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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, 0.4 mi from Jackson Square
10.0 out of 10, Exceptional, (1,009 reviews)
"Great staff, breakfast and happy hour. "
United States
Tina
The price is £221
includes taxes & fees
25 May - 26 May
Almond Tree Inn Hotel - Adults Only

The Gardens Hotel

The Gardens Hotel
4.0 star property
Downtown Key West, 0.2 mi from Jackson Square
9.8 out of 10, Exceptional, (1,005 reviews)
"Breakfasts were great and they had a very good selection of drinks at the bar."
United States
Dennis
The price is £231
includes taxes & fees
11 May - 12 May
The Gardens Hotel

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.2 mi from Jackson Square
9.8 out of 10, Exceptional, (1,004 reviews)
"Great accommodations and great staff"
United States
Julian
The price is £296
includes taxes & fees
25 May - 26 May
The Marquesa Hotel

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Historic Seaport, 0.2 mi from Jackson Square
9.8 out of 10, Exceptional, (948 reviews)
"Defiantly would stay again and so close to everything"
United States
kelly
The price is £199
includes taxes & fees
14 May - 15 May
Simonton Court Historic Inn & Cottages

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Uptown - Upper Duval, 0.4 mi from Jackson Square
9.8 out of 10, Exceptional, (1,002 reviews)
"Breakfast menu was fresh, rooms were cleaned every day, staff couldn’t have been nicer."
United States
Thomas L
The price is £203
includes taxes & fees
17 May - 18 May
Orchid Key Inn - Adults Only

The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West, 0.4 mi from Jackson Square
9.8 out of 10, Exceptional, (172 reviews)
"Great location "
United Kingdom
Lucy
The price is £226
includes taxes & fees
11 May - 12 May
The Conch House Heritage Inn

H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Uptown - Upper Duval, 0.6 mi from Jackson Square
9.8 out of 10, Exceptional, (603 reviews)
"This resort was in the perfect location for exploring Key West. Highly recommend!"
United States
Barton
The price is £338
includes taxes & fees
2 Jun - 3 Jun
H2O Suites - Adults Only

Douglas House - Adults Only

Douglas House - Adults Only
3.0 star property
Uptown - Upper Duval, 0.5 mi from Jackson Square
9.6 out of 10, Exceptional, (383 reviews)
"Great location, helpful staff and fun people. Would stay here again…the pool and room were fantastic"
United States
Scott
The price is £144
includes taxes & fees
4 Jun - 5 Jun
Douglas House - Adults Only

L'Habitation Guest House

L'Habitation Guest House
2.5 star property
Historic Seaport, 0.1 mi 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 £153
includes taxes & fees
25 May - 26 May
L'Habitation Guest House

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, < 0.1 mi from Jackson Square
9.4 out of 10, Exceptional, (525 reviews)
"Great location, pleasant staff & cute pool. "
United States
julie
The price is £217
includes taxes & fees
1 Jun - 2 Jun
Coco Plum Inn

Duval House

Duval House
3.0 star property
Downtown Key West, 0.3 mi 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 £180
includes taxes & fees
8 Jun - 9 Jun
Duval House

Santa Maria Suites

Santa Maria Suites
4.0 star property
Uptown - Upper Duval, 0.7 mi from Jackson Square
9.6 out of 10, Exceptional, (1,004 reviews)
"Great hotel and room. Very clean, great location."
United States
Cindy
The price is £329
includes taxes & fees
1 Jun - 2 Jun
Santa Maria Suites

The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West, 0.7 mi 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 £167
includes taxes & fees
11 May - 12 May
The Grand Guesthouse

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.5 mi from Jackson Square
9.4 out of 10, Exceptional, (1,012 reviews)
"Quant little bungalow in great location - heated pool and outside breakfast were very welcoming. "
United States
Peter
The price is £187
includes taxes & fees
1 Jun - 2 Jun
Westwinds Inn

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
3.5 star property
Old Town Key West, 0.6 mi from Jackson Square
9.4 out of 10, Exceptional, (1,030 reviews)
"Excellent place and convenience was perfect"
United States
Bonnie
The price is £156
includes taxes & fees
2 Jun - 3 Jun
Silver Palms Inn & Historic Homes

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns
3.5 star property
Old Town Key West, 0.3 mi 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 £251
includes taxes & fees
1 Jun - 2 Jun
Ella's Cottages - Key West Historic Inns

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.2 mi from Jackson Square
9.2 out of 10, Wonderful, (1,154 reviews)
"Good fresh breakfast, great location and a nice pool. "
United States
Joseph
The price is £170
includes taxes & fees
17 May - 18 May
Heron House - Adult Only

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West, 0.3 mi from Jackson Square
9.2 out of 10, Wonderful, (1,107 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 £243
includes taxes & fees
25 May - 26 May
Opal Key Resort & Marina, Key West

The Garden House

The Garden House
3.0 star property
Historic Seaport, 0.3 mi from Jackson Square
9.2 out of 10, Wonderful, (699 reviews)
"A great relaxing stay"
United States
Dennis
The price is £149
includes taxes & fees
14 May - 15 May
The Garden House

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only
3.5 star property
Downtown Key West, 0.3 mi from Jackson Square
9.2 out of 10, Wonderful, (1,009 reviews)
"Great stay"
United States
Michael
The price is £186
includes taxes & fees
26 May - 27 May
Paradise Inn Key West - Adults Only
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
1,009 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,005 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,004 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
948 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,002 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 1734 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 1734 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.