Cheap flights To Islamorada (MIA) from $41

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Cheap Flights to Islamorada from $41 One Way, $82 Round Trip

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

Wed, Sep 16 - Fri, Sep 18
TPA
Tampa Intl.
EYW
Key West Intl.
$82 Roundtrip, found 7 hours ago
$82
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Tampa Intl. to Key West Intl., returning Fri, Sep 18, priced at $82 found 7 hours ago
Mon, Aug 24 - Thu, Aug 27
TPA
Tampa Intl.
EYW
Key West Intl.
$84 Roundtrip, found 19 hours ago
$84
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Mon, Aug 24 from Tampa Intl. to Key West Intl., returning Thu, Aug 27, priced at $84 found 19 hours ago
Wed, Sep 16 - Fri, Sep 18
TPA
Tampa Intl.
EYW
Key West Intl.
$87 Roundtrip, found 7 hours ago
$87
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Tampa Intl. to Key West Intl., returning Fri, Sep 18, priced at $87 found 7 hours ago
Thu, Aug 20 - Mon, Aug 24
TPA
Tampa Intl.
EYW
Key West Intl.
$89 Roundtrip, found 1 hour ago
$89
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Aug 20 from Tampa Intl. to Key West Intl., returning Mon, Aug 24, priced at $89 found 1 hour ago
Wed, Sep 16 - Fri, Sep 18
TPA
Tampa Intl.
EYW
Key West Intl.
$92 Roundtrip, found 7 hours ago
$92
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Tampa Intl. to Key West Intl., returning Fri, Sep 18, priced at $92 found 7 hours ago
Thu, Aug 20 - Mon, Aug 24
TPA
Tampa Intl.
EYW
Key West Intl.
$94 Roundtrip, found 10 hours ago
$94
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Thu, Aug 20 from Tampa Intl. to Key West Intl., returning Mon, Aug 24, priced at $94 found 10 hours ago
Sun, Aug 30 - Tue, Sep 1
TPA
Tampa Intl.
EYW
Key West Intl.
$97 Roundtrip, found 8 hours ago
$97
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Sun, Aug 30 from Tampa Intl. to Key West Intl., returning Tue, Sep 1, priced at $97 found 8 hours ago
Mon, Jul 13 - Thu, Jul 16
TPA
Tampa Intl.
EYW
Key West Intl.
$97 Roundtrip, found 5 hours ago
$97
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Mon, Jul 13 from Tampa Intl. to Key West Intl., returning Thu, Jul 16, priced at $97 found 5 hours ago
Mon, Jul 6 - Wed, Jul 8
TPA
Tampa Intl.
EYW
Key West Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Mon, Jul 6 from Tampa Intl. to Key West Intl., returning Wed, Jul 8, priced at $98 found 2 days ago
Mon, Sep 14 - Thu, Sep 17
MCO
Orlando Intl.
EYW
Key West Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Mon, Sep 14 from Orlando Intl. to Key West Intl., returning Thu, Sep 17, priced at $102 just found

Islamorada Flight Information

Traveling To
Islamorada
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$82
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.
Nobu Hotel Miami Beach
5.0-star property

Nobu Hotel Miami Beach

Aug 21 - Aug 24

3 night stay

Detroit (DTW) to Miami (MIA)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $908, price is now $490 per person
$490
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

Jul 31 - Aug 6

6 night stay

Detroit (DTW) to Miami (MIA)

American Airlines • Roundtrip • Coach
Price was $27,133, price is now $13,305 per person
$13,305
per person
found 10 hours ago
Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

Jul 31 - Aug 6

6 night stay

Detroit (DTW) to Miami (MIA)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,286, price is now $738 per person
$738
per person
found 1 day ago
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See all available trips from Detroit to Islamorada
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Islamorada premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
The 27 Wynwood
4.0-star property

The 27 Wynwood

9.4/10 Exceptional! (17 reviews)

Aug 7 - Aug 11

4 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,033, price is now $702 per person
$702
per person
found 1 day ago
Fontainebleau Miami Beach
4.5-star property

Fontainebleau Miami Beach

8.4/10 Very Good! (8,366 reviews)

Aug 20 - Aug 25

5 night stay

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

Frontier Airlines • Non-stop • PremiumEconomy

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

JetBlue Airways • Non-stop • PremiumEconomy
Price was $1,465, price is now $944 per person
$944
per person
found 1 day ago
Overall experience was great! However, they need to fire the current house keeping. They’re lazy and you walk into a dirty room with stains and hair everywhere . Thank God they upgraded me to a one bedroom suite which made me give them a 5 star. There were dozens of people complaining of dirty rooms. Fire management if they cannot hire quality housekeepers.

Reviewed on Jun 2, 2026

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,563 reviews)

Aug 7 - Aug 11

4 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,132, price is now $1,397 per person
$1,397
per person
found 1 day ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

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See all available trips from Chicago to Islamorada
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Islamorada business class 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

8.6/10 Excellent! (1,011 reviews)

Aug 7 - Aug 14

7 night stay

New York (NYC) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $1,625, price is now $923 per person
$923
per person
found 18 hours ago
We had a very nice stay. The staff is very friendly and the room was nice. Would stay again.

Reviewed on Jun 28, 2026

Nobu Hotel Miami Beach
5.0-star property

Nobu Hotel Miami Beach

8.6/10 Excellent! (1,418 reviews)

Aug 7 - Aug 14

7 night stay

New York (NYC) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,009, price is now $1,037 per person
$1,037
per person
found 18 hours ago
Location is great. Room is starting to look tired with some fraying in the carpet and a damaged bed frame that they used a screw to reatach. Mirror in bathroom was delaminating and the faucet was scratched and chipped. They say overnight valet is $60 but they charged me $80 because I had an SUV. They include a 22% service charge in everything you order even though the pool side service was mediocre at best. Waiter acted offended when we asked him to clear the dirty plates.

Reviewed on Jul 17, 2025

Eden Roc Miami Beach
4.5-star property

Eden Roc Miami Beach

8.6/10 Excellent! (3,293 reviews)

Aug 7 - Aug 14

7 night stay

New York (NYC) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $1,865, price is now $1,012 per person
$1,012
per person
found 18 hours ago
Very communicative hotel. Super friendly and professional

Reviewed on Mar 8, 2026

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See all available trips from New York to Islamorada
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Islamorada first class flight packages

Price found within the past 48 hours. Click for updated prices.
The 27 Wynwood
4.0-star property

The 27 Wynwood

9.4/10 Exceptional! (17 reviews)

Aug 10 - Aug 14

4 night stay

New York (JFK) to Miami (MIA)

Delta • Roundtrip • FirstClass
Price was $1,354, price is now $995 per person
$995
per person
found 1 day ago
Nobu Hotel Miami Beach
5.0-star property

Nobu Hotel Miami Beach

8.6/10 Excellent! (1,418 reviews)

Aug 13 - Aug 16

3 night stay

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

United • FirstClass

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

Frontier Airlines • FirstClass
Price was $1,434, price is now $1,017 per person
$1,017
per person
found 11 hours ago
Location is great. Room is starting to look tired with some fraying in the carpet and a damaged bed frame that they used a screw to reatach. Mirror in bathroom was delaminating and the faucet was scratched and chipped. They say overnight valet is $60 but they charged me $80 because I had an SUV. They include a 22% service charge in everything you order even though the pool side service was mediocre at best. Waiter acted offended when we asked him to clear the dirty plates.

Reviewed on Jul 17, 2025

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,563 reviews)

Aug 13 - Aug 16

3 night stay

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

United • FirstClass

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

Frontier Airlines • FirstClass
Price was $2,088, price is now $1,526 per person
$1,526
per person
found 11 hours ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

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See all available trips from New York to Islamorada
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Islamorada

Orbitz is your one stop for guaranteed low prices on Islamorada flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

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Orbitz will find you discount air fare for flights to Islamorada and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Islamorada Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

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Our state of the art mobile apps will allow you to book cheap flights to Islamorada from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

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 $82 to $102 this week. The most affordable one-way ticket was $41, coming from Tampa (TPA).
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.