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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, (1,000 reviews)
"Close to everything great stay!"
United States
Cindy
The price is ฿13,524
฿15,214 total
includes taxes & fees
29 Mar - 30 Mar
Almond Tree Inn Hotel - Adults Only

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, (922 reviews)
"Great location. Cool vibe. "
United States
Becky
The price is ฿13,065
฿14,699 total
includes taxes & fees
19 Apr - 20 Apr
Simonton Court Historic Inn & Cottages

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)
"A little slice of heaven nestled amongst quaint downtown location. Quiet and relaxing atmosphere perfect Key West getaway."
United States
Wendall
The price is ฿14,057
฿15,814 total
includes taxes & fees
22 Apr - 23 Apr
The Gardens 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 stay!"
United States
David
The price is ฿13,409
฿15,085 total
includes taxes & fees
29 Mar - 30 Mar
Orchid Key Inn - Adults Only

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, (592 reviews)
"Very nice place. Great location. "
United States
Colleen Tom
The price is ฿19,614
฿24,276 total
includes taxes & fees
19 Apr - 20 Apr
H2O Suites - 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, (384 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 ฿6,920
฿8,604 total
includes taxes & fees
1 Apr - 2 Apr
Tropical Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (1,002 reviews)
"Beautiful neighborhood. Friendly staff, easy location to everything and spacious rooms"
United States
Suzy Alpert
The price is ฿12,495
฿14,057 total
includes taxes & fees
30 Mar - 31 Mar
Weatherstation 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, (1,001 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 ฿9,680
฿11,709 total
includes taxes & fees
29 Mar - 30 Mar
The Grand Guesthouse

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, (1,002 reviews)
"The property is beautiful and the location is perfect. It has a lovely chill Key West vibe. Management is on-site and helpful."
United States
Ann Elizabeth
The price is ฿11,171
฿12,567 total
includes taxes & fees
29 Mar - 30 Mar
Ambrosia Key West

Silver Palms Inn

Silver Palms Inn
3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.4 out of 10, Exceptional, (1,029 reviews)
"Nice Stay"
United States
Terry
The price is ฿9,106
฿12,455 total
includes taxes & fees
1 Apr - 2 Apr
Silver Palms Inn

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, (452 reviews)
"Perfect location!"
United States
Amelita
The price is ฿13,143
฿16,455 total
includes taxes & fees
5 Apr - 6 Apr
Ella's Cottages - Key West Historic Inns

Caribbean House

Caribbean House
3.0 star property
Bahama Village, 0.4 km from Jackson Square
9.2 out of 10, Wonderful, (338 reviews)
"Very convenient location."
United States
Miguel
The price is ฿7,049
฿8,749 total
includes taxes & fees
29 Mar - 30 Mar
Caribbean House

Southernmost House

Southernmost House
4.0 star property
Uptown - Upper Duval, 1.1 km from Jackson Square
9.4 out of 10, Exceptional, (1,000 reviews)
"Terrific small hotel on beach"
United States
Dan
The price is ฿10,452
฿15,903 total
includes taxes & fees
19 Apr - 20 Apr
Southernmost House

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, (893 reviews)
"Nice little quaint place, great breakfast, the roosters are something to be desired tho, crow all hours of the night"
United States
Jody
The price is ฿12,417
฿15,627 total
includes taxes & fees
16 Apr - 17 Apr
Ridley House - Key West Historic Inns

The Garden House

The Garden House
3.0 star property
Historic Seaport, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (688 reviews)
"Room was spotless, breakfast by the pool is a plus, host is always attentive to making everything right!"
United States
Robert
The price is ฿12,547
฿14,825 total
includes taxes & fees
27 Apr - 28 Apr
The Garden House

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, (1,221 reviews)
"Great accommodations and staff ! "
United States
Raymond
The price is ฿13,143
฿16,455 total
includes taxes & fees
5 Apr - 6 Apr
Winslow's Bungalows - 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, (1,072 reviews)
"We were very pleased with our room and the property. We will definitely be staying here again."
United States
Colleen
The price is ฿12,495
฿15,356 total
includes taxes & fees
19 Apr - 20 Apr
Opal Key Resort & Marina, Key West

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, (1,005 reviews)
"A great place to stay on the island!"
United States
Andy
The price is ฿14,657
฿18,566 total
includes taxes & fees
27 Apr - 28 Apr
The Marker Key West Harbor Resort

The Saint Hotel Key West, Autograph Collection, Adult Only

The Saint Hotel Key West, Autograph Collection, Adult Only
3.5 star property
Historic Seaport, 0.2 km from Jackson Square
9.0 out of 10, Wonderful, (356 reviews)
"Fantastic spot, close to everything, but just far enough away. "
United States
Ruth
The price is ฿13,393
฿15,067 total
includes taxes & fees
30 Mar - 31 Mar
The Saint Hotel Key West, Autograph Collection, Adult Only

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Downtown Key West, 0.3 km from Jackson Square
9.0 out of 10, Wonderful, (1,126 reviews)
"Great location and great accommodation "
United States
robert
The price is ฿5,999
฿7,900 total
includes taxes & fees
1 Apr - 2 Apr
Heron House - Adult 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
Free daily continental breakfast
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,000 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
922 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,002 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,000 reviews
View
Courtyard
H2O Suites - Adults Only
3.5 star property
9.8
Exceptional
592 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 1744 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 1744 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, 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 Film Society and Red Barn Theater.