Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West
Price was $1,044, price is now $832 per person
$832
per person
May 11 - May 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Contra House Key West
Price was $5,776, price is now $4,449 per person
$4,449
per person
May 17 - May 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free WiFi, free parking, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Key West Hotel
Save 100% on your flight
Price was $2,303, price is now $1,663 per person
$1,663
per person
May 27 - May 31
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.
Hyatt Vacation Club at Sunset Harbor, Key West
Save 100% on your flight
Price was $1,966, price is now $1,447 per person
$1,447
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. 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 $2,173, price is now $1,603 per person
$1,603
per person
May 8 - May 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Casa Marina Key West, Curio Collection by Hilton
Price was $1,619, price is now $1,199 per person
$1,199
per person
May 28 - Jun 1
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
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 are located nearby.
Southernmost Beach Resort and Guesthouses
Save 100% on your flight
Price was $1,791, price is now $1,360 per person
$1,360
per person
May 11 - May 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 South Beach are located nearby.
Sea Breeze by Brightwild Off-street Parking
Save 100% on your flight
Price was $3,066, price is now $2,359 per person
$2,359
per person
May 15 - May 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this apartment in Key West. Enjoy free parking. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Caribbean House
Price was $1,440, price is now $1,109 per person
$1,109
per person
May 15 - May 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 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.
Poolside Retreat by Brightwild Cottage w Pool
Save 100% on your flight
Price was $2,046, price is now $1,606 per person
$1,606
per person
May 15 - May 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this apartment in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Palmgale House in Key West
Save 100% on your flight
Price was $6,195, price is now $4,876 per person
$4,876
per person
May 17 - May 22
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free parking and an outdoor pool. Popular attractions Duval Street and Smathers Beach are located nearby.
Floralee House in Key West
Save 100% on your flight
Price was $5,981, price is now $4,773 per person
$4,773
per person
May 17 - May 22
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free parking and a garden. 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 ...
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. ...
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. ...
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 ...
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 ...
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 ...
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 ...
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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