Search Deals onJackson 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
Price was $1,085, price is now $871 per person
$871
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this 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.
Hyatt Vacation Club at Windward Pointe, Key West
Price was $1,559, price is now $1,150 per person
$1,150
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Save 100% on your flight
Price was $2,405, price is now $1,799 per person
$1,799
per person
Jun 27 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Stay at this 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.
The Key West Hotel
Save 100% on your flight
Price was $1,773, price is now $1,332 per person
$1,332
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $2,931, price is now $2,212 per person
$2,212
per person
Jun 23 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Smathers Beach are located nearby.
Casa Marina Key West, Curio Collection by Hilton
Save 100% on your flight
Price was $1,669, price is now $1,267 per person
$1,267
per person
Jun 20 - Jun 26
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach are located nearby.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Save 100% on your flight
Price was $2,984, price is now $2,275 per person
$2,275
per person
Jun 23 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, a beach locale, and concierge services. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Hyatt Vacation Club at Sunset Harbor, Key West
Price was $1,254, price is now $972 per person
$972
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located nearby.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Save 100% on your flight
Price was $1,881, price is now $1,479 per person
$1,479
per person
Jun 23 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Stay at this cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Gardens Hotel
Price was $1,490, price is now $1,197 per person
$1,197
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Hyatt Vacation Club at Beach House, Key West
Price was $1,395, price is now $1,129 per person
$1,129
per person
Jun 14 - Jun 18
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Save 100% on your flight
Price was $3,389, price is now $2,757 per person
$2,757
per person
Jun 17 - Jun 21
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum 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
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 helpful staff and the clean ...
Southernmost Beach Resort and Guesthouses
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 ...
Opal Key Resort & Marina, Key West
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. ...
Pier House Resort & Spa
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 ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
The Cabana Inn Key West - Adults Only
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. ...
Pegasus International Hotel
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 ...
Heron House - Adult Only
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 ...
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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