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Jackson Square Vacation Packages

Jackson Square Flight + Hotel Packages

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

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Price was $1,582, price is now $1,171 per person
$1,171
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Save 100% on your flight
Price was $2,565, price is now $1,448 per person
$1,448
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South 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 $2,129, price is now $1,473 per person
$1,473
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $2,215, price is now $1,562 per person
$1,562
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
The Key West Hotel

The Key West Hotel

3 out of 5
Save 100% on your flight
Price was $2,471, price is now $1,747 per person
$1,747
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!

3 out of 5
Save 100% on your flight
Price was $3,203, price is now $2,301 per person
$2,301
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

3 out of 5
Save 100% on your flight
Price was $3,915, price is now $2,828 per person
$2,828
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5
Save 100% on your flight
Price was $2,883, price is now $2,084 per person
$2,084
per person
Jul 11 - Jul 16
found 24 hours ago
Roundtrip non-stop flight included
Memphis (MEM) 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.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 out of 5
Save 100% on your flight
Price was $3,726, price is now $2,714 per person
$2,714
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, a beach locale, and concierge services. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Amelia Home by Avantstay In Historic Old Town w/ Pool

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5
Save 100% on your flight
Price was $4,201, price is now $3,080 per person
$3,080
per person
Jun 30 - Jul 5
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Save 100% on your flight
Price was $3,925, price is now $2,889 per person
$2,889
per person
Jun 30 - Jul 5
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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 Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $1,748, price is now $1,325 per person
$1,325
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.

3-4 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was $912, price is now $727 per person
$727
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $1,716, price is now $1,215 per person
$1,215
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 $1,307, price is now $1,015 per person
$1,015
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Key West (EYW)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was $916, price is now $733 per person
$733
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Key West (EYW)

5-7 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,565, price is now $1,448 per person
$1,448
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $2,129, price is now $1,473 per person
$1,473
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
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 $2,215, price is now $1,562 per person
$1,562
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $2,471, price is now $1,747 per person
$1,747
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
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 ...
Southernmost Beach Resort and Guesthouses
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
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. ...
Opal Key Resort & Marina, Key West
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
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 ...
Pier House Resort & Spa
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
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 ...
Casa Marina Key West, Curio Collection by Hilton
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
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
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
See all 2,663 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.