Book Exclusive Islamorada Vacation Packages

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Islamorada flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Arya Hotel & Suites Coconut Grove, WorldHotels, Distinctive

Arya Hotel & Suites Coconut Grove, WorldHotels, Distinctive

4 out of 5
Coconut Grove
Price was CA $1,251, price is now CA $701 per person
CA $701
per person
May 29 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
Stay at this hotel in Miami. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brickell City Centre and Bayside Marketplace are located nearby.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $2,940, price is now CA $1,318 per person
CA $1,318
per person
May 19 - May 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
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. Popular attractions Florida Keys Dive Center and Mangrove Marina are located nearby.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $4,123, price is now CA $2,099 per person
CA $2,099
per person
May 9 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
Book a stay at this beach aparthotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and laundry facilities. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was CA $1,601, price is now CA $894 per person
CA $894
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
President Hotel

President Hotel

3.5 out of 5
South Beach
Price was CA $1,555, price is now CA $873 per person
CA $873
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

Top Islamorada hotels deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Free cancellation
Reserve now, pay when you stay
The price is CA $416 per night
CA $416
CA $568 total
Apr 12 - Apr 13
includes taxes & 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 in our reviews. Popular attractions Florida Keys Brewing Co. and MoradaWay Arts & Cultural District are located nearby.
On private beach
Pool
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
The price is CA $321 per night
CA $321
CA $438 total
Apr 12 - Apr 13
includes taxes & fees
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. Popular attractions History of Diving Museum and Windley Key Fossil Reef Geological State Park are located nearby.
On private beach
Pool
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
The price is CA $335 per night
CA $335
CA $477 total
Mar 22 - Mar 23
includes taxes & 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 our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
On private beach
Pool
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
Free cancellation
Reserve now, pay when you stay
The price is CA $443 per night
CA $443
CA $591 total
Apr 12 - Apr 13
includes taxes & 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. Popular attractions Keys History & Discovery Center and Islamorada Brewery & Distillery are located nearby.
On private beach
Pool
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
Free cancellation
Reserve now, pay when you stay
The price is CA $473 per night
CA $473
CA $622 total
Mar 23 - Mar 24
includes taxes & 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 in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and History of Diving Museum are located nearby.
On private beach
Pool
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
Free cancellation
Reserve now, pay when you stay
The price is CA $346 per night
CA $346
CA $489 total
Mar 22 - Mar 23
includes taxes & 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 rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
On private beach
Pool
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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.

Popular places to visit

Theater of the Sea

Theater of the Sea

Take the kids to visit the sea life you'll find at Theater of the Sea during your trip to Islamorada. Take in the entertainment choices and beautiful sunsets in this family-friendly area.

Theater of the Sea
Islamorada_BudnMarysDiveCenter_6069243-0004

Bud n' Mary's Dive Center

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

Bud n' Mary's Dive Center
Anne\'s Beach featuring a bridge

Anne's Beach

If a restful vacation is part of your travel plans, Anne's Beach might be the perfect place to seek out during your trip to Islamorada.

Anne's Beach

Islamorada Vacations

If you're going to Islamorada and you don't really know much about it, you don't need to worry — we'll let you in on the basics!

Islamorada is located 170 miles (274 kilometers) to the northeast of Havana, a significant city.

At last count, the population of this area of Florida Keys was 7,000.

Places to visit in Islamorada

If you've got an inquiring mind, stop by History of Diving Museum. You never know what you'll find out here! Need some more ideas? We all dote on our fuzzy and feathery friends, but how about getting familiar with those who are a tad more scaly and slippery? Meet some of the most magnificent occupants of the marine world at Theater of the Sea. And that's not all. Hurricane Monument offers a space for reflection and solitude. Learn about the importance of this memorial and find out more about how, when and why it was erected.

Where do you fly into for Islamorada?

While you're arranging your upcoming Islamorada escape, keep in mind that the closest terminal, Homestead Air Reserve Base Airport (HST), is about 40 miles (64 kilometers) north of the city center. Book your flight, fill up your luggage and get set for some exciting new adventures!

Frequently asked questions

How much are vacation packages to Islamorada?
Prepare to be surprised — you can vacation in Islamorada for a paltry CA $701. Allow Travelocity to save you time and money with our excellent vacation packages. With flights, hotels and experiences all available at our one-stop shop, what's stopping you?
How long should my Islamorada vacation be?
There's no rule when it comes to how long you should spend in Islamorada, but many people decide to stay around 3 nights. Got some wiggle room in your travel dates? Extend your vacation by a few more nights. That way, you'll have loads of time to explore the area's off-the-beaten-path gems as well.
Where can I get the best vacation package deals for Islamorada?
No matter how you like to travel, Travelocity can help you get your hands on an unbeatable Islamorada package deal. The only thing you need to do is pick and choose between our 400 air carriers and 665,000 properties across the globe.
Why should I purchase my Islamorada vacation bundle via Travelocity?
We've got 24/7 support, excellent service and a Price Match Guarantee. Life is one big journey — and we have enticing destinations for you to journey to in all four corners of the globe. Explore with us and your bank balance will thank you for it.
Can I save on my Islamorada car rental if I combine it with a hotel or flight?
Absolutely — combine your hotel, car and flight into an Islamorada vacation package and you'll save a tidy sum. With so much to discover in and around Islamorada, that rental car will come in handy. Once you've buckled up, turn up the tunes and head to PortMiami, a well-known sight about 100 kilometersfrom Islamorada.
What is the best time of year to go to Islamorada?
Visiting in the least busy months, , comes with a few upsides — think cheaper hotels and flights and less pushing past hordes of strangers. But there's magic in the destination in the peak season. More events are likely to be on and more attractions will be open in . If you're on a tight budget, typically has the cheapest hotel rates. You can expect to pay more for a room in .
What is there to do in Islamorada?
Theater of the Sea should be at the top of your must-see list. Once you've crossed off this top attraction, simply wander the streets of Islamorada and find out what makes this vibrant city tick.
Where should I stay when visiting Islamorada?
The Hadley House Islamorada (2.0 stars) and the Coconut Cove Resort and Marina (2.0 stars) are ideal options if you're visiting Islamorada on a tight budget.
Can I go on vacation to Islamorada at this time?
Don't fly off to Islamorada without the facts about travel restrictions and quarantine policies. Travelocity's Covid-19 Travel Advisor can fill you in. It has all the information you need to make your getaway as stress-free as possible.

Photos of local treasures

Browse Islamorada vacation photos for more inspiration

Islamorada which includes tropical scenes and a sandy beach
Islamorada which includes tropical scenes and a sandy beach
Islamorada showing a sandy beach
Islamorada showing a bay or harbor
Islamorada showing outdoor eating as well as a small group of people

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