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 $2,036, price is now $1,510 per person
$1,510
per person
Mar 6 - Mar 13
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.
The Key West Hotel
Price was $5,002, price is now $3,143 per person
$3,143
per person
Mar 6 - Mar 13
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.
Oceans Edge Key West Resort, Hotel & Marina
Price was $2,760, price is now $1,751 per person
$1,751
per person
Mar 6 - Mar 13
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.
Havana Cabana at Key West
Price was $2,256, price is now $1,566 per person
$1,566
per person
Mar 6 - Mar 13
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.
Blue Flamingo Resort Key West
Price was $2,288, price is now $1,607 per person
$1,607
per person
Mar 6 - Mar 13
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.
Southernmost Beach Resort and Guesthouses
Price was $3,314, price is now $2,373 per person
$2,373
per person
Mar 6 - Mar 13
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 $7,043, price is now $5,346 per person
$5,346
per person
Mar 13 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
The Perry Hotel & Marina Key West
Price was $2,580, price is now $2,039 per person
$2,039
per person
Mar 24 - Mar 29
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.
Pier House Resort & Spa
Save 100% on your flight
Price was $3,229, price is now $2,556 per person
$2,556
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
The Reach Key West, Curio Collection by Hilton
Price was $2,627, price is now $2,091 per person
$2,091
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Price was $3,242, price is now $2,583 per person
$2,583
per person
Mar 3 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Hyatt Vacation Club at Windward Pointe, Key West
Price was $2,255, price is now $1,797 per person
$1,797
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip non-stop 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.
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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