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.
Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jun. 15 - Jun. 20
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this hotel in Fort Lauderdale. Enjoy free WiFi, parking (surcharge), and a garden. Popular attractions Fort Lauderdale Beach and Las Olas Beach are located nearby.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Jul. 21 - Jul. 25
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Stay at this 5-star luxury hotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby.
Mayfair House Hotel & Garden

Mayfair House Hotel & Garden

4.5 out of 5
Coconut Grove
Save 100% on your flight
per person
Aug. 1 - Aug. 5
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
Book a stay at this boutique hotel in Miami. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Brickell City Centre and Bayside Marketplace 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
per person
Aug. 4 - Aug. 11
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
Stay at this 5-star luxury condo 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.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jun. 27 - Jul. 2
Roundtrip non-stop flight included
Buffalo (BUF) to Miami (MIA)
Stay at this 4-star beach hotel in Fort Lauderdale. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fort Lauderdale Beach and Las Olas Beach are located nearby.

Top Islamorada hotels deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $407 per night
CA $407
per night
Jun. 16 - Jun. 17
Book a stay at this beach 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 Matecumbe United Methodist Church and Florida Keys Brewing Co. are located nearby.
Hot tub
Pool
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $272 per night
CA $272
per night
May 19 - May 20
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions History of Diving Museum and Windley Key Fossil Reef Geological State Park are located nearby.
Pet-friendly
Pool
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is CA $393 per night
CA $393
per night
May 19 - May 20
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the restaurant in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.
Pet-friendly
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 $400 per night
CA $400
per night
May 19 - May 20
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). 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.
Pet-friendly
Pool
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $205 per night
CA $205
per night
May 28 - May 29
Stay at this hotel in Islamorada. Enjoy free breakfast, a marina, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions History of Diving Museum and Matecumbe United Methodist Church are located nearby.
Pet-friendly
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 $325 per night
CA $325
per night
May 22 - May 23
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Matecumbe United Methodist Church and Florida Keys Brewing Co. are located nearby.
Hot tub
Pet-friendly
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.

Popular places to visit

Image for Theater of the Sea

Theater of the Sea

4/5(6 reviews)

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
Image for Anne's Beach

Anne's Beach

4/5(14 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.

Anne's Beach
Image for Founders Park

Founders Park

3.5/5(2 reviews)

Enjoy the beautiful sunsets and explore Founders Park, a lovely green space in Islamorada. Wander the seaside and beautiful beaches in this family-friendly area.

Founders Park

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 $539. 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.