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
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 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.
A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

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
€248
includes taxes & fees
11 Oct - 12 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 neon sign for Orchid Key Inn with a 'VACANCY' sign below it.

2. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Uptown - Upper Duval, 0.6 km from Jackson Square
United Kingdom
Lisa
€233
includes taxes & fees
12 Oct - 13 Oct
Orchid Key Inn - Adults Only
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.

3. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Uptown - Upper Duval, 1.1 km from Jackson Square
United States
yessy
€253
includes taxes & fees
25 Oct - 26 Oct
Southernmost House - Adult Exclusive
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.
A two-story yellow house with a porch, white railings, and green shutters.

4. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West, 0.9 km from Jackson Square
United States
sam
€222
includes taxes & fees
11 Oct - 12 Oct
Silver Palms Inn & Historic Homes
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.
A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

5. Eden House

Eden House
Historic Seaport, 0.9 km from Jackson Square
United States
Angie
€144
includes taxes & fees
11 Oct - 12 Oct
Eden House
A breakfast setup with wine bottles, fruits, and pastries on a tray by a door with a view of a staircase and greenery.
A spacious kitchen with wooden cabinets and a dining area with a round table and chairs.
A patio with sun loungers, a table with an umbrella, and potted plants.
A pool area with lounge chairs, a wicker basket, and a staircase leading to an upper level.

6. The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only
Downtown Key West, < 0.1 km from Jackson Square
United States
Donna
€211
includes taxes & fees
14 Oct - 15 Oct
The Cabana Inn Key West - Adults Only
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.
A person standing by a window overlooking a beach with palm trees and the ocean.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

7. Margaritaville Beach House Key West

Margaritaville Beach House Key West
3.2 km from Jackson Square
United States
Richard
€266
includes taxes & fees
15 Oct - 16 Oct
Margaritaville Beach House Key West
A hotel with a swimming pool, balconies, and a view of the sea.
A balcony with a view of the ocean, a table, chairs, and a railing.
A marina with jet skis docked in front of a hotel with a dock and a boat in the background.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

8. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Historic Seaport, 0.7 km from Jackson Square
United States
Jennifer
€304
includes taxes & fees
25 Oct - 26 Oct
Hyatt Centric Key West Resort and Spa
Room
Terrace/patio
Rooftop terrace
A two-story building with a porch, a brown door, and a sign for 'The Independent Inn'.

9. The Independent Inn - Formerly Heron House Court

The Independent Inn - Formerly Heron House Court
Historic Seaport, 1 km from Jackson Square
United States
Michael
€158
includes taxes & fees
12 Oct - 13 Oct
The Independent Inn - Formerly Heron House Court
A modern bathroom with a toilet, a sink with a mirror, and a framed picture on the wall.
A spacious lobby with a checkered floor, a central seating area with wicker chairs, a large potted plant, and a staircase with a metal railing.
A modern hotel entrance with a black and white striped curtain, wicker furniture, potted plants, and a sign for the Autograph Collection.
A beach with clear turquoise water, snorkelers, and a large building in the background.

10. La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
Historic Seaport, 0.2 km from Jackson Square
United States
THOMAS
€250
includes taxes & fees
12 Oct - 13 Oct
La Concha Key West, Autograph Collection
A swimming pool with clear water, surrounded by lush greenery and palm trees.
A covered porch with white columns and wicker furniture.
A yellow building with a blue door and shutters, a number '302' on the wall, and a small porch area.
A bedroom with a bed, a nightstand, a lamp, a window with shutters, and a wall with coral patterns.

11. Tranquility Guest House

Tranquility Guest House
Bahama Village, 0.3 km from Jackson Square
United States
Sandra
€211
includes taxes & fees
14 Oct - 15 Oct
Tranquility Guest House
A poolside area with lounge chairs, a small pool, and a white building with a balcony.
A reception area with a wooden reception desk, a brown leather couch, and a mural of palm trees on the wall.
A bedroom with a bed, a ceiling fan, a window with blinds, a painting, and a nightstand with a lamp.
A pool area with lounge chairs, a hot tub, and a deck with a railing.

12. Seascape Tropical Inn - Adult Exclusive

Seascape Tropical Inn - Adult Exclusive
Downtown Key West, 0.5 km from Jackson Square
United States
Julia
€171
includes taxes & fees
11 Oct - 12 Oct
Seascape Tropical Inn - Adult Exclusive
A gated entrance with a gazebo, palm trees, and a brick pathway leading to a building with a red roof.
A bedroom with a large bed, wooden headboard, two bedside lamps, and a floral wall art piece.
A poolside area with lounge chairs and umbrellas, a bar, and a staircase leading to a house.
A waterfront property with a white facade, palm trees, and a street view.

13. Duval Inn

Duval Inn
Downtown Key West, 0.3 km from Jackson Square
United States
Arnold J
€185
includes taxes & fees
11 Oct - 12 Oct
Duval Inn
A deck with sun loungers and a railing overlooking the sea.
A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.
A beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, and a clear blue sky.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the sea.

14. Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Uptown - Upper Duval, 1 km from Jackson Square
United States
Krystle
€212
includes taxes & fees
11 Oct - 12 Oct
Southernmost Beach Resort and Guesthouses
A beach with a wooden pier, palm trees, and beach umbrellas.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.
A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.
An outdoor dining area with tables and chairs, overlooking the ocean.

15. The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Uptown - Upper Duval, 1.2 km from Jackson Square
United States
Darlene
€239
includes taxes & fees
25 Oct - 26 Oct
The Reach Key West, Curio Collection by Hilton
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.
A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

16. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Casa Marina, 1.6 km from Jackson Square
United States
Coni
€277
includes taxes & fees
25 Oct - 26 Oct
Casa Marina Key West, Curio Collection by Hilton
A poolside area with lounge chairs, a staircase leading to a balcony, and a pool.
A beige sofa with two pillows, flanked by two wooden side tables with lamps and potted plants, against a white wall with a framed picture of a tree.
A Southernmost Inn with a porch, a sign indicating vacancy, and a staircase leading to the entrance.
A dining area with round tables and wicker chairs, a ceiling fan, and a bar area in the background.

17. The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only
Uptown - Upper Duval, 1 km from Jackson Square
United States
Anthony
€160
includes taxes & fees
14 Oct - 15 Oct
The Southernmost Inn - Adults Only
A balcony with a view of a street, a bench, and a potted plant.
A hotel lobby with a bar area, seating, and a fireplace.
A bar area with a Pegasus International Hotel sign, round tables, and metal chairs.
A reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.

18. Pegasus International Hotel

Pegasus International Hotel
Downtown Key West, 0.2 km from Jackson Square
United States
Karla
€189
includes taxes & fees
12 Oct - 13 Oct
Pegasus International Hotel
A neatly made bed with white linens and a blue throw blanket, a bedside table with a lamp, and an air conditioning unit mounted on the wall.
A youth hostel with a white exterior, a blue awning, and a white picket fence.
A shower with white subway tiles and a black shower curtain.
A motel sign, parked bicycles, and a building with a covered porch.

19. Seashell Motel

Seashell Motel
Casa Marina, 1.3 km from Jackson Square
United States
Yuliya
€132
includes taxes & fees
12 Oct - 13 Oct
Seashell Motel
A covered outdoor seating area with wicker chairs and a glass table, overlooking a lush garden with palm trees and a pool.
A wooden door with a fire alarm, a white door with shutters, and a patterned carpet.
A covered outdoor area with wicker furniture, a pool, and surrounding palm trees.
A spacious living room with a large leather sofa, green armchairs, and a red and white patterned rug. There are framed botanical prints on the wall and a view into the dining area through glass doors.

20. Curry House

Curry House
Old Town Key West, 0.6 km from Jackson Square
United States
donald
€239
includes taxes & fees
14 Oct - 15 Oct
Curry House
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
1,004 reviews
View
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
Southernmost House - Adult Exclusive
9.4
Exceptional
1,000 reviews
View
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
Silver Palms Inn & Historic Homes
9.4
Exceptional
1,042 reviews
View
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
Eden House
9.0
Wonderful
1,002 reviews
View

Top Jackson Square Hotel Reviews

The Gardens Hotel

The Gardens Hotel

10/10 Excellent
"Absolutely love this place. Visited here last year and will plan again to be back soon. Very welcoming and is just beautiful. I can’t say enough about everyone that works there. Always a fantastic time,"
Barbara 4-night trip
Posted 6 hours ago
The Gardens Hotel
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool

Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool

10/10 Excellent
"This place was amazing! Lots of space for 8 people and each room has a bathroom. Beds were comfortable and everything was clean. Right in the middle of the island so everything is walking distance. Would definitely go back!"
Kristy W. 3-night trip
Posted 14 hours ago
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
Pier House Resort & Spa

Pier House Resort & Spa

8/10 Good
"Guest BEWARE, didn't think there would be a surcharge, but there was. A total of $262. and no one said anything. When we checked in and the asked for a credit card, I asked why, they said for unexpectedly occurred charges, nothing about surcharges. So PLEASE beware"
Connie 4-night trip
Posted 1 day ago
Pier House Resort & Spa
Duval House

Duval House

10/10 Excellent
"Fun place to stay!! Very nice staff."
Cliff 3-night trip
Posted 1 day ago
Duval House
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"Our room was spacious and clean. We loved the uniqueness of the hotel and the proximity to all the bars and restaurants on Duvall street."
Blaire 1-night trip
Posted 1 day ago
The Cabana Inn Key West - Adults Only
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

10/10 Excellent
"The staff were friendly and helpful."
Jeff 2-night trip
Posted 2 days ago
Paradise Inn Key West - Adults Only
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Perfect! Great surroundings, staff & people! Convenient to get to everything!"
Diahann 5-night trip
Posted 2 days ago
Southernmost Beach Resort and Guesthouses
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Wonderful place at a great location"
THOMAS 2-night trip
Posted 3 days ago
La Concha Key West, Autograph Collection
Heron House - Adult Only

Heron House - Adult Only

10/10 Excellent
"I’ve been to Key West many times, the Heron House is by far the best property we have stayed at. Perfect location to walk to Duval, Mallory Square. Great pool, friendly staff."
Erin 3-night trip
Posted 8 days ago
Heron House - Adult Only

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.
See properties

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, 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, 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, Key West Film Society and The Key West Theater.

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