Hotels near Jackson Square

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
8 May - 9 May
Tomorrow
9 May - 10 May
This weekend
8 May - 10 May
Next weekend
15 May - 17 May

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Jackson Square hotels

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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, (1,005 reviews)
"Great staff, breakfast and happy hour. "
United States
Tina
The price is RM1,135
RM1,277 total
includes taxes & fees
10 May - 11 May
Almond Tree Inn Hotel - Adults Only
Minibar, in-room safe, individually decorated, individually furnished

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, (945 reviews)
"Very unique, great staff, and great location"
United States
Jason
The price is RM1,130
RM1,271 total
includes taxes & fees
1 Jun - 2 Jun
Simonton Court Historic Inn & Cottages
Property grounds

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)
"Breakfast menu was fresh, rooms were cleaned every day, staff couldn’t have been nicer."
United States
Thomas L
The price is RM1,146
RM1,290 total
includes taxes & fees
25 May - 26 May
Orchid Key Inn - Adults Only
Front of property

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, (978 reviews)
"This was a lovely well stocked, and comfortable stay."
United States
Pat
The price is RM665
RM748 total
includes taxes & fees
12 May - 13 May
L'Habitation Guest House
Exterior

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, (377 reviews)
"Great location, helpful staff and fun people. Would stay here again…the pool and room were fantastic"
United States
Scott
The price is RM701
RM867 total
includes taxes & fees
2 Jun - 3 Jun
Douglas House - Adults Only
Balcony view

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, (1,001 reviews)
"We absolutely loved staying here!"
United States
Victoria E
The price is RM985
RM1,109 total
includes taxes & fees
13 May - 14 May
Island City House Hotel
Free WiFi, bed sheets

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, (143 reviews)
"The staff and other guests were very friendly. The room was spacious and the bed was comfortable. "
United States
Annette
The price is RM700
RM944 total
includes taxes & fees
13 May - 14 May
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Terrace/patio

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, (337 reviews)
"It was nice. Get a smart tv 😂"
United States
Robert
The price is RM1,208
RM1,359 total
includes taxes & fees
20 May - 21 May
Marrero's Guest Mansion
Property grounds

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,034 reviews)
"Very clean and convenient staff was very nice will stay again "
United States
Brian
The price is RM700
RM871 total
includes taxes & fees
12 May - 13 May
Duval House
Porch

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (1,152 reviews)
"Good fresh breakfast, great location and a nice pool. "
United States
Joseph
The price is RM582
RM788 total
includes taxes & fees
11 May - 12 May
Heron House - Adult Only
Outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

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, (471 reviews)
"Cute place. Great location to everything on Duval. Service was great and friendly."
United States
DJS Darren Jay
The price is RM1,017
RM1,342 total
includes taxes & fees
1 Jun - 2 Jun
Ella's Cottages - Key West Historic Inns
Lobby sitting area

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.8 km from Jackson Square
9.4 out of 10, Exceptional, (1,009 reviews)
"Quant little bungalow in great location - heated pool and outside breakfast were very welcoming. "
United States
Peter
The price is RM932
RM1,049 total
includes taxes & fees
3 Jun - 4 Jun
Westwinds Inn
2 outdoor pools, pool loungers

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, (1,002 reviews)
"Nice suites , staff very friendly. Conveniently located. Check your room bills carefully. "
United States
Kristine
The price is RM1,325
RM1,755 total
includes taxes & fees
7 Jun - 8 Jun
Santa Maria Suites
Outdoor pool

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1,028 reviews)
"Excellent place and convenience was perfect"
United States
Bonnie
The price is RM507
RM834 total
includes taxes & fees
10 May - 11 May
Silver Palms Inn & Historic Homes
Courtyard

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, (1,003 reviews)
"This is a great place to stay, quiet and nice accommodations. Awesome little courtyard for breakfast."
United States
Jacqueline
The price is RM706
RM892 total
includes taxes & fees
11 May - 12 May
The Grand Guesthouse
Front of property – evening/night

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, (1,099 reviews)
"Loved the location and the prximity to so many things we wanted to visit. The pool and services there were great!"
United States
Pamela
The price is RM1,013
RM1,293 total
includes taxes & fees
25 May - 26 May
Opal Key Resort & Marina, Key West
Outdoor pool

The Key West Hotel

The Key West Hotel
3.0 star property
Historic Seaport, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (552 reviews)
"Great location"
United States
David
The price is RM1,309
RM1,688 total
includes taxes & fees
12 May - 13 May
The Key West Hotel
Exterior

Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns
3.5 star property
Historic Seaport, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (908 reviews)
"Staff was amazing from check in to check out. Located in a great location, close to everything but far enough its not loud while sleeping."
United States
Brennan
The price is RM898
RM1,209 total
includes taxes & fees
26 May - 27 May
Ridley House - Key West Historic Inns
Front of property

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
4.0 star property
Old Town Key West, 0.8 km from Jackson Square
9.2 out of 10, Wonderful, (1,270 reviews)
"Wonderful hotel and loved the atmosphere, hospitality and ability to walk everywhere. Would definitely stay here again!"
United States
Michelle
The price is RM939
RM1,255 total
includes taxes & fees
25 May - 26 May
Winslow's Bungalows - Key West Historic Inns
Exterior

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
4.0 star property
Historic Seaport, 0.7 km from Jackson Square
9.2 out of 10, Wonderful, (1,004 reviews)
"Great place to stay. Friendly staff well kept property. Great food as well"
United States
Bradley
The price is RM910
RM1,270 total
includes taxes & fees
25 May - 26 May
The Marker Key West Harbor Resort
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.
View all properties

Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,005 reviews
View
Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
945 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,001 reviews
View
Front of property
L'Habitation Guest House
2.5 star property
9.4
Exceptional
978 reviews
View
Exterior
Douglas House - Adults Only
3.0 star property
9.6
Exceptional
377 reviews
View

Top Jackson Square Hotel Reviews

The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

10/10 Excellent
"Very helpful and courteous staff. They made the available travel resources easy to access with personal guidance."
Tom 4-night trip
Posted 9 hours ago
The Cabana Inn Key West - Adults Only

Hotels near other Jackson Square attractions

KEY WEST, FLORIDA, USA - September 2012: San Carlos institute is a historic Key West building also known as "La casa de Cuba"

San Carlos Institute - Casa Cuba

4.3/5 (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

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 1741 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 Pier House Resort & Spa.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1741 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 Mel Fisher Maritime Museum feature a variety of fascinating exhibits to see while you're in town. Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum 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 Film Society and Red Barn Theater.