Key West Jackson Square Hotels

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Check prices for these dates

Tonight
21 Feb - 22 Feb
Tomorrow
22 Feb - 23 Feb
Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar

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Our top choices for Jackson Square hotels

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, (910 reviews)
"Great stay, clean room, and amazing staff!"
United States
Jennifer
The price is HK$2,866
HK$3,225 total
includes taxes & fees
8 Mar - 9 Mar
Simonton Court Historic Inn & Cottages
Free daily continental breakfast

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, (1,001 reviews)
"Excellent hotel in a great location just off Duval Street. The staff were very attentive, rooms clean. "
United Kingdom
Stephen
The price is HK$4,354
HK$4,898 total
includes taxes & fees
1 Mar - 2 Mar
Almond Tree Inn Hotel - Adults Only
Exterior detail

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, (1,000 reviews)
"Wonderful all around! "
United States
Elena
The price is HK$5,530
HK$6,221 total
includes taxes & fees
28 Feb - 1 Mar
The Gardens Hotel
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, (1,006 reviews)
"Clean room, great breakfast and nice staff"
United States
Tari
The price is HK$4,318
HK$4,858 total
includes taxes & fees
1 Mar - 2 Mar
Orchid Key Inn - Adults Only
Self-parking (surcharge) 15.00 per night

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, (252 reviews)
"Awsome staff great location "
United States
Jeffrey
Key West Villas
Terrace/patio

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, (153 reviews)
"Large clean room and excellent staff! Made for a great stay. "
United States
Daniel
The price is HK$3,826
HK$4,304 total
includes taxes & fees
25 Feb - 26 Feb
The Conch House Heritage Inn
Sports facility

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (377 reviews)
"Nice place to stay "
United States
yulio
The price is HK$3,209
HK$3,805 total
includes taxes & fees
23 Feb - 24 Feb
Tropical Inn
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, (942 reviews)
"Great location "
United States
Scott
The price is HK$2,826
HK$3,179 total
includes taxes & fees
24 Mar - 25 Mar
L'Habitation Guest House
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, (1,011 reviews)
"Great place! "
United States
David
The price is HK$2,962
HK$3,500 total
includes taxes & fees
5 Mar - 6 Mar
Duval House
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, (1,007 reviews)
"Excellent stay"
United States
Emily Barbara
The price is HK$3,488
HK$3,924 total
includes taxes & fees
16 Mar - 17 Mar
Island City House Hotel
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, (335 reviews)
"Location very good Staff friendly Pool not well maintained Breakfast and happy hour lacking compared to others"
United States
Scott
The price is HK$3,899
HK$4,387 total
includes taxes & fees
10 Mar - 11 Mar
Marrero's Guest Mansion
Courtyard

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, (586 reviews)
"Great place!!"
United States
Joel
The price is HK$5,697
HK$6,936 total
includes taxes & fees
22 Mar - 23 Mar
H2O Suites - Adults Only
3 outdoor pools, a heated pool, pool loungers

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, (1,006 reviews)
"Great place to stay"
United States
Melody
The price is HK$2,982
HK$3,355 total
includes taxes & fees
3 Mar - 4 Mar
Ambrosia Key West
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, (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
View from property

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.8 km from Jackson Square
9.4 out of 10, Exceptional, (1,007 reviews)
"This was a great location, staff is very friendly and helpful. Rooms are nice and pools areas are lovely."
United States
Frances
Westwinds Inn
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, (438 reviews)
"Excellent food, location, friendly staff and pool was awesome."
United States
Karen
The price is HK$3,899
HK$4,782 total
includes taxes & fees
5 Mar - 6 Mar
Ella's Cottages - Key West Historic Inns
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, (1,001 reviews)
"Great location and really nice room. Def stay here again. "
United States
Daniel
The Grand Guesthouse
Outdoor pool

The Key West Hotel

The Key West Hotel
2.5 star property
Historic Seaport, 0.3 km from Jackson Square
9.2 out of 10, Wonderful, (532 reviews)
"Great location, very clean, and great staff"
United States
William
The price is HK$3,297
HK$4,139 total
includes taxes & fees
24 Feb - 25 Feb
The Key West Hotel
View from room

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, (1,055 reviews)
"Awsome resort. Great food and staff"
United States
Doug
The price is HK$4,486
HK$5,354 total
includes taxes & fees
22 Mar - 23 Mar
Opal Key Resort & Marina, Key West
Front of property

Caribbean House

Caribbean House
3.0 star property
Bahama Village, 0.4 km from Jackson Square
9.2 out of 10, Wonderful, (323 reviews)
"Cute little place. "
United States
Wendy
The price is HK$2,642
HK$3,168 total
includes taxes & fees
23 Feb - 24 Feb
Caribbean House
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.
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Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages
2.5 star property
9.8
Exceptional
910 reviews
View
Free daily continental breakfast
Almond Tree Inn Hotel - Adults Only
3.5 star property
10.0
Exceptional
1,001 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,000 reviews
View
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,006 reviews
View
Self-parking (surcharge) 15.00 per night
Key West Villas
3.5 star property
9.8
Exceptional
252 reviews
View

Top Jackson Square Hotel Reviews

NYAH Key West - Adults Only

NYAH Key West - Adults Only

10/10 Excellent
"Great location! Amazing price. Can’t wait to stay here again. Easy going and polite staff. Clean pools and hot tub. The room had some wear and tear but you don’t go to Key West to stay in the room! Balcony was an excellent surprise and the breakfast! Happy Hour is cheap and fun! Thank you!!"
Cassandra 3-night trip
Posted 1 day ago
NYAH 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

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
Vibrant atmosphere at Duval Street showcases Key West's historic charm and cultural richness in Florida's lively district

Duval Street

4.5/5 (9,716 reviews)
Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.
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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 1732 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 1732 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 Fort East Martello Museum and Gallery 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.