Search Deals on
Jackson Square Vacation Packages

Jackson Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,776, price is now $1,002 per person
$1,002
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
Stay at this 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.
The Key West Hotel

The Key West Hotel

2.5 out of 5
Save 100% on your flight
Price was $4,245, price is now $2,371 per person
$2,371
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop 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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $3,265, price is now $1,902 per person
$1,902
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,947, price is now $1,170 per person
$1,170
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Save 100% on your flight
Price was $2,526, price is now $1,632 per person
$1,632
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop 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 Southernmost Point are located nearby.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Save 100% on your flight
Price was $2,618, price is now $1,696 per person
$1,696
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $2,468, price is now $1,614 per person
$1,614
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Save 100% on your flight
Price was $1,722, price is now $1,181 per person
$1,181
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
Save 100% on your flight
Price was $1,593, price is now $1,112 per person
$1,112
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
Save 100% on your flight
Price was $1,880, price is now $1,348 per person
$1,348
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop 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.
Fitch Lodge - Key West Historic Inns

Fitch Lodge - Key West Historic Inns

3.5 out of 5
Save 100% on your flight
Price was $2,621, price is now $1,887 per person
$1,887
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $3,068, price is now $2,239 per person
$2,239
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop 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 Southernmost Point are located nearby.

3-4 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,391, price is now $901 per person
$901
per person
Feb 5 - Feb 8
found 7 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,963, price is now $1,758 per person
$1,758
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $1,975, price is now $1,290 per person
$1,290
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,081, price is now $1,395 per person
$1,395
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)

5-7 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,776, price is now $1,002 per person
$1,002
per person
Feb 1 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $4,245, price is now $2,371 per person
$2,371
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $3,265, price is now $1,902 per person
$1,902
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Key West (EYW)
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,947, price is now $1,170 per person
$1,170
per person
Jan 31 - Feb 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)

Jackson Square Last Minute Hotel Deals

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
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 ...
La Concha Key West, Autograph Collection
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
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. ...
The Cabana Inn Key West - Adults Only
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
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 ...
Heron House - Adult Only
Pegasus International Hotel

Pegasus International Hotel

2.5 out of 5
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 ...
Pegasus International Hotel
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
511 Caroline St Key West FL
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean ...
Amsterdam's Curry Mansion Inn
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
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 helpful staff in our reviews. ...
Hyatt Centric Key West Resort and Spa
Marrero's Guest Mansion

Marrero's Guest Mansion

3.5 out of 5
410 Fleming Street Key West FL
Stay at this B&B in Key West. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located ...
Marrero's Guest Mansion
Coco Plum Inn

Coco Plum Inn

3 out of 5
611 Whitehead Street Key West FL
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. ...
Coco Plum Inn
See all 2,749 properties in Jackson Square
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.