Cheap flights To Islamorada (MIA) from $29

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Cheap Flights to Islamorada from $29 One Way, $59 Round Trip

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

Sat, Jan 31 - Tue, Feb 3
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$59 Roundtrip, found 1 hour ago
$59
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jan 31 from John F. Kennedy Intl. to Miami Intl., returning Tue, Feb 3, priced at $59 found 1 hour ago
Sat, Feb 21 - Wed, Mar 4
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$60 Roundtrip, found 15 hours ago
$60
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from John F. Kennedy Intl. to Miami Intl., returning Wed, Mar 4, priced at $60 found 15 hours ago
Wed, Jan 28 - Wed, Feb 4
BOS
Logan Intl.
MIA
Miami Intl.
$60 Roundtrip, found 1 hour ago
$60
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Jan 28 from Logan Intl. to Miami Intl., returning Wed, Feb 4, priced at $60 found 1 hour ago
Tue, Jan 27 - Thu, Jan 29
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$63 Roundtrip, found 1 hour ago
$63
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jan 27 from John F. Kennedy Intl. to Miami Intl., returning Thu, Jan 29, priced at $63 found 1 hour ago
Tue, Feb 10 - Wed, Feb 11
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Feb 10 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Feb 11, priced at $63 just found
Fri, Feb 20 - Sat, Feb 28
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$142 Roundtrip, found 15 hours ago
$142
Roundtrip
found 15 hours ago
Select Delta flight, departing Fri, Feb 20 from John F. Kennedy Intl. to Miami Intl., returning Sat, Feb 28, priced at $142 found 15 hours ago
Fri, Feb 20 - Sat, Feb 28
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$142 Roundtrip, found 15 hours ago
$142
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Fri, Feb 20 from John F. Kennedy Intl. to Miami Intl., returning Sat, Feb 28, priced at $142 found 15 hours ago
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
EYW
Key West Intl.
$143 Roundtrip, found 3 days ago
$143
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Feb 2 from Logan Intl. to Key West Intl., returning Mon, Feb 9, priced at $143 found 3 days ago
Tue, Feb 10 - Wed, Feb 11
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$151 Roundtrip, just found
$151
Roundtrip
just found
Select United flight, departing Tue, Feb 10 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Feb 11, priced at $151 just found
Tue, Feb 10 - Thu, Feb 12
BOS
Logan Intl.
MIA
Miami Intl.
$175 Roundtrip, found 1 hour ago
$175
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Feb 10 from Logan Intl. to Miami Intl., returning Thu, Feb 12, priced at $175 found 1 hour ago

Islamorada Flight Information

Traveling To
Islamorada
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines, Delta, United, Southwest Airlines, JetBlue Airways
Flight Price
$59
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.
Beach Park Hotel
3.0-star property

Beach Park Hotel

Feb 14 - Feb 17

3 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,167, price is now $527 per person
$527
per person
found 1 day ago
Creekside Inn
2.5-star property

Creekside Inn

Feb 12 - Feb 17

5 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,577, price is now $728 per person
$728
per person
found 1 day ago
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

Feb 26 - Mar 1

3 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Coach

Miami (MIA) to Boston (BOS)

Frontier Airlines • Coach
Price was $1,278, price is now $636 per person
$636
per person
found 1 day ago
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See all available trips from Boston to Islamorada
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Islamorada premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.4/10 Very Good! (1,001 reviews)

Feb 13 - Feb 19

6 night stay

Boston (BOS) to Miami (MIA)

Delta • PremiumEconomy

Miami (MIA) to Boston (BOS)

American Airlines • PremiumEconomy
Price was $2,920, price is now $1,882 per person
$1,882
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 2026

The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

8/10 Very Good! (1 review)

Feb 13 - Feb 19

6 night stay

Boston (BOS) to Miami (MIA)

Delta • PremiumEconomy

Miami (MIA) to Boston (BOS)

American Airlines • PremiumEconomy
Price was $27,751, price is now $14,796 per person
$14,796
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Islamorada
View all trips

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)

Mar 7 - Mar 10

3 night stay

Boston (BOS) to Miami (MIA)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,464, price is now $1,592 per person
$1,592
per person
found 1 day ago
There were quite a few issues — the bathroom door and the safe were broken, the beach chairs on the beach couldn’t be used, and we had to carry folding chairs and towels provided by the hotel down to the beach. There was also only one slow elevator, and even though we booked Park Central, we were actually put in the building next door. Still, the staff were all friendly and helpful, the room was clean, and the breakfast was good.

Reviewed on Dec 23, 2025

The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

8/10 Very Good! (1 review)

Mar 5 - Mar 9

4 night stay

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

American Airlines • Non-stop roundtrip • FirstClass
Price was $19,531, price is now $10,404 per person
$10,404
per person
found 5 hours ago
1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,365 reviews)

Mar 7 - Mar 10

3 night stay

Boston (BOS) to Miami (MIA)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,407, price is now $2,165 per person
$2,165
per person
found 1 day ago
This property is amazing. Food was great, staff was friendly and welcoming. We enjoyed our stay.

Reviewed on Jun 10, 2025

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Islamorada

Save more on flights to Islamorada while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Islamorada

Now it is easier than ever to find a discount Islamorada flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

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We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Islamorada flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Islamorada a breeze.

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 $59 to $175 this week. The most affordable one-way ticket was $29, coming from New York (JFK).
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.