 total

includes taxes & fees

16 Sept - 17 Sept

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 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.

9. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Alissa

HK$885

HK$1,191 total

includes taxes & fees

13 Sept - 14 Sept

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

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

10. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

June Young

HK$2,188

HK$2,991 total

includes taxes & fees

13 Sept - 14 Sept

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 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 hotel with a pool, bicycles, and lush greenery.

11. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

Shawn

HK$628

HK$1,236 total

includes taxes & fees

16 Sept - 17 Sept

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

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.

A grand staircase with ornate railings and a chandelier.

12. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

Mark

HK$1,092

HK$2,221 total

includes taxes & fees

24 Sept - 25 Sept

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

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

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

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.

13. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Kate

HK$1,053

HK$1,184 total

includes taxes & fees

27 Sept - 28 Sept

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

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

A swimming pool with a white picket fence, surrounded by lounge chairs and potted plants.

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

14. Weatherstation Inn

Truman Annex, 0.3 km from Jackson Square

Svetlana

HK$1,325

HK$1,491 total

includes taxes & fees

17 Sept - 18 Sept

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

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

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.

15. Ella's Cottages - Key West Historic Inns

Old Town Key West, 0.5 km from Jackson Square

Susannah

HK$1,568

HK$2,161 total

includes taxes & fees

13 Sept - 14 Sept

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

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 pool area with lounge chairs and a small palm tree.

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

16. Marrero's Guest Mansion

Downtown Key West, < 0.1 km from Jackson Square

Michael

HK$1,717

HK$1,932 total

includes taxes & fees

23 Sept - 24 Sept

A building with a white exterior, a large red awning, and a gated entrance.

A small, enclosed porch with a chair and a table, surrounded by lush greenery and a white lattice fence.

A paved pathway lined with various plants and trees, leading to a building with a beige exterior.

A spacious kitchen with a dining area, large windows, and a view of the outdoors.

17. Authors of Key West Guest House

The Meadows, 1.2 km from Jackson Square

Idamis

HK$582

HK$655 total

includes taxes & fees

28 Sept - 29 Sept

A wooden deck with wicker furniture, a white staircase, and a lush garden area.

A two-story house with a balcony, surrounded by palm trees and a clear blue sky.

A hotel room with a large bed, a view of a swimming pool, and a balcony with outdoor seating.

A bedroom with a large bed, a view of a swimming pool, and an open door leading to an outdoor seating area.

18. Heron House - Adult Only

Downtown Key West, 0.3 km from Jackson Square

Natalia

HK$912

HK$1,287 total

includes taxes & fees

13 Sept - 14 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 garden with a stone pathway, a wooden fence, and various tropical plants.

19. Alexander Palms Court

Casa Marina, 1.2 km from Jackson Square

Andrew

HK$1,112

HK$1,251 total

includes taxes & fees

14 Sept - 15 Sept

A bright green porch with hanging planters, a wooden chair, and a railing.

A brightly colored Caribbean house with a balcony, a sign indicating it's for rent, and bicycles parked outside.

A bar area with a wooden counter, colorful decorations, and a sign with motivational ocean-themed text.

A marina with multiple boats docked, wooden pilings, and a dock with ropes.

20. Caribbean House

Bahama Village, 0.4 km from Jackson Square

David

HK$930

HK$1,242 total

includes taxes & fees

13 Sept - 14 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 1,016 reviews	View
The Gardens Hotel	9.8 Exceptional 1,000 reviews	View
The Marquesa Hotel	9.8 Exceptional 1,004 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,015 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 651 reviews	View

Top Jackson Square Hotel Reviews

Pier House Resort & Spa

10/10 Excellent

"What a great resort! Everything you need from a beach resort and more. The beautiful beach with NO sargassum. Clean, well maintained pool and common areas. Friendly staff. Delicious food and drinks. One of the best places I've ever stayed."

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"We've stayed here before and really enjoyed it. The property location is great walking to Duval Street and other restaurants around. The rooms were clean, the bed was pretty comfortable. Free espresso pods available in the rooms, I think I saw some tea too. There are 2 coffee shops in a 3-5 minute walking distance too. Bottles of water (to purchase) but the pool has a water machine. 2/3 pools open (the main one closed for renovations) but with music, the vibe was fun. There are also fun daily activities. The cafe is located right on the beach, which is nice, but sadly the smell of old, wet seaweed is off- putting, Front desk staff were friendly and accomodating ( we were able to check in an hour earlier - granted it's not in season). Only downfall is the expensive overnight parking fee!"

Opal Key Resort & Marina, Key West

10/10 Excellent

"Beautiful resort right on the water and very close to everything. Super clean room and hotel, professional and very friendly staff. Huge pool, restaurant and multiple bars on site. We loved our stay!"

Winslow's Bungalows - Key West Historic Inns

8/10 Good

"Check in was very easy and the front desk staff was very friendly. I loved the landscaping of the grounds and how each dwelling felt private and secluded. Our bungalow was nice. I wish there was a coffee maker in the room though, that was a little disappointing. The free breakfast was better than I expected with lots of things to choose from. The bartenders were super friendly and the bar/pool area was relaxing. We were able to easily walk anywhere we wanted to go and we could be on Duval Street in less than 10 minutes. There was also a CVS about 1/2 a block away for any things you need to pick up. I would definitely want to stay here again and I would recommend to anyone else visiting Key West."

Duval House

10/10 Excellent

"Cold rooms!"

The Gardens Hotel

10/10 Excellent

"This was our first time at the Garden House and we LOVED it! Everything about the place was outstanding. So much, that we booked again to stay there in October, 2026. The staff, drinks, food, grounds....Everything is just wonderful.l"

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"Loved the stay. Definitely will be back"

Duval Inn

10/10 Excellent

"The location is great. Close to Duval street, but didn’t hear any noise! Staff was welcoming & accommodating. Pool area is adorable! Breakfast was great, lots to choose from. The room, clean & bed comfy! One of favorites so far, we will return!"

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

Key West Jackson Square Hotels

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. The Gardens Hotel

3. The Marquesa Hotel

4. Orchid Key Inn - Adults Only

5. H2O Suites - Adults Only

6. Island City House Hotel

7. Douglas House - Adults Only

8. Duval House

9. The Grand Guesthouse

10. Santa Maria Suites

11. Silver Palms Inn & Historic Homes

12. Southernmost House - Adult Exclusive

13. Ambrosia Key West

14. Weatherstation Inn

15. Ella's Cottages - Key West Historic Inns

16. Marrero's Guest Mansion

17. Authors of Key West Guest House

18. Heron House - Adult Only

19. Alexander Palms Court

20. Caribbean House

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Pier House Resort & Spa

Southernmost Beach Resort and Guesthouses

Opal Key Resort & Marina, Key West

Winslow's Bungalows - Key West Historic Inns

Duval House

The Gardens Hotel

Hyatt Centric Key West Resort and Spa

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