Vacations in Key West

Boston (BOS)
Key West
Mon 10/16
Thu 10/19
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Key West vacation information

Top vacation (Flight+Hotel) $614
Family vacation (Flight+Hotel) $582
Romantic vacation (Flight+Hotel) $578
Luxury vacation (Flight+Hotel) $708

Key West vacation price trends

Estimated package price

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2 travelers Flight to Key West 3 nights at hotel
Median hotel rate + Median airfare from United States

Why should you book a vacation package to Key West?

Located off Florida's stunning Caribbean coastline, the 7 miles of sandy beaches that comprise Key West are not to be missed. Ensure you have the mental bandwidth to do your vacation itinerary justice by booking a Key West flight and hotel package. The extra savings could come in handy for that next round of Pina Coladas!

Key West

There are many points of interest along Key West, including Ernest Hemingway's home, Dry Tortugas National Park, Martello Towers, and the Key West Aquarium. A rental car is the easiest way to travel at your leisure between these popular cultural attractions.


When should you book a vacation package to Key West?

The best time to visit is between March and May before the heat and crowds of summer tourists arrive. However some of the most popular cultural festivals include Ernest Hemingway Days, Goombay Festival, and Fantasy Fest, which take place in the summer and fall.


Where should you stay in Key West during your vacation?For any vacation type in Key West:

Ocean Key Resort-A Noble House Resort lets you soak in the island's charm with a barside pool, private cabanas, and uninterrupted views of the Caribbean. Located on Key West's biggest island, it's easy to connect via rental car from Key West International Airport.

Hilton Garden Inn is part of the renowned collection of Keys hotels which features year-round outdoor pools, modern tropical décor, and friendly knowledgeable staff. Consider taking a lyft, uber, or taxi from Key West International Airport to avoid paying parking fees.

For family vacations in Key West:


The Marker Waterfront Resort is one of the newest hotel additions to Key West, providing updated amenities and an intuitive layout. Keyshuttles will transport the whole family from the airport to your hotel's front door from Key West, Fort Lauderdale, or Miami International Airport.

Southernmost Beach Resort on Duval Street is close to boutique shops, art galleries, eclectic restaurants, and non-stop nightlife. Daily bike rentals are also available from several locations to keep your family entertained and active on your Key West getaway.

For romantic vacations in Key West:

Chelsea House Hotel is a quiet historic inn with an acre of botanical gardens so you can travel back in time to the days when Ernest Hemingway called these islands home. The VIP concierge can help guide you towards your best transportation options on the island.

The Gardens Hotel offers intimate cottages with tropical verandahs for a romantic beach vacation in Key West. This hotel is located just 3.7 miles from EYW Airport.

For luxury vacations in Key West:

Crown Plaza Key West-LA Concha is a historical landmark situated on the popular Duval Street. It puts you within easy reach of Key West's most popular shopping district. Key West International Airport is just a few miles away and easily accessible by taxi.

Hyatt Centric Key West Resort and Spa offers sweeping views of the Caribbean, docks, Mallory Square, and the Key West Aquarium. You can easily rent a car at Key West International Airport for added flexibility when travelling around the islands, however Hyatt Centric Key West charges a $20-a-night parking fee for guests.

For budget vacations in Key West:

Fairfield Inn & Suites by Marriott Key West is one of the few hotels that also offers free breakfast with your nightly rate. Easily hop on the trolley which stops in front of the hotel for a new vantage point of the city when traveling between different locations on the island or to Key West International Airport.

Eden House and Suites is a 4-star guest house in the old city that prides itself on old-fashioned customer service coupled with modern comforts to help you find your home away from home. In addition to a heated pool, Eden House also offers guests waterfalls, hammocks, swings, and a garden café on-site.