Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort
Price was $1,700, price is now $1,275 per person
$1,275
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $2,348, price is now $1,570 per person
$1,570
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
The Key West Hotel
Save 100% on your flight
Price was $3,817, price is now $2,574 per person
$2,574
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Southernmost Beach Resort and Guesthouses
Save 100% on your flight
Price was $2,622, price is now $1,942 per person
$1,942
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Save 100% on your flight
Price was $4,027, price is now $3,014 per person
$3,014
per person
Mar 16 - Mar 20
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $2,614, price is now $1,983 per person
$1,983
per person
Mar 21 - Mar 28
found 15 hours ago
Roundtrip flight included
Hartford (BDL) 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.
Havana Cabana at Key West
Price was $1,995, price is now $1,527 per person
$1,527
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Save 100% on your flight
Price was $3,646, price is now $2,796 per person
$2,796
per person
Mar 5 - Mar 11
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) 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.
Blue Flamingo Resort Key West
Price was $1,881, price is now $1,446 per person
$1,446
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this family-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 Perry Hotel & Marina Key West
Save 100% on your flight
Price was $2,265, price is now $1,763 per person
$1,763
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Winslow's Bungalows - Key West Historic Inns
Price was $2,000, price is now $1,572 per person
$1,572
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Lighthouse Hotel - Key West Historic Inns
Price was $1,967, price is now $1,547 per person
$1,547
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
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
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 ...
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. ...
Duval House
815 Duval St Key West FL
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
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 ...
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 ...
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 ...
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. ...
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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