Search Hotels Near Jackson Square, Key West

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
23 Mar - 24 Mar
Tomorrow
24 Mar - 25 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Jackson Square hotels

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)
"Close to everything great stay!"
United States
Cindy
The price is 10.346.420 ₫
11.639.722 ₫ total
includes taxes & fees
29 Mar - 30 Mar
Almond Tree Inn Hotel - 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, (253 reviews)
"Awsome staff great location "
United States
Jeffrey
Key West Villas
Queen with Pool View | 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, (920 reviews)
"Great location. Cool vibe. "
United States
Becky
The price is 10.493.700 ₫
11.805.544 ₫ total
includes taxes & fees
15 Apr - 16 Apr
Simonton Court Historic Inn & Cottages
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, (1,002 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 11.213.531 ₫
12.615.321 ₫ total
includes taxes & fees
22 Apr - 23 Apr
The Gardens Hotel
Exterior

The Marquesa Hotel

The Marquesa Hotel
3.5 star property
Old Town Key West, 0.3 km from Jackson Square
9.8 out of 10, Exceptional, (1,001 reviews)
"Great accommodations and great staff"
United States
Julian
The price is 13.123.700 ₫
16.243.669 ₫ total
includes taxes & fees
25 Mar - 26 Mar
The Marquesa 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, (1,001 reviews)
"Wonderful stay! Want to come back!"
United States
Deborah
The price is 10.254.370 ₫
11.536.166 ₫ total
includes taxes & fees
29 Mar - 30 Mar
Orchid Key Inn - Adults Only
Veranda Room | 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, (159 reviews)
"Large clean room and excellent staff! Made for a great stay. "
United States
Daniel
The price is 9.884.592 ₫
11.120.166 ₫ total
includes taxes & fees
13 Apr - 14 Apr
The Conch House Heritage Inn
Audubon Room - Adult Exclusive | Terrace/patio

The Mermaid & Alligator

The Mermaid & Alligator
3.5 star property
Old Town Key West, 0.8 km from Jackson Square
9.8 out of 10, Exceptional, (292 reviews)
"The breakfast was delicious freshly made specials each morning. The pool is more of an oversized hot tub than a cool pool but it was relaxing anyway."
United States
marie
The Mermaid & Alligator
Cigar House King Suite w/ Poolside porch | 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, (1,001 reviews)
"We absolutely loved staying here!"
United States
Victoria E
The price is 9.599.445 ₫
10.799.375 ₫ total
includes taxes & fees
31 Mar - 1 Apr
Island City House Hotel
Exterior

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, (327 reviews)
"Great quiet location, short walk to all major points of interest. Friendly staff and excellent amenities "
United States
Tsvetelina
The price is 7.259.455 ₫
8.983.574 ₫ total
includes taxes & fees
31 Mar - 1 Apr
Douglas House - Adults Only
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, (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 8.351.302 ₫
10.052.649 ₫ total
includes taxes & fees
24 Mar - 25 Mar
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, (954 reviews)
"Nice place with a great staff. Would definitely stay here again. also, it was in a fantastic location"
United States
Michael
The price is 7.337.700 ₫
8.255.044 ₫ total
includes taxes & fees
26 Mar - 27 Mar
L'Habitation Guest House
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, (590 reviews)
"Lovely property!"
United States
Jesse
The price is 15.753.700 ₫
19.498.163 ₫ total
includes taxes & fees
19 Apr - 20 Apr
H2O Suites - Adults Only
Outdoor pool

Coco Plum Inn

Coco Plum Inn
3.0 star property
Downtown Key West, 0.1 km from Jackson Square
9.4 out of 10, Exceptional, (500 reviews)
"Great location, clean room, amazing staff!! The property was so cozy and intimate- the breakfast was great too. "
United States
Arturo
The price is 8.792.616 ₫
9.891.693 ₫ total
includes taxes & fees
29 Mar - 30 Mar
Coco Plum Inn
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, (337 reviews)
"It was nice. Get a smart tv 😂"
United States
Robert
The price is 12.334.700 ₫
13.876.669 ₫ total
includes taxes & fees
5 Apr - 6 Apr
Marrero's Guest Mansion
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
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
Premium bedding, iron/ironing board, free WiFi, bed sheets

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 9.967.700 ₫
11.213.663 ₫ total
includes taxes & fees
1 Apr - 2 Apr
Weatherstation Inn
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, (1,012 reviews)
"Very good breakfast and staff"
United States
Gerald
The price is 7.800.643 ₫
9.341.173 ₫ total
includes taxes & fees
24 Mar - 25 Mar
Duval House
King Suite | 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, (1,002 reviews)
"Beautiful property and friendly staff. Was very peaceful."
United States
Carmen
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, (449 reviews)
"Perfect location!"
United States
Amelita
The price is 11.024.960 ₫
13.734.649 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Ella's Cottages - Key West Historic Inns
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.
View all properties

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
1,001 reviews
View
Self-parking (surcharge) 15.00 per night
Key West Villas
3.5 star property
9.8
Exceptional
253 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
920 reviews
View
Exterior detail
The Gardens Hotel
4.0 star property
9.8
Exceptional
1,002 reviews
View
Exterior
The Marquesa Hotel
3.5 star property
9.8
Exceptional
1,001 reviews
View

Top Jackson Square Hotel Reviews

Pegasus International Hotel

Pegasus International Hotel

10/10 Excellent
"Loved the room, loved the location, things provided in the room were great. A little weird when room service just puts new towels in and changes a trash bin. Never changed or made the bed"
kirk 4-night trip
Posted 2 hours ago
Pegasus International 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 beautiful beaches or experience its lively festivals.
See properties
Duval street sign in Key West at sunset, Florida

Duval Street

4.5/5 (9,716 reviews)
With a visit to Duval Street, a favourite shopping spot in Key West, you can find the perfect gifts to bring home. Wander the seaside or discover the area's beautiful sunsets.
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 1744 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 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.