Islamorada Holidays

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Islamorada Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
27 Mar - 30 Mar
found 6 hours ago
Return flight included
New York (NYC) to Miami (MIA)
8.4/10 Very Good! (733 reviews)
Decent sized, reasonably attractive room. Good location. 2 min. walk to Starbucks. Walgreens one block away. Basic breakfast served at different hotel one block away. Might very well return. 8/10

Reviewed on 9 Feb,2025

Hotel Colonnade Coral Gables, Autograph Collection

Hotel Colonnade Coral Gables, Autograph Collection

4 out of 5
Coral Gables Section
per person
27 Mar - 30 Mar
found 6 hours ago
Return flight included
New York (NYC) to Miami (MIA)
9.2/10 Wonderful! (1,004 reviews)
Hotel needs renovation. Loud wedding downstairs.

Reviewed on 9 Feb,2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
27 Mar - 30 Mar
found 6 hours ago
Return flight included
New York (NYC) to Miami (MIA)
8/10 Very Good! (1,027 reviews)
I liked the decorations of the property and the friendly staff.

Reviewed on 16 Feb,2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
27 Mar - 30 Mar
found 6 hours ago
Return flight included
New York (NYC) to Miami (MIA)
9.2/10 Wonderful! (1,059 reviews)
We loved our stay. Beautiful and amazing staff.

Reviewed on 16 Feb,2025

Avalon Hotel

Avalon Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
27 Mar - 30 Mar
found 6 hours ago
Return flight included
New York (NYC) to Miami (MIA)
9/10 Wonderful! (1,015 reviews)
This place is such a hidden gem, I hate for it to become too popular! Affordable, clean, one of the best locations on Ocean drive. Best key lime and cheesecake desserts on Ocean drive. And the grouper was amazing.

Reviewed on 15 Feb,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

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

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 16 kilometres 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.

Top hotels in Islamorada

Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is S$527 per night from 25 Feb to 26 Feb
S$527
includes taxes & fees
25 Feb - 26 Feb
9/10 Wonderful! (1,404 reviews)
"The hotel is in great condition, very clean and the staff is amazing! The breakfast is a game changer! There's an omelet station!!! Pools were nice and the fact we could bring our boat made it perfect. Couple restaurants close by also great!"

Reviewed on 17 Feb,2025

Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is S$596 per night from 23 Feb to 24 Feb
S$596
includes taxes & fees
23 Feb - 24 Feb
8.8/10 Excellent! (1,211 reviews)
"We really enjoyed our stay at Amara Cay Resort. Wonderful staff, very helpful and knowledgeable. Gorgeous location on the Atlantic side of Islamorada. Beautiful pool area and tiki bar."

Reviewed on 12 Feb,2025

Amara Cay 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 S$596 per night from 23 Feb to 24 Feb
S$596
includes taxes & fees
23 Feb - 24 Feb
9/10 Wonderful! (1,029 reviews)
Cheeca Lodge
"We had an amazing relaxing trip . It is beautiful and impeccably maintained. Anna at the front desk was so nice. Maureen the concierge was so helpful and sweet. Cassandra was our favorite waitress. We will definitely go back,"

Reviewed on 10 Feb,2025

Cheeca Lodge & Spa
See all 2,245 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.

Frequently asked questions

How much does an Islamorada holiday package cost?
You can snap up a holiday package to this destination from S$967 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.

Popular places to visit

Founders Park showing modern architecture, theatre scenes and a 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
History of Diving Museum

History of Diving Museum

Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts.

History of Diving Museum

Sunset Drive Beach

Why not spend a lazy afternoon at Sunset Drive Beach during your trip to Islamorada?

Sunset Drive Beach

What to do in Islamorada

Day Tour Glass Bottom Boat In Islamorada

Day Tour Glass Bottom Boat In Islamorada

S$109
per adult
Day Tour Glass Bottom Boat In Islamorada
Original Snorkel and Sandbar Combo in Islamorada

Original Snorkel and Sandbar Combo in Islamorada

S$199
per adult
90% of travellers recommend
Original Snorkel and Sandbar Combo in Islamorada
Private 3-Hour Islamorada Sandbar Tour

Private 3-Hour Islamorada Sandbar Tour

S$678
per traveller
100% of travellers recommend
Private 3-Hour Islamorada Sandbar Tour
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.