Islamorada Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
A pier extending into calm waters with a covered seating area and a sandy beach.

Matecumbe

6 out of top 10 points of interest in this area

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Robbieā€™s of Islamorada are top sights worth seeing.

Find hotels in Matecumbe

Find the Best Islamorada Vacation Packages

Islamorada Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is SARĀ 817 per night from Aug 12 to Aug 13
SARĀ 817
SARĀ 1,194 total
12 Aug - 13 Aug
includes taxes & fees
Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is SARĀ 574 per night from Aug 17 to Aug 18
SARĀ 574
SARĀ 921 total
17 Aug - 18 Aug
includes taxes & fees
Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is SARĀ 528 per night from Aug 16 to Aug 17
SARĀ 528
SARĀ 805 total
16 Aug - 17 Aug
includes taxes & fees
9.4/10 Exceptional! (1,743 reviews)
"Great pool and beach area"

Reviewed on 18 July 2026

Chesapeake Beach Resort
See all 2,152 properties in Islamorada
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)
Anne's Beach offers shallow, calm waters and a scenic boardwalk winding through mangroves. Enjoy the covered pavilions for picnicking or launch your paddleboard into the crystal-clear waters of the Florida Keys.
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Frequently asked questions

How much does an Islamorada vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation to Islamorada costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Islamorada?
If you'd like to score a cheap Islamorada vacation package, consider traveling in September, October and November. You'll typically find better rates on hotels and airfares during these months ā€” ideal for a budget-friendly getaway.
How to find the best Islamorada package deals?
Finding a cheap Islamorada package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Islamorada package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Islamorada vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still have the freedom to create a personalized Islamorada vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Islamorada?
If you have your Islamorada vacation dates locked in, book early to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Islamorada?

  1. Pick your travel dates: What you plan to do in Islamorada and your preferred season will help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and experiences. Your hotel will probably be the largest expense during your trip to Islamorada.
  3. Work out your trip length: Think about how long you want to spend discovering Islamorada. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Islamorada vacation package.