Vacations Close To Jackson Square

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Jackson Square Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
New Town
per person
Jun 16 - Jun 20
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Jun 16 - Jun 20
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
per person
Jun 16 - Jun 20
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)

Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Jun 16 - Jun 20
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
per person
Jun 16 - Jun 20
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
per person
Jun 16 - Jun 20
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
per person
Jun 16 - Jun 20
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)

Douglas House

Douglas House

3 out of 5
Old Town Key West
per person
Jun 16 - Jun 20
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)

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Best Lodging Options Near Jackson Square

Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
1319 Duval Street, Key West, FL
1.07 km from Jackson Square
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. ...
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St, Key West, FL
0.18 km from Jackson Square
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 ...
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St, Key West, FL
0.71 km from Jackson Square
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. ...
Duval House

Duval House

3 out of 5
815 Duval St, Key West, FL
0.42 km from Jackson Square
Stay at this 3-star B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. ...
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

4 out of 5
245 Front Street, Key West, FL
0.51 km from Jackson Square
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 ...
Heron House - Adult Only

Heron House - Adult Only

3.5 out of 5
512 Simonton St, Key West, FL
0.3 km from Jackson Square
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 ...
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane, Key West, FL
0.06 km from Jackson Square
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 ...
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
420 Margaret Street, Key West, FL
0.71 km from Jackson Square
Stay at this 3-star guesthouse in Key West. Enjoy free breakfast, 3 outdoor pools, and a rooftop terrace. Our guests praise the pool and the helpful staff in ...
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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.