Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,005, price is now $622 per person
$622
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Breezy Bungalow by Avantstay Close 2 Zachary Taylor State Park & Beach w/ Shared Pool Week Long Stays
Price was $3,755, price is now $3,010 per person
$3,010
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy balconies, cable/satellite TV service, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only
Price was $2,892, price is now $2,360 per person
$2,360
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star beach cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays
Price was $3,975, price is now $3,259 per person
$3,259
per person
Oct 18 - Oct 25
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.
Lavender Jungle by Avantstay Great Location w/ Patio & Shared Pool! Week Long Stays Only
Price was $2,770, price is now $2,272 per person
$2,272
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy a beach locale, patios, and in-room washers/dryers. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
Price was $3,673, price is now $3,019 per person
$3,019
per person
Oct 18 - Oct 25
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 air conditioning. Popular attractions Duval Street and Mallory Square are located nearby.
Parrot Perch by Avantstay Old Town Key West w/ Shared Pool Week Long Stays Only
Price was $2,786, price is now $2,292 per person
$2,292
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3.5-star cottage in Key West. Enjoy free parking, concierge services, and balconies. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Key West Charming by Avantstay Communal Pool Gated Community Near Fort Zachary Taylor Park Week Long Stays
Price was $3,014, price is now $2,509 per person
$2,509
per person
Oct 18 - Oct 25
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 Ernest Hemingway Home and Museum are located nearby.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,541, price is now $1,032 per person
$1,032
per person
Oct 26 - Nov 2
found 1 day ago
Roundtrip non-stop 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 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.
Amelia Home by Avantstay In Historic Old Town w/ Pool
Save 100% on your flight
Price was $5,345, price is now $3,723 per person
$3,723
per person
Nov 3 - Nov 8
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Save 100% on your flight
Price was $2,759, price is now $2,053 per person
$2,053
per person
Nov 3 - Nov 8
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Smathers Beach are located nearby.
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
Save 100% on your flight
Price was $1,449, price is now $1,111 per person
$1,111
per person
Oct 13 - Oct 18
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star villa in Key West. Enjoy free parking, a beach locale, 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
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. ...
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. ...
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 ...
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 ...
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 ...
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 ...
Heron House - Adult Only
512 Simonton St, Key West, FL
Stay at this 3.5-star 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 ...
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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