Cheap Flights to Islamorada from $39
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How Much Does it Cost To Fly To Islamorada?
The cheapest prices found with in the last 7 days for return flights were $88 and $39 for one-way flights to Islamorada for the period specified. Prices and availability are subject to change. Additional terms apply
DFW
Dallas-Fort Worth Intl.
MIA
Miami Intl.
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
SFO
San Francisco Intl.
MIA
Miami Intl.
$170 Roundtrip, found 6 hours ago
$170
Roundtrip
found 6 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Miami | August 11 to August 11 | $88 |
| PHL | Miami | July 26 to August 20 | $96 |
| LGA | Miami | August 25 to September 1 | $177 |
| EWR | Miami | August 25 to September 1 | $197 |
| ORD | Miami | August 8 to August 10 | $225 |
| BOS | Miami | August 29 to September 6 | $227 |
| BOS | Key West | July 19 to July 28 | $263 |
| LAX | Key West | September 1 to September 5 | $277 |
| ORD | Key West | August 3 to August 8 | $319 |
| LAX | Miami | July 29 to July 31 | $319 |
| JFK | Key West | July 11 to July 18 | $329 |
| EWR | Key West | June 6 to June 13 | $334 |
| LGA | Key West | July 8 to July 14 | $336 |
| ATL | Key West | July 24 to July 29 | $339 |
| TTN | Key West | August 1 to August 8 | $442 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LGA | Miami | May 30 to June 12 | $378 |
| LGA | Miami | May 30 to June 12 | $378 |
| DTW | Key West | May 29 to June 2 | $385 |
| ATL | Miami | May 29 to June 5 | $392 |
| DTW | Miami | May 31 to June 5 | $408 |
| EWR | Downtown Miami | May 29 to June 9 | $421 |
| JFK | Miami | May 31 to June 2 | $446 |
| BOS | Miami | May 30 to June 3 | $449 |
| LGA | Key West | May 30 to June 3 | $456 |
| JFK | Key West | May 30 to June 3 | $456 |
| LGA | Key West | May 30 to June 3 | $456 |
| EWR | Key West | May 30 to June 3 | $468 |
| PHL | Key West | May 29 to June 1 | $500 |
| LAX | Miami | May 31 to June 4 | $531 |
| BOS | Key West | May 30 to May 31 | $879 |
Islamorada Flight Information
Traveling to | Islamorada |
|---|---|
Lowest Price | $88 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Islamorada Accommodation Deals
Conch On Inn Motel
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 ...
Creekside Inn
90611 Old Highway Tavernier FL
$159 nightly
The price is $179 total per night from Jun 1 to Jun 2
$179 total
Jun 1 - Jun 2
Total with taxes and 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. ...
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$264 nightly
The price is $297 total per night from Jun 2 to Jun 3
$297 total
Jun 2 - Jun 3
Total with taxes and 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! (1,315 reviews)
"amenities were great, clean hotel, lots of fun."
Reviewed on May 24, 2026
Save an average of 15% on thousands of hotels when you're signed in
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$172 nightly
The price is $194 total per night from Jun 25 to Jun 26
$194 total
Jun 25 - Jun 26
Total with taxes and 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! (1,008 reviews)
"Everything was clean and tidy. Rooms were nice. Shower head was loose so some water was leaking from the top and pouring down. Not bad though."
Reviewed on May 26, 2026
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
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$264 nightly
The price is $297 total per night from Jun 2 to Jun 3
$297 total
Jun 2 - Jun 3
Total with taxes and 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! (1,315 reviews)
"amenities were great, clean hotel, lots of fun."
Reviewed on May 24, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$267 nightly
The price is $301 total per night from May 31 to Jun 1
$301 total
May 31 - Jun 1
Total with taxes and 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! (1,280 reviews)
"Absolutely beautiful! The pool was amazing and we could have stayed at the resort and never left and had an amazing vacation! The location was convenient, and feeding the tarpon and great food nearby makes this hotel a win!"
Reviewed on May 26, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$282 nightly
The price is $313 total per night from May 28 to May 29
$313 total
May 28 - May 29
Total with taxes and 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 room wasn’t the most luxurious and needed work. The pool needs a reface as well, but the location and the boat ramp was great and we were able to get across to the sand bar in no time! The staff was helpful, the location is absolutely amazing, the scenery is amazing, and the convenience of launching ..."
Reviewed on May 25, 2026
Save an average of 15% on thousands of hotels when you're signed in
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
84001 Overseas Hwy Islamorada FL
$319 nightly
The price is $359 total per night from Jun 2 to Jun 3
$359 total
Jun 2 - Jun 3
Total with taxes and 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! (198 reviews)
"My only suggestion is to clean the garbage littered in the beach-lounging area. There’s also litter in the ocean (under Little Limon deck) that we picked up and a strong smell of sewage that hits the nostrils as soon as we exit our room or walk towards the Tiki bar. The ice cream place also needs ..."
Reviewed on May 16, 2026
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
82100 Overseas Highway Islamorada FL
$289 nightly
The price is $325 total per night from Jun 23 to Jun 24
$325 total
Jun 23 - Jun 24
Total with taxes and 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. ...
9.4/10 Exceptional! (1,022 reviews)
Families like: Outdoor pools, miniature golf, on the beach, bicycle rentals
Travelers say...
"Amazing!! Nothing bad to say at all"
Reviewed on May 26, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$267 nightly
The price is $301 total per night from May 31 to Jun 1
$301 total
May 31 - Jun 1
Total with taxes and 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! (1,280 reviews)
"Absolutely beautiful! The pool was amazing and we could have stayed at the resort and never left and had an amazing vacation! The location was convenient, and feeding the tarpon and great food nearby makes this hotel a win!"
Reviewed on May 26, 2026
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$255 nightly
The price is $287 total per night from May 31 to Jun 1
$287 total
May 31 - Jun 1
Total with taxes and 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! (1,003 reviews)
"$65 daily resort fee is excessive."
Reviewed on May 25, 2026
Save an average of 15% on thousands of hotels when you're signed in
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$264 nightly
The price is $297 total per night from Jun 2 to Jun 3
$297 total
Jun 2 - Jun 3
Total with taxes and 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! (1,315 reviews)
Families like: Outdoor pools, kids club, playground, game room
Travelers say...
"amenities were great, clean hotel, lots of fun."
Reviewed on May 24, 2026
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.
Islamorada flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
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See all available trips from Philadelphia to Islamorada
View all tripsIslamorada flight + hotel packages - business class flights
Price found within the past 48 hours. Click for updated prices.
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See all available trips from Philadelphia to Islamorada
View all tripsIslamorada flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Islamorada
View all tripsNeed a Car For After Your Flight?
Compact
MIAMI, USA
$4
$13 total
found 18 hours ago
Economy
MIAMI, USA
$4
$13 total
found 18 hours ago
Midsize
MIAMI, USA
$4
$14 total
found 18 hours ago
Standard
Miami, Florida, USA
$7
$19 total
found 18 hours ago
Lowest prices found within the past 18 hours. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
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!
More Ways To Wander
Islamorada Hotels
Find the perfect hotel after your flight
Islamorada Vacation Rentals
Great Deals on alternative accommodations
Islamorada Car Rentals
Affordable cars to get you around town
Islamorada Vacations
Save more by combining flights, hotels and cars
Things to do in Islamorada
Activities, attractions and tours
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