Cheap Flight Deals to Islamorada FL from CA $255

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How to find cheap flights to Islamorada?

The cheapest prices found with in the last 7 days for return flights were CA $82 and CA $255 for one-way flights to Islamorada for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
ATLMiamiMay 10 to May 15CA $82
PHLMiamiMay 4 to May 8CA $89
EWRMiamiJuly 21 to August 5CA $131
EWRMiamiJuly 21 to August 5CA $131
LGAMiamiMay 13 to May 16CA $133
ORDMiamiMay 11 to May 14CA $192
JFKMiamiMay 7 to May 12CA $271
DTWMiamiJuly 7 to July 14CA $273
BOSMiamiMay 16 to May 20CA $277
LAXMiamiMay 23 to May 29CA $437
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLMiamiApril 25 to April 28CA $156
EWRMiamiApril 25 to May 2CA $274
EWRMiamiApril 25 to May 2CA $274
ORDMiamiApril 26 to May 2CA $315
BOSMiamiApril 25 to April 28CA $447
JFKMiamiApril 25 to May 9CA $458
LGAMiamiApril 24 to May 3CA $487
DTWMiamiApril 26 to April 28CA $538
LAXMiamiApril 25 to May 2CA $752
*Prices include taxes and fees

Your guide to flights to Islamorada, FL

American Airlines, Air Transat fly to Islamorada, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Islamorada FL currently costs between CA $82 and CA $752. Prices vary, but for the best fares, travel in May when prices are at their lowest.  

Top tips for finding cheap flights to Islamorada  

The cheapest flight for a round trip to Islamorada is currently CA $82. When you search for flights to Islamorada, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Islamorada for nearby days.  The cheapest month to travel to Islamorada is January from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Islamorada 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Islamorada with Travelocity 

We have top deals on plane tickets even for last minute flights to Islamorada, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Islamorada for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Islamorada

Conch On Inn Motel

Conch On Inn Motel

2 out of 5
103 Caloosa Street Tavernier FL
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Old Road Gallery and Florida Keys Dive Center are ...
Opens in a new windowConch On Inn Motel
Creekside Inn

Creekside Inn

2.5 out of 5
90611 Old Highway Tavernier FL
The price is CA $590 per night from Apr 25 to Apr 26
CA $590
CA $664 total
Apr 25 - Apr 26
includes taxes & fees
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (1,009 reviews)
Really liked the canal view and the pool was really nice.

Reviewed on Apr 21, 2026

Opens in a new windowCreekside Inn
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $334 per night from May 11 to May 12
CA $334
CA $476 total
May 11 - May 12
includes taxes & fees
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,318 reviews)
For the price per night you would think the rooms would look better than a standard hotel room.

Reviewed on Apr 20, 2026

Opens in a new windowCheeca Lodge & Spa
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Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
The price is CA $196 per night from May 6 to May 7
CA $196
CA $265 total
May 6 - May 7
includes taxes & fees
Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
8.2/10 Very Good! (1,009 reviews)
Amazing hotel

Reviewed on Apr 20, 2026

Opens in a new windowFisher Inn Resort & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $334 per night from May 11 to May 12
CA $334
CA $476 total
May 11 - May 12
includes taxes & fees
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,318 reviews)
For the price per night you would think the rooms would look better than a standard hotel room.

Reviewed on Apr 20, 2026

Opens in a new windowCheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is CA $372 per night from May 4 to May 5
CA $372
CA $518 total
May 4 - May 5
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,267 reviews)
No clean room every day

Reviewed on Apr 16, 2026

Opens in a new windowAmara Cay Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
The price is CA $222 per night from Apr 22 to Apr 23
CA $222
CA $298 total
Apr 22 - Apr 23
includes taxes & fees
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,003 reviews)
The place over charges this is not a resort it’s more like a motel I payed over $1200 for two nights and I feel this place shouldn’t charge more than $250 a night. Also be aware there was a resort fee the kayaks weren’t working and the office was always closed. Will not be going back.

Reviewed on Apr 20, 2026

Opens in a new windowDrop Anchor
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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
The price is CA $347 per night from May 4 to May 5
CA $347
CA $481 total
May 4 - May 5
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (185 reviews)
We loved everthing about this resort! We just wish we had stayed longer! We stayed in The Cove. It was secluded and quiet! A perfect get away!

Reviewed on Apr 16, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Islamorada

Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
The price is CA $291 per night from May 17 to May 18
CA $291
CA $419 total
May 17 - May 18
includes taxes & fees
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,005 reviews)
Ate breakfast outside the hotel

Reviewed on Apr 19, 2026

Opens in a new windowIslander Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is CA $372 per night from May 4 to May 5
CA $372
CA $518 total
May 4 - May 5
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,267 reviews)
No clean room every day

Reviewed on Apr 16, 2026

Opens in a new windowAmara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
The price is CA $282 per night from Apr 29 to Apr 30
CA $282
CA $417 total
Apr 29 - Apr 30
includes taxes & fees
Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
8.6/10 Excellent! (1,009 reviews)
It was simply stunning. Beautiful location, great facilities, spacious apartment and for a family of 5 the door key card being on the wristband is genius. Thank you for a wonderful stay

Reviewed on Apr 21, 2026

Opens in a new windowLa Siesta Resort & Villas
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Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is CA $334 per night from May 11 to May 12
CA $334
CA $476 total
May 11 - May 12
includes taxes & fees
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,318 reviews)
For the price per night you would think the rooms would look better than a standard hotel room.

Reviewed on Apr 20, 2026

Opens in a new windowCheeca Lodge & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Islamorada Flight and Hotel Packages

Islamorada flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
President Hotel
Creekside Inn
1 Hotel South Beach
Don't see what you're looking for?
See all available trips from Montreal to Islamorada
View all trips

Islamorada flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Miami Beach
Fontainebleau Miami Beach
Carillon Miami Wellness Resort
Don't see what you're looking for?
See all available trips from Toronto to Islamorada
View all trips

Need a car after flight to Islamorada?

Frequently asked questions

Which airlines fly to Islamorada?
There are plenty of airline companies that advertise flights to and from Islamorada — 20 to be exact. Highly rated ones include:

  • American Airlines
  • Delta Air Lines
  • Spirit Airlines

Where to stay in Islamorada
Every magnificent journey begins with just one step — along with a comfortable place to lay your weary head! Book your Islamorada accommodations through Travelocity and you'll have 615 options to pick from.Have a thing for the fancier things in life? Then spend your nights in style at the Cheeca Lodge & Spa. If you'd prefer to be more economical with your accommodations, consider a budget option like the Hadley House Islamorada.
Places to visit in Islamorada
0 Need some more ideas? 0 And that's not all. 0
How to get through airport security fast when traveling to Islamorada
Your trip to Islamorada starts as soon as you've finished the security checks. Here are some hints and tips to make sure you get through quickly:

  • Airport security staff will expect to see your travel ID and boarding pass as part of their checks. Have them in an accessible place, so they're all ready for inspection.
  • Wallets, belts and power banks should be put in a tray for X-raying. If you enter the body scanner with any one of these items, you'll be asked to turn back and remove them.
  • Everyday electronics such as phones, laptops and cameras will need to be put through the X-ray machine separately. Be sure to have them within easy reach.
  • When it comes to flying with gels or liquids, each passenger is allowed a quart-sized clear resealable bag to transport containers no larger than 3.4 ounces (100 milliliters).
  • Undo your shoelaces before approaching the body scanner. Depending on the type of shoes you're wearing, security may tell you to remove them.
  • The list of non-permissible items is forever updating. Browse your airline's official website for what is not allowed on board their flights.

Plane Tickets To Islamorada

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Islamorada. Browse through our inventory to explore a wide range of cheap flights to Islamorada to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Islamorada as you anxiously await to exit the plane and explore what Islamorada has to offer. Considering all the amazing local food and culture in Islamorada, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Islamorada to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Islamorada without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Islamorada with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Islamorada today!

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.