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Our top choices for Jackson Square hotels

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
3.5 star property
Downtown Key West, 0.6 km from Jackson Square
10.0 out of 10, Exceptional, (1,003 reviews)
"Excellent hotel in a great location just off Duval Street. The staff were very attentive, rooms clean. "
United Kingdom
Stephen
The price is Rp9.677.952
Rp10.887.696 total
includes taxes & fees
25 Mar - 26 Mar
Almond Tree Inn Hotel - Adults Only

The Gardens Hotel

The Gardens Hotel
4.0 star property
Downtown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,000 reviews)
"Wonderful all around! "
United States
Elena
The price is Rp13.023.651
Rp14.651.607 total
includes taxes & fees
7 Mar - 8 Mar
The Gardens Hotel

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Historic Seaport, 0.4 km from Jackson Square
9.8 out of 10, Exceptional, (912 reviews)
"Great stay, clean room, and amazing staff!"
United States
Jennifer
The price is Rp7.208.058
Rp8.109.064 total
includes taxes & fees
8 Mar - 9 Mar
Simonton Court Historic Inn & Cottages

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,003 reviews)
"Great accommodations and great staff"
United States
Julian
The price is Rp9.560.338
Rp11.700.577 total
includes taxes & fees
24 Mar - 25 Mar
The Marquesa Hotel

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Uptown - Upper Duval, 0.6 km from Jackson Square
9.8 out of 10, Exceptional, (1,008 reviews)
"Clean room, great breakfast and nice staff"
United States
Tari
The price is Rp9.009.232
Rp10.135.387 total
includes taxes & fees
1 Mar - 2 Mar
Orchid Key Inn - Adults Only

The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West, 0.7 km from Jackson Square
9.8 out of 10, Exceptional, (154 reviews)
"Large clean room and excellent staff! Made for a great stay. "
United States
Daniel
The price is Rp8.427.883
Rp9.481.369 total
includes taxes & fees
25 Feb - 26 Feb
The Conch House Heritage Inn

Douglas House

Douglas House
3.0 star property
Uptown - Upper Duval, 0.8 km from Jackson Square
9.6 out of 10, Exceptional, (293 reviews)
"Great place with a perfect location. "
United States
Brandon
The price is Rp5.966.669
Rp7.383.752 total
includes taxes & fees
10 Mar - 11 Mar
Douglas House

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
3.5 star property
Old Town Key West, 1.1 km from Jackson Square
9.8 out of 10, Exceptional, (142 reviews)
"We absolutely loved finding this gem to stay on our first visit to Key West. Great location, wonderful staff, and excellent room. "
United States
Sammy
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (378 reviews)
"Nice place to stay "
United States
yulio
The price is Rp6.760.789
Rp8.025.979 total
includes taxes & fees
2 Mar - 3 Mar
Tropical Inn

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Historic Seaport, 0.2 km from Jackson Square
9.4 out of 10, Exceptional, (942 reviews)
"Great location "
United States
Scott
The price is Rp6.075.939
Rp6.835.390 total
includes taxes & fees
2 Mar - 3 Mar
L'Habitation Guest House

Island City House Hotel

Island City House Hotel
3.0 star property
Historic Seaport, 0.6 km from Jackson Square
9.6 out of 10, Exceptional, (1,008 reviews)
"Excellent stay"
United States
Emily Barbara
The price is Rp7.360.116
Rp8.280.026 total
includes taxes & fees
26 Mar - 27 Mar
Island City House Hotel

Marrero's Guest Mansion

Marrero's Guest Mansion
3.5 star property
Downtown Key West, < 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (335 reviews)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is Rp8.384.198
Rp9.432.307 total
includes taxes & fees
10 Mar - 11 Mar
Marrero's Guest Mansion

H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Uptown - Upper Duval, 1 km from Jackson Square
9.8 out of 10, Exceptional, (586 reviews)
"Great place!!"
United States
Joel
The price is Rp12.248.658
Rp14.913.875 total
includes taxes & fees
22 Mar - 23 Mar
H2O Suites - Adults Only

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,014 reviews)
"Great place! "
United States
David
The price is Rp6.367.958
Rp7.525.196 total
includes taxes & fees
5 Mar - 6 Mar
Duval House

Ambrosia Key West

Ambrosia Key West
3.5 star property
Old Town Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,006 reviews)
"Great place to stay"
United States
Melody
The price is Rp6.091.859
Rp6.853.341 total
includes taxes & fees
3 Mar - 4 Mar
Ambrosia Key West

The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,001 reviews)
"Great location and really nice room. Def stay here again. "
United States
Daniel
The Grand Guesthouse

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
3.5 star property
Old Town Key West, 0.5 km from Jackson Square
9.4 out of 10, Exceptional, (439 reviews)
"Excellent food, location, friendly staff and pool was awesome."
United States
Karen
The price is Rp8.383.358
Rp10.281.962 total
includes taxes & fees
2 Mar - 3 Mar
Ella's Cottages - Key West Historic Inns

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (1,058 reviews)
"Awsome resort. Great food and staff"
United States
Doug
The price is Rp9.644.348
Rp11.511.554 total
includes taxes & fees
22 Mar - 23 Mar
Opal Key Resort & Marina, Key West

Santa Maria Suites

Santa Maria Suites
4.0 star property
Uptown - Upper Duval, 1.2 km from Jackson Square
9.6 out of 10, Exceptional, (1,004 reviews)
"Very nice place unfortunately weather wasn’t great so didn’t use the pool staff was very nice and husband loved the muffins and dove bars every day "
United States
Michelle
The price is Rp12.416.678
Rp15.102.898 total
includes taxes & fees
3 Mar - 4 Mar
Santa Maria Suites

Caribbean House

Caribbean House
3.0 star property
Bahama Village, 0.4 km from Jackson Square
9.2 out of 10, Wonderful, (325 reviews)
"Cute little place. "
United States
Wendy
The price is Rp6.074.427
Rp7.253.781 total
includes taxes & fees
1 Mar - 2 Mar
Caribbean House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Jackson Square Hotel Reviews

Hotels near other Jackson Square attractions

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 1732 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 1732 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, Audubon House and Tropical Gardens 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 Waterfront Playhouse, Key West Film Society and Red Barn Theater.