Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star 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.
Pier House Resort & Spa
Save 100% on your flight
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
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. Popular attractions Duval Street and Mallory Square are located nearby.
Orchid Key Inn - Adults Only
Save 100% on your flight
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3.5-star 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.
Sundown Refuge by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays
Save 100% on your flight
per person
May 7 - May 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Mallory Square are located nearby.
Easy Livin' by Avantstay Key West Home w/ Pool & BBQ Week Long Stays Only
Save 100% on your flight
per person
Apr 29 - May 6
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy free parking, concierge services, and balconies. Popular attractions Duval Street and Mallory Square are located nearby.
Artist Garden by Avantstay Great Location w/ Balcony, Outdoor Dining, Shared Pool & Bbq! Week Long Stays
Save 100% on your flight
per person
May 7 - May 14
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Mallory Square are located nearby.
Fitch Lodge - Key West Historic Inns
Save 100% on your flight
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 3.5-star 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.
Beach House Condo by Avantstay Communal Pool Gated Community Great Location Week Long Stays
Save 100% on your flight
per person
Apr 29 - May 6
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy free parking, a private beach, and concierge services. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Shipyard Treasure by Avantstay Communal Pool Gated Community Great Location Week Long Stays
Save 100% on your flight
per person
Apr 24 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star 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.
Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only
Save 100% on your flight
per person
Apr 24 - May 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star cottage in Key West. Enjoy balconies, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Southernmost Beach Resort
Save 100% on your flight
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
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. Popular attractions Duval Street and South Beach are located nearby.
The Perry Hotel & Marina Key West
Save 100% on your flight
per person
Apr 25 - Apr 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star 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.
3-4 Night Vacations in Jackson Square
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Jackson Square
Price found within the past 48 hours. Click for updated prices.
Jackson Square Last Minute Hotel Deals
Southernmost Beach Resort
1319 Duval Street, Key West, FL
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. ...
Pier House Resort & Spa
1 Duval St, Key West, FL
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. ...
La Concha Key West, Autograph Collection
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 bar and the helpful staff ...
Opal Key Resort & Marina, Key West
245 Front Street, Key West, FL
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 ...
Duval House
815 Duval St, Key West, FL
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. ...
NYAH Key West - Adults Only
420 Margaret Street, Key West, FL
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 ...
The Cabana Inn Key West - Adults Only
413 Applerouth Lane, Key West, FL
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 ...
Heron House - Adult Only
512 Simonton St, Key West, FL
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 ...
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.
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Hotels Near Points of Interest in Jackson Square
- Hotels near Duval Street
- Hotels near Smathers Beach
- Hotels near Mallory Square
- Hotels near Southernmost Point
- Hotels near Ernest Hemingway Home and Museum
- Hotels near South Beach
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near Key West Golf Club
- Hotels near Clarence S. Higgs Memorial Beach Park
- Hotels near Stock Island Yacht Club & Marina
- Hotels near Harry S. Truman Little White House
- Hotels near Key West Lighthouse and Keeper's Quarters Museum
- Hotels near Florida Keys National Marine Sanctuary
- Hotels near Key West Butterfly and Nature Conservatory
- Hotels near Key West Tropical Forest and Botanical Garden
- Hotels near Florida Keys Eco - Discovery Center
Car Rentals in Jackson Square
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