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
Save 100% on your flight
Price was $1,068, price is now $733 per person
$733
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
The Key West Hotel
Price was $2,584, price is now $1,386 per person
$1,386
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,435, price is now $846 per person
$846
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,416, price is now $837 per person
$837
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, free parking, 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.
Lighthouse Hotel - Key West Historic Inns
Save 100% on your flight
Price was $1,979, price is now $1,188 per person
$1,188
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Ella's Cottages - Key West Historic Inns
Save 100% on your flight
Price was $1,991, price is now $1,201 per person
$1,201
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,373, price is now $856 per person
$856
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this 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.
Winslow's Bungalows - Key West Historic Inns
Save 100% on your flight
Price was $1,789, price is now $1,150 per person
$1,150
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Southernmost Beach Resort and Guesthouses
Save 100% on your flight
Price was $2,288, price is now $1,583 per person
$1,583
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
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 reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Casa Marina Key West, Curio Collection by Hilton
Save 100% on your flight
Price was $2,295, price is now $1,615 per person
$1,615
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) 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 Southernmost Point are located nearby.
Ibis Bay Beach Resort
Save 100% on your flight
Price was $1,194, price is now $849 per person
$849
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Pier House Resort & Spa
Save 100% on your flight
Price was $2,914, price is now $2,133 per person
$2,133
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
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 in our reviews. 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
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 ...
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. ...
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 ...
Amsterdam's Curry Mansion Inn
511 Caroline St Key West FL
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean ...
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 ...
Marrero's Guest Mansion
410 Fleming Street Key West FL
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located ...
Coco Plum Inn
611 Whitehead Street Key West FL
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. ...
The Saint Hotel Key West, Autograph Collection, Adult Only
417 Eaton Street Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Popular attractions Duval Street and ...
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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