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Islamorada

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Islamorada Flights as Low as $55

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Cheap Flights to Islamorada

Fall in love at first flight with your vacation to Islamorada by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Islamorada on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Islamorada, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Islamorada

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Islamorada with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the MIA airport.

What is the cheapest month to fly to Islamorada?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Islamorada are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Islamorada?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Islamorada.

What airport is best to fly into Islamorada?

When you’re planning your trip to Islamorada, convenience is the name of the game. Luckily, Islamorada Florida Keys Marathon Airport is nearby so you can deplane and get going on checking off everything on your Islamorada must-do list.

How much are flights to Islamorada?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Islamorada on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $55, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Islamorada?

The trick to saving a stack of cash on your flight to Islamorada? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $55 right now, why wait?

Islamorada Flight Information
Destination airport
Miami Intl.
Destination airport IATA code
MIA
Roundtrip price
$73

Last Minute Hotel Deals in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
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! (1,310 reviews)
Amazing! Loved everything can’t wait to go back!!

Reviewed on Apr 5, 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,690 reviews)
Beautiful property and the beach is nice, calm, and quiet. The made to order breakfasts every morning were absolutely amazing and delicious! My only complaint was that we explored Islamorada and did adventures during the day off the property. When we came back after dinnertime, we wanted to use some ...

Reviewed on Apr 7, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
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)
Great

Reviewed on Mar 30, 2026

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
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! (1,010 reviews)
My husband and I stayed here for our baby moon, and we honestly couldn’t recommend this place more! After doing a painful amount of research, it was difficult to decide between this resort and a few other ones we found, but I am so glad we went with The Islander. The grounds are beautiful, the staff ...

Reviewed on Apr 6, 2026

Islander Resort
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
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! (181 reviews)
Pool staff great. Too windy to do beach activities our trip unfortunately. Hotel room was great. Beautiful views. Check in was an unfortunate process. We were hoping for an early check in, instead didn’t get checked in till after our guaranteed 4PM.

Reviewed on Apr 4, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
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)
We had a wonderful stay in the BOTE House. Perfect for a small family and dogs with the fenced in yard. The staff was great and very accommodating. The access to the other resorts and amenities is also a huge plus. We will definitely be back!

Reviewed on Apr 6, 2026

La Siesta Resort & Villas
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
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! (1,005 reviews)
We stayed in the King Oceanfront Suite and it was perfect. Clean, modern, nice big balcony. The grounds were well kept and there were plenty of water sports equipment for use. The breakfast is not very plentiful or varied but not a reason to keep me from staying here! I would definitely recommend ...

Reviewed on Apr 6, 2026

Fisher Inn Resort & Marina
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy Islamorada FL
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
7.6/10 Good! (1,000 reviews)
Very nice room in the pool villa, property was nice but not impressive. Front desk lady was unfriendly. Could have been better with friendlier staff.

Reviewed on Apr 6, 2026

Hadley Resort and 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.