Islamorada Vacation Packages

Top Islamorada hotel deals

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$179

per night

Apr 30 - May 1

This smoke-free hotel's private beach and 2 outdoor pools are some of the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. There's a computer station and multilingual staff can provide around-the-clock assistance.

Pet friendly

Pool

Cheeca Lodge & Spa

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

Free Cancellation

Reserve now, pay when you stay

$290

per night

May 23 - May 24

This smoke-free resort features a private beach, a golf course, and a full-service spa. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities.

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$250

per night

Apr 28 - Apr 29

A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. Unwind with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and an area shuttle. You'll appreciate the gym, poolside bar, and laundry facilities.

La Siesta Resort & Villas

80241 Overseas Highway, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$266

per night

Apr 30 - May 1

The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, and a 24-hour front desk and wedding services are also provided.

Pet friendly

Breakfast available

Islander Resort

82100 Overseas Highway, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$258

per night

May 6 - May 7

This hotel features a private beach, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Enjoy the 24-hour gym and perks like free self parking and free WiFi.

Hadley Resort and Marina

82749 Overseas Hwy, Islamorada, FL

Free Cancellation

Reserve now, pay when you stay

$125

per night

May 12 - May 13

A marina and an outdoor pool are featured at this traditional hotel. Guests will appreciate freebies like on-the-go breakfast and free self parking. A business center, a terrace, and a garden are also on offer.

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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

4.5/5(215 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

3.5/5(139 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

4.5/5(137 reviews)

Play soccer, baseball and volleyball just meters from the Atlantic Ocean before you dive into the water at this family-friendly beach park.

Frequently asked questions

How much are vacation packages to Islamorada?

With vacation packages available from just , you won’t need to blow out the credit card for your getaway to Islamorada. Travelocity is here to help. Bundle flights, hotels and experiences into a convenient package and score some impressive discounts. The more you book, the greater the savings.

How long should my Islamorada vacation be?

Around 3 nights is what many visitors book for their Islamorada vacation. That’s a good starting point, but there’s so much more to explore if you give yourself a couple of extra days.

Where can I get the best vacation package deals for Islamorada?

You can snap up amazing Islamorada package deals with Travelocity. Pick and choose from 400 airlines and 1,000,000 worldwide properties and turn those vacation dreams into reality.

Why should I book my Islamorada vacation bundle with Travelocity?

Whether you’re planning a month-long vacation or a last-minute weekend trip, we have plenty of exciting destinations to choose from at a good price. And on top of that, we provide 24/7 assistance, high-quality service and a Price Match Guarantee. Save yourself time and money and book your dream vacation today.

Will I save money on my Islamorada car rental if I book it with a hotel or flight?

With an Islamorada vacation package, you can bundle your hotel, car and flight bookings and save loads. If you can’t wait to explore the best of this fabulous city, why not make a beeline for PortMiami? This top sight is 65 mi from Islamorada. With your own rental car, you’ll be there belong long.

What is the best time of year to go to Islamorada?

November, December and January are the months when most travelers visit, while April, September and October are usually quieter. If you’re traveling with a limited budget, consider visiting during . is usually regarded as the most expensive time of the year to stay here.

What is there to do in Islamorada?

While venturing off the beaten track is no doubt rewarding, you shouldn’t ignore the well-known sights that make a place famous. Theater of the Sea and Bud n Marys Dive Center are a couple of them in Islamorada.

Where should I stay when visiting Islamorada?

If you’re after someplace comfortable to spend your nights, have a look at the Postcard Inn Beach Resort & Marina. It’s the top pick for many travelers.