Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
Price was $1,215, price is now $967 per person
$967
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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
Save 100% on your flight
Price was $1,380, price is now $986 per person
$986
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,634, price is now $1,178 per person
$1,178
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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 $2,128, price is now $1,556 per person
$1,556
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $2,641, price is now $1,932 per person
$1,932
per person
Jun 27 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. 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 $1,767, price is now $1,340 per person
$1,340
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) 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.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,873, price is now $1,504 per person
$1,504
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), 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.
Coconut Beach Resort
Price was $2,015, price is now $1,617 per person
$1,617
per person
Jun 13 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
The Gardens Hotel
Save 100% on your flight
Price was $1,986, price is now $1,606 per person
$1,606
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Grand Guesthouse
Price was $1,994, price is now $1,615 per person
$1,615
per person
Jun 13 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Save 100% on your flight
Price was $3,309, price is now $2,682 per person
$2,682
per person
Jun 18 - Jun 22
found 17 hours ago
Roundtrip non-stop flight included
Memphis (MEM) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Marker Key West Harbor Resort
Price was $1,559, price is now $1,265 per person
$1,265
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. 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
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 ...
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 ...
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. ...
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 ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and South Beach ...
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. ...
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 ...
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 ...
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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