The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

Hotels near Jackson Square Key West

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Where to stay near Jackson Square?

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

1. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Colleen

$192

$272 total

includes taxes & fees

Sep 28 - Sep 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 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.

2. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

Jim

$163

$183 total

includes taxes & fees

Sep 14 - Sep 15

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.

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

3. H2O Suites - Adults Only

Uptown - Upper Duval, 1 km from Jackson Square

Barton

$279

$381 total

includes taxes & fees

Sep 13 - Sep 14

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

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.

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

4. Duval House

Downtown Key West, 0.4 km from Jackson Square

Wendy S

$99

$133 total

includes taxes & fees

Sep 16 - Sep 17

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

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

5. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

kenneth

$174

$196 total

includes taxes & fees

Sep 13 - Sep 14

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 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.

6. Coco Plum Inn

Downtown Key West, 0.1 km from Jackson Square

julie

$152

$171 total

includes taxes & fees

Sep 14 - Sep 15

A white building with green shutters and a white picket fence.

A modern kitchen with white cabinetry, a central island, and a view of the outdoors.

A pool area with lounge chairs, a small table, and a thatched umbrella.

A hotel room with a large bed, a sitting area, and multiple bookshelves filled with books.

7. Ridley House - Key West Historic Inns

Historic Seaport, 0.5 km from Jackson Square

Rosa

$200

$276 total

includes taxes & fees

Sep 13 - Sep 14

A pool area with a wooden deck, lounge chairs, and umbrellas.

A wooden signboard with the text "The Key West Hotel" and "COME HIDE" on a brick pathway surrounded by lush greenery.

An outdoor bar area with a thatched roof, multiple seating arrangements, and a pool in the background.

A hotel sign with the text "The Key West Hotel" and "COME HIDE" in gold lettering.

8. The Key West Hotel

Historic Seaport, 0.3 km from Jackson Square

Deborah S.

$321

$434 total

includes taxes & fees

Sep 13 - Sep 14

A poolside area with lounge chairs, a small pool, and a white building with a balcony.

A white building with a sign reading "The StarCare Inn" and a "No Vacancies" sign.

A pool area with lounge chairs, a hot tub, and a deck with a railing.

A bedroom with a bed, a ceiling fan, a window with blinds, a painting, and a nightstand with a lamp.

9. Seascape Tropical Inn - Adult Exclusive

Downtown Key West, 0.5 km from Jackson Square

Diana

$119

$185 total

includes taxes & fees

Sep 25 - Sep 26

A two-story building with a porch, a front door, and a mailbox.

A swimming pool with a wooden deck and metal handrails, surrounded by lush greenery and potted plants.

A living room with a ceiling fan, a sofa, a TV, and a bookshelf.

A bedroom with a bed, bedside tables, a dresser, a mirror, and a window with curtains.

10. The Independent Inn - Formerly Heron House Court

Historic Seaport, 1 km from Jackson Square

Jose

$106

$152 total

includes taxes & fees

Sep 13 - Sep 14

A dining table with plates of food, a drink, and a view of a pool and palm trees.

A beach with a palm tree and two chairs.

A person standing by a window overlooking a beach with palm trees and the ocean.

A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

11. Margaritaville Beach House Key West

3.2 km from Jackson Square

Paraskevi

$178

$263 total

includes taxes & fees

Sep 28 - Sep 29

A swimming pool with clear water, surrounded by lush greenery and palm trees.

A yellow building with a blue door and shutters, a number '302' on the wall, and a small porch area.

A bathroom with a white sink, three bottles of body lotion, and a white towel.

A covered porch with white columns and wicker furniture.

12. Tranquility Guest House

Bahama Village, 0.3 km from Jackson Square

"We had a great stay. If you're looking for a quiet place of of Duval, I highly recommend this place. It's not a fancy place but the rooms are clean, the beds are comfortable and the pool is lovely. The location is fantastic! Walking distance to several nice restaurants and bars. Stores nearby. The hosts communicate very well. Anything we needed, they were on it right away with a text and let us know when to expect them. We will be booking here for our future stays."

Dianna

$67

$164 total

includes taxes & fees

Sep 16 - Sep 17

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

A spacious lobby with green sofas, a coffee table, and a dining area.

A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

13. Casa Marina Key West, Curio Collection by Hilton

Casa Marina, 1.6 km from Jackson Square

Taylor

$227

$323 total

includes taxes & fees

Sep 22 - Sep 23

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.

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

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.

14. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 0.6 km from Jackson Square

mario

$163

$183 total

includes taxes & fees

Sep 15 - Sep 16

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 couple walking along a poolside pathway surrounded by lush greenery.

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

15. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Daniel

$190

$214 total

includes taxes & fees

Sep 21 - Sep 22

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

16. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

Craig

$90

$111 total

includes taxes & fees

Sep 15 - Sep 16

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 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.

17. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Harriett C

$128

$169 total

includes taxes & fees

Sep 13 - Sep 14

A pool area with lounge chairs and palm trees.

A sign for Santa Maria Resort surrounded by lush greenery 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.

18. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

"My husband and I stayed at this hotel in April, and we had a wonderful experience. The room was clean, comfortable, and well-maintained, and the staff was friendly and welcoming throughout our stay. We especially appreciated the excellent customer service and the relaxing atmosphere. The location was convenient, and everything we needed was easily accessible. The hotel exceeded our expectations and made our trip even more enjoyable. We would definitely stay here again and highly recommend it...

Rebecca

$279

$381 total

includes taxes & fees

Sep 13 - Sep 14

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 hotel with a pool, bicycles, and lush greenery.

19. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

Dennis

$89

$168 total

includes taxes & fees

Sep 13 - Sep 14

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

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.

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

20. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

Mary Anne

$149

$294 total

includes taxes & fees

Oct 1 - Oct 2

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Compare popular hotels close to Jackson Square

Property	Property class	Guest rating
The Marquesa Hotel	9.8 Exceptional 1,000 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,000 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 652 reviews	View
Duval House	9.6 Exceptional 1,092 reviews	View
Island City House Hotel	9.6 Exceptional 999 reviews	View

Other landmarks 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)

San Carlos Institute - Casa Cuba is just one of the attractions in Old Town Key West, Key West so you might want to stop by during your trip. Why not take a stroll along the beaches and watch the sunset while you're here? If you want to experience more of the culture Key West has to offer, head to Duval Street, Harry S. Truman Little White House, and Mel Fisher Maritime Museum.

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A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)

If you want to give your credit card some exercise, head out to Duval Street, a popular place for shoppers in Key West Historic District. Splash some more cash at We Cycle Key West and Mallory Dock.

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We Cycle Key West

We Cycle Key West is a famous shop in Old Town Key West and is definitely worth popping into during your stay in Key West. Splash some more cash at Duval Street and Mallory Dock.

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St. Paul's Episcopal Church

9.0/10 (73 reviews)

Key West Historic District is home to St. Paul's Episcopal Church, so why not stop by during your stay in Key West. Why not take a stroll along the beaches and watch the sunset while you're here?

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Key West Film Society

7.6/10 (9 reviews)

If you want to see a show while you're in town, try and grab some tickets at Key West Film Society in Key West Historic District. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy the show and want to see another, Waterfront Playhouse, Red Barn Theater, and The Key West Theater are all a short walk away.

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The Key West Theater

The Key West Theater is a venue in Key West Historic District. If you enjoy the show and want to see another, Waterfront Playhouse, Red Barn Theater, and Key West Film Society are all a short walk away.

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Red Barn Theater

8.0/10 (10 reviews)

If you want to see a show while you're in town, try and grab some tickets at Red Barn Theater in Key West Historic District. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy the show and want to see another, Waterfront Playhouse, Key West Film Society, and The Key West Theater are all a short walk away.

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Hellings House Museum

Hellings House Museum is just one of the attractions in Key West Historic District, Key West so you might want to stop by during your trip. If you want to experience more of the culture Key West has to offer, head to Mel Fisher Maritime Museum, Harry S. Truman Little White House, and Key West Shipwreck Museum.

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