Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Weatherstation Inn
Price was $1,351, price is now $976 per person
$976
per person
Oct 12 - Oct 16
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Book a stay at this boutique B&B in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Hyatt Vacation Club at Sunset Harbor, Key West
Price was $1,650, price is now $1,032 per person
$1,032
per person
Oct 5 - Oct 9
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square are located nearby.
The Key West Hotel
Save 100% on your flight
Price was $3,180, price is now $1,998 per person
$1,998
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
Island View 1BR Residence With Balcony
Price was $1,613, price is now $1,121 per person
$1,121
per person
Oct 12 - Oct 16
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this aparthotel in Key West. Popular attractions Duval Street and Smathers Beach are located nearby.
Banana's Foster Guesthouse
Price was $1,467, price is now $1,040 per person
$1,040
per person
Oct 12 - Oct 16
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, laundry facilities, and a picnic area. Popular attractions Duval Street and Mallory Square are located nearby.
Ocean Front One Bedroom Residence
Price was $1,719, price is now $1,222 per person
$1,222
per person
Oct 12 - Oct 16
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this aparthotel in Key West. Popular attractions Duval Street and Smathers Beach are located nearby.
New Rose Petal Petite Suite - Pool Parking
Price was $1,662, price is now $1,198 per person
$1,198
per person
Oct 5 - Oct 9
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this apartment in Key West. Enjoy free parking. Popular attractions Duval Street and Mallory Square are located nearby.
The Marker Key West Harbor Resort
Save 100% on your flight
Price was $2,153, price is now $1,595 per person
$1,595
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
The Grenada Suite Pool View Private Balcony
Price was $1,597, price is now $1,187 per person
$1,187
per person
Oct 5 - Oct 9
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this apartment in Key West. Enjoy free parking and a fitness center. Popular attractions Duval Street and Smathers Beach are located nearby.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Save 100% on your flight
Price was $2,834, price is now $2,162 per person
$2,162
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Stay at this cottage in Key West. Enjoy free parking, a beach locale, and concierge services. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Ambrosia Key West
Price was $1,409, price is now $1,089 per person
$1,089
per person
Oct 12 - Oct 16
found 20 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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.
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
Save 100% on your flight
Price was $2,287, price is now $1,780 per person
$1,780
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy free parking, a beach locale, and balconies. 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 and Guesthouses
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 ...
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 helpful staff and the clean ...
The Cabana Inn Key West - Adults Only
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. ...
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 helpful staff in our reviews. ...
Pier House Resort & Spa
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 ...
Heron House - Adult Only
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 ...
Opal Key Resort & Marina, Key West
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. ...
Tranquility Guest House
302 Angela st Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, a garden, and cable TV channels. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located ...
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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