Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
per person
Jun 18 - Jun 22
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.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
per person
Jun 2 - Jun 7
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 WiFi, free parking, 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.
Pier House Resort & Spa
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop 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.
Havana Cabana at Key West - Adults Only
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Southwinds Motel
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Fairfield Inn and Suites by Marriott Key West
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Southernmost Beach Resort
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop 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.
Courtyard by Marriott Key West Waterfront
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star beach hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
Save 100% on your flight
per person
Jun 13 - Jun 18
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 Smathers Beach are located nearby.
Hyatt Vacation Club at Windward Pointe, Key West
per person
Jun 18 - Jun 22
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 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.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Save 100% on your flight
per person
Jun 12 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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 Ernest Hemingway Home and Museum are located nearby.
The Grand Guesthouse
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and South 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. ...
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 ...
Hyatt Centric Key West Resort and Spa
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 bar in our reviews. Popular ...
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 ...
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. ...
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 ...
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 ...
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
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Car Rentals in Jackson Square
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