Islamorada Holidays from £599

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Your Islamorada Holiday

The laid-back lifestyle and spectacular views are just the beginning of the things Islamorada has to offer. Enjoy the sights and sounds of this captivating city the way you want with a customised Islamorada holiday package. You'll want to do some exploring during your trip to Islamorada. Make time for popular attractions like Theatre of the Sea, Bud n Marys Dive Centre and Founders Park. Check out Expedia's wide range of travel options and start organising your dream holiday to Islamorada today.

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
Price was £1,040, price is now £599 per person
£599
per person
22 Sept - 28 Sept
found 17 hours ago
Return flight included
London (LON) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.

Reviewed on 16 Aug 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
Price was £15,480, price is now £7,030 per person
£7,030
per person
22 Sept - 28 Sept
found 16 hours ago
Return flight included
London (LON) 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
Price was £4,323, price is now £2,338 per person
£2,338
per person
27 Oct - 3 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
9.4/10 Exceptional! (1,245 reviews)
Went for a family trip. Lots of healthy food options.

Reviewed on 17 Aug 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was £1,789, price is now £1,050 per person
£1,050
per person
20 Sept - 27 Sept
found 23 hours ago
Return flight included
Birmingham (BHX) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
We had a wonderful time here. It was very family friendly with the lazy river, pool and easy beach access. They had fun events like a kids glow party with spelling bee and coconut race. My daughter had a blast. The staff were beyond accommodating, especially Andrew by the pool, Jean by the beach and Donte. I don’t have some of the names but everyone spoiled my daughter with fruit and ice cream any room she walked into and made her feel like a princess. We would definitely come back!

Reviewed on 20 Aug 2025

Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Save 100% on your flight
Price was £1,833, price is now £1,120 per person
£1,120
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LON) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
First time there. Definitely will return.

Reviewed on 19 Aug 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 Anne's Beach are top sights worth seeing.

Find hotels in Matecumbe

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

Top hotels in Islamorada

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 £138 per night from 21 Sept to 22 Sept
£138
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (1,501 reviews)
"Excellent location on the ocean and everything was really perfect. will stay there again"

Reviewed on 17 Aug 2025

Chesapeake Beach Resort
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 £176 per night from 24 Aug to 25 Aug
£176
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,158 reviews)
"Great place. Feel like rooms can be updated to a modern appea"

Reviewed on 20 Aug 2025

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 £189 per night from 1 Sept to 2 Sept
£189
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,241 reviews)
"The views, the staff and service were very pleasant. We loved our stay overall."

Reviewed on 19 Aug 2025

Amara Cay Resort
See all 2,178 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

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
Ft. Lauderdale to Key West Bus Tour w/ 6 hours of free time in KW

Ft. Lauderdale to Key West Day Trip Quality Day Tours

£166
per adult
Ft. Lauderdale to Key West Day Trip Quality Day Tours
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.

* 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.