A coastal road with a beach on one side and a marina with boats on the other.

$38 Cheap Flights to Summerland Key, FL

View $38 flight on Sun, Nov 8, 2026Opens in a new window

Popular airlines to Summerland Key

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How much is the cheapest flight to Summerland Key?

Prices were available within the past 7 days and start at $38 for one-way flights and $87 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
American Airlines
Delta
United
Frontier Airlines

Alternative airports near Summerland Key

Prices were available within the past 7 days. Prices and availability are subject to change.

Find the cheapest month to fly from Columbus (CMH) to Miami (MIA)

From $139 - $530 per traveler.

What you need to know for your flight to Summerland Key

Flights to Summerland Key at a glance

Getting to Summerland Key is easy; you can choose from a variety of full-service or budget airlines. Compare travel times and select the best option that fits your budget and schedule while planning your visit to the city's iconic attractions and neighborhoods. Look for cheap Summerland Key flights to find the best deals!

  • Major airport near Summerland Key: Key West International Airport (EYW)
  • Flights per week: 1,350+ flights arriving at Summerland Key airport
  • Number of airlines that fly to Summerland Key: around 5+ carriers

Popular airport near Summerland Key

Summerland Key is an inviting island city that perfectly caters to outdoor enthusiasts and families seeking fun beach vacations. With its stunning scenery and adventurous activities, it’s no wonder why travelers flock to this destination. Conveniently, the area is accessible via a major airport, making it easy to find flights to Summerland Key.

  • Key West International Airport (EYW): Situated in Monroe County, Florida, approximately 21 miles from Summerland Key, this airport facilitates both domestic and international travel. It connects to over 155 domestic cities and three international locations, with options for upgrading to first class and premium economy seating for enhanced comfort, varying by route and airline. Key airlines serving this airport include American Airlines, Delta, and United.

Top routes to Summerland Key

  • Boston (BOS) to Summerland Key (EYW), with one-way flight options from around $110
  • Newark (EWR) to Summerland Key (EYW), with one-way airfare from around $120
  • Philadelphia (PHL) to Summerland Key (EYW), with one-way fares starting at around $200
  • Chicago (ORD/MDW) to Summerland Key (EYW), with one-way tickets available from around $120
  • Tampa (TPA) to Summerland Key (EYW), with one-way airfare from around $45

Cheapest routes to Summerland Key

  • Tampa (TPA) to Summerland Key (EYW), with low-cost one-way tickets from around $45
  • Orlando (MCO) to Summerland Key (EYW), with budget one-way fares from around $50
  • Fort Lauderdale (FLL) to Summerland Key (EYW), with budget one-way fares from around $65
  • Akron (CAK) to Summerland Key (EYW), with low one-way fares from around $85
  • Raleigh (RDU) to Summerland Key (EYW), with budget one-way fares from around $90

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Summerland Key

  • American Airlines: Servicing Key West International Airport (EYW), American Airlines represents about 59% of arrivals to Summerland Key. The typical one-way fare hovers around $270, and travelers may find first class as a premium cabin option depending on the route.
  • Delta: Operating flights to Key West International Airport (EYW), Delta contributes roughly 24% of arrivals to Summerland Key. Average one-way fares are about $280, with premium cabin options that may include both premium economy and first class based on the route.
  • United: Flying into Key West International Airport (EYW), United accounts for nearly 12% of arrivals to Summerland Key. The average fare for a one-way ticket is around $280, with first class available as a premium cabin option depending on the route.
  • JetBlue Airways: JetBlue services Key West International Airport (EYW) and accounts for approximately 2% of arrivals to Summerland Key. The average one-way fare is close to $240, with premium cabin options that may feature premium economy depending on the route.
  • Breeze: Operating flights to Key West International Airport (EYW), Breeze captures about 2% of arrivals to Summerland Key. Travelers can expect an average one-way fare of around $130, making it a budget-friendly option for those heading to the area.

Best time to fly to Summerland Key

The most popular months for travelers to fly to Summerland Key are February, March, and April, when peak temperatures in Summerland Key can reach up to 76.8°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 83.7°F and typically the lowest average one-way fare (around $217), roughly 14% cheaper than the yearly average. Looking for additional cheaper months to fly? August, July, and January offer average one-way fares roughly ranging from $222 to $236, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnyAverage$236
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnyHigh$276
March73.2°F (22.9°C)No Rain (Dry)Mostly SunnyHigh$297
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnyHigh$283
May79.3°F (26.3°C)Light RainMostly SunnyAverage$246
June82.6°F (28.1°C)Light RainMostly SunnyAverage$251
July84.0°F (28.9°C)Light RainMostly SunnyAverage$228
August84.4°F (29.1°C)Light RainMostly SunnyLow$222
September83.7°F (28.7°C)Light RainMostly SunnyLow$217
October80.8°F (27.1°C)Light RainMostly SunnyLow$247
November76.6°F (24.8°C)Light RainMostly SunnyAverage$261
December73.8°F (23.2°C)No Rain (Dry)Mostly SunnyAverage$285

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Summerland Key

Getting some of the best deals on flights to Summerland Key is all about timing and flexibility. Here are some key tips to help you save:

  1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
  3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Summerland Key hotel and flight deals.
  4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
  5. Earn miles—you can earn airline miles when you book your Summerland Key flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Summerland Key

Summerland Key welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Summerland Key efficiently:

  • Public transportation: From Key West International Airport, Key West Seaport, a seaport, is located about 3.7 miles away by car, providing convenient access for travelers heading to the water.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Summerland Key, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Summerland Key is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Summerland Key on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay in Summerland Key

  • Cutthroat Harbor Estates: Located around the area of Summerland Key, Cutthroat Harbor Estates is a delightful neighborhood perfect for families and beach lovers. Enjoy the peaceful atmosphere while exploring nearby attractions like Florida Keys Beaches, Venture Key, and Upper Sugarloaf Key. This area offers various outdoor experiences, making it an excellent choice for a beach vacation or family outing. Visitors can also find shopping venues and resorts nearby, enhancing their stay with convenient amenities.
  • Sugarloaf Shores: Sugarloaf Shores is located around the area of Summerland Key and is ideal for those seeking outdoor and beach experiences. This charming neighborhood features recreational areas and golf courses, making it a great spot for both relaxation and activity. Key points of interest include Florida Keys Beaches, Upper Sugarloaf Sound, and Upper Sugarloaf Key. Whether you're looking to lounge by the water or enjoy a round of golf, Sugarloaf Shores has something to offer every traveler.
  • Bay Point: Bay Point is located around the area of Summerland Key, offering a blend of outdoor adventures and family-friendly activities. This neighborhood is well-suited for those who enjoy shopping, as there are several shopping areas and recreational spots nearby. Explore local landmarks such as Florida Keys Beaches, Lower Sugarloaf Sound, and Upper Sugarloaf Key. With its diverse attractions, Bay Point provides an inviting atmosphere for visitors looking to immerse themselves in the unique charm of the Florida Keys.

Tips for short-haul flights to Summerland Key

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

  • Pack light and skip checked bags—with budget airlines, traveling with just a carry-on is often more economical. Save space by using mini toiletries, wearing your bulkiest clothing, and efficiently planning your outfits. This strategy also allows you to bypass the wait at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights might not provide in-flight entertainment options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself entertained. Remember to fully charge your devices before you board.
  • Arrive at the airport in plenty of time—even for short or domestic flights, it's advisable to get there at least 1.5 to 2 hours before departure, taking into account traffic and security lines.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Summerland Key

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

  • Select your seat in advance—for longer flights, choosing your seat can greatly enhance your comfort. Full-service airlines typically allow you to select your seat for free once online check-in opens, which is usually 24–48 hours before your flight. Some airlines may provide seat selection options even earlier.
  • Arrive at the airport in plenty of time—ensure you arrive at the airport at least 3 hours before departure for international flights to accommodate check-in, security, and immigration procedures.
  • Relax at the airport—if you find yourself with extra time, take the opportunity to browse the shops, grab a coffee, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and available.
  • Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and adjusting your sleep schedule to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time at your arrival destination to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Summerland Key?
The cheapest month to fly to Summerland Key is September when demand is low. Off-peak months are typically when you'll find cheap flights. To save money, avoid flying during school breaks and public holidays.
Which US cities have the cheapest flights to Summerland Key?
Get cheap flights to Summerland Key from New York, Atlanta and Chicago. These cities typically offer the best fares to this top destination. But keep in mind that demand, seasonality and stopovers will also have an influence on rates, so remain flexible and book when you see a bargain.
Which US cities fly direct to Summerland Key?
Choose from 63 US cities providing direct flights to Summerland Key. When you book on Expedia, click on the "Direct flights only" filter to compare nonstop itineraries. Fly to Summerland Key from any of these cities:
  • New York
  • Atlanta
  • Chicago
  • Dallas
  • Newark
How to find a cheap flight to Summerland Key?
Book your trip early to score cheap flights to Summerland Key. Also, consider visiting during off-season months like September and October. If you fly on a Thursday, you'll save an average of 16% compared to departing on a Sunday.* Save time checking every day and track your flight prices using the Expedia app. We'll notify you when fares drop.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Summerland Key?
While booking in advance is usually the easiest way to save cash, don't panic if your Summerland Key vacation is last minute. It's still possible to find cheap flights to Summerland Key, especially if your plans have a little leeway. Try changing your trip dates, looking at different ticket types or jetting out of an alternative airport.
How far in advance should I book a flight to Summerland Key?
To snap up some of the biggest savings on domestic journeys, book your flight to Summerland Key 28 days ahead of your travel dates. For international flights, search for your ticket two to four months in advance. This improves your chances of locking in the departure dates and times you want.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Summerland Key?
You can save an average of 8% if you buy plane tickets on a Sunday rather than Fridays, which tend to be the priciest day to book.* When it comes to getting a cheap flight to Summerland Key, timing makes a difference.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Summerland Key?
There are 4 carriers connecting Summerland Key with 13 airports across the world. The primary gateway to this city is Key West Intl. Airport (EYW). Travel with any of these leading airlines to Summerland Key:
  • American Airlines
  • Delta Air Lines
  • Silver Airways
  • United Airlines
Where do you fly into Summerland Key?
Key West Intl. Airport (EYW) is the main airport for travelers flying to Summerland Key. Or you could arrive at Marathon, FL (MTH-Florida Keys Marathon). Compare fares between the two airports to find the cheapest or easiest way to fly to Summerland Key.
How far is the airport from central Summerland Key?
If you're flying into Key West Intl. Airport (EYW), you'll be around 20 mi west of the center of Summerland Key.
Can I save money by booking a Summerland Key trip package?
Bundle your accommodations and flights and you could save hundreds of dollars. Plus, you can add extras like car rentals and tours to your Summerland Key flight and hotel package deal. With Expedia, it's a breeze to book all your Summerland Key travel arrangements in one place.
Can I change or cancel my flight to Summerland Key?
If you reserved your flight to Summerland Key in the last 24 hours, you can typically cancel or change it for free. After that, additional costs may apply depending on the airline's rules and restrictions. For more information, head to our Customer Service Portal. Keep in mind that some flights are non-refundable, so you may be issued a credit toward future flights rather than a direct refund. During your search on Expedia, select the "No cancel fee" or "Changes included" boxes to see fares with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

Book with confidence

Tips to find the cheapest flights to Summerland Key

The cheapest day to fly

Get started finding a cheap flight to Summerland Key on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

September is the cheapest month to fly to Summerland Key. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Summerland Key. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Summerland Key, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Summerland Key

The lowest price for round-trip flights to Summerland Key in 2026 starts from from $87, while one-way tickets start from from $38. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Summerland Key. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Summerland Key

Southwest Airlines, Frontier Airlines, JetBlue Airways, American Airlines, United, Delta are just some of the airlines that can typically offer cheap tickets to Summerland Key. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Summerland Key and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Summerland Key, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Summerland Key. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Summerland Key plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Summerland Key

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Summerland Key.

Stopover savings

The cheapest tickets to Summerland Key are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Summerland Key. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Summerland Key for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Summerland Key. Simply download the free Expedia app to your smart device and activate Summerland Key flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Summerland Key. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Tips to find the cheapest flights to Summerland Key

Travel information

Destination airport
Miami Intl.
Destination airport IATA code
MIA
Destination city name
Miami
Roundtrip price
$87

Trending flights to Summerland Key

Prices were available within the past 7 days and start at $38 for one-way flights and $87 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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