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Jackson Square Vacation Packages

Jackson Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Price was $1,859, price is now $1,486 per person
$1,486
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
The Key West Hotel

The Key West Hotel

3 out of 5
Price was $3,414, price is now $2,365 per person
$2,365
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Southernmost Point are located nearby.
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was $2,627, price is now $1,895 per person
$1,895
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Price was $2,863, price is now $2,090 per person
$2,090
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
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 $3,715, price is now $2,748 per person
$2,748
per person
Jul 15 - Jul 22
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) 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.
Coconut Beach Resort

Coconut Beach Resort

2.5 out of 5
Price was $2,563, price is now $1,974 per person
$1,974
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy free WiFi, free parking, and a private beach. Our guests praise 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
Price was $4,127, price is now $3,191 per person
$3,191
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was $2,182, price is now $1,702 per person
$1,702
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
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 $3,476, price is now $2,716 per person
$2,716
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Price was $2,414, price is now $1,913 per person
$1,913
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). 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 Gardens Hotel

The Gardens Hotel

4 out of 5
Price was $2,342, price is now $1,864 per person
$1,864
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Price was $2,301, price is now $1,839 per person
$1,839
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Price was $1,321, price is now $1,076 per person
$1,076
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

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

3 out of 5
Old Town Key West
Price was $3,646, price is now $2,707 per person
$2,707
per person
Jul 5 - Jul 9
found 12 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

3 out of 5
Old Town Key West
Price was $2,412, price is now $1,809 per person
$1,809
per person
Jul 5 - Jul 9
found 12 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was $2,154, price is now $1,617 per person
$1,617
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,468, price is now $1,018 per person
$1,018
per person
Jul 7 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Key West (EYW)
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Price was $3,414, price is now $2,365 per person
$2,365
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

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

3 out of 5
Old Town Key West
Save 100% on your flight
Price was $4,130, price is now $2,951 per person
$2,951
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip flight included
New York (NYC) 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
Price was $2,627, price is now $1,895 per person
$1,895
per person
Jun 29 - Jul 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
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
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
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
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
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
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
See all 2,657 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.