Exclusive Jackson Square Vacation Deals
Jackson Square vacation package deals
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
Sep 13 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.
Orchid Key Inn - Adults Only
Old Town Key West
Save 100% on your flight
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Enjoy the hot tub and free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and dry cleaning are also offered.
Almond Tree Inn Hotel - Adults Only
Old Town Key West
Save 100% on your flight
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free continental breakfast each morning.
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Frequently asked questions
Top Jackson Square hotel deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
$244 nightly
The price is $275 total per night
$275 total
Aug 25 - Aug 26
Total includes taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Pool
Spa
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$283 nightly
The price is $318 total per night
$318 total
Aug 13 - Aug 14
Total includes taxes and fees
This eco-certified resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Pool
Spa
La Concha Key West, Autograph Collection
430 Duval St, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$233 nightly
The price is $262 total per night
$262 total
Aug 17 - Aug 18
Total includes taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
Pool
Pet friendly
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.