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Jackson Square Vacation Packages

Jackson Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
Hyatt Vacation Club at Sunset Harbor, Key West
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
The Key West Hotel
Fitch Lodge - Key West Historic Inns
Coconut Beach Resort
Hyatt Vacation Club at Windward Pointe, Key West
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Hyatt Vacation Club at Beach House, Key West
Amelia Home by Avantstay In Historic Old Town w/ Pool
Winslow's Bungalows - Key West Historic Inns
Bananas Foster by Brightwild Epic Guesthouse

3-4 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
The Key West Hotel
Amelia Home by Avantstay In Historic Old Town w/ Pool
Coconut Beach Resort

5-7 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
Coconut Beach Resort
Hyatt Vacation Club at Windward Pointe, Key West
The Key West Hotel
Hyatt Vacation Club at Beach House, Key West

Jackson Square Last Minute Hotel Deals

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
La Concha Key West, Autograph Collection
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
Hyatt Centric Key West Resort and Spa
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street Key West FL
Stay at this hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opal Key Resort & Marina, Key West
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
Stay at this guesthouse in Key West. Enjoy free breakfast, parking (surcharge), and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. ...
The Cabana Inn Key West - Adults Only
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St Key West FL
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Heron House - Adult Only
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
501 Southard Street Key West FL
Stay at this hotel in Key West. Enjoy free breakfast, free parking, and a rooftop terrace. Our guests praise the helpful staff and the property condition in ...
Pegasus International Hotel
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St Key West FL
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
Pier House Resort & Spa
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.