Cheap Flights to Islamorada from $29
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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 $50 and $29 for one-way flights to Islamorada for the period specified. Prices and availability are subject to change. Additional terms apply
LGA
LaGuardia
MIA
Miami Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| BOS | Miami | January 27 to January 28 | $50 |
| ATL | Miami | February 3 to February 7 | $50 |
| LGA | Miami | January 31 to February 7 | $59 |
| LGA | Miami | January 31 to February 7 | $59 |
| JFK | Miami | February 4 to February 11 | $59 |
| EWR | Miami | January 31 to February 4 | $63 |
| ATL | Key West | January 26 to January 30 | $126 |
| LAX | Miami | January 31 to February 7 | $146 |
| BOS | Key West | February 20 to February 24 | $156 |
| LGA | Key West | January 29 to February 5 | $192 |
| ORD | Key West | February 5 to February 20 | $203 |
| PHL | Key West | February 1 to February 6 | $205 |
| EWR | Key West | February 1 to February 5 | $210 |
| JFK | Key West | February 4 to February 8 | $235 |
| LAX | Key West | February 4 to February 11 | $257 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| PHL | Miami | January 18 to January 29 | $104 |
| ATL | Miami | January 17 to January 18 | $126 |
| EWR | Miami | January 17 to January 30 | $158 |
| EWR | Miami | January 17 to January 30 | $158 |
| ORD | Miami | January 18 to January 21 | $159 |
| BOS | Miami | January 17 to January 21 | $203 |
| DTW | Miami | January 17 to January 22 | $210 |
| ATL | Key West | January 18 to January 25 | $273 |
| PHL | Key West | January 18 to January 22 | $321 |
| BOS | Key West | January 18 to January 22 | $340 |
| EWR | Key West | January 18 to January 22 | $381 |
| EWR | Key West | January 18 to January 22 | $381 |
| LGA | Key West | January 17 to January 21 | $460 |
| JFK | Key West | January 18 to January 22 | $460 |
| LAX | Key West | January 17 to January 31 | $475 |
Islamorada Flight Information
Traveling to | Islamorada |
|---|---|
Lowest Price | $50 |
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 ...
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
Creekside Inn
90611 Old Highway Tavernier FL
$169 nightly
The price is $190 total per night from Jan 13 to Jan 14
$190 total
Jan 13 - Jan 14
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. ...
7.8/10 Good! (1,001 reviews)
The staff were very friendly and helpful
Reviewed on Jan 5, 2026
Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82 Islamorada FL
$320 nightly
The price is $361 total per night from Jan 29 to Jan 30
$361 total
Jan 29 - Jan 30
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! (1,287 reviews)
Generally nice place. Leftover food and drinks in our hotel refrigerator upon arrival. Understaffed at dining facilities meaning long waits and order mistakes.
Reviewed on Jan 8, 2026
Save an average of 15% on thousands of hotels when you're signed in
Fisher Inn Resort & Marina
84951 Overseas Hwy Islamorada FL
$200 nightly
The price is $225 total per night from Jan 19 to Jan 20
$225 total
Jan 19 - Jan 20
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! (1,009 reviews)
Todo ok
Reviewed on Jan 4, 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
$320 nightly
The price is $361 total per night from Jan 29 to Jan 30
$361 total
Jan 29 - Jan 30
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! (1,287 reviews)
Generally nice place. Leftover food and drinks in our hotel refrigerator upon arrival. Understaffed at dining facilities meaning long waits and order mistakes.
Reviewed on Jan 8, 2026
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$288 nightly
The price is $325 total per night from Jan 20 to Jan 21
$325 total
Jan 20 - Jan 21
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! (1,260 reviews)
This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back
Reviewed on Jan 10, 2026
Drop Anchor
84959 Overseas Highway, 222 Islamorada FL
$216 nightly
The price is $238 total per night from Jan 19 to Jan 20
$238 total
Jan 19 - Jan 20
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. ...
8.6/10 Excellent! (1,000 reviews)
The staff was personable, great location, having the bicycles and kayaks were a great touch
Reviewed on Jan 1, 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
$356 nightly
The price is $400 total per night from Jan 21 to Jan 22
$400 total
Jan 21 - Jan 22
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 ...
8.8/10 Excellent! (123 reviews)
Amazing place - so much variety
Reviewed on Jan 6, 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
$365 nightly
The price is $410 total per night from Jan 29 to Jan 30
$410 total
Jan 29 - Jan 30
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. ...
9.2/10 Wonderful! (1,007 reviews)
Families like: Outdoor pools, miniature golf, on the beach, bicycle rentals
Travelers say...
Clean room and resort. So much to do. Absolutely beautiful
Reviewed on Dec 28, 2025
Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$288 nightly
The price is $325 total per night from Jan 20 to Jan 21
$325 total
Jan 20 - Jan 21
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! (1,260 reviews)
This resort exceed our expectations. Wonderful for families , very clean and amazing staff. We did a free fishing lesson with captain Patrick and he was wonderful-also great with kids. Loved the free water taxi to visit the sister resorts . We will definitely be back
Reviewed on Jan 10, 2026
La Siesta Resort & Villas
80241 Overseas Highway Islamorada FL
$272 nightly
The price is $307 total per night from Jan 14 to Jan 15
$307 total
Jan 14 - Jan 15
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! (1,002 reviews)
Staff were nice, the bathroom needs an upgrade and more water pressure
Reviewed on Jan 7, 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
$320 nightly
The price is $361 total per night from Jan 29 to Jan 30
$361 total
Jan 29 - Jan 30
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! (1,287 reviews)
Families like: Outdoor pools, kids club, playground, game room
Travelers say...
Generally nice place. Leftover food and drinks in our hotel refrigerator upon arrival. Understaffed at dining facilities meaning long waits and order mistakes.
Reviewed on Jan 8, 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
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Islamorada flight + hotel packages - premium economy flights
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Islamorada flight + hotel packages - business class flights
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See all available trips from Philadelphia to Islamorada
View all tripsIslamorada flight + hotel packages - first class flights
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Need a Car For After Your Flight?
Compact
Miami, Florida, USA
$1
$2 total
found 2 days ago
Economy
Miami, Florida, USA
$1
$2 total
found 2 days ago
Midsize
Miami, Florida, USA
$1
$2 total
found 2 days ago
Fullsize
Miami, Florida, USA
$2
$4 total
found 2 days ago
Lowest prices found within the past 2 days. 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
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Things to do in Islamorada
Activities, attractions and tours
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