Key West Jackson Square Hotels

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Jackson Square

Almond Tree Inn Hotel - Adults Only

3.5 star property
10.0 out of 10, Exceptional, (1009)
"Beautiful quaint property with outstanding staff. Loved our visit and would highly recommend "
The price is HK$1,524
HK$1,715 total
includes taxes & fees
17 Sept - 18 Sept
Almond Tree Inn Hotel - Adults Only

The Gardens Hotel

4.0 star property
9.8 out of 10, Exceptional, (1001)
"Great property and location!"
The price is HK$1,504
HK$1,692 total
includes taxes & fees
18 Sept - 19 Sept
The Gardens Hotel

The Marquesa Hotel

3.5 star property
9.8 out of 10, Exceptional, (1008)
"Beautiful, clean property! Would definitely stay there again!"
The price is HK$1,052
HK$1,577 total
includes taxes & fees
30 Sept - 1 Oct
The Marquesa Hotel

Simonton Court Historic Inn & Cottages

2.5 star property
9.8 out of 10, Exceptional, (822)
"Friendly staff good continental breakfast."
The price is HK$1,004
HK$1,129 total
includes taxes & fees
16 Sept - 17 Sept
Simonton Court Historic Inn & Cottages

Key West Villas

3.5 star property
9.8 out of 10, Exceptional, (237)
"Owners are incredible hosts. They’ve basically thought of everything. Space and grounds are very clean safe and comfortable! We will definitely be back!"
Key West Villas

Coco Plum Inn

3.0 star property
9.6 out of 10, Exceptional, (444)
"Would stay again. "
The price is HK$1,183
HK$1,331 total
includes taxes & fees
16 Sept - 17 Sept
Coco Plum Inn

Orchid Key Inn - Adults Only

3.5 star property
9.8 out of 10, Exceptional, (1007)
"Excellent friendly staff and beautiful property. "
The price is HK$1,438
HK$1,618 total
includes taxes & fees
21 Sept - 22 Sept
Orchid Key Inn - Adults Only

The Conch House Heritage Inn

3.5 star property
9.8 out of 10, Exceptional, (132)
"We really enjoyed our stay"
The price is HK$1,579
HK$1,777 total
includes taxes & fees
16 Sept - 17 Sept
The Conch House Heritage Inn

The Mermaid & Alligator

3.5 star property
9.8 out of 10, Exceptional, (258)
"Absolutely loved staying here and are already looking at dates to come back!"
The Mermaid & Alligator

L'Habitation Guest House

2.5 star property
9.4 out of 10, Exceptional, (887)
"Great place close to lots of fun and shopping. Excellent staff, very friendly and attentive. Will stay there again!"
The price is HK$678
HK$763 total
includes taxes & fees
16 Sept - 17 Sept
L'Habitation Guest House

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

3.5 star property
9.8 out of 10, Exceptional, (114)
"Staff (Olga, Zana, Tim) went out of their way to make sure that all of our stay was excellent "
The price is HK$973
HK$1,317 total
includes taxes & fees
16 Sept - 17 Sept
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Island City House Hotel

3.0 star property
9.6 out of 10, Exceptional, (1002)
"Great location. Appreciated having access to a pool and liked the separate living area with kitchen amenities. "
The price is HK$1,157
HK$1,302 total
includes taxes & fees
16 Sept - 17 Sept
Island City House Hotel

H2O Suites - Adults Only

3.5 star property
9.8 out of 10, Exceptional, (558)
"We had an amazing time here! Very clean and the staff was unbelievable!! I highly recommend this place!! Great location, updated facilities just amazing!! "
The price is HK$2,015
HK$2,617 total
includes taxes & fees
22 Sept - 23 Sept
H2O Suites - Adults Only

Douglas House

3.0 star property
9.6 out of 10, Exceptional, (167)
"Such a beautiful property. "
The price is HK$881
HK$1,026 total
includes taxes & fees
30 Sept - 1 Oct
Douglas House

Weatherstation Inn

2.5 star property
9.4 out of 10, Exceptional, (955)
"We LOVE the Weatherstation!! It’s so quiet and clean but a very short walk to all the action in Key West. The breakfast croissants are wonderful! Beautiful decorated rooms. Staff is exceptionally friendly and accommodating. We can’t wait to go back."
The price is HK$1,225
HK$1,379 total
includes taxes & fees
18 Sept - 19 Sept
Weatherstation Inn

Marrero's Guest Mansion

3.5 star property
9.4 out of 10, Exceptional, (333)
"Part of a 10 day anniversary celebration! The service and convenience could not have been any better! Marrero’s felt like home and we were very happy with our stay!"
The price is HK$1,548
HK$1,742 total
includes taxes & fees
16 Sept - 17 Sept
Marrero's Guest Mansion

Ambrosia Key West

3.5 star property
9.4 out of 10, Exceptional, (1001)
"Loved staying here, such a cute place and the location was close to Duval St."
The price is HK$1,250
HK$1,406 total
includes taxes & fees
16 Sept - 17 Sept
Ambrosia Key West

Duval House

3.0 star property
9.4 out of 10, Exceptional, (1016)
"Great place to stay and friendly staff"
The price is HK$926
HK$1,209 total
includes taxes & fees
17 Sept - 18 Sept
Duval House

Tropical Inn

3.5 star property
9.4 out of 10, Exceptional, (345)
"Great spot "
The price is HK$859
HK$1,161 total
includes taxes & fees
18 Sept - 19 Sept
Tropical Inn

Ella's Cottages - Key West Historic Inns

3.5 star property
9.4 out of 10, Exceptional, (375)
"Loved our stay. "
The price is HK$1,394
HK$1,962 total
includes taxes & fees
22 Sept - 23 Sept
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Jackson Square Hotel Reviews

Destinations near Key West

Duval Street
Duval Street

Duval Street

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.

Oldest House Museum and Garden
Oldest House Museum and Garden

Oldest House Museum and Garden

With its period décor and vintage documents, South Florida’s oldest house provides an impression of life in the Florida Keys archipelago in the 19th century

Ernest Hemingway Home and Museum
Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 1762 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 Hyatt Centric Key West Resort and Spa and Southernmost Beach Resort and Guesthouses.

How many hotels can I expect to find close to Jackson Square?

Expedia has 1762 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 Saint Mary Star of the Sea 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.