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13 Dec - 14 Dec
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14 Dec - 15 Dec
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19 Dec - 21 Dec
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Our top choices for Jackson Square hotels

Queen Deluxe ADA | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Almond Tree Inn Hotel - Adults Only

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, (1000)
"Very nice & peaceful with a wonderful staff. Our second time staying here"
United States
Sandra
The price is Rp3.798.617
Rp4.273.444 total
includes taxes & fees
17 Dec - 18 Dec
Almond Tree Inn Hotel - Adults Only
Exterior detail
The Gardens Hotel

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, (1001)
"Amazing hotel, the perfect Key West vibe. Clean rooms, delicious breakfast. We will come back again"
United States
Isis
The price is Rp5.421.784
Rp6.099.507 total
includes taxes & fees
15 Dec - 16 Dec
The Gardens Hotel
Exterior
The Marquesa Hotel

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Historic Seaport, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1001)
"Perfect place to stay. "
United States
Paulette
The price is Rp7.141.134
Rp8.970.196 total
includes taxes & fees
17 Dec - 18 Dec
The Marquesa Hotel
Queen with Pool View | Minibar, in-room safe, individually decorated, individually furnished
Simonton Court Historic Inn & Cottages

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, (878)
"The staff was really nice"
United States
doug
The price is Rp2.646.714
Rp2.977.553 total
includes taxes & fees
17 Dec - 18 Dec
Simonton Court Historic Inn & Cottages
Property grounds
Orchid Key Inn - Adults Only

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, (1000)
"Great location and amazing staff!"
United States
Charles
The price is Rp3.798.617
Rp4.273.444 total
includes taxes & fees
17 Dec - 18 Dec
Orchid Key Inn - Adults Only
Front of property
L'Habitation Guest House

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, (921)
"Great place close to all. Manager was very helpful in recommending how to get around the island, what to do and where to eat."
United States
Robert
The price is Rp2.271.605
Rp2.555.430 total
includes taxes & fees
15 Dec - 16 Dec
L'Habitation Guest House
Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave | Free WiFi, bed sheets
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

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, (130)
"Great place to stay always clean an the employees are very respectful "
United States
Charles
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Deluxe Suite, 1 King Bed, Private Pool | View from room
H2O Suites - 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, (581)
"Great place!!"
United States
Joel
The price is Rp4.986.124
Rp6.735.019 total
includes taxes & fees
16 Dec - 17 Dec
H2O Suites - Adults Only
Premium bedding, iron/ironing board, free WiFi, bed sheets
Weatherstation Inn

Weatherstation Inn

Weatherstation Inn
2.5 star property
Truman Annex, 0.3 km from Jackson Square
9.4 out of 10, Exceptional, (993)
"Wonderful property safe neighborhood convenient to all activities would stay here again."
United States
William
The price is Rp3.645.474
Rp4.101.159 total
includes taxes & fees
16 Dec - 17 Dec
Weatherstation Inn
3 outdoor pools, a heated pool, pool loungers
Ambrosia Key West

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, (1000)
"Great location, room, pool, and breakfast. Would recommend."
United States
Francis
The price is Rp3.664.617
Rp4.122.694 total
includes taxes & fees
16 Dec - 17 Dec
Ambrosia Key West
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

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, (406)
"Enjoyed everything about our stay at Ellas, and the front desk gentleman was the best. Breakfast was a special treat. Will stay again."
United States
Donna
The price is Rp3.656.461
Rp4.956.306 total
includes taxes & fees
17 Dec - 18 Dec
Ella's Cottages - Key West Historic Inns
Outdoor pool
Silver Palms Inn

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, (1018)
"We had a wonderful stay and it was a convenient location for all the activities along Duval Street. The room was clean & comfortable with a great breakfast."
United States
Susanne
The price is Rp2.232.229
Rp3.634.987 total
includes taxes & fees
18 Dec - 19 Dec
Silver Palms Inn
2 outdoor pools, pool loungers
Santa Maria Suites

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, (1000)
"Awesome place we loved it"
United States
Josh
The price is Rp5.809.454
Rp7.659.241 total
includes taxes & fees
17 Dec - 18 Dec
Santa Maria Suites
Exterior
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
4.0 star property
Historic Seaport, 0.2 km from Jackson Square
9.0 out of 10, Wonderful, (283)
"Hotel staff was amazing. Room was spotless! Excellent place to stay! Will definitely stay here again in the future! "
United States
Tracy
The price is Rp3.811.934
Rp4.850.229 total
includes taxes & fees
16 Dec - 17 Dec
La Concha Key West, Autograph Collection
Exterior
Ridley House - Key West Historic Inns

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, (856)
"Room was clean, staff were awesome."
United States
Bridget
The price is Rp3.750.332
Rp5.063.429 total
includes taxes & fees
15 Dec - 16 Dec
Ridley House - Key West Historic Inns
BBQ/picnic Area
Banana's Foster Guesthouse

Banana's Foster Guesthouse

Banana's Foster Guesthouse
2.0 star property
Historic Seaport, 0.5 km from Jackson Square
9.0 out of 10, Wonderful, (7)
"The room was spotless and very comfortable."
United States
KARLA
Banana's Foster Guesthouse
Outdoor pool, pool loungers
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Historic Seaport, 0.7 km from Jackson Square
9.2 out of 10, Wonderful, (1004)
"Great stay."
United States
Sarit
The price is Rp6.974.674
Rp9.138.738 total
includes taxes & fees
17 Dec - 18 Dec
Ocean Key Resort - A Noble House Resort
Exterior
The Marker Key West Harbor Resort

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, (1006)
"Fantastic staff, great breakfast"
United States
Kelly
The price is Rp3.430.741
Rp4.908.281 total
includes taxes & fees
16 Dec - 17 Dec
The Marker Key West Harbor Resort
Front of property – evening/night
Opal Key Resort & Marina, Key West

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, (1020)
"Our stay was great!"
United States
Richard
The price is Rp4.644.234
Rp5.880.366 total
includes taxes & fees
16 Dec - 17 Dec
Opal Key Resort & Marina, Key West
Food and drink
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only
3.0 star property
Downtown Key West, < 0.1 km from Jackson Square
8.8 out of 10, Excellent, (1002)
"Rooms are clean, staff was friendly and pool was refreshing. "
United States
Wendy
The Cabana 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.
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Top Jackson Square Hotel Reviews

Pegasus International Hotel

Pegasus International Hotel

10/10 Excellent
"Wonderful place to stay right in the heart of Key West. The pool and deck area are nice and cozy for a relaxing time. "
Daniel 2-night trip
Posted 10 days ago
Pegasus International Hotel
The Marquesa Hotel

The Marquesa Hotel

10/10 Excellent
"So conveniently situated. Beautiful property and room!"
Kathleen 2-night trip
Posted 12 days ago
The Marquesa Hotel

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 seaside 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.
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 1756 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 Winslow's Bungalows - Key West Historic Inns.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1756 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 Key West Historic Seaport are some of the local landmarks to explore. You can check out the local talent at Red Barn Theater, Waterfront Playhouse and Key West Film Society.

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