Cheap flights To Summerland Key (MIA) from $29

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Summerland Key from $29 One Way, $58 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Jan 13 - Sat, Jan 24
LGA
LaGuardia
MIA
Miami Intl.
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jan 13 from LaGuardia to Miami Intl., returning Sat, Jan 24, priced at $58 found 1 hour ago
Sat, Mar 7 - Sat, Mar 14
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Mar 7 from John F. Kennedy Intl. to Miami Intl., returning Sat, Mar 14, priced at $58 found 2 hours ago
Wed, Jan 7 - Fri, Jan 9
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Jan 7 from John F. Kennedy Intl. to Miami Intl., returning Fri, Jan 9, priced at $59 just found
Thu, Jan 15 - Thu, Jan 29
LGA
LaGuardia
MIA
Miami Intl.
$66 Roundtrip, found 18 hours ago
$66
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, Jan 15 from LaGuardia to Miami Intl., returning Thu, Jan 29, priced at $66 found 18 hours ago
Tue, Jan 20 - Wed, Jan 28
LGA
LaGuardia
MIA
Miami Intl.
$69 Roundtrip, found 2 days ago
$69
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Jan 20 from LaGuardia to Miami Intl., returning Wed, Jan 28, priced at $69 found 2 days ago
Fri, Jan 23 - Sat, Jan 31
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jan 23 from Newark Liberty Intl. Airport to Miami Intl., returning Sat, Jan 31, priced at $82 just found
Tue, Jan 13 - Wed, Jan 21
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$117 Roundtrip, just found
$117
Roundtrip
just found
Select American Airlines flight, departing Tue, Jan 13 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Jan 21, priced at $117 just found
Tue, Jan 13 - Wed, Jan 21
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$123 Roundtrip, just found
$123
Roundtrip
just found
Select United flight, departing Tue, Jan 13 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Jan 21, priced at $123 just found
Tue, Jan 13 - Wed, Jan 21
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$123 Roundtrip, just found
$123
Roundtrip
just found
Select Delta flight, departing Tue, Jan 13 from John F. Kennedy Intl. to Miami Intl., returning Wed, Jan 21, priced at $123 just found
Sat, Jan 31 - Tue, Feb 10
LGA
LaGuardia
MIA
Miami Intl.
$151 Roundtrip, found 5 hours ago
$151
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Jan 31 from LaGuardia to Miami Intl., returning Tue, Feb 10, priced at $151 found 5 hours ago

Summerland Key Flight Information

Traveling To
Summerland Key
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines, United, Delta, Southwest Airlines
Flight Price
$58
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Summerland Key economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hawks Cay Resort
4.0-star property

Hawks Cay Resort

Jan 19 - Jan 22

3 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $803, price is now $391 per person
$391
per person
found 1 day ago
The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

Jan 27 - Jan 31

4 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $20,256, price is now $9,224 per person
$9,224
per person
found 1 day ago
Flow Miami Hotel
3.5-star property

Flow Miami Hotel

Jan 23 - Jan 29

6 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Coach

Miami (MIA) to Boston (BOS)

Spirit Airlines • Coach
Price was $2,021, price is now $984 per person
$984
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Summerland Key
View all trips

Summerland Key premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

9/10 Wonderful! (1,736 reviews)

Jan 30 - Feb 1

2 night stay

Boston (BOS) to Key West (EYW)

Delta • Non-stop • PremiumEconomy

Key West (EYW) to Boston (BOS)

American Airlines • Non-stop • PremiumEconomy
Price was $998, price is now $747 per person
$747
per person
found 11 hours ago
great property, transportation to key west great, missing an additional dining option. Everything else was fantastic

Reviewed on Sep 21, 2025

Lighthouse Hotel - Key West Historic Inns
3.5-star property

Lighthouse Hotel - Key West Historic Inns

9/10 Wonderful! (831 reviews)

Jan 30 - Feb 1

2 night stay

Boston (BOS) to Key West (EYW)

Delta • Non-stop • PremiumEconomy

Key West (EYW) to Boston (BOS)

American Airlines • Non-stop • PremiumEconomy
Price was $1,521, price is now $1,082 per person
$1,082
per person
found 11 hours ago
This place is a much better place to stay than places closer to the cruise ship pier or off or whitehead or duval

Reviewed on Sep 22, 2024

Southernmost Beach Resort and Guesthouses
4.0-star property

Southernmost Beach Resort and Guesthouses

8.6/10 Excellent! (2,844 reviews)

Jan 30 - Feb 1

2 night stay

Boston (BOS) to Key West (EYW)

Delta • Non-stop • PremiumEconomy

Key West (EYW) to Boston (BOS)

American Airlines • Non-stop • PremiumEconomy
Price was $1,376, price is now $985 per person
$985
per person
found 11 hours ago
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.

Reviewed on Nov 1, 2025

Don't see what you're looking for?
See all available trips from Boston to Summerland Key
View all trips

Summerland Key first class flight packages

Price found within the past 48 hours. Click for updated prices.
Pelican Hotel
4.0-star property

Pelican Hotel

9.2/10 Wonderful! (394 reviews)

Jan 26 - Jan 30

4 night stay

Detroit (DTW) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $1,533, price is now $1,019 per person
$1,019
per person
found 6 hours ago
My recent stay at the Pelican Hotel was nothing short of delightful. The location is truly exceptional — perfectly situated to enjoy the very best of the area. From the moment I arrived, the warm and friendly atmosphere made me feel completely at ease. The service was impeccable. Both room service and management were consistently professional and courteous, with special appreciation to Oscar, whose attentiveness and genuine hospitality made a lasting impression. The dining experience was outstanding. Every meal was a pleasure, but the fried octopus deserves special mention — perfectly prepared and absolutely unforgettable. The rooms themselves were a highlight: comfortable, thoughtfully appointed, and each with its own unique design that adds charm and character to the stay. The complimentary cocktails were another memorable touch — expertly made and thoroughly enjoyable. Overall, my time at the Pelican Hotel was a wonderful experience from start to finish. I look forward to returning and will gladly book again without hesitation.

Reviewed on Aug 11, 2025

Fontainebleau Miami Beach
4.5-star property

Fontainebleau Miami Beach

8.2/10 Very Good! (7,303 reviews)

Jan 26 - Jan 30

4 night stay

Detroit (DTW) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,691, price is now $1,865 per person
$1,865
per person
found 6 hours ago
Great place to visit

Reviewed on Nov 30, 2025

President Hotel
3.5-star property

President Hotel

8.4/10 Very Good! (1,775 reviews)

Jan 26 - Jan 30

4 night stay

Detroit (DTW) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $1,483, price is now $1,036 per person
$1,036
per person
found 6 hours ago
Best hotel on south beach.

Reviewed on Nov 21, 2025

Don't see what you're looking for?
See all available trips from Detroit to Summerland Key
View all trips

Summerland Key

Finding cheap flights to Summerland Key is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Summerland Key flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Summerland Key through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Summerland Key—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Summerland Key flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Summerland Key with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

Frequently asked questions

Which airlines fly to Summerland Key?
Search for a flight that suits your budget among the 20 airlines that run services to and from Key West Intl. Airport (EYW). The easiest way to save on airfares is to book early. Take a look at these popular domestic air carriers and score a fantastic deal today:

  • American Airlines - 118 flights to Summerland Key per month
  • Silver Airways - 57 flights to Summerland Key per month
  • Delta - 45 flights to Summerland Key per month

What is the best airport to fly to in Summerland Key?
Key West Intl. Airport (EYW) is the gateway to the city, so the only thing you'll need to make a decision about will be the aisle seat or the window seat. Downtown Summerland Key is around 20 miles away and where many visitors choose to book a hotel.
How much is a flight to Summerland Key?
Last week, prices hovered between $58 and $151 for a return trip to Summerland Key. One-way tickets from New York (JFK) sank as low as $29 during the same time period.
How to book the cheapest flight to Summerland Key?
Using Orbitz, you'll find some of the most impressive flight deals around from a wide range of airlines. But if you'd like to heighten your chances of snapping up cheap flights to Summerland Key, here are some tips to bear in mind:

  • Depending on where you're leaving from, click on the 'Nearby airports' function (located under the departure and arrival form fields). Sometimes, alternative departure points offer cheaper airfares.
  • If your plans aren't etched in stone, click on the 'Show flexible dates' option to check out the flight deals for a range of departure dates. If you find a suitable cheaper fare, go with it.
  • You can also select the 'Show options' function to filter results for your preferred airline, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you want to fly.
  • If you've worked out your travel dates, book your flight. Fares normally become more expensive as the departure date gets closer.
  • Consider combining your flights, hotels and car rentals into an Orbitz package to save money.
  • Flying during peak season often means pricey airfares. Try to travel outside of popular periods, such as Easter, Thanksgiving and school breaks.

How long is a flight to Summerland Key?
The destination you're leaving from and whether you have a layover will determine your flight time. However, these top routes to Summerland Key will give you a clearer idea:

  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Key West Intl. Airport (EYW) - 2 hours and 5 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Key West Intl. Airport (EYW) - 1 hour and 49 minutes
  • Miami, FL (MIA-Miami Intl.) to Key West Intl. Airport (EYW) - 59 minutes

What is the best time to book a flight to Summerland Key?
If you can, purchase your seats to Summerland Key in January. This is the best month to reserve low airfares, closely followed by February and August. With a little organizing, you're bound to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Summerland Key?
If you're after inexpensive airfares to Summerland Key, the best days to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), a terrific flight deal will be all yours.
What is the cheapest day of the week to fly to Summerland Key?
Look into departing early in the week to score cheap flights to Summerland Key. Orbitz data from 2020 shows Monday is normally the most inexpensive day to take off, followed by Tuesday. Saturdays were shown to have the highest airfares. This is probably because many travelers choose to begin their escape on a weekend.
What is the cheapest month to fly to Summerland Key?
If you're flexible with your travel dates, think about leaving sometime in August. Orbitz data has found that this is generally the best month to fly out if you're looking for cheap flights to Summerland Key. As you might imagine, fares increase in the busy month of June and flights get snapped up quickly.
Which airlines allow free cancellation?
We understand that plans change and flexibility matters. That's why you can easily search for flights that include free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll show you fares more flexible than a crayon left in the sun!
What do I need for the flight to Summerland Key?
Nothing's more fun than jetting somewhere new, but it's good to be prepared. These top tips will help get your trip off to a good start:

  • Your travel documents are the most important items you'll need to have with you on your flight. To avoid any confusion at check-in time, make sure that the information on your ticket matches your government-issued ID.
  • Take some activities to pass the time on your journey to Summerland Key. Magazines, books and electronic devices like laptops and e-readers will do the trick. Remember to take a water bottle as well. Even on a short flight, it's important to stay well-hydrated.
  • Whatever the weather outside, plane cabins can get seriously cold. Take a hoodie on board to keep yourself nice and toasty.

How many direct flights are there to Summerland Key?
Multiple airlines fly nonstop into Summerland Key, with approximately 49 direct flights each month to select from. These well-known operators include American Airlines, Silver Airways and Delta Air Lines.
How do I get cheap first-class/business deals to Summerland Key?
There are ways of booking first or business-class airfares to Summerland Key that won't burn a hole through your budget. Grab a seat in the pointy end of the plane for less with these handy tips:

  • Flexibility is essential. By being open to other travel dates, you'll have better odds of picking up a rewarding deal on first or business-class airfares.
  • A lot of low-cost carriers have superb business-class seating without the hefty fees.
  • Bid for an upgrade in online auctions (if available) or upgrade your ticket with points earned through loyalty programs.

How to get into Summerland Key from the airport?
Driving is one option. Budget, Thrifty Car Rental and Dollar are three car rental branches located at Key West Intl. Airport (EYW). After picking up a Key West Intl. Airport (EYW) car rental, you can zoom straight from EYW airport to downtown Summerland Key, about 20 miles to the east. Alternatively, if you'd prefer to book a set of wheels from the city center, browse through our Summerland Key car rentals.
What is the best time to go to Summerland Key?
Travelers come from every direction to go to Summerland Key in April, July and December. So if you'd love to experience this fantastic destination during its busiest months, this is the time to go. Like most places in the Northern Hemisphere, summer begins June 20 in Summerland Key, with average daily temperatures floating between 80 ºF and 85 ºF.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.