Islamorada Holidays from £836

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to £195 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Islamorada Holiday

With one of our holiday packages to Islamorada, you'll discover endless opportunities for adventure and relaxation. There's plenty to enjoy, including its laid-back lifestyle and spectacular views. Make your trip to Islamorada even more fun by including some sightseeing. Theatre of the Sea, Bud n Marys Dive Centre and Founders Park are some of the popular attractions worth exploring. Don't put off visiting this destination any longer. The ultimate Islamorada holiday is only a few clicks away with Expedia.

The Latest Islamorada Holiday Deals

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
19 Jun - 26 Jun
Return flight included
London (LON) to Miami (MIA)
9/10 Wonderful! (1,012 reviews)
The rooms are spacious. The property is gorgeous. Just all around great experience.

Reviewed on 17 Apr 2024

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
27 May - 3 Jun
Return flight included
London (LON) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
The location is very nice. Rooms were small.

Reviewed on 17 Apr 2024

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
27 May - 3 Jun
Return flight included
London (LON) to Miami (MIA)
8.2/10 Very Good! (635 reviews)
Hotel staff are friendly and helpful. Staff offered to store one's luggage as check out is at 11:00AM. Breakfast is served at a sister hotel a few blocks away on Ocean Drive. There is water, tea and coffee available throughout the day. My concerns about my stay related to the temperature of the room which was too cold and one could not adjust thermostat, which was on the wall, but it did nothing to affect the overall temperature of the room. Added to that, the maximum temperature for the hot water was much too low, although there was very hot water in the sink but did not transfer to the shower. The television in the room was difficult to operate with the remote and we could not figure out how to change the channel on the cable. The YouTube option was a functional substitute.

Reviewed on 4 Apr 2024

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
per person
27 May - 3 Jun
Return flight included
London (LON) to Miami (MIA)
8/10 Very Good! (1,184 reviews)
Beautiful location and property

Reviewed on 16 Apr 2024

Fontainebleau Miami Beach Private Luxury Suites

Fontainebleau Miami Beach Private Luxury Suites

4 out of 5
Mid Beach
Save 100% on your flight
per person
27 May - 3 Jun
Return flight included
London (LON) to Miami (MIA)
7.6/10 Good! (44 reviews)
There was a cleaning fee, which I was not aware of. I only stayed one night. The fee was half of what I paid for the room.

Reviewed on 15 Feb 2024

The Gates Hotel South Beach - a DoubleTree by Hilton

The Gates Hotel South Beach - a DoubleTree by Hilton

4 out of 5
South Beach
per person
27 May - 3 Jun
Return flight included
London (LON) to Miami (MIA)
7.6/10 Good! (1,016 reviews)
Our time was wonderful. Scott was a great help at checkout! Will definitely return.

Reviewed on 15 Apr 2024

Prices and availability subject to change. Additional terms may apply.

Islamorada Beach Holiday

Take a break from life's daily stresses and relax on your Islamorada holiday. Few things are more rejuvenating than a cool ocean breeze and the sound of waves lapping at the shore. Plan your trip to Islamorada the quick and easy way by locking in one of our Islamorada packages. Many people opt to base themselves near Anne's Beach, a must-see only 10 miles from the downtown area.

Things You Should Know About Islamorada

  • Spend your getaway by the water and let the stresses of daily life drift away with the ocean breeze. Check out our Islamorada beach hotels and indulge in a little beachside bliss.
  • Have a look at Angler's Reef Resort by KeysCaribbean and Blue Water Retreat by RedAwning. These private holiday homes might just be ideal for your stay in Islamorada.
  • Roughly 7,100 people reside in Islamorada. If you're after tips about what to see and do in this area, why not strike up a conversation with some of the friendly locals? Our Islamorada things to do page is also a handy source of information.
  • Islamorada holiday deals are a terrific way to save on exciting experiences. Some ideas, including Theatre of the Sea, Founders Park and Anne's Beach, belong at the very top of your sightseeing list.

Islamorada Essential Information

Language
English
Currency
U.S dollars
Population
7,100
Max Temp Winter
24ºC
Max Temp Summer
29ºC
Top Sights
Theatre of the Sea, Annes Beach and Windley Key Fossil Reef Geological State Park

Our guide on where to stay in Islamorada

Check out a few of the areas and neighbourhoods we love in Islamorada Learn more about Islamorada
Islamorada showing a beach bar

Matecumbe

5 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 Anne's Beach are top sights worth seeing.

Find hotels in Matecumbe

Our pick of the best Islamorada Hotel Deals

Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
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 ...
8.8/10 Excellent! (1,290 reviews)
"My husband and I stayed 1 night in a VILLA . It was awesome from the kitchen to the bedroom to the bathroom . Super clean , excellent quality from top to bottom . Would definitely stay there again"

Reviewed on 15 Apr 2024

Chesapeake Beach Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
4 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Stay at this beach resort in Islamorada. Enjoy free parking, 3 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,000 reviews)
"Great property!"

Reviewed on 15 Apr 2024

Cheeca Lodge & Spa
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
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 their ...
8.8/10 Excellent! (1,249 reviews)
Amazing
"Great"

Reviewed on 16 Apr 2024

Amara Cay Resort
See all 2,101 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Islamorada holiday with Expedia?
Expedia has your back for every detail of your next Islamorada trip. You’ll always get the best prices around, but when you bundle your accommodation, airfares and/or car hire into a holiday package, you’ll score even more savings. Want to truly make the most of your escape? Add a few exciting activities and tours to your package. We offer flexible cancellation policies on almost all bookings, so you won’t need to worry if your plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Islamorada?
Islamorada is a popular place in November, December and January. If you’re not into large crowds and prefer a calmer pace, book your escape for April, September and October. To get an idea of the type of weather to expect, the average temperature during the day in January, the coolest month in Islamorada, is 21ºC. The warmest period here is August, when temperatures reach around 29ºC.
What are the top hotels for my holiday in Islamorada?
If you’d like to stay in the Venetian Shores neighbourhood, Postcard Inn Beach Resort & Marina and Sunset Inn are in-demand options. Lower Matecumbe Beach is another well-known Islamorada area. We recommend Sunset Inn or Islander Resort if you prefer this part of town.
How do I get a cheap holiday to Islamorada?
Bundle your flights and hotels with Expedia to save on your next getaway. With more than 400 airlines and 321,000 hotels globally, your Islamorada holiday can be tailored exactly to suit your travel style. With all that extra money, why not add a few awesome activities and tours? It’s an easy way to unlock even more savings. Your dream getaway to Islamorada is closer than you thought! Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Islamorada holiday?
There are so many places to check out while having a holiday in Islamorada. Theatre of the Sea, Annes Beach, Bud n Marys Dive Centre and Founders Park are among this destination’s key attractions.
What is the best area to stay in when on holiday in Islamorada?
If you plan to check out Theatre of the Sea, maximise your time sightseeing and lock in a stay close by. It’s one of the most popular attractions in Islamorada.
Do I need a visa for my Islamorada holiday?
Research the latest information on official government websites. Your nationality and whether you’re travelling for business, study or leisure will determine if you’ll need a visa for Islamorada. Get familiar with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow enough time for processing. Some visas can take many weeks or even months to obtain, depending on the country.
What should I wear on my Islamorada holiday?
First, think about the types of things you’ll be doing during your Islamorada holiday and select versatile pieces that can be mixed and matched. For fashion inspiration or information on any dress codes, look up style blogs or relevant social media accounts. Pack your bags with confidence by monitoring the local weather conditions in Islamorada. August brings the warmest temperatures, with daytime averages of 29ºC, while January days average 21ºC, making it the coolest time of the year.
What does an Expedia Islamorada holiday include?
Hotels, flights and a cool set of wheels for all your road trip adventures. Simply pick and choose your favourite bundle and gain access to great discounts. Once you’ve made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to organising your Islamorada break, you’re the boss! Explore a wide range of property types and pick one that suits your group size and travel needs. The most in-demand rentals here are private holiday homes and condos. With Expedia, it’s easy to tailor-make your Islamorada escape however you want.
Does Expedia offer Book Now, Pay Later Islamorada holidays?
Your bank balance shouldn’t prevent you from going on holiday, so Expedia has come up with a solution to help. Now that we’ve partnered with online lender Klarna, it’s easier than ever to book a fabulous getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna’s manageable payment plans. If paying across multiple instalments works for you, pick this option at checkout.
  • No-deposit holidays: When you see an unbeatable deal but don’t have the full amount yet, Klarna’s no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your escape.

Can I choose my airline with an Islamorada Expedia holiday?
Yes, you’re in control. We have access to over 400 partner airlines around the world, so you can design your Islamorada holiday according to your travel needs.

Discover the most popular places to visit in Islamorada

Image for Theater of the Sea

Theater of the Sea

4.5/5(5 reviews)

Swim with the dolphins and sharks and feed the crocodiles and sea turtles near the lagoon of this vast interactive park for marine mammals.

Theater of the Sea
Image for 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
Image for Founders Park

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

Unmissable things to do in Islamorada

Image for Salty Keys Snorkel and Sandbar Activity

Salty Keys Snorkel and Sandbar Activity

£127
Per adult
Salty Keys Snorkel and Sandbar Activity
Image for Half Day Private Boat Tour

Half Day Private Boat Tour

£712
Per adult
Half Day Private Boat Tour
Image for Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours

Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours

£297
Per adult
Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours
See all activities in Islamorada

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.