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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 Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Price was $1,349, price is now $1,061 per person
$1,061
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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 $3,820, price is now $2,686 per person
$2,686
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Price was $1,623, price is now $1,273 per person
$1,273
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
Price was $1,405, price is now $1,118 per person
$1,118
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
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 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 $3,535, price is now $2,824 per person
$2,824
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
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
Price was $2,666, price is now $2,133 per person
$2,133
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Smathers Beach are located nearby.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Price was $2,826, price is now $2,267 per person
$2,267
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Ambrosia Key West

Ambrosia Key West

3.5 out of 5
Price was $1,760, price is now $1,415 per person
$1,415
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Stay at this B&B 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.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Price was $2,730, price is now $2,220 per person
$2,220
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Book a stay at this spa 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.
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 $2,575, price is now $2,100 per person
$2,100
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

3 out of 5
Price was $2,090, price is now $1,706 per person
$1,706
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Book a stay at this beach 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.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $2,651, price is now $2,171 per person
$2,171
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Price was $2,534, price is now $1,944 per person
$1,944
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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 $3,820, price is now $2,686 per person
$2,686
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
Sky Suites Retreat by Brightwild 2 Stunning Condos

Sky Suites Retreat by Brightwild 2 Stunning Condos

2 out of 5
Old Town Key West
Save 100% on your flight
Price was $6,950, price is now $5,276 per person
$5,276
per person
Nov 13 - Nov 17
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Key West (EYW)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was $2,826, price is now $2,267 per person
$2,267
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)

5-7 Night Vacations in Jackson Square

Price found within the past 48 hours. Click for updated prices.
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
Key West Historic District
Price was $1,909, price is now $1,413 per person
$1,413
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) 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 $4,198, price is now $2,719 per person
$2,719
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) to Key West (EYW)
The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $3,314, price is now $2,494 per person
$2,494
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 $3,055, price is now $2,380 per person
$2,380
per person
Nov 12 - Nov 17
found 22 hours ago
Roundtrip flight included
Charlotte (CLT) 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 spa 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
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
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
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
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
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
Winslow's Bungalows - Key West Historic Inns
Duval House

Duval House

3 out of 5
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 ...
Duval House
See all 2,599 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.