Exclusive Jackson Square Vacation Deals
Jackson Square vacation package deals
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,074, price is now $675 per person
$675
per person
Nov 13 - Nov 17
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.
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,526, price is now $930 per person
$930
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $3,153, price is now $1,960 per person
$1,960
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,591, price is now $994 per person
$994
per person
Oct 22 - Oct 28
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.
Ridley House - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $2,662, price is now $1,671 per person
$1,671
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free buffet breakfast each morning. Concierge services are provided for your convenience.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,101, price is now $702 per person
$702
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop 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.
Frequently asked questions
Top Jackson Square hotel deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Free Cancellation
$230 nightly
The price is $259 total per night
$259 total
Sep 22 - Sep 23
Total with 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
Pier House Resort & Spa
1 Duval St, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$387 nightly
The price is $435 total per night
$435 total
Sep 22 - Sep 23
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.
On private beach
Pool
La Concha Key West, Autograph Collection
430 Duval St, Key West, FL
Free Cancellation
Reserve now, pay when you stay
$208 nightly
The price is $234 total per night
$234 total
Oct 5 - Oct 6
Total with 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.