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Boston to Key West Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Boston to Key West

Departure Arrival Travel dates Round-trip
BOS EYW Fri, Sep 19 - Mon, Sep 22 $415
BOS EYW Thu, Sep 11 - Tue, Sep 16 $416
BOS EYW Fri, Sep 19 - Mon, Sep 22 $440
BOS EYW Thu, Sep 11 - Tue, Sep 16 $534
BOS EYW Thu, Aug 7 - Sun, Aug 17 $2,109
BOS EYW Thu, Aug 7 - Sun, Aug 17 $3,354

Boston and Key West airports and terminals

Airports in Boston MA, US
map of airports in Boston
  • 1

    Boston Logan Airport (BOS)

    Distance from City Center: 3 miles

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Airports in Key West FL, US
map of airports in Key West
  • 1

    Key West International (EYW)

    Distance from City Center: 2.9 miles

  • 2

    Miami Airport (MIA)

    Distance from City Center: 128.3 miles

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Cheap flights from Boston to Key West

Sun Mon Tue Wed Thu Fri Sat
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$468
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31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Key West Airport Hotels

Hotel only $225

Hyatt Windward Pointe

4 stars
4.4 / 5 45 reviews

3675 South Roosevelt Blvd Map

...Transportation Key West International Airport (0.2 mi/0.3 km).... On the southeast side of Key West, the Hyatt Windward Pointe offers a secluded getaway with residential-style accommodations... More

Hotel only $191

Sunrise Suites Resort

3 stars
3.6 / 5 115 reviews

3685 Seaside Drive Map

Save 25%

...Transportation Key West International Airport (1.1 mi./1.8 km).... Secluded Key West vacation rentals near beach offer kitchens, Wi-Fi Sunrise Suites Resort Key West offers all the convenience... More

Hotel only $170

Doubletree' Grand Key Resort

3 stars
4.1 / 5 205 reviews

3990 S. Roosevelt Blvd Map

Includes breakfast for two adults & two children

...Transportation Key West International Airport (1.1 mi./1.8 km).... Mid-range rooms and suites with free shuttle service and pet policy The Green Lodging-certified Doubletree Grand Key Resort... More

Hotel only $175

Sheraton Suites Key West

4 stars
4.1 / 5 180 reviews

2001 South Roosevelt Boulevard Map

Save 40% on your stay

...Transportation Key West International Airport (1.1 mi./1.8 km).... The airport adjacent hotel offers suites decorated in Caribbean colors, and the property has undergone a recent renovation... More

Hotel only $160

Coconut Mallory Resort and Marina by Kees Vacations

3 stars
3.7 / 5 54 reviews

1445 S. Roosevelt Blvd. Map

...Located just after the entrance to the island, the resort sits near the Key West airport and less than five miles from Mallory Square and the popular attractions along Duval Street....... More

Hotel only $169

Ibis Bay Resort

2 stars
3.4 / 5 63 reviews

3101 North Roosevelt Blvd Map

Located just outside of Old Town Key West, the Ibis Bay Resort provides a true feel of Key West with great food, fun, and excitement, while still giving you the rest and relaxation that brought you... More

August

Lowest roundtrip airfare in August from Boston to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Aug 11 Boston (BOS) Key West (EYW) United Airlines $468
Earn $4.68
Return Fri, Aug 15 Key West (EYW) Boston (BOS) United Airlines
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September

Cheapest weekend flights in September from Boston to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Sep 19 Boston (BOS) Key West (EYW) United Airlines $415
Earn $4.15
Return Mon, Sep 22 Key West (EYW) Boston (BOS) United Airlines

Lowest roundtrip airfare in September from Boston to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Sep 19 Boston (BOS) Key West (EYW) United Airlines $415
Earn $4.15
Return Mon, Sep 22 Key West (EYW) Boston (BOS) United Airlines
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October

Lowest roundtrip airfare in October from Boston to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 7 Boston (BOS) Key West (EYW) United Airlines $512
Earn $5.12
Return Tue, Oct 14 Key West (EYW) Boston (BOS) United Airlines

Best one-week trip in October from Boston to Key West

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 7 Boston (BOS) Key West (EYW) United Airlines $512
Earn $5.12
Return Tue, Oct 14 Key West (EYW) Boston (BOS) United Airlines
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Flights to Key West

Boston Logan International Airport

The Boston Logan International Airport is located at 1 Harborside Drive, approximately four miles from downtown Boston. Numerous airlines service the airport, including US Airways, Virgin America, JetBlue and British Airways. Orbitz.com can help you find cheap flights from Boston. The website searches and displays your flight choices, so you can book one with a cheap rate.

Parking and Transportation

If you need to leave your car at the airport while you travel, there are several parking lots available. Most of the lots cost $27 per day to park; however, the airport does have an economy parking lot that offers long-term parking for $18 per day. There are shuttles that run from all of the parking lots to the airport terminals. The subway runs from downtown Boston to the airport. The trip takes between 35 and 45 minutes and costs $2. Taxicab services from downtown Boston to the airport cost between $25 and $45, depending on the length of the trip. The Orbitz.com website has the tools you need to reserve a rental car at your destination. This way, you don't have to wait at the airport. Your car will be ready for you when you arrive.

Dining at the Airport

When you use Orbitz.com to book cheap flights from Boston, you don't have to worry about your travel arrangements. This gives you plenty of time to grab a quick meal before you board your plane. The airport has a variety of dining options available, including Johnny Rockets, Vineyard Grille and Wolfgang Puck Gourmet Express.

Key West International Airport

With warm weather, amazing views, and dozens of outdoor activities, Key West is a popular vacation spot. Looking for cheap flights to Key West doesn't have to be stressful. Orbitz.com offers discounts on flights to the island from many locations. Key West International Airport is the only airport in this area. Several major airlines operate out of the airport, including Southwest Airlines, Delta Air Lines, American Eagle and US Airways Express.

Getting to Downtown

Since the airport is only two miles from downtown, you can get to almost any downtown spot within 10 to 20 minutes. Many travelers rent a car from one of the companies operating out of the airport, such as Thrifty, Enterprise or Budget. You can also take the Keys Shuttle, which is a large bus that makes stops at the airport throughout the day and drops off passengers at multiple spots around Key West.

Key West Weather

The late spring through late fall is the rainy season in Key West, and the area has more than 50 rainy days throughout this season. Temperatures during the summer can easily reach the high 80s or low 90s, while winter temperatures typically range from the mid 60s to low 70s. When you book your air ticket, make sure that you plan ahead for wet weather.

Festivals and Events

Top local events include Bike Week, Fantasy Fest, Key West Race Week, Hemingway Days Festival, and Key West Songwriters Festival. With Orbitz.com, you can get deals on your hotel room, rental car and on cheap flights to Key West. No matter when you visit, you can make your travel arrangements quickly.