Cheap Flight Deals to Islamorada FL from CA $54

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Islamorada?

The cheapest prices found with in the last 7 days for return flights were CA $107 and CA $54 for one-way flights to Islamorada for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
ORDMiamiMay 27 to May 29CA $107
LGAMiamiMay 14 to May 21CA $114
LGAMiamiMay 14 to May 21CA $114
BOSMiamiMay 22 to May 25CA $137
PHLMiamiMay 31 to June 7CA $150
DTWMiamiJune 9 to June 12CA $151
EWRMiamiMay 11 to May 15CA $152
ATLMiamiMay 19 to May 25CA $165
JFKMiamiMay 17 to May 20CA $204
LAXMiamiMay 24 to May 31CA $301
DTWKey WestMay 7 to May 20CA $488
PHLKey WestMay 10 to May 13CA $779
BOSKey WestJune 30 to July 5CA $797
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLMiamiMay 4 to May 5CA $186
BOSMiamiMay 3 to May 10CA $277
DTWMiamiMay 4 to May 9CA $280
ORDMiamiMay 3 to May 7CA $295
EWRMiamiMay 3 to May 10CA $300
EWRMiamiMay 3 to May 10CA $300
LGAMiamiMay 3 to May 10CA $308
JFKMiamiMay 4 to May 6CA $438
PHLMiamiMay 3 to May 5CA $625
DTWKey WestMay 3 to May 26CA $800
*Prices include taxes and fees

Your guide to flights to Islamorada, FL

Spirit Airlines, Delta fly to Islamorada, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Islamorada FL currently costs between CA $107 and CA $800. 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 $107. 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 May 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 ...
7.6/10 Good! (483 reviews)
"The room was about 90° when we got there and never did cool off for two days we were there. Water pressure in the bathroom was bad. And one of the owners gave us a real bad attitude when we inquired about checking out a little bit late on our last day. We will never go back there again I would not ..."

Reviewed on Aug. 6, 2018

Conch On Inn Motel
Creekside Inn Islamorada

Creekside Inn Islamorada

2.5 out of 5
90611 Old Highway, Tavernier, FL
The price is CA $231 per night from May 11 to May 12
CA $231
CA $260 total
includes taxes & fees
May 11 - May 12
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! (1,000 reviews)
"This was an amazing stay. I loved the low key vibe, the canal and views. Well stay again 100%"

Reviewed on Apr. 26, 2025

Creekside Inn Islamorada
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is CA $375 per night from May 21 to May 22
CA $375
CA $515 total
includes taxes & fees
May 21 - May 22
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,066 reviews)
"Great spot. Restaurants on Location."

Reviewed on Apr. 24, 2025

Cheeca Lodge & Spa
Save an average of 15% on thousands of hotels when you're signed in
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
The price is CA $248 per night from May 11 to May 12
CA $248
CA $324 total
includes taxes & fees
May 11 - May 12
Stay at this 3.5-star beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (998 reviews)
"Didn’t like that the room had no full length mirror"

Reviewed on Apr. 29, 2025

Fisher 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, Marker 82, Islamorada, FL
The price is CA $375 per night from May 21 to May 22
CA $375
CA $515 total
includes taxes & fees
May 21 - May 22
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,066 reviews)
"Great spot. Restaurants on Location."

Reviewed on Apr. 24, 2025

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is CA $300 per night from May 4 to May 5
CA $300
CA $429 total
includes taxes & fees
May 4 - May 5
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,188 reviews)
"Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down."

Reviewed on Apr. 30, 2025

Amara Cay Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
The price is CA $206 per night from May 1 to May 2
CA $206
CA $280 total
includes taxes & fees
May 1 - May 2
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,002 reviews)
Good price and clean
"Great place. I enjoyed the beach area and how we could walk to a few good dive bars w live music. Very clean and included a kitchen snd good size shower. Only complaint would be the blinds did not close all the way and parking lot coyld see in at night."

Reviewed on Apr. 23, 2025

Drop Anchor
Save an average of 15% on thousands of hotels when you're signed in
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
The price is CA $375 per night from May 4 to May 5
CA $375
CA $514 total
includes taxes & fees
May 4 - May 5
Stay at this 3.5-star beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
"We loved the hotel. Perfect weekend getaway with our dog. It really is pet friendly and everyone is super nice. Loved all the dinning options as well as the amount of different spaces to be at. Definitely will be coming back!"

Reviewed on Apr. 19, 2025

Three 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 $331 per night from May 12 to May 13
CA $331
CA $459 total
includes taxes & fees
May 12 - May 13
Stay at this 4-star 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. ...
9/10 Wonderful! (1,005 reviews)
"The place was lovely"

Reviewed on Apr. 28, 2025

Islander Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is CA $300 per night from May 4 to May 5
CA $300
CA $429 total
includes taxes & fees
May 4 - May 5
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,188 reviews)
"Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down."

Reviewed on Apr. 30, 2025

Amara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
The price is CA $279 per night from May 12 to May 13
CA $279
CA $406 total
includes taxes & fees
May 12 - May 13
Stay at this 4-star 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! (1,003 reviews)
"The views are amazing!!!!"

Reviewed on Apr. 25, 2025

La Siesta Resort & Villas
Save an average of 15% on thousands of hotels when you're signed in
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is CA $375 per night from May 21 to May 22
CA $375
CA $515 total
includes taxes & fees
May 21 - May 22
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,066 reviews)
"Great spot. Restaurants on Location."

Reviewed on Apr. 24, 2025

Cheeca 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.
Amara Cay Resort
The Retreat Collection at 1 Hotel & Homes South Beach
Hawks Cay Resort
Don't see what you're looking for?
See all available trips from Toronto to Islamorada
View all trips

Islamorada flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Beachcomber Resort & Club
Costa Hollywood Beach Resort
citizenM Miami South Beach
Don't see what you're looking for?
See all available trips from Halifax 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!

*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.