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Key West Express Vacation Packages

Key West Express Flight + Hotel Packages

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
per person
Jun 4 - Jun 8
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 4-star golf aparthotel in Estero. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby. Discover genuine guest reviews for Hyatt Vacation Club at Coconut Cove, Bonita Springs along with the latest prices and availability – book now.
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 14
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita Springs Public Beach are located nearby. Discover genuine guest reviews for GullWing Beach Resort, in South Island neighborhood, along with the latest prices and availability – book now.
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 14
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star beach condo in Fort Myers. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Key West Express and Sanibel Island Southern Beach are located nearby. Discover genuine guest reviews for Resort Harbour Properties along with the latest prices and availability – book now.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
per person
Jun 8 - Jun 15
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Stay at this beach resort in Captiva. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Popular attractions Captiva Beach and Captiva Chapel By the Sea are located nearby. Discover genuine guest reviews for Tween Waters Island Resort & Spa along with the latest prices and availability – book now.
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 14
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hertz Arena and Coconut Point Mall are located nearby. Discover genuine guest reviews for Embassy Suites by Hilton Fort Myers Estero along with the latest prices and availability – book now.
The Boat House

The Boat House

2 out of 5
Save 100% on your flight
per person
May 24 - May 28
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this hotel in Marco Island. Enjoy free WiFi, free parking, and a terrace. Our guests praise the clean rooms in our reviews. Popular attractions Pelican Pier Marina and Cannon Beach are located nearby. Discover genuine guest reviews for The Boat House along with the latest prices and availability – book now.
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 8
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this beach hotel in Naples. Enjoy 3 outdoor pools, 3 restaurants, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Vanderbilt Beach and Naples Zoo at Caribbean Gardens are located nearby. Discover genuine guest reviews for Naples Grande Beach Resort, in Park Shore neighborhood, along with the latest prices and availability – book now.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Save 100% on your flight
per person
Jun 14 - Jun 19
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this beach resort in Naples. Enjoy 2 restaurants, a private beach, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby. Discover genuine guest reviews for LaPlaya Beach & Golf Resort - A Noble House Resort, in Vanderbilt Beach neighborhood, along with the latest prices and availability – book now.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
per person
Jun 9 - Jun 14
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby. Discover genuine guest reviews for Hilton Garden Inn Ft Myers along with the latest prices and availability – book now.
South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
per person
Jun 8 - Jun 15
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Stay at this beach resort in Captiva. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Jungle Drums and McCarthy's Marina are located nearby. Discover genuine guest reviews for South Seas Resort along with the latest prices and availability – book now.
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 8
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this business-friendly condo in Naples. Enjoy free WiFi, free parking, and breakfast. Our guests praise the pool and the restaurant in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby. Discover genuine guest reviews for Bellasera Resort, in Old Naples neighborhood, along with the latest prices and availability – book now.
Homewood Suites by Hilton Fort Myers Airport/FGCU

Homewood Suites by Hilton Fort Myers Airport/FGCU

3 out of 5
per person
Jun 9 - Jun 14
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Gulf Coast Town Center and Hertz Arena are located nearby. Discover genuine guest reviews for Homewood Suites by Hilton Fort Myers Airport/FGCU along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

3-4 Night Vacations in Key West Express

Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
per person
May 29 - Jun 1
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
The Boat House

The Boat House

2 out of 5
Save 100% on your flight
per person
May 24 - May 28
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
Park Shore
Save 100% on your flight
per person
May 29 - Jun 1
Roundtrip flight included
Columbus (CMH) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
May 24 - May 27
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Prices and availability subject to change. Additional terms may apply.

5-7 Night Vacations in Key West Express

GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
South Island
Save 100% on your flight
per person
Jun 9 - Jun 14
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 14
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
per person
Jun 8 - Jun 15
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
per person
Jun 9 - Jun 14
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Prices and availability subject to change. Additional terms may apply.

Key West Express Last Minute Hotel Deals

Latitude 26 Waterfront Boutique Resort - Fort Myers Beach
Latitude 26 Waterfront Boutique Resort - Fort Myers Beach
2.5 out of 5
17990 San Carlos Blvd, Fort Myers Beach, FL
Stay at this hotel in Fort Myers Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Latitude 26 Waterfront Boutique Resort - Fort Myers Beach
Margaritaville Beach Resort Fort Myers
Margaritaville Beach Resort Fort Myers
4 out of 5
251 Crescent Street, Fort Myers Beach, FL
Stay at this 4-star beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Ostego Bay ...
Margaritaville Beach Resort Fort Myers
The Lighthouse Resort Inn & Suites
The Lighthouse Resort Inn & Suites
3 out of 5
1051 5th St, Fort Myers Beach, FL
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. Popular ...
The Lighthouse Resort Inn & Suites
DiamondHead Beach Resort
DiamondHead Beach Resort
3.5 out of 5
2000 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our ...
DiamondHead Beach Resort
Pink Shell Beach Resort and Marina
Pink Shell Beach Resort and Marina
4 out of 5
275 Estero Blvd, Fort Myers Beach, FL
Stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 2 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool in our ...
Pink Shell Beach Resort and Marina
Matanzas Inn Bayside Resort and Marina
Matanzas Inn Bayside Resort and Marina
3 out of 5
414 Crescent Street, Fort Myers Beach, FL
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a terrace. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Matanzas Inn Bayside Resort and Marina
Edison Beach House
Edison Beach House
3.5 out of 5
830 Estero Blvd., Fort Myers Beach, FL
Stay at this 3.5-star beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and a terrace. Our guests praise the helpful staff and the clean ...
Edison Beach House
Harbour House At The Inn
Harbour House At The Inn
3 out of 5
450 Old San Carlos Blvd, Fort Myers Beach, FL
Stay at this 3-star hotel in Fort Myers Beach. Enjoy free WiFi, a marina, and a business center. Our guests praise the clean rooms in our reviews. Popular attractions ...
Harbour House At The Inn
See all 10,383 properties in Key West Express
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.

Book the perfect getaway to Key West Express

With Hotwire, booking your next trip to Fort Myers Beach is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Key West Express while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Key West Express flight and hotel package for as low as $466.

Living it up in Fort Myers Beach means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Key West Express, Fort Myers Beach vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Key West Express for some of the best accommodations and flight deals.

FAQs about cheap Key West Express packages:

How to get cheap vacation deals to Key West Express?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $144.

How much are Key West Express packages?

Vacation packages to Key West Express vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $466.

How to find cheap car rentals near Key West Express?

Hotwire partners with some of the most reliable car rental companies in Fort Myers Beach to bring you the best car rental deals in Key West Express for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Key West Express now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Key West Express right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

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