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

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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 accommodations"
United States
Jimmy
The price is ฿6,292
฿7,078 total
includes taxes & fees
1 Jul - 2 Jul
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, (1,002 reviews)
"Whole place is great"
United States
Joseph
The price is ฿6,642
฿7,472 total
includes taxes & fees
12 Jul - 13 Jul
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, (992 reviews)
"Perfcet location and walk to everything , we very much enjoyed our stay!"
United States
Rita
The price is ฿4,639
฿5,219 total
includes taxes & fees
28 Jul - 29 Jul
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, (263 reviews)
"This was the best place we have stayed at in Key West! It was super quiet but only a block from Duval. The owners really put a lot of care into the place and are super nice! Definitely would stay there again! "
United States
Jennifer
The price is ฿6,879
฿7,739 total
includes taxes & fees
29 Jun - 30 Jun
Key West Villas

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)
"Friendly and helpful staff, and the rooms were exceptionally clean and comfortable. Everything was well-maintained, and the overall experience was wonderful. I will definitely be coming back again!"
United States
Helia
The price is ฿7,822
฿10,678 total
includes taxes & fees
21 Jul - 22 Jul
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, (1,000 reviews)
"Great boutique hotel in the perfect location !! "
United States
Michael
The price is ฿5,833
฿6,562 total
includes taxes & fees
28 Jun - 29 Jun
Orchid Key Inn - Adults Only

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (413 reviews)
"Very friendly staff and a prime location."
United States
Akhenaton
The price is ฿6,259
฿7,875 total
includes taxes & fees
8 Jul - 9 Jul
Tropical Inn

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, (432 reviews)
"Great stay"
United States
Matthew
The price is ฿2,869
฿3,550 total
includes taxes & fees
20 Jul - 21 Jul
Douglas House - Adults Only

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, (997 reviews)
"Loved the location, breakfast and clean room. Staff, Drew, very friendly and helpful. Will definitely stay here again."
United States
Richard
The price is ฿3,575
฿4,022 total
includes taxes & fees
28 Jun - 29 Jun
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, (1,000 reviews)
"I love this Hotel. Great location, safe m, convenient. The staff is very accommodating."
United States
Paul
The price is ฿6,350
฿7,143 total
includes taxes & fees
20 Jul - 21 Jul
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, (337 reviews)
"Service and hospitality were exceptional. Will stay again. "
United States
Don
The price is ฿6,639
฿7,469 total
includes taxes & fees
20 Jul - 21 Jul
Marrero's Guest Mansion

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (1,004 reviews)
"Quaint place to stay with access to there other more resort style property made for an amazing experience."
United States
Bret
The price is ฿5,971
฿6,718 total
includes taxes & fees
6 Jul - 7 Jul
Weatherstation Inn

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, (620 reviews)
"We had a wonderful stay!"
United States
Elizabeth
The price is ฿10,975
฿14,599 total
includes taxes & fees
26 Jul - 27 Jul
H2O Suites - Adults Only

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, (539 reviews)
"Loved the property and staff was super friendly."
United States
Brinkley
The price is ฿5,874
฿6,609 total
includes taxes & fees
28 Jun - 29 Jun
Coco Plum Inn

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, (1,001 reviews)
"Great location and breakfast"
United States
Lori
The price is ฿5,391
฿6,065 total
includes taxes & fees
5 Jul - 6 Jul
Ambrosia Key West

Duval House

Duval House
3.0 star property
Downtown Key West, 0.4 km from Jackson Square
9.4 out of 10, Exceptional, (1,043 reviews)
"Great location and clean rooms. Breakfast staff is so sweet! Will stay here again for sure!!"
United States
Wendy S
The price is ฿3,638
฿4,810 total
includes taxes & fees
1 Jul - 2 Jul
Duval House

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, (1,155 reviews)
The price is ฿3,959
฿5,566 total
includes taxes & fees
5 Jul - 6 Jul
Heron House - Adult Only

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.8 km from Jackson Square
9.4 out of 10, Exceptional, (1,002 reviews)
"Great location!!"
United States
Kelly
The price is ฿5,557
฿6,252 total
includes taxes & fees
29 Jun - 30 Jun
Westwinds Inn

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)
"we had a great stay, rented bikes"
United States
Duncan
The price is ฿4,014
฿5,350 total
includes taxes & fees
8 Jul - 9 Jul
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, (485 reviews)
"Breakfast was delicious!! Fresh breads, fruit, meat and cheese, etc. Staff super friendly!!"
United States
Michelle
The price is ฿7,343
฿9,951 total
includes taxes & fees
14 Jul - 15 Jul
Ella's Cottages - Key West Historic Inns
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.

Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,003 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,002 reviews
View
Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
992 reviews
View
Front of property
Key West Villas
3.5 star property
9.8
Exceptional
263 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,000 reviews
View

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 1722 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 1722 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 Curry Mansion Museum 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.