Hotels near Jackson Square, Key West

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

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

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

Michelle

S$235

includes taxes & fees

23 Aug - 24 Aug

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

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

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

A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.

2. Key West Villas

Downtown Key West, 0.3 km from Jackson Square

Margaret

S$372

includes taxes & fees

3 Sept - 4 Sept

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 spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

3. The Mermaid & Alligator

Old Town Key West, 0.8 km from Jackson Square

Johnny

S$280

includes taxes & fees

24 Aug - 25 Aug

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

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

S$231

includes taxes & fees

23 Aug - 24 Aug

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 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.

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

Shermeka

S$485

includes taxes & fees

7 Sept - 8 Sept

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

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.

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

6. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Darrell

S$395

includes taxes & fees

8 Sept - 9 Sept

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

A narrow room with a bed, a potted plant, and a window with blinds.

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.

7. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Old Town Key West, 1.1 km from Jackson Square

Jaime

S$193

includes taxes & fees

22 Aug - 23 Aug

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 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.

8. Duval House

Downtown Key West, 0.4 km from Jackson Square

Melissa

S$173

includes taxes & fees

31 Aug - 1 Sept

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 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.

9. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Paul

S$245

includes taxes & fees

8 Sept - 9 Sept

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 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.

10. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Travis

S$225

includes taxes & fees

23 Aug - 24 Aug

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.

11. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

Nila

S$485

includes taxes & fees

23 Aug - 24 Aug

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.

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

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

12. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

Shawn

S$207

includes taxes & fees

25 Aug - 26 Aug

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

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.

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

13. Authors of Key West Guest House

The Meadows, 1.2 km from Jackson Square

Kasi

S$122

includes taxes & fees

23 Aug - 24 Aug

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

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

14. Marrero's Guest Mansion

Downtown Key West, < 0.1 km from Jackson Square

Michael

S$313

includes taxes & fees

31 Aug - 1 Sept

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

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

15. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Jenina

S$270

includes taxes & fees

24 Aug - 25 Aug

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

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

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

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

16. Heron House - Adult Only

Downtown Key West, 0.3 km from Jackson Square

Lindsay

S$198

includes taxes & fees

26 Aug - 27 Aug

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

A yellow building with a door marked '7'.

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.

17. Alexander Palms Court

Casa Marina, 1.2 km from Jackson Square

Julianne

S$243

includes taxes & fees

3 Sept - 4 Sept

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

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

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

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

18. Opal Key Resort & Marina, Key West

Old Town Key West, 0.5 km from Jackson Square

Melissa

S$420

includes taxes & fees

30 Aug - 31 Aug

A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

A marina with various boats docked, including a green and white boat named 'Jolly Roger'.

A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

A tropical setting with palm trees and a building with a white facade and dark roof.

19. The Marker Key West Harbor Resort

Historic Seaport, 0.7 km from Jackson Square

Danny Lee

S$319

includes taxes & fees

1 Sept - 2 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.

20. Caribbean House

Bahama Village, 0.4 km from Jackson Square

William

S$207

includes taxes & fees

23 Aug - 24 Aug

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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 1,020 reviews	View
Key West Villas	9.8 Exceptional 275 reviews	View
The Mermaid & Alligator	9.8 Exceptional 313 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,017 reviews	View
H2O Suites - Adults Only	9.8 Exceptional 641 reviews	View

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

8/10 Good

"Parking and resort fees expensive for what you get."

Duval House

10/10 Excellent

"Fantastic location with parking. The property is like no other on Duval."

Hyatt Centric Key West Resort and Spa

8/10 Good

"The staff was friendly and we upgraded our room once we arrived (for a fee) and the room was great! I will say I was a little disappointed on the “beach”. There was a small access spot to the water which was very rocky and even had a sign to wear water shoes."

La Concha Key West, Autograph Collection

10/10 Excellent

"We had a wonderful stay at La Concha Hotel in Key West! The location on Duval Street was one of the biggest highlights..it was within perfect walking distance of so many of Key West’s attractions, restaurants, bars, and things to do, which made exploring the area incredibly convenient. Having onsite parking was also a huge benefit, especially in Key West where parking can be difficult to find. The hotel bar was excellent, and the staff throughout the hotel were incredibly friendly and welcoming. Overall, La Concha was a great choice for a Key West stay, especially if you want to be right in the heart of everything!"

Simonton Court Historic Inn & Cottages

10/10 Excellent

"Everything is amazing. Love this hotel"

Tranquility Guest House

10/10 Excellent

"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."

Marrero's Guest Mansion

10/10 Excellent

"Awesome place to stay!"

Opal Key Resort & Marina, Key West

10/10 Excellent

"This hotel was really truly excellent. We thoroughly enjoyed our stay."

Weatherstation Inn

10/10 Excellent

"Nice place"

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 1675 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 Hyatt Centric Key West Resort and Spa.

How many hotels can I expect to find close to Jackson Square?

Expedia has 1675 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, 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, Key West Historic Seaport and Fort Zachary Taylor Historic State Park 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.

Hotels near Jackson Square

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

2. Key West Villas

3. The Mermaid & Alligator

4. Orchid Key Inn - Adults Only

5. H2O Suites - Adults Only

6. The Marquesa Hotel

7. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

8. Duval House

9. Island City House Hotel

10. The Grand Guesthouse

11. Santa Maria Suites

12. Silver Palms Inn & Historic Homes

13. Authors of Key West Guest House

14. Marrero's Guest Mansion

15. Ambrosia Key West

16. Heron House - Adult Only

17. Alexander Palms Court

18. Opal Key Resort & Marina, Key West

19. The Marker Key West Harbor Resort

20. Caribbean House

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Southernmost Beach Resort and Guesthouses

Duval House

Hyatt Centric Key West Resort and Spa

La Concha Key West, Autograph Collection

Simonton Court Historic Inn & Cottages

Tranquility Guest House

Marrero's Guest Mansion

Opal Key Resort & Marina, Key West

Weatherstation 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