Islamorada Vacations 2025 from CA $1,758

Islamorada flight + hotel packages

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

Banana Bay Resort & Marina

Save 100% on your flight

per person

Feb. 11 - Feb. 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

Stay at this 3-star golf hotel in Marathon. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the bar in our reviews. Popular attractions Sombrero Beach and Florida Keys Country Club are located nearby.

EAST Miami

Downtown Miami

per person

Feb. 27 - Mar. 4

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Miami (MIA)

Stay at this 5-star luxury hotel in Miami. Enjoy free WiFi, 4 outdoor pools, and 2 restaurants. Our guests praise the pool and the restaurant in our reviews. Popular attractions Brickell City Centre and Bayside Marketplace are located nearby.

Villas At Hawks Cay Resort

per person

Feb. 11 - Feb. 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

Stay at this 4-star beach resort in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Popular attractions Little Conch Key and Walkers Island are located nearby.

Hawks Cay Resort

Save 100% on your flight

per person

Feb. 11 - Feb. 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Miami (MIA)

Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Little Conch Key and Walkers Island are located nearby.

1 Hotel South Beach

South Beach

per person

Feb. 27 - Mar. 5

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) 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.

Top Islamorada hotels deals

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $408

CA $554 total

includes taxes & fees

5 Jan - 6 Jan 2025

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 bar in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby.

On private beach

Pool

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $326

CA $438 total

includes taxes & fees

20 Jan - 21 Jan 2025

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 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

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $365

CA $508 total

includes taxes & fees

8 Jan - 9 Jan 2025

Stay at this 5-star 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 Matecumbe United Methodist Church and Florida Keys Brewing Co. are located nearby.

On private beach

Pool

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $343

CA $482 total

includes taxes & fees

5 Jan - 6 Jan 2025

Stay at this 4-star 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

Islander Resort

82100 Overseas Highway, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $389

CA $528 total

includes taxes & fees

20 Jan - 21 Jan 2025

Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 restaurants. 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

Hadley Resort and Marina

82749 Overseas Hwy, Islamorada, FL

Free cancellation

Reserve now, pay when you stay

CA $257

CA $336 total

includes taxes & fees

6 Jan - 7 Jan 2025

Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Islamorada Brewery & Distillery and History of Diving Museum 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

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.

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.

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.

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 $1,758. 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.