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

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Check prices for these dates

Tonight
23 Sep - 24 Sep
Tomorrow
24 Sep - 25 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

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

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Downtown Key West, 0.6 km from Jackson Square
United States
John
4.585.144 ₫
5.158.287 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Almond Tree Inn Hotel - Adults Only
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 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

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.6 km from Jackson Square
United States
Nicholas
6.274.818 ₫
7.059.170 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Orchid Key Inn - Adults Only
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 colonial-style building with a porch, surrounded by lush tropical vegetation.

3. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.3 km from Jackson Square
United States
Forrest
5.828.986 ₫
6.557.609 ₫ total
includes taxes & fees
30 Sept - 1 Oct
The Gardens Hotel
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 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.

4. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.3 km from Jackson Square
United States
Darrell
5.948.330 ₫
8.155.183 ₫ total
includes taxes & fees
24 Sept - 25 Sept
The Marquesa Hotel
A porch with a white railing, a bench, and a flag.
A pool area with lounge chairs and a dining table, surrounded by palm trees and a house with a porch.
A living room with a sofa, a glass coffee table, a TV, and a painting on the wall.
A spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.

5. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 0.7 km from Jackson Square
United States
John
4.620.264 ₫
5.197.797 ₫ total
includes taxes & fees
5 Oct - 6 Oct
The Conch House Heritage Inn
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
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.
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.

6. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West, 1.1 km from Jackson Square
United States
Nestor
2.321.839 ₫
3.587.729 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Alexander's Guesthouse - Adult Exclusive
A gated entrance to Villas Key West with a brick pathway leading to the gate.
A house with a porch, a table, and a door with a number '6'.
A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

7. Key West Villas

Key West Villas
Downtown Key West, 0.3 km from Jackson Square
United States
Margaret
Key West Villas
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.
A modern hotel room with a bed, sofa, coffee table, and artwork.

8. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1 km from Jackson Square
United States
Kourosh
7.258.185 ₫
9.921.472 ₫ total
includes taxes & fees
27 Sept - 28 Sept
H2O Suites - Adults Only
A bedroom with a four-poster bed, a wooden desk, wicker chairs, and a view of the outdoors.
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.
A pool area with lounge chairs and candles, surrounded by palm trees and a building in the background.

9. Tropical Inn

Tropical Inn
Downtown Key West, 0.4 km from Jackson Square
United States
Molly
2.509.667 ₫
3.473.783 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Tropical Inn
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 garden with a pond, rocks, and various plants.

10. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.6 km from Jackson Square
United States
Osvaldo
Island City House Hotel
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.
A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.
A wooden deck with lush greenery and a pool area.

11. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 0.8 km from Jackson Square
United States
michael
2.654.178 ₫
3.284.546 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Douglas House - Adults Only
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

The Grand Guesthouse
Old Town Key West, 1.2 km from Jackson Square
United States
Alissa
2.935.446 ₫
3.952.877 ₫ total
includes taxes & fees
28 Sept - 29 Sept
The Grand Guesthouse
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 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.

13. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 km from Jackson Square
United States
Brian
The Mermaid & Alligator
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.
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.

14. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.8 km from Jackson Square
United States
Tricia
3.024.243 ₫
3.402.273 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Westwinds Inn
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.

15. Duval House

Duval House
Downtown Key West, 0.4 km from Jackson Square
United States
Anne
2.810.160 ₫
3.720.861 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Duval House
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 two-story yellow house with a porch, white railings, and green shutters.
A hotel with a pool, bicycles, and lush greenery.

16. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 km from Jackson Square
United States
sam
2.083.802 ₫
4.100.485 ₫ total
includes taxes & fees
28 Sept - 29 Sept
Silver Palms Inn & Historic Homes
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.
A garden with a stone pathway, a wooden fence, and various tropical plants.
A yellow building with a door marked '7'.
A room with a bed, a desk, a chair, a lamp, a painting of a boat on water, and a view of the sea.

17. Alexander Palms Court

Alexander Palms Court
Casa Marina, 1.2 km from Jackson Square
United States
Andrew
3.102.289 ₫
3.490.173 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Alexander Palms Court
A wooden deck with wicker furniture and a white railing, surrounded by lush tropical vegetation.
A swimming pool with a white picket fence, surrounded by lounge chairs and potted plants.
A pathway leading to a building with a white facade, surrounded by lush greenery and palm trees.
A breakfast tray with croissants, orange juice, and coffee on a table by a window with a view of a pool and greenery.

18. Weatherstation Inn

Weatherstation Inn
Truman Annex, 0.3 km from Jackson Square
United States
Svetlana
4.397.380 ₫
4.947.053 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Weatherstation Inn
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 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.

19. Ambrosia Key West

Ambrosia Key West
Old Town Key West, 0.4 km from Jackson Square
United States
Tricia
3.492.513 ₫
3.929.078 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Ambrosia Key West
A gated entrance with lush green foliage and a white picket fence.
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.
A hotel room with a large bed, two bedside tables, a ceiling fan, and two framed pictures on the wall.

20. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.1 km from Jackson Square
3.492.514 ₫
3.929.046 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Coco Plum Inn
View all properties

Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only
10.0
Exceptional
1,006 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,002 reviews
View
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
The Gardens Hotel
9.8
Exceptional
1,002 reviews
View
A two-story house with a covered porch, a brick pathway, and a large tree.
The Marquesa Hotel
9.8
Exceptional
1,001 reviews
View
A porch with a white railing, a bench, and a flag.
The Conch House Heritage Inn
9.8
Exceptional
189 reviews
View

Top Jackson Square Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"The resort was well maintained, the staff very friendly, the beach, pool and restaurant made for an amazing vacation."
Cheryl 5-night trip
Posted 2 hours ago
Pier House Resort & Spa
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"Don’t spend the extra money for oceanfront or expect to use the beach if you are traveling from April - October. Beach was closed and very stinky. Staff says it happens every year during those months. Most areas of the resort you couldn’t smell it except the cafe and the part of the resort near the ocean. Large pool was also closed but they said that was an emergency repair. Overall, helpful staff and good property. Would stay again but wouldn’t stay on that side of the resort."
Jennifer 4-night trip
Posted 4 hours ago
Southernmost Beach Resort and Guesthouses
The Gardens Hotel

The Gardens Hotel

10/10 Excellent
"Beautiful place, very nice pool, nice spacious rooms. Wonderful staff."
Valerie 4-night trip
Posted 5 hours ago
The Gardens Hotel
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"This property was the perfect spot for seeing all of Key West. We had a brief problem with our door and the team was so responsive and apologetic and offered things to make it right. Have already recommended to friends and family in the 24hrs of being home."
Tammi 3-night trip
Posted 16 hours ago
Winslow's Bungalows - Key West Historic Inns
Heron House - Adult Only

Heron House - Adult Only

8/10 Good
"It was all about location for me"
Levi 3-night trip
Posted 17 hours ago
Heron House - Adult Only
Duval House

Duval House

10/10 Excellent
"Loved the chilled pool!"
Alicia 4-night trip
Posted 2 days ago
Duval House
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"Great stay. Clean and well Maintained. Friendly staff."
ALEASE 3-night trip
Posted 2 days ago
The Cabana Inn Key West - Adults Only
Douglas House - Adults Only

Douglas House - Adults Only

10/10 Excellent
"We spent a weekend at Douglas House. Very convenient. The staff was amazing and very knowledgeable. We will stay there again"
Penny 1-night trip
Posted 2 days ago
Douglas House - Adults Only
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"Always love staying at the Opal."
SHANNON 6-night trip
Posted 2 days ago
Opal Key Resort & Marina, Key West

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)
With a visit to Duval Street, a favourite shopping spot in Key West, you can find the perfect gifts to bring home. Wander the seaside or discover the area's beautiful sunsets.
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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.
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.