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 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.

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

P11,480

P12,915 total

includes taxes & fees

Sep 30 - Oct 1

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

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

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.

2. Orchid Key Inn - Adults Only

Uptown - Upper Duval, 0.6 km from Jackson Square

Nicholas

P11,492

P12,929 total

includes taxes & fees

Sep 30 - Oct 1

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

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.

A couple walking along a poolside pathway surrounded by lush greenery.

3. The Gardens Hotel

Downtown Key West, 0.3 km from Jackson Square

Forrest

P16,341

P18,384 total

includes taxes & fees

Oct 1 - Oct 2

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 pool area with a clear view of a house in the background, surrounded by palm trees and greenery.

4. Simonton Court Historic Inn & Cottages

Historic Seaport, 0.4 km from Jackson Square

William

P10,570

P11,891 total

includes taxes & fees

Sep 30 - Oct 1

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 pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.

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.

5. Alexander's Guesthouse - Adult Exclusive

Old Town Key West, 1.1 km from Jackson Square

Nestor

P13,556

P17,822 total

includes taxes & fees

Oct 4 - Oct 5

A porch with a white railing, a bench, and a flag.

A spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.

A living room with a sofa, a glass coffee table, a TV, and a painting on the wall.

A two-story white house with green shutters, a wooden door, and a white picket fence.

6. The Conch House Heritage Inn

Old Town Key West, 0.7 km from Jackson Square

John

P11,845

P13,326 total

includes taxes & fees

Sep 30 - Oct 1

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

A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.

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

7. The Marquesa Hotel

Old Town Key West, 0.3 km from Jackson Square

Darrell

P16,806

P22,421 total

includes taxes & fees

Sep 30 - Oct 1

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.

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

8. H2O Suites - Adults Only

Uptown - Upper Duval, 1 km from Jackson Square

Corey

P17,431

P23,826 total

includes taxes & fees

Sep 30 - Oct 1

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.

9. Douglas House - Adults Only

Uptown - Upper Duval, 0.8 km from Jackson Square

michael

P8,351

P10,334 total

includes taxes & fees

Sep 30 - Oct 1

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.

10. Duval House

Downtown Key West, 0.4 km from Jackson Square

Christopher

P6,185

P8,301 total

includes taxes & fees

Sep 30 - Oct 1

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

A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

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 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.

11. Tropical Inn

Downtown Key West, 0.4 km from Jackson Square

Natalie

P7,686

P10,208 total

includes taxes & fees

Oct 1 - Oct 2

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 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.

12. The Grand Guesthouse

Old Town Key West, 1.2 km from Jackson Square

Travis

P7,048

P9,491 total

includes taxes & fees

Sep 30 - Oct 1

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

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

13. Island City House Hotel

Historic Seaport, 0.6 km from Jackson Square

Osvaldo

P13,942

P15,685 total

includes taxes & fees

Oct 25 - Oct 26

A room with a bed, a ceiling fan, and a window with blinds.

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

A room with a yellow armchair, a glass coffee table, and a view of a wooden deck and tropical plants.

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

14. The Mermaid & Alligator

Old Town Key West, 0.8 km from Jackson Square

Adam

P11,246

P12,651 total

includes taxes & fees

Sep 30 - Oct 1

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.

15. Santa Maria Suites

Uptown - Upper Duval, 1.2 km from Jackson Square

Anthony

P15,556

P21,718 total

includes taxes & fees

Sep 30 - Oct 1

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.

16. Southernmost House - Adult Exclusive

Uptown - Upper Duval, 1.1 km from Jackson Square

yessy

P8,703

P17,698 total

includes taxes & fees

Oct 25 - Oct 26

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 garden with a stone pathway, a wooden fence, and various tropical plants.

A yellow building with a door marked '7'.

17. Alexander Palms Court

Casa Marina, 1.2 km from Jackson Square

Andrew

P7,450

P8,382 total

includes taxes & fees

Sep 30 - Oct 1

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.

A hotel with a pool, bicycles, and lush greenery.

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.

18. Silver Palms Inn & Historic Homes

Old Town Key West, 0.9 km from Jackson Square

sam

P5,567

P10,480 total

includes taxes & fees

Sep 30 - Oct 1

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

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.

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.

19. Ambrosia Key West

Old Town Key West, 0.4 km from Jackson Square

Tricia

P8,387

P9,436 total

includes taxes & fees

Sep 30 - Oct 1

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

20. Weatherstation Inn

Truman Annex, 0.3 km from Jackson Square

Svetlana

P10,570

P11,891 total

includes taxes & fees

Oct 1 - Oct 2

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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 1,007 reviews	View
Orchid Key Inn - Adults Only	9.8 Exceptional 1,005 reviews	View
The Gardens Hotel	9.8 Exceptional 1,005 reviews	View
Simonton Court Historic Inn & Cottages	9.8 Exceptional 1,001 reviews	View
Alexander's Guesthouse - Adult Exclusive	9.8 Exceptional 170 reviews	View

Top Jackson Square Hotel Reviews

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"We had a wonderful stay at Hyatt Centric Key West Resort & Spa! The pool was a perfect place to relax, and we especially loved seeing the rescued turtles - such a unique and memorable part of the property. The location could not be better: everything we wanted to explore in Key West was within easy walking distance. It was incredibly convenient to enjoy the sights, restaurants, and lively atmosphere without needing a car. We would gladly stay here again!"

The Cabana Inn Key West - Adults Only

10/10 Excellent

"This hotel has become my go-to place in KW! Great location and well maintained. In fact, there was always someone cleaning/repairing. The day manager Sayed Ali went way above and beyond to be helpful. I highly recommend"

La Concha Key West, Autograph Collection

10/10 Excellent

"Hotel is very conveniently located to old town Key West. The renovations that have been made to the hotel really make it a very fun place to stay."

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"A+"

The Gardens Hotel

10/10 Excellent

"It is a GREAT property in Key West, right in the center of the action."

Duval House

10/10 Excellent

"*"

Winslow's Bungalows - Key West Historic Inns

8/10 Good

"Good location, walking distance to most of the Old Town. Good breakfast. Lots of outdoor furniture for lounging under tropical trees. Most rooms have covered decks with outdoor furniture so you can still be outdoors if you're waiting out a rainstorm. My bathroom floor needed mopping before I got there."

Ocean Key Resort - A Noble House Resort

10/10 Excellent

"Loved the decor! The lobby, lobby bar and deck were so cute! I specially picked this resort and the room fur the decor-very tropical and fabulous! But honestly, the staff is what made this resort so great! From the front desk, to concierge, to the staff at Hot Tin Roof, to the pool bartender/ they all went above and beyond!"

Pier House Resort & Spa

10/10 Excellent

"Great location and superb private beach"

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 search for that perfect souvenir at We Cycle Key West during your trip to 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 stay in 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 biking trails.

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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.

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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.

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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 biking. If you're looking for a convenient place to stay, check out the 1672 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 1672 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.

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

Check prices for these dates

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Our top choices for Jackson Square hotels

1. Almond Tree Inn Hotel - Adults Only

2. Orchid Key Inn - Adults Only

3. The Gardens Hotel

4. Simonton Court Historic Inn & Cottages

5. Alexander's Guesthouse - Adult Exclusive

6. The Conch House Heritage Inn

7. The Marquesa Hotel

8. H2O Suites - Adults Only

9. Douglas House - Adults Only

10. Duval House

11. Tropical Inn

12. The Grand Guesthouse

13. Island City House Hotel

14. The Mermaid & Alligator

15. Santa Maria Suites

16. Southernmost House - Adult Exclusive

17. Alexander Palms Court

18. Silver Palms Inn & Historic Homes

19. Ambrosia Key West

20. Weatherstation Inn

Compare popular hotels close to Jackson Square

Top Jackson Square Hotel Reviews

Hyatt Centric Key West Resort and Spa

The Cabana Inn Key West - Adults Only

La Concha Key West, Autograph Collection

Southernmost Beach Resort and Guesthouses

The Gardens Hotel

Duval House

Winslow's Bungalows - Key West Historic Inns

Ocean Key Resort - A Noble House Resort

Pier House Resort & Spa

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