Islamorada Holidays from £788

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Top Islamorada Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
per person
2 Sept - 6 Sept
found 1 day ago
Return flight included
London (LON) to Miami (MIA)
9.6/10 Exceptional! (5 reviews)
Quiet.Lobby was nice and smelled amazing. Staff was good. Loved the gym/studio. Dislikes: No hot water in the shower. Lobby smelled amazing but wasn’t consistent throughout the building.

Reviewed on 17 Jul 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
1 Sept - 8 Sept
found 19 hours ago
Return flight included
London (LGW) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
6 Oct - 13 Oct
found 20 hours ago
Return direct flight included
Manchester (MAN) to Miami (MIA)
9.4/10 Exceptional! (1,212 reviews)
Beautiful hotel and experience.

Reviewed on 16 Jul 2025

EAST Miami

EAST Miami

5 out of 5
Downtown Miami
Save 100% on your flight
per person
9 Oct - 16 Oct
found 8 hours ago
Return flight included
London (LHR) to Miami (MIA)
9.2/10 Wonderful! (3,202 reviews)
Very good experience

Reviewed on 17 Jul 2025

iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
Save 100% on your flight
per person
5 Sept - 11 Sept
found 6 hours ago
Return direct flight included
Edinburgh (EDI) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
The property was in a very populated area with lots of shops, restaurants and nightlife (if that’s your thing). The studio was very clean and there were no issues at all. Unlike hotel rooms, I could not hear what was happening right next door, so it was quiet as well. I would stay here again.

Reviewed on 12 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

Popular places to visit

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.

What to do in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

£110
per adult
90% of travellers recommend
Original Snorkel and Sandbar Combo in Islamorada
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch

Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch

£183
per adult
Ft Lauderdale to Islamorada Tour with Boat Ride and Lunch
Islamorada: Multi-Activity Private Boat Charter

4 Hour – Snorkel & Sandbar Adventure

£441
per traveller
4 Hour – Snorkel & Sandbar Adventure
See all activities in Islamorada

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.