Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Caribbean House
Save 100% on your flight
Price was $788, price is now $542 per person
$542
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 3-star B&B in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise 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
Save 100% on your flight
Price was $1,356, price is now $798 per person
$798
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 3.5-star 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.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,870, price is now $1,171 per person
$1,171
per person
Dec 2 - Dec 9
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 3.5-star eco-certified 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.
Winslow's Bungalows - Key West Historic Inns
Save 100% on your flight
Price was $1,173, price is now $753 per person
$753
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 4-star 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.
The Key West Hotel
Save 100% on your flight
Price was $3,253, price is now $2,161 per person
$2,161
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Fitch Lodge - Key West Historic Inns
Save 100% on your flight
Price was $878, price is now $602 per person
$602
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Lighthouse Hotel - Key West Historic Inns
Save 100% on your flight
Price was $1,073, price is now $740 per person
$740
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Margaritaville Beach House Key West
Save 100% on your flight
Price was $948, price is now $666 per person
$666
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant in our reviews. 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 $1,105, price is now $790 per person
$790
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 4-star 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.
Fairfield Inn & Suites by Marriott Key West at the Keys Collection
Price was $869, price is now $633 per person
$633
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, room service, and a fitness center. 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 $1,220, price is now $895 per person
$895
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays
Save 100% on your flight
Price was $2,523, price is now $1,855 per person
$1,855
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the bar in our reviews. Popular ...
Southernmost Beach Resort and Guesthouses
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. ...
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 ...
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. ...
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 ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Stay at this 4-star beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue, Key West, FL
Stay at this 4-star 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 ...
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 ...
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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