Islamorada Trip

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Top Islamorada Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
25 Sept - 1 Oct
found 19 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Overall, the property is great and it’s very close to the beach , the Check in staff was great and friendly. And the bedrooms are renovated very good . However, the bathroom has a sliding door which is glass when you are in the bathroom, your shadow can be seen by the person that is in the bedroom.

Reviewed on 23 Jul 2025

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
25 Sept - 1 Oct
found 19 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (800 reviews)
friendly staff, clean rooms, 1 block away from the beach

Reviewed on 22 Jul 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
25 Sept - 1 Oct
found 19 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,636 reviews)
We were greeted by Henry at the front desk, he was the sweetest! Most helpful person I encountered in my entire visit to Miami. He gave you all the information you needed plus some. He was attending multiple people at once so noone was waiting for a simple request. When we got to the room I did notice they did not sweep throughout the room but for the most part it smelled really clean and sanitized. We were about 3 minutes from a Starbucks, dinning options, and the beach.

Reviewed on 23 Jul 2025

The Gabriel Miami South Beach, Curio Collection by Hilton

The Gabriel Miami South Beach, Curio Collection by Hilton

4 out of 5
South Beach
Save 100% on your flight
per person
25 Sept - 1 Oct
found 19 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
Wonderful property and right in the middle of all the action in South Beach. Awesome they had two pools, one in courtyard then an amazing rooftop pool with incredible views! Bathrooms were nice and clean up on rooftop too! Only complaint would be room was pretty hot even with AC, just can’t seem to cool the room enough. Not sure if that’s extremely common for Miami since it’s so how they can’t keep up or what, but that was the same at another hotel we stayed downtown last year. Other than that, great hotel and would absolutely stay there again if going back to South Beach!

Reviewed on 20 Jul 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
25 Sept - 1 Oct
found 19 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,329 reviews)
Great clean hotel and convenient location but very noisy and AC location blowing directly on bed ….

Reviewed on 23 Jul 2025

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Islamorada showing a beach bar

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 Florida Keys Brewing Co. are top sights worth seeing.

Find hotels in Matecumbe

Islamorada Beach Holiday

Relax along the shoreline and feel the wind through your hair during your Islamorada holiday. If it's your first time, why not collect some unique seashells as a souvenir of your trip to Islamorada? Spend your nights near Anne's Beach, a popular stretch of coast just 14 kilometres from the town centre. We also offer fantastic Islamorada packages closer to Sunset Drive Beach, another great nearby option.

Things You Should Know About Islamorada

  • Escape the daily grind at one of our Islamorada beach hotels. The sound of the waves and seagulls cawing high in the sky are just a few clicks away.
  • If you're searching for lots of room to spread out and relax, Islamorada private holiday homes are a great choice. After a much-needed family getaway or a few nights escape with your best friends? Treasure Harbour and Bud N' Mary's Fishing Marina will fit the bill.
  • Roughly 7,100 people reside in Islamorada. If you're after a few helpful tips on what to see and do during your stay, have a chat to some of the friendly locals or have a look at our Islamorada things to do page.

Top hotels in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₹22,209 per night from 11 Aug to 12 Aug
₹22,209
₹30,816 total
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,137 reviews)
"Stayed here for one night. Unfortunately the weather wasn’t great so we didn’t get to experience the pool areas and such. We walked around the grounds at night in the rain and it was still breath taking. Would love to stay longer the next time I am back in the area."

Reviewed on 20 Jul 2025

Cheeca Lodge & Spa
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 ₹15,349 per night from 5 Aug to 6 Aug
₹15,349
₹22,126 total
5 Aug - 6 Aug
includes taxes & fees
9/10 Wonderful! (1,488 reviews)
Chesapeake is Amazing - Gets better every trip
"We have been coming here for 5 years and the place gets better and better. Every year we come they have added new amenities. The beach and pools are amazing and the location makes it easy to go anywhere in the Keys quickly. If you are looking for a great resort for a great price in this area it is ..."

Reviewed on 22 Jul 2025

Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is ₹17,965 per night from 11 Aug to 12 Aug
₹17,965
₹26,041 total
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Perfect gateaway with my husband! THANKS EXPEDIA FOR A GREAT PRICE in a wonderful place! we enjoyed it every minute. WE will back soon!"

Reviewed on 19 Jul 2025

Islander Resort
See all 2,190 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.

Popular places to visit

Anne's Beach

Anne's Beach

4.5/5(3 reviews)

If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.

Anne's Beach
Founders Park showing modern architecture, a garden and theatre scenes

Founders Park

3.5/5(2 reviews)

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

Founders Park
Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.

Frequently asked questions

How much does an Islamorada holiday package cost?
You can snap up a holiday package to this destination from ₹30,602 on Expedia. However, how much your holiday to Islamorada costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Islamorada?
You can generally find lower prices and greater availability in September, October and November. Browse our cheap Islamorada holiday packages and you could get some great off-season discounts.
How many days is enough for Islamorada?
We'd recommend booking an Islamorada holiday for at least 3 days. This will give you enough time to visit top attractions such as Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park, and explore neighbourhoods like Matecumbe and Plantation Key. You could even slot in one or two day trips from Islamorada.
Is it worth booking a holiday package to Islamorada?
Islamorada has all the ingredients you need for a fantastic getaway — walking trails, views and family-friendly attractions are just the start. Whether you'd like to check out attractions such as Theatre of the Sea and Hurricane Monument, or take the path less traveled, there's plenty to see and do on your Islamorada holiday.
How to find the best Islamorada package deals?
Use Expedia's filter tool to help you find some tempting Islamorada package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Islamorada package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book an Islamorada holiday as a package?
You can enjoy significant savings on your Islamorada escape by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Islamorada?
If you're considering a spur-of-the-moment Islamorada getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Islamorada?

  1. Choose when to go: Check your diary and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Islamorada.
  2. Set your budget: Factor in expenses like food, flights and transportation when working out how much to save for your trip to Islamorada. Then, select a hotel that works with your budget, whether that's a low-cost option or a swankier getaway.
  3. Decide your trip length: Think about how much time you want to spend exploring Islamorada. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your airfare and accommodation: After you've nailed down your travel dates and duration, lock in the right Islamorada holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.