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Islamorada flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Park Royal Miami Beach managed by Accor

Park Royal Miami Beach managed by Accor

2.5 out of 5
North Beach
Price was CA $1,646, price is now CA $740 per person
CA $740
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Miami Beach Boardwalk and Lincoln Road Mall are located nearby.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $15,485, price is now CA $8,358 per person
CA $8,358
per person
Oct 10 - Oct 13
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
Book a stay at this luxury aparthotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Balfour Miami Beach, a Registry Collection Hotel

Balfour Miami Beach, a Registry Collection Hotel

4 out of 5
South Beach
Price was CA $2,064, price is now CA $1,164 per person
CA $1,164
per person
Nov 7 - Nov 14
found 5 hours ago
Roundtrip flight included
Ottawa (YOW) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area are located nearby.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was CA $1,531, price is now CA $864 per person
CA $864
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) 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 Lincoln Road Mall are located nearby.
The Local House

The Local House

3.5 out of 5
South Beach
Price was CA $2,972, price is now CA $1,707 per person
CA $1,707
per person
Nov 7 - Nov 14
found 5 hours ago
Roundtrip flight included
Ottawa (YOW) to Miami (MIA)
Book a stay at this boutique hotel in Miami Beach. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean Drive and Collins Avenue Shopping Area 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 $206 per night
CA $206
CA $332 total
Sep 15 - Sep 16
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 Lorelei Restaurant & Cabana Bar 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 $154 per night
CA $154
CA $251 total
Oct 5 - Oct 6
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 $198 per night
CA $198
CA $324 total
Sep 30 - Oct 1
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
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 $253 per night
CA $253
CA $385 total
Sep 10 - Sep 11
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 Hog Heaven 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 $270 per night
CA $270
CA $397 total
Sep 30 - Oct 1
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 Lorelei Restaurant & Cabana Bar are located nearby.
On private beach
Pool
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
Free cancellation
Reserve now, pay when you stay
The price is CA $175 per night
CA $175
CA $242 total
Sep 21 - Sep 22
includes taxes & 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 our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and Hog Heaven 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.

Stay near popular Islamorada attractions

A sandy beach with green vegetation and a calm sea.

Anne's Beach

7.8/10 (597 reviews)
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.
See properties

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 $740. 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

A beach with palm trees and white lounge chairs under a clear blue sky.
A beach with white lounge chairs, a covered pavilion, and palm trees.
A wooden dock extending into calm waters, surrounded by sandy beach and palm trees.
A waterfront with palm trees, a dock, and a small boat.
A colorful shop with various fish decorations, a sign that says "You bring the tequila, I'll bring the bad decisions," and a display of mugs and other items.

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