Cheap flights To Islamorada (MIA) from $29

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

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

Thu, Feb 19 - Thu, Feb 26
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$58 Roundtrip, found 17 hours ago
$58
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Raleigh - Durham Intl. to Miami Intl., returning Thu, Feb 26, priced at $58 found 17 hours ago
Sat, Feb 14 - Sat, Feb 21
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 14 from Raleigh - Durham Intl. to Miami Intl., returning Sat, Feb 21, priced at $59 just found
Thu, Feb 5 - Sun, Feb 8
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$63 Roundtrip, found 3 hours ago
$63
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Feb 5 from Raleigh - Durham Intl. to Miami Intl., returning Sun, Feb 8, priced at $63 found 3 hours ago
Fri, Jan 9 - Fri, Jan 16
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$64 Roundtrip, found 4 days ago
$64
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Raleigh - Durham Intl. to Miami Intl., returning Fri, Jan 16, priced at $64 found 4 days ago
Fri, Jan 2 - Fri, Jan 9
MCO
Orlando Intl.
EYW
Key West Intl.
$102 Roundtrip, found 11 hours ago
$102
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Fri, Jan 2 from Orlando Intl. to Key West Intl., returning Fri, Jan 9, priced at $102 found 11 hours ago
Sat, Jan 3 - Wed, Jan 7
TPA
Tampa Intl.
EYW
Key West Intl.
$110 Roundtrip, found 4 hours ago
$110
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sat, Jan 3 from Tampa Intl. to Key West Intl., returning Wed, Jan 7, priced at $110 found 4 hours ago
Sat, Jan 24 - Fri, Jan 30
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$117 Roundtrip, found 7 hours ago
$117
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Jan 24 from Raleigh - Durham Intl. to Miami Intl., returning Fri, Jan 30, priced at $117 found 7 hours ago
Mon, Jan 19 - Fri, Jan 30
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$117 Roundtrip, found 17 hours ago
$117
Roundtrip
found 17 hours ago
Select Delta flight, departing Mon, Jan 19 from Raleigh - Durham Intl. to Miami Intl., returning Fri, Jan 30, priced at $117 found 17 hours ago
Wed, Dec 31 - Wed, Jan 7
MCO
Orlando Intl.
MIA
Miami Intl.
$124 Roundtrip, found 6 hours ago
$124
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Dec 31 from Orlando Intl. to Miami Intl., returning Wed, Jan 7, priced at $124 found 6 hours ago
Fri, Jan 23 - Sun, Jan 25
TPA
Tampa Intl.
MIA
Miami Intl.
$128 Roundtrip, found 5 days ago
$128
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Jan 23 from Tampa Intl. to Miami Intl., returning Sun, Jan 25, priced at $128 found 5 days ago

Islamorada Flight Information

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

Book Your Flight & Hotel Together & Save

Islamorada economy flight packages

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

Pelican Hotel

Jan 22 - Jan 26

4 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,218, price is now $571 per person
$571
per person
found 1 day ago
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

Feb 5 - Feb 9

4 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Coach

Miami (MIA) to Boston (BOS)

American Airlines • Coach
Price was $1,805, price is now $831 per person
$831
per person
found 1 day ago
President Hotel
3.5-star property

President Hotel

Jan 22 - Jan 26

4 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,192, price is now $579 per person
$579
per person
found 1 day ago
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Islamorada premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Park Central South Beach
4.0-star property

Park Central South Beach

8.6/10 Excellent! (385 reviews)

Jan 22 - Jan 25

3 night stay

Boston (BOS) to Miami (MIA)

Delta • Roundtrip • PremiumEconomy
Price was $1,205, price is now $823 per person
$823
per person
found 1 day ago
Service was great. Staff was super attentive and helpful. Room was clean. Outlets were tricky as one wasn't working and learned the hardway when my phone lost its charge in the morning. Beach was right across the street. I liked they put a towel and water bottle in the backpack beach chairs.

Reviewed on Dec 10, 2025

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • PremiumEconomy

Key West (EYW) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Save 100% on your flight
Price was $3,510, price is now $2,216 per person
$2,216
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

Hyatt Vacation Club at Windward Pointe, Key West
3.5-star property

Hyatt Vacation Club at Windward Pointe, Key West

9.6/10 Exceptional! (1,002 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • PremiumEconomy

Key West (EYW) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Price was $2,015, price is now $1,395 per person
$1,395
per person
found 1 day ago
Pool and service was great!!! Staff always pleasant and helpful!

Reviewed on Dec 6, 2025

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Islamorada first class flight packages

Price found within the past 48 hours. Click for updated prices.
Park Central South Beach
4.0-star property

Park Central South Beach

8.6/10 Excellent! (385 reviews)

Jan 29 - Feb 3

5 night stay

Philadelphia (PHL) to Miami (MIA)

American Airlines • Non-stop • FirstClass

Miami (MIA) to Philadelphia (PHL)

Delta • Non-stop • FirstClass
Price was $1,823, price is now $1,242 per person
$1,242
per person
found 1 day ago
Service was great. Staff was super attentive and helpful. Room was clean. Outlets were tricky as one wasn't working and learned the hardway when my phone lost its charge in the morning. Beach was right across the street. I liked they put a towel and water bottle in the backpack beach chairs.

Reviewed on Dec 10, 2025

Seacoast Suites on Miami Beach
3.5-star property

Seacoast Suites on Miami Beach

6.4/10 (1,352 reviews)

Jan 24 - Jan 30

6 night stay

Philadelphia (PHL) to Miami (MIA)

American Airlines • FirstClass

Miami (MIA) to Philadelphia (PHL)

Delta • FirstClass
Price was $3,486, price is now $2,531 per person
$2,531
per person
found 9 hours ago
Would stay here again!

Reviewed on Jun 21, 2024

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (ORD) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,124, price is now $2,195 per person
$2,195
per person
found 7 hours ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

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Islamorada

Orbitz uses cutting edge mobile technology to help get you the best deals on Islamorada flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Islamorada Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Islamorada, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Islamorada can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Islamorada. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Islamorada to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

Frequently asked questions

Which airlines fly to Islamorada?
You can pick from 20 airlines with flights to Miami Intl. Airport (MIA), the leading airport in the city. With plenty of options, you're bound to find a fabulous deal. Here are a few of the most well-known international airlines that'll get you to Islamorada:

  • American Airlines - 1,841 flights to Islamorada per month
  • Copa Airlines - 105 flights to Islamorada per month
  • LATAM Airlines - 86 flights to Islamorada per month

How much is a flight to Islamorada?
If you're after round-trip flights, fares ranged from $58 to $128 this week. The most affordable one-way ticket was $29, coming from Raleigh (RDU).
How to book the cheapest flight to Islamorada?
Snapping up cheap flights to Islamorada is as simple as booking your ticket with Orbitz. But if you want to make sure you're getting the best flight deals around, here are some suggestions worth following:

  • Consider alternative airports to save money. Enter your preferred departure and arrival points in the form fields, then choose the 'Nearby airports' function below. It will list the available options.
  • If you're flexible with when you take off, click on the 'Show flexible dates' link. It'll bring up flight deals for the days around your selected departure. Ticket prices often vary depending on the day of the week.
  • Hit 'Show options' to narrow down your search results. You can choose your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • If you've sorted your travel dates, don't delay booking. Prices generally rise as the departure date nears.
  • Bundle your hotels, flights and car rental into a money-saving package deal. Save your hard-earned cash for things you're really excited about, like exploring every corner of Islamorada.
  • Flying during the busy season can mean higher airfares. If possible, plan your vacation outside of popular dates, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Islamorada?
If your schedule allows, purchase your seats to Islamorada in January. This is the best month to reserve low airfares, closely followed by February and August. With a little planning, you're bound to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Islamorada?
Make a booking on a Tuesday, Wednesday or Saturday. Generally, these are the cheapest days of the week to purchase tickets to Islamorada. The vacation of your dreams starts with a great flight deal!
What is the cheapest day of the week to fly to Islamorada?
You can nab cheap flights to Islamorada by hopping on a plane on a Monday, according to Orbitz data from 2020. Tuesday is the next most affordable day, while Saturday has the most costly airfares. Whether you prefer to save cash or take off on whichever day is convenient, you'll always find a wonderful deal with Orbitz.
What is the cheapest month to fly to Islamorada?
Get set to jet for less in August. This is generally the best month to get on a plane if you're after cheap flights to Islamorada, Orbitz data shows. The most expensive time to fly is June, so avoid this month if possible.
Which airlines allow free cancellation?
When searching for your Islamorada flights on Orbitz, choose "Filter by flexible change policies." This filter will show you all the airlines offering free cancellation and no change fees. Breathe easy knowing that if your travel dates change, your reservation can too.
What do I need for the flight to Islamorada?
The secret to a successful flight is being well prepared. Here are some useful tips to help you get ready for take off:

  • Whether you print it out beforehand or use an electronic one, you'll need your boarding pass to step foot on the plane. You'll also need some kind of government-issued ID. If you're flying internationally, make sure your passport is valid and you've looked into visa requirements.
  • Take some activities to keep you busy on your trip to Islamorada. Books and electronic devices like laptops and tablets are ideal. Don't forget to take a bottle of water with you too. Even on short flights, it's important to remain well-hydrated.
  • It can get cold on the plane. If you'd prefer not to shiver your way through the flight, bring an extra layer.

How do I get cheap first-class/business deals to Islamorada?
Savvy travelers are pros at finding business or first-class fares to Islamorada without the sky-high price tag. You can do the same with these practical tips:

  • Be flexible with your travel dates and hold out for sales or exclusive offers on first or business-class airfares.
  • Plenty of budget airlines nowadays offer superb business-class seating that doesn't cost the earth.
  • Make the most of your airline's frequent flyer program and upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

What is the best time to go to Islamorada?
People come from all over the place to go to Islamorada in November, December and January. So if you love the idea of exploring this incredible destination in the busy months, this is the time to go. Like many places in the Northern Hemisphere, the summer begins June 20 in Islamorada, with average daily temperatures hovering between 80 ºF and 85 ºF.
Travel tips for Islamorada

  • Downtown Islamorada has plenty of terrific attractions. Favorites like Theater of the Sea and Hurricane Monument will keep your feet moving and the sightseer in you happy.
  • If you're in the mood for a fun day trip, there are more sights to mark off a short commute from the hustle and bustle. Find out why Sombrero Beach and John Pennekamp Coral Reef State Park are on the travel itineraries of many Islamorada visitors.
  • Like to wander the streets of Monroe County's other great cities? Book a car rental and drive to Key West or Marathon. With your own set of wheels, getting to those off-radar destinations will also be a snap.

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.