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Our top choices for Jackson Square hotels

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, (1,004 reviews)
"Great stay"
United States
Julia
The price is 9.469.468 ₫
10.653.151 ₫ total
includes taxes & fees
10 May - 11 May
Orchid Key Inn - Adults Only

The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West, 0.7 km from Jackson Square
9.8 out of 10, Exceptional, (163 reviews)
"Large clean room and excellent staff! Made for a great stay. "
United States
Daniel
The price is 10.050.199 ₫
11.306.474 ₫ total
includes taxes & fees
27 Apr - 28 Apr
The Conch House Heritage Inn

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, (963 reviews)
"This was a lovely well stocked, and comfortable stay."
United States
Pat
The price is 5.136.242 ₫
5.778.338 ₫ total
includes taxes & fees
30 Apr - 1 May
L'Habitation Guest House

Tropical Inn

Tropical Inn
3.5 star property
Downtown Key West, 0.4 km from Jackson Square
9.6 out of 10, Exceptional, (392 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 5.566.062 ₫
6.920.311 ₫ total
includes taxes & fees
19 Apr - 20 Apr
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, (353 reviews)
"We really enjoyed our stay at the Douglas House, great location and the staff was very friendly and gave wonderful tips on great places to dine. Would highly recommend choosing Douglas House for your stay."
United States
Timothy
The price is 6.228.263 ₫
7.707.476 ₫ total
includes taxes & fees
6 May - 7 May
Douglas House - Adults Only

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, (999 reviews)
"We absolutely loved staying here!"
United States
Victoria E
The price is 8.631.952 ₫
9.710.946 ₫ total
includes taxes & fees
4 May - 5 May
Island City House Hotel

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)
"Staff very courteous and friendly, public spaces lovely."
United States
Paul
The price is 5.902.122 ₫
7.727.803 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

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, (594 reviews)
"Very nice place. Great location. "
United States
Colleen Tom
The price is 12.088.683 ₫
15.377.516 ₫ total
includes taxes & fees
11 May - 12 May
H2O Suites - Adults Only

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)
"It was nice. Get a smart tv 😂"
United States
Robert
The price is 9.454.983 ₫
10.636.988 ₫ total
includes taxes & fees
6 May - 7 May
Marrero's Guest Mansion

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)
"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 7.408.640 ₫
8.334.719 ₫ total
includes taxes & fees
19 Apr - 20 Apr
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, (1,019 reviews)
"Great place, great location, great staff"
United States
Victoria
The price is 6.294.782 ₫
7.647.897 ₫ total
includes taxes & fees
12 May - 13 May
Duval House

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, (1,002 reviews)
"The location is pretty good, it's about a mile and a little bit more to Mallory square, but there are many things to see along the way. It has a nice Key West vibe to it, especially having the breakfast outside in the morning. And coffee is available 24 hours which we like"
United States
Glenn
The price is 7.692.432 ₫
9.312.412 ₫ total
includes taxes & fees
19 Apr - 20 Apr
The Grand Guesthouse

Westwinds Inn

Westwinds Inn
3.5 star property
Historic Seaport, 0.8 km from Jackson Square
9.4 out of 10, Exceptional, (1,011 reviews)
"Room was clean and the staff was very friendly. Garden area and pool were peaceful. Would definitely stay here again."
United States
Bryan
The price is 7.348.023 ₫
8.266.527 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Westwinds Inn

Silver Palms Inn

Silver Palms Inn
3.5 star property
Old Town Key West, 0.9 km from Jackson Square
9.2 out of 10, Wonderful, (1,027 reviews)
"Great location and very nice ataff"
Australia
fernando
The price is 4.716.957 ₫
7.084.654 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Silver Palms Inn

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, (1,127 reviews)
"Great location and great accommodation "
United States
robert
The price is 5.049.593 ₫
6.612.858 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Heron House - Adult Only

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, (463 reviews)
"Perfect location!"
United States
Amelita
The price is 11.561.943 ₫
14.340.760 ₫ total
includes taxes & fees
29 Apr - 30 Apr
Ella's Cottages - Key West Historic Inns

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, (1,001 reviews)
"Wonderful pool "
United States
lloyd
The price is 11.561.943 ₫
14.784.935 ₫ total
includes taxes & fees
11 May - 12 May
Santa Maria Suites

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only
3.5 star property
Downtown Key West, 0.5 km from Jackson Square
9.2 out of 10, Wonderful, (1,001 reviews)
"Clean, quiet, close to everything we wanted to do!"
United States
leighanne
The price is 5.311.910 ₫
7.160.800 ₫ total
includes taxes & fees
30 Apr - 1 May
Paradise Inn Key West - Adults Only

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
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 8.406.770 ₫
12.790.894 ₫ total
includes taxes & fees
30 Apr - 1 May
Southernmost House - Adult Exclusive

Caribbean House

Caribbean House
3.0 star property
Bahama Village, 0.4 km from Jackson Square
9.2 out of 10, Wonderful, (345 reviews)
"Very convenient location."
United States
Miguel
The price is 6.518.934 ₫
7.992.226 ₫ total
includes taxes & fees
19 Apr - 20 Apr
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.

Compare popular hotels close to Jackson Square

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Property grounds
Orchid Key Inn - Adults Only
3.5 star property
9.8
Exceptional
1,004 reviews
View
Veranda Room | Terrace/patio
The Conch House Heritage Inn
3.5 star property
9.8
Exceptional
163 reviews
View
Front of property
L'Habitation Guest House
2.5 star property
9.4
Exceptional
963 reviews
View
11 Gecko's Garden - Adults Only | Premium bedding, pillow-top beds, individually decorated
Tropical Inn
3.5 star property
9.6
Exceptional
392 reviews
View
Exterior
Douglas House - Adults Only
3.0 star property
9.6
Exceptional
353 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 1735 hotels and other accommodation options you'll find within a mile.
How many hotels can I expect to find close to Jackson Square?
Expedia has 1735 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 Waterfront Playhouse, Key West Film Society and Red Barn Theater.