Cheap Flight Deals to Islamorada FL from CA $199

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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 $100 and CA $199 for one-way flights to Islamorada for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSMiamiDecember 31 to January 8CA $100
EWRMiamiJanuary 8 to January 14CA $109
EWRMiamiJanuary 8 to January 14CA $109
PHLMiamiJanuary 6 to January 8CA $117
ORDMiamiJanuary 22 to January 25CA $140
ATLMiamiJanuary 7 to January 13CA $150
JFKMiamiFebruary 11 to February 15CA $180
BOSKey WestMarch 5 to March 11CA $364
JFKKey WestJanuary 1 to January 9CA $489
JFKKey WestJanuary 1 to January 9CA $489
EWRKey WestDecember 31 to January 7CA $531
ORDKey WestJanuary 1 to January 8CA $551
DTWKey WestMarch 3 to March 12CA $570
LAXKey WestDecember 29 to January 7CA $773
ATLKey WestDecember 27 to January 1CA $846
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
BOSMiamiDecember 20 to December 21CA $288
DTWMiamiDecember 22 to December 25CA $510
ORDMiamiDecember 21 to December 31CA $620
EWRMiamiDecember 20 to December 27CA $638
EWRMiamiDecember 20 to December 27CA $638
LGAMiamiDecember 20 to December 27CA $654
JFKMiamiDecember 20 to December 27CA $718
PHLMiamiDecember 21 to December 22CA $756
EWRKey WestDecember 21 to December 24CA $783
EWRKey WestDecember 21 to December 24CA $783
PHLKey WestDecember 22 to December 31CA $800
LAXMiamiDecember 20 to January 2CA $874
ATLKey WestDecember 22 to January 1CA $894
JFKKey WestDecember 22 to December 31CA $949
DTWKey WestDecember 22 to December 25CA $969
*Prices include taxes and fees

Your guide to flights to Islamorada, FL

Porter Airlines, American Airlines 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 $100 and CA $969. Prices vary, but for the best fares, travel in January 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 $100. 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 ...
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 6 Aug. 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 $168 per night from Dec. 19 to Dec. 20
CA $168
CA $189 total
includes taxes & fees
19 Dec - 20 Dec
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! (1,007 reviews)
"Nice location on the creek with manatees in the canal"

Reviewed on 16 Dec. 2024

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 $360 per night from Dec. 20 to Dec. 21
CA $360
CA $502 total
includes taxes & fees
20 Dec - 21 Dec
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! (1,004 reviews)
"We had a wedding nearby and couldn’t get a stay there since it was all booked. We are glad we couldn’t stay this since Cheeca was above what we could have imagined."

Reviewed on 13 Dec. 2024

Cheeca 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 $226 per night from Dec. 19 to Dec. 20
CA $226
CA $301 total
includes taxes & fees
19 Dec - 20 Dec
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 ...
7.6/10 Good! (1,000 reviews)
"Mrs. S, the check in staff is friendly, very professional and she remembered my name from my last stay. This is what great customer service is all about. I love this property."

Reviewed on 13 Dec. 2024

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 $360 per night from Dec. 20 to Dec. 21
CA $360
CA $502 total
includes taxes & fees
20 Dec - 21 Dec
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! (1,004 reviews)
"We had a wedding nearby and couldn’t get a stay there since it was all booked. We are glad we couldn’t stay this since Cheeca was above what we could have imagined."

Reviewed on 13 Dec. 2024

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is CA $356 per night from Dec. 19 to Dec. 20
CA $356
CA $496 total
includes taxes & fees
19 Dec - 20 Dec
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! (1,197 reviews)
"I loved our room, the tiki bar and pool. Staff was friendly and it was a great location. Definitely will stay here again if in the area."

Reviewed on 18 Dec. 2024

Amara Cay Resort
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
The price is CA $172 per night from Dec. 19 to Dec. 20
CA $172
CA $243 total
includes taxes & fees
19 Dec - 20 Dec
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! (1,000 reviews)
"Amazing place! Beautiful area with great amenities. Only thing was really stiff beds. But if you like very firm mattresses…it’s a 5 star. That aside …we will definitely be back!!"

Reviewed on 6 Dec. 2024

Drop 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

3 out of 5
84001 Overseas Hwy, Islamorada, FL
The price is CA $552 per night from Dec. 19 to Dec. 20
CA $552
CA $716 total
includes taxes & fees
19 Dec - 20 Dec
Stay at this 3-star beach resort in Islamorada. Enjoy free WiFi, a private beach, and a marina. Our guests praise the helpful staff and the clean rooms in our ...
8/10 Very Good! (1,001 reviews)
"Excellent and amazing property. I love this resort. Will be back"

Reviewed on 11 Dec. 2024

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 $411 per night from Jan. 13 to Jan. 14
CA $411
CA $541 total
includes taxes & fees
13 Jan - 14 Jan 2025
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,002 reviews)
"Excellent.yes will book again."

Reviewed on 12 Dec. 2024

Islander Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is CA $356 per night from Dec. 19 to Dec. 20
CA $356
CA $496 total
includes taxes & fees
19 Dec - 20 Dec
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! (1,197 reviews)
"I loved our room, the tiki bar and pool. Staff was friendly and it was a great location. Definitely will stay here again if in the area."

Reviewed on 18 Dec. 2024

Amara Cay Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
The price is CA $557 per night from Dec. 21 to Dec. 22
CA $557
CA $722 total
includes taxes & fees
21 Dec - 22 Dec
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)
"Great resort!!"

Reviewed on 14 Dec. 2024

La Siesta Resort & Villas
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Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is CA $360 per night from Dec. 20 to Dec. 21
CA $360
CA $502 total
includes taxes & fees
20 Dec - 21 Dec
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! (1,004 reviews)
"We had a wedding nearby and couldn’t get a stay there since it was all booked. We are glad we couldn’t stay this since Cheeca was above what we could have imagined."

Reviewed on 13 Dec. 2024

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.
Mayfair House Hotel & Garden
The Retreat Collection at 1 Hotel & Homes South Beach
Waterfront House with Boat Dock
Don't see what you're looking for?
See all available trips from Montreal to Islamorada
View all trips

Islamorada flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Solé Miami, A Noble House Resort
Carillon Miami Wellness Resort
Trump International Beach Resort
Don't see what you're looking for?
See all available trips from Toronto to Islamorada
View all trips

Islamorada flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
Hotel Greystone - Adults Only
EAST Miami
1 Hotel South Beach
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!

*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.