Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Lighthouse Hotel - Key West Historic Inns
Save 100% on your flight
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Douglas House
Save 100% on your flight
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Easy Livin' by Avantstay Key West Home w/ Pool & BBQ Week Long Stays Only
Save 100% on your flight
per person
Apr 29 - May 6
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy free parking, concierge services, and balconies. Popular attractions Duval Street and Mallory Square are located nearby.
The Perry Hotel & Marina Key West
Save 100% on your flight
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Southernmost Beach Resort
Save 100% on your flight
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Save 100% on your flight
per person
May 2 - May 7
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Smathers Beach are located nearby.
Pier House Resort & Spa
Save 100% on your flight
per person
May 1 - May 5
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Havana Cabana at Key West - Adults Only
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Commodore s Compound by Brightwild Huge Home
Save 100% on your flight
per person
May 8 - May 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this apartment in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Mallory Square are located nearby.
Heron House Court - Adult Only
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, a rooftop terrace, and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays
Save 100% on your flight
per person
May 2 - May 9
found 24 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Mallory Square are located nearby.
3-4 Night Vacations in Jackson Square
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Jackson Square
Price found within the past 48 hours. Click for updated prices.
Jackson Square Last Minute Hotel Deals
Southernmost Beach Resort
1319 Duval Street, Key West, FL
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
Pier House Resort & Spa
1 Duval St, Key West, FL
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
La Concha Key West, Autograph Collection
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 bar and the helpful staff ...
Opal Key Resort & Marina, Key West
245 Front Street, Key West, FL
Stay at this 4-star hotel in Key West. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
Duval House
815 Duval St, Key West, FL
Stay at this 3-star B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. ...
NYAH Key West - Adults Only
420 Margaret Street, Key West, FL
Stay at this 3-star guesthouse in Key West. Enjoy free breakfast, 3 outdoor pools, and a rooftop terrace. Our guests praise the pool and the helpful staff in ...
The Cabana Inn Key West - Adults Only
413 Applerouth Lane, Key West, FL
Stay at this 3-star guesthouse in Key West. Enjoy free breakfast, parking (surcharge), and daily housekeeping. Our guests praise the breakfast and the pool in ...
Heron House - Adult Only
512 Simonton St, Key West, FL
Stay at this 3.5-star 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 ...
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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Hotels Near Points of Interest in Jackson Square
- Hotels near Duval Street
- Hotels near Smathers Beach
- Hotels near Mallory Square
- Hotels near Southernmost Point
- Hotels near Ernest Hemingway Home and Museum
- Hotels near South Beach
- Hotels near Fort Zachary Taylor Historic State Park
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- Hotels near Key West Lighthouse and Keeper's Quarters Museum
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Car Rentals in Jackson Square
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