Search Deals onJackson Square Vacation Packages
Jackson Square Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Havana Cabana at Key West - Adults Only
Save 100% on your flight
per person
Jun 10 - Jun 17
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.
Southernmost Beach Resort
Save 100% on your flight
per person
Jun 10 - Jun 17
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.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip non-stop 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
Jun 10 - Jun 17
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.
The Perry Hotel & Marina Key West
Save 100% on your flight
per person
Jun 10 - Jun 17
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, 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.
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
per person
May 24 - May 28
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 Ernest Hemingway Home and Museum are located nearby.
Winslow's Bungalows - Key West Historic Inns
Save 100% on your flight
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star hotel 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.
Bishop Hotel Key West
Save 100% on your flight
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 4-star guesthouse in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Douglas House
Save 100% on your flight
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this 3-star guesthouse in Key West. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Fitch Lodge - Key West Historic Inns
Save 100% on your flight
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip non-stop 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.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
per person
Jun 5 - Jun 9
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Key West (EYW)
Stay at this 3.5-star cottage in Key West. Enjoy free parking, concierge services, and premium TV channels. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Ibis Bay Beach Resort
Save 100% on your flight
per person
Jun 10 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool 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. ...
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.
Discover Other Travel Deals
- Legoland Florida
- Universal Studios Hollywood®
- Legoland California
- Broadway New York
- The Wizarding World of Harry Potter
- Sanibel Captiva Island
- Paseo de España
- Universal Studios Florida
- San Antonio SeaWorld
- Siargao Island
- Australia Zoo
- Busch Gardens Tampa Bay
- SeaWorld® Orlando
- Tolantongo Caves
- Eleuthera and Harbour Island
- Biltmore Estate
- Blue Lagoon
- Swiss Alps
- Silver Dollar City
- Lackland Air Force Base
- Grand Teton National Park
- San Diego Zoo
- Holy Land Experience
- Grand Ole Opry
- Ark Encounter
- Levi's Stadium
- Breckenridge Ski Resort
- Alcatraz Island
- Six Flags Magic Mountain
- Walt Disney World®
- Dollywood
- Kalahari Waterpark Resort
- Giza Pyramid Complex
- Casino at Don Laughlin's Riverside Resort
- Hoover Dam
- Hollywood Beach
- Faisalabad Clock Tower
- Venice Beach Boardwalk
- Blue Lagoon Beach
- Moraine Lake
- Hotels with a Pool in Key West
- Beach Hotels in Key West
- Historic Hotels in Key West
- Family Hotels in Key West
- Hotels with Free Parking in Key West
- Romantic Hotels in Key West
- Apartment Hotel in Key West
- Hotels with Hot Tubs in Key West
- Luxury Hotels in Key West
- Resorts & Hotels with Spas in Key West
- Key West Hotels
- Florida Keys Hotels
- Summerland Key Hotels
- South Florida Hotels
- Gulf Coast Hotels
- Stock Island Hotels
- Sugarloaf Key Hotels
- Southeastern United States Hotels
- Gulf of Mexico Hotels
- Raccoon Key Hotels
- Dredgers Key Hotels
- Cow Key Hotels
- Lower Keys Hotels
- Fleming Key Hotels
- The South Hotels
Hotels Near Points of Interest in Jackson Square
- Hotels near Duval Street
- Hotels near Mallory Square
- Hotels near Smathers Beach
- Hotels near Southernmost Point
- Hotels near South Beach
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near Clarence S. Higgs Memorial Beach Park
- Hotels near Key West Golf Club
- Hotels near Stock Island Yacht Club & Marina
- Hotels near Harry S. Truman Little White House
- Hotels near Florida Keys National Marine Sanctuary
- Hotels near Key West Butterfly and Nature Conservatory
- Hotels near Key West Lighthouse and Keeper's Quarters Museum
- Hotels near Key West Tropical Forest and Botanical Garden
- Hotels near Florida Keys Eco - Discovery Center
Car Rentals in Jackson Square
- Car rentals in Key West
- Car rentals in Florida Keys
- Car rentals in Summerland Key
- Car rentals in South Florida
- Car rentals in Gulf Coast
- Car rentals in Stock Island
- Car rentals in Sugarloaf Key
- Car rentals in Southeastern United States
- Car rentals in Gulf of Mexico
- Car rentals in Raccoon Key
- Car rentals in Dredgers Key
- Car rentals in Cow Key
- Car rentals in Lower Keys
- Car rentals in Fleming Key
- Car rentals in The South