Florida may have travel restrictions in place due to COVID-19.

Islamorada Vacation Packages

Choose two or more items and save on your trip:

Top Islamorada Flight + Hotel Deals

Solé Miami, A Noble House Resort
EAST Miami
W Fort Lauderdale
The L Hotel
1 Hotel South Beach

2021 Islamorada vacation deals

Selina Miami River
Holiday Inn Express Doral
EAST Miami
Odyssey of South Beach Apart Hotel
EVEN Hotel Miami - Airport

Top Hotels in Islamorada

Islander Resort
Islander Resort
3 out of 5
82100 Overseas Highway, Islamorada, FL
Free cancellationReserve now, pay when you stay
The price is CA $261 per night from Jan 18 to Jan 19
4.5/5Wonderful! (983 reviews)

"Very nice property with beautiful ocean view.. awesome Oceanside availability to sit and relax"…"

Reviewed on Jan. 8, 2021

Islander Resort
Amara Cay Resort
Amara Cay Resort
3.5 out of 5
80001 Overseas Hwy, Islamorada, FL
Free cancellationReserve now, pay when you stay
The price is CA $277 per night from Jan 31 to Feb 1
4.4/5Wonderful! (994 reviews)

"Went here on my Honeymoon in Dec 2020 and it was amazing. We had an ocean front suite that was very spacious, clean, and very well designed. The amenities and beach front property were great."…"

Reviewed on Jan. 3, 2021

Amara Cay Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free cancellationReserve now, pay when you stay
The price is CA $315 per night from Jan 17 to Jan 18
4.4/5Excellent! (991 reviews)

"Beautiful property. Things close early like the beach...would be nice if night time activities were more abundant."…"

Reviewed on Jan. 11, 2021

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.

Top things to do in Islamorada

Islamorada Beach Vacation

Take a break from life's daily stresses and relax on your Islamorada vacation. Few things are more rejuvenating than a cool ocean breeze and the sound of waves lapping at the shore. Plan your trip to Islamorada the quick and easy way by locking in one of our Islamorada packages. Many people opt to base themselves near Anne's Beach, a must-see only 10 miles (16 km) from the downtown area.

Things You Should Know About Islamorada

  • Spend your getaway by the water and let the stresses of daily life drift away with the ocean breeze. Check out our Islamorada beach hotels and indulge in a little beachside bliss.
  • Have a look at Angler's Reef Resort by KeysCaribbean and Blue Water Retreat by RedAwning. These private vacation homes might just be ideal for your stay in Islamorada.
  • Roughly 7,100 people reside in Islamorada. If you're after tips about what to see and do in this area, why not strike up a conversation with some of the friendly locals? Our Islamorada things to do page is also a handy source of information.
  • Islamorada vacation deals are a terrific way to save on exciting experiences. Some ideas, including Theater of the Sea, Founders Park and Anne's Beach, belong at the very top of your sightseeing list.

Frequently asked questions

How much does an Islamorada vacation package cost?
Browse and book everything in one place with our Islamorada vacation packages, which start from only CA $1,121. Pick the hotels and flights that match your travel plans. Then, add on a couple of sightseeing activities for an one-of-a-kind getaway.
If I'm not able to travel, can I cancel my Islamorada vacation package?
It’s hard to predict what tomorrow might bring, so it’s comforting to know that you can cancel or change your Islamorada vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for more information.
How do I get a cheap travel package to Islamorada?
You can save up to C$590 if you combine your hotels, car rentals and flights into an Islamorada vacation package. Sometimes cheap means fewer options. But not with Expedia. We offer more than 400 air carriers and 321,000 hotels across the world, which means you’ll always have plenty of variety to choose from. Like to save even more? Add some fun activities to your package deal to unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
What are the top hotels in Islamorada?
Tropical Paradise in Venetian Shores. Luxury Heated Pool / Spa, 4 Bikes & Kayak will make an ideal base for your Islamorada adventures. Located in Venetian Shores, it’s one of the area’s best hotels.
When is the best time of year to visit Islamorada?
The answer depends on you. If you’re hoping to get the best deal, visit in September. Hotels and airfares are generally more reasonable around this time of year than they are in March. If you want to experience the buzz of Islamorada during peak season, lock in your adventure for July, June, August. December, November, October is usually a quieter time of year.
How far in advance should I book my Islamorada vacation?
Travelers are generally able to browse international airfares on Expedia up to 12 months prior to departure. Booking last minute? With a stroke of luck, there’s a still a chance you can nab an affordable ticket just weeks before your journey.
What does an Expedia Islamorada travel package include?
Hotels, flights and a reliable car for all your road trip adventures. Simply pick and choose your favorite bundle and get access to great discounts. Once you’ve made your booking, add on a few tours and activities and watch your savings stack up. When it comes to planning your Islamorada trip, the choice is all yours!
What should I know before booking an Islamorada travel package?
Whether it’s adventure or relaxation you’re craving, an Islamorada vacation package lets you plan your escape your way. Plus, you’ll get access to great discounts just for combining your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Does Expedia offer Book Now, Pay Later Islamorada vacation packages?
Expedia works with online lender Affirm to help minimize any financial stress related to your trip. This may be useful if your reason for travel arose unexpectedly. Book Now, Pay Later and spread the price of your activities and hotel package over numerous installments.
Can I choose my airline with an Islamorada Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Simply select your preferred air carrier and put together your ideal Islamorada escape.

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