Hotels near Jackson Square

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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)
"Close to everything great stay!"
United States
Cindy
The price is RM1,663
RM1,870 total
includes taxes & fees
22 Mar - 23 Mar
Almond Tree Inn Hotel - Adults Only

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, (1,000 reviews)
"Great accommodations and great staff"
United States
Julian
The price is RM1,847
RM2,300 total
includes taxes & fees
17 Mar - 18 Mar
The Marquesa Hotel

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, (1,001 reviews)
"The Gardens Hotel is an oasis in Key West. Walkable to anywhere you want to go in Old Town. Staff is amazing!"
United States
Jean
The price is RM2,344
RM2,637 total
includes taxes & fees
28 Mar - 29 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, (918 reviews)
"Room was very clean,well furnished and staff were all very friendly. This was our 6th time staying here and it never disappoints."
United States
Thomas
The price is RM1,572
RM1,768 total
includes taxes & fees
15 Apr - 16 Apr
Simonton Court Historic Inn & Cottages

Key West Villas

Key West Villas
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (253 reviews)
"Awsome staff great location "
United States
Jeffrey
The price is RM1,344
RM1,512 total
includes taxes & fees
6 Apr - 7 Apr
Key West Villas

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, (1,001 reviews)
"Wonderful stay! Want to come back!"
United States
Deborah
The price is RM1,663
RM1,870 total
includes taxes & fees
22 Mar - 23 Mar
Orchid Key Inn - Adults Only

Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Uptown - Upper Duval, 0.8 km from Jackson Square
9.6 out of 10, Exceptional, (317 reviews)
"Great quiet location, short walk to all major points of interest. Friendly staff and excellent amenities "
United States
Tsvetelina
The price is RM931
RM1,153 total
includes taxes & fees
22 Mar - 23 Mar
Douglas House - 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, (156 reviews)
"Large clean room and excellent staff! Made for a great stay. "
United States
Daniel
The price is RM1,480
RM1,665 total
includes taxes & fees
13 Apr - 14 Apr
The Conch House Heritage Inn

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (382 reviews)
"This place is a gem with Lovely accommodations,peaceful pooland great staff we will always come back when in KW. "
United States
Garda
The price is RM1,585
RM1,881 total
includes taxes & fees
22 Mar - 23 Mar
Tropical Inn

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, (1,002 reviews)
"We absolutely loved staying here!"
United States
Victoria E
The price is RM1,482
RM1,667 total
includes taxes & fees
23 Mar - 24 Mar
Island City House Hotel

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (494 reviews)
"Great location, clean room, amazing staff!! The property was so cozy and intimate- the breakfast was great too. "
United States
Arturo
The price is RM1,343
RM1,511 total
includes taxes & fees
14 Apr - 15 Apr
Coco Plum 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, (951 reviews)
"Nice place with a great staff. Would definitely stay here again. also, it was in a fantastic location"
United States
Michael
The price is RM1,099
RM1,236 total
includes taxes & fees
14 Apr - 15 Apr
L'Habitation Guest House

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, (588 reviews)
"Very nice, very clean with great staff and convenient parking. The "private" pools are all in a courtyard so you can make awkward eye contact with the"
United States
Jessica
The price is RM2,556
RM3,142 total
includes taxes & fees
5 Apr - 6 Apr
H2O Suites - Adults Only

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, (336 reviews)
"It was nice. Get a smart tv 😂"
United States
Robert
The price is RM1,887
RM2,123 total
includes taxes & fees
5 Apr - 6 Apr
Marrero's Guest Mansion

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,005 reviews)
"Great place in an excellent location! Staff were lovely, had a great time."
United Kingdom
Maurice
The price is RM1,217
RM1,454 total
includes taxes & fees
24 Mar - 25 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, (1,003 reviews)
"Great place to stay"
United States
Melody
The price is RM1,403
RM1,578 total
includes taxes & fees
23 Mar - 24 Mar
Ambrosia Key West

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (1,001 reviews)
"Beautiful neighborhood. Friendly staff, easy location to everything and spacious rooms"
United States
Suzy Alpert
The price is RM1,572
RM1,768 total
includes taxes & fees
22 Mar - 23 Mar
Weatherstation Inn

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

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, (446 reviews)
"Perfect location!"
United States
Amelita
The price is RM1,768
RM2,188 total
includes taxes & fees
5 Apr - 6 Apr
Ella's Cottages - Key West Historic Inns

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)
"We loved our stay here. The room was very clean and the staff was very kind and helpful. Loved the courtyard where we enjoyed our continental breakfast. "
United States
Mabel
The price is RM1,805
RM2,129 total
includes taxes & fees
17 Mar - 18 Mar
The Grand Guesthouse
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 1745 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, The Cabana Inn Key West - Adults Only is one of the top choices for your stay based on our traveller data, and this guest house offers free breakfast and an outdoor pool. Other good options close by include Southernmost Beach Resort and Guesthouses and Opal Key Resort & Marina, Key West.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1745 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, Key West Historic Seaport and Fort Zachary Taylor Historic State Park are some of the local landmarks to explore. You can check out the local talent at Waterfront Playhouse, Key West Burlesque Theater and Key West Film Society.