Book Exclusive Islamorada Vacation Packages

Choose one or more items to build your trip:

Islamorada flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Pantera Rosa

Pantera Rosa

4 out of 5
South Beach
Price was CA $1,221, price is now CA $738 per person
CA $738
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
Stay at this aparthotel in Miami Beach. Enjoy free WiFi, valet parking (surcharge), and an in-room coffeemaker. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.
Nobu Hotel Miami Beach

Nobu Hotel Miami Beach

5 out of 5
Mid Beach
Price was CA $2,058, price is now CA $1,078 per person
CA $1,078
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Book a stay at this luxury resort in Miami Beach. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. 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 $23,636, price is now CA $12,722 per person
CA $12,722
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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.
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was CA $1,669, price is now CA $969 per person
CA $969
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip 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 pool in our reviews. Popular attractions Miami Beach Boardwalk and Lincoln Road Mall are located nearby.
Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Price was CA $1,239, price is now CA $752 per person
CA $752
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, 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.

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 $305 per night
CA $305
CA $446 total
Aug 6 - Aug 7
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.
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 $212 per night
CA $212
CA $341 total
Aug 17 - Aug 18
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.
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 $205 per night
CA $205
CA $310 total
Aug 16 - Aug 17
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.
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 $366 per night
CA $366
CA $506 total
Aug 12 - Aug 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 Lorelei Restaurant & Cabana Bar are located nearby.
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 $291 per night
CA $291
CA $429 total
Aug 10 - Aug 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.
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 $236 per night
CA $236
CA $368 total
Aug 16 - Aug 17
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.
Don't see what you're looking for?
See all available properties in Islamorada
View all properties
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 $738. 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.

Explore More Ways to Travel with Travelocity