Top 10 Hotels Near 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 reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

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.

1. Almond Tree Inn Hotel - Adults Only

Downtown Key West, 0.6 km from Jackson Square

John

RM659

RM741 total

includes taxes & fees

30 Sept - 1 Oct

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

A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.

2. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Forrest

RM1,145

RM1,289 total

includes taxes & fees

26 Oct - 27 Oct

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 building with a neon sign that reads "Orchid Key Inn."

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.

3. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

Nicholas

RM659

RM741 total

includes taxes & fees

30 Sept - 1 Oct

A modern interior with a staircase, a sofa set, a wooden table, and a television.

A spacious room with a large bed, a sofa, a chair, a small table, and a television.

A courtyard with two green lounge chairs, a palm tree, and a building with a white facade and lattice window design.

A pathway flanked by lush green foliage leading to a gated entrance.

4. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.4 km from Jackson Square

William

RM771

RM868 total

includes taxes & fees

29 Sept - 30 Sept

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

5. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Osvaldo

RM627

RM706 total

includes taxes & fees

27 Sept - 28 Sept

A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.

A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden deck with a view of a lush garden and a pool.

A wooden door with glass panels, leading to an interior space with furniture and plants.

A cozy room with a wicker chair, a small table with a bottle and glasses, and a view of a yellow room through an open door.

6. Tropical Inn

Downtown Key West, 0.4 km from Jackson Square

Molly

RM394

RM545 total

includes taxes & fees

27 Sept - 28 Sept

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

A two-story building with a white picket fence, a mailbox, and a small tree in front.

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.

7. Duval House

Downtown Key West, 0.4 km from Jackson Square

Christopher

RM441

RM583 total

includes taxes & fees

5 Oct - 6 Oct

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

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.

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

8. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Alissa

RM460

RM620 total

includes taxes & fees

27 Sept - 28 Sept

A tropical outdoor area with palm trees, hanging plants, 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.

A large, two-story building with a balcony, surrounded by dense tropical foliage.

9. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

michael

RM513

RM635 total

includes taxes & fees

5 Oct - 6 Oct

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 cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.

10. The Mermaid & Alligator

Old Town Key West, 0.8 km from Jackson Square

Brian

RM734

RM826 total

includes taxes & fees

28 Sept - 29 Sept

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 pool area with a covered seating area, palm trees, and a small pavilion.

A room with a bed, a desk, a chair, a lamp, a painting of a boat on water, and a view of the sea.

11. Alexander Palms Court

Casa Marina, 1.2 km from Jackson Square

Andrew

RM487

RM547 total

includes taxes & fees

27 Sept - 28 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 cozy living room with a wooden ceiling, a sofa set, two side tables with lamps, and framed artwork on the wall.

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

12. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Tricia

RM549

RM617 total

includes taxes & fees

27 Sept - 28 Sept

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 hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.

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

13. Coco Plum Inn

Downtown Key West, 0.1 km from Jackson Square

Jake

RM548

RM616 total

includes taxes & fees

28 Sept - 29 Sept

A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.

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

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.

14. Westwinds Inn

Historic Seaport, 0.8 km from Jackson Square

Tricia

RM570

RM641 total

includes taxes & fees

27 Sept - 28 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.

15. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

sam

RM327

RM643 total

includes taxes & fees

28 Sept - 29 Sept

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 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.

16. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

yessy

RM569

RM1,157 total

includes taxes & fees

18 Oct - 19 Oct

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.

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

A living room with a spiral staircase, a sofa, a chair, a coffee table, and a view of an outdoor seating area.

17. Ella's Cottages - Key West Historic Inns

Old Town Key West, 0.5 km from Jackson Square

tracy

RM1,020

RM1,354 total

includes taxes & fees

6 Oct - 7 Oct

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

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

18. Marrero's Guest Mansion

Downtown Key West, < 0.1 km from Jackson Square

Michael

RM1,036

RM1,166 total

includes taxes & fees

29 Sept - 30 Sept

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

A hotel entrance with a sign reading "Heron House Office."

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.

19. Heron House - Adult Only

Downtown Key West, 0.3 km from Jackson Square

Fernando

RM475

RM670 total

includes taxes & fees

27 Sept - 28 Sept

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

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

RM411

RM564 total

includes taxes & fees

27 Sept - 28 Sept

View all properties

Compare popular hotels close to Jackson Square

Property	Property class	Guest rating
Almond Tree Inn Hotel - Adults Only	10.0 Exceptional 1,006 reviews	View
The Gardens Hotel	9.8 Exceptional 1,002 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,003 reviews	View
Simonton Court Historic Inn & Cottages	9.8 Exceptional 1,001 reviews	View
Island City House Hotel	9.6 Exceptional 999 reviews	View

Top Jackson Square Hotel Reviews

Douglas House - Adults Only

10/10 Excellent

"Unique boutique experience."

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"From before we arrived we already knew we chose the right place to stay! We had questions about parking our motorcycle on property and there was no hesitation to share information and also connect with us. The staff is great. We are recommending this location and properties to friends and family. Next time we’re in town, 100% this will be the place we stay. Location is great and the property is fun to explore. Thank you all for making our stay memorable!"

Duval House

10/10 Excellent

"Love the Duval House! Beautiful and lush tropical property with pool, very friendly staff, excellent continental breakfast in a great location."

Pier House Resort & Spa

8/10 Good

"La ubicacion es excelente, solo que el hotel esta un poco dejado, le falta cariño, pero el personal es muy atento y hemos tenido una muy buena estancia en Key West,"

Pegasus International Hotel

10/10 Excellent

"The hotel was located on duval street walking distance to everything Key West, the room was great and amenities were also great. Check in and out was easy and fast."

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"The facility was beautiful and the amenities were great! just keep in mind it is a walk to the seaport and the main part of Duval, which became a little too far to walk back in forth, which we knew it would be a walk when we booked it."

The Gardens Hotel

10/10 Excellent

"Beautiful place, very nice pool, nice spacious rooms. Wonderful staff."

Heron House - Adult Only

8/10 Good

"It was all about location for me"

The Cabana Inn Key West - Adults Only

10/10 Excellent

"Great stay. Clean and well Maintained. Friendly staff."

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 1672 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 1672 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 Red Barn Theater, Waterfront Playhouse and Key West Film Society.

Hotels near Jackson Square

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Treat yourself

Be picky

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Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

2. The Gardens Hotel

3. Orchid Key Inn - Adults Only

4. Simonton Court Historic Inn & Cottages

5. Island City House Hotel

6. Tropical Inn

7. Duval House

8. The Grand Guesthouse

9. Douglas House - Adults Only

10. The Mermaid & Alligator

11. Alexander Palms Court

12. Ambrosia Key West

13. Coco Plum Inn

14. Westwinds Inn

15. Silver Palms Inn & Historic Homes

16. Southernmost House - Adult Exclusive

17. Ella's Cottages - Key West Historic Inns

18. Marrero's Guest Mansion

19. Heron House - Adult Only

20. Caribbean House

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Douglas House - Adults Only

Winslow's Bungalows - Key West Historic Inns

Duval House

Pier House Resort & Spa

Pegasus International Hotel

Southernmost Beach Resort and Guesthouses

The Gardens Hotel

Heron House - Adult Only

The Cabana Inn Key West - Adults Only

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