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

Key West Hotel Guide - Jackson Square hotels in Key West, United States of America.

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Check prices for these dates

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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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 building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.
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

Almond Tree Inn Hotel - Adults Only
Downtown Key West, 0.6 km from Jackson Square
United States
Michelle
€161
includes taxes & fees
30 Aug - 31 Aug
Almond Tree Inn Hotel - Adults Only
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 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 building with a neon sign that reads "Orchid Key Inn."

2. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.6 km from Jackson Square
United States
Nicholas
€168
includes taxes & fees
30 Aug - 31 Aug
Orchid Key Inn - Adults Only
A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.
A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.
A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.
A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

3. Artist House Key West

Artist House Key West
Historic Seaport, 0.3 km from Jackson Square
United States
NATHAN
€141
includes taxes & fees
10 Sept - 11 Sept
Artist House Key West
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 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.

4. The Gardens Hotel

The Gardens Hotel
Downtown Key West, 0.3 km from Jackson Square
United States
Salvatore
€194
includes taxes & fees
31 Aug - 1 Sept
The Gardens Hotel
A modern interior with a staircase, a sofa set, a wooden table, and a television.
A pathway flanked by lush green foliage leading to a gated entrance.
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.

5. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Historic Seaport, 0.4 km from Jackson Square
United States
Robin
€124
includes taxes & fees
26 Aug - 27 Aug
Simonton Court Historic Inn & Cottages
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 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.

6. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West, 0.8 km from Jackson Square
United States
Johnny
€189
includes taxes & fees
30 Aug - 31 Aug
The Mermaid & Alligator
A tropical outdoor area with palm trees, hanging plants, and string lights.
A wooden deck with lush greenery and a pool area.
An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.
A large, two-story building with a balcony, surrounded by dense tropical foliage.

7. Douglas House - Adults Only

Douglas House - Adults Only
Uptown - Upper Duval, 0.8 km from Jackson Square
United Kingdom
Dylan
€83
includes taxes & fees
7 Sept - 8 Sept
Douglas House - Adults Only
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 pool area with lounge chairs and a dining table, surrounded by palm trees and a house with a porch.

8. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West, 0.7 km from Jackson Square
United States
John
€160
includes taxes & fees
26 Aug - 27 Aug
The Conch House Heritage Inn
A modern outdoor area with a pool, lounge chairs, and a bar area.
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.
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.

9. H2O Suites - Adults Only

H2O Suites - Adults Only
Uptown - Upper Duval, 1 km from Jackson Square
United States
Shermeka
€327
includes taxes & fees
7 Sept - 8 Sept
H2O Suites - Adults Only
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 poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.
A covered porch with white wicker furniture and a blue floor, surrounded by lush tropical plants.

10. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West, 0.3 km from Jackson Square
United States
Darrell
€266
includes taxes & fees
8 Sept - 9 Sept
The Marquesa Hotel
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.
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.

11. Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Old Town Key West, 1.1 km from Jackson Square
United States
Jaime
€121
includes taxes & fees
25 Aug - 26 Aug
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
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 lush garden with a variety of tropical plants and a paved walkway.

12. Duval House

Duval House
Downtown Key West, 0.4 km from Jackson Square
United States
Melissa
€117
includes taxes & fees
31 Aug - 1 Sept
Duval House
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.

13. Island City House Hotel

Island City House Hotel
Historic Seaport, 0.6 km from Jackson Square
United States
Paul
€163
includes taxes & fees
31 Aug - 1 Sept
Island City House Hotel
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.

14. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West, 1.2 km from Jackson Square
United States
Travis
€129
includes taxes & fees
25 Aug - 26 Aug
The Grand Guesthouse
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 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.

15. Tropical Inn

Tropical Inn
Downtown Key West, 0.4 km from Jackson Square
United States
Joel
€146
includes taxes & fees
27 Aug - 28 Aug
Tropical Inn
A pool area with lounge chairs and palm trees.
A sign for Santa Maria Resort surrounded by lush greenery 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.

16. Santa Maria Suites

Santa Maria Suites
Uptown - Upper Duval, 1.2 km from Jackson Square
United States
Nila
€327
includes taxes & fees
25 Aug - 26 Aug
Santa Maria Suites
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 exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.
The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.

17. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 km from Jackson Square
United States
Shawn
€131
includes taxes & fees
25 Aug - 26 Aug
Silver Palms Inn & Historic Homes
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 two-story house with a white exterior, a green roof, and a staircase leading to the upper floor.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.

18. Westwinds Inn

Westwinds Inn
Historic Seaport, 0.8 km from Jackson Square
United States
Karen
€128
includes taxes & fees
31 Aug - 1 Sept
Westwinds Inn
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 swimming pool with lounge chairs, a covered deck, and a view of lush greenery.
A white colonial-style building with a balcony, surrounded by palm trees and a white picket fence.

19. Coco Plum Inn

Coco Plum Inn
Downtown Key West, 0.1 km from Jackson Square
United States
Jake
€144
includes taxes & fees
30 Aug - 31 Aug
Coco Plum Inn
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 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.

20. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.1 km from Jackson Square
United States
Mark
€243
includes taxes & fees
13 Sept - 14 Sept
Southernmost House - Adult Exclusive
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
1,021 reviews
View
A pool area with lounge chairs and a table, surrounded by palm trees.
Orchid Key Inn - Adults Only
9.8
Exceptional
1,019 reviews
View
A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.
Artist House Key West
9.8
Exceptional
452 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
1,005 reviews
View
A modern interior with a staircase, a sofa set, a wooden table, and a television.
Simonton Court Historic Inn & Cottages
9.8
Exceptional
1,005 reviews
View

Top Jackson Square Hotel Reviews

Tranquility Guest House

Tranquility Guest House

8/10 Good
"Nice place. Very quiet and peaceful. Some minor amenities would be helpful (coffee pot in the room, ice machine)."
Richard 3-night trip
Posted less than an hour ago
Tranquility Guest House
Duval House

Duval House

10/10 Excellent
"Our stay was perfect. Convenient to Duval Street. The staff was very helpful."
Jason 4-night trip
Posted less than an hour ago
Duval House
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

8/10 Good
"Everything was great, however, the AC in our room was very loud. I asked my friends and it wasn’t the same for them. We stayed in one of the ocean view room. By the way, the view was great!! Excellent room to watch the beautiful sunset."
Gustavo 1-night trip
Posted less than an hour ago
Opal Key Resort & Marina, Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"We thoroughly enjoyed our stay at Pier House. The location can't be beat--walking distance to most attractions, and golf carts are available onsite for going farther, such as Fort Zachary Taylor. We were treated with complete attention to any of our requests and questions. We typically select a resort with at least a guest laundry, if no in-room washer/dryer, but the laundry service was efficient and reasonably priced. The daily refreshing of linens was nice--seems like that has to be requested at many resorts now or is only after a few nights. They did a good job keeping the sargassum out of the Pier House swimming area and off the beach. Several of the ice machines didn't work, minor inconvenience. We would absolutely stay there again."
Rita 5-night trip
Posted 3 hours ago
Pier House Resort & Spa
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"The pool had fun activities all the days we were there. The food was really good at the restaurant on site."
Lauren 4-night trip
Posted 13 hours ago
Southernmost Beach Resort and Guesthouses
Coco Plum Inn

Coco Plum Inn

10/10 Excellent
"Excellent will definitely come back"
Zenaida 4-night trip
Posted 18 hours ago
Coco Plum Inn
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"Beautiful stay, spacious room. Pool was refreshing and clean. Quiet place with friendly staff. Close to everything."
George P 2-night trip
Posted 1 day ago
Heron House - Adult Only
The Gardens Hotel

The Gardens Hotel

10/10 Excellent
"Tortoises on property blew me away! Along with beautiful pool area. 4 poster king bed. Huge bathroom with spa tub and rain shower. Every member of the staff was super friendly and accommodating. Awesome poolside bar with live music during happy hour. Looking forward to our next trip here.....which we've already booked. Wish I would've found this place years ago."
Eldon 3-night trip
Posted 2 days ago
The Gardens Hotel
Marrero's Guest Mansion

Marrero's Guest Mansion

10/10 Excellent
"Awesome place to stay!"
Michael 4-night trip
Posted 7 days ago
Marrero's Guest Mansion

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.
See properties
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.
See properties

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 1677 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 1677 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 Donkey Milk House 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.

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