Islamorada Holidays from NZ$1,899

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The Latest Islamorada Holiday Deals

Prices and availability subject to change. Additional terms may apply.
The Gardens Hotel

The Gardens Hotel

4 out of 5
Key West Historic District
Save 100% on your flight
per person
16 Jun - 21 Jun
Return direct flight included
Toronto (YYZ) to Key West (EYW)
9.6/10 Exceptional! (901 reviews)
Beautiful property.Breakfast excellent. Staff helpful and friendly. Would like vending machines for snacks and drinks. No room service

Reviewed on 19 Apr. 2024

Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
per person
16 Jun - 21 Jun
Return direct flight included
Toronto (YYZ) to Key West (EYW)
7.8/10 Good! (1,614 reviews)
I have mixed feelings about my stay at the Ibis Bay Resort. First off it is one of the more reasonably priced accommodations in Key West. They have great amenities, such as their large clean pool, free continental breakfast and free transport to and from old town. You can also rent golf carts, scooters, bicycles, and they offer a few different tours. Unfortunately, we were quite disappointed with our room. We booked the queen bed courtyard room on the 2nd floor. They did a lovely job decorating the tiny room but the room was extremely damp and smelly. The carpet was old and most likely the cause of the smell. The air conditioning system ran continuously and was very loud. The venetian blinds let in a lot of light from the outside hallway and didn’t provide much privacy at night. In order to fit our luggage, we moved the patio chairs and bistro table to the outside hallway. This is an old motel that has been nicely decorated but requires a lot more than paint to bring it up to modern standards. So would I stay here again? Maybe, but I would definitely upgrade to a larger room on the main floor with an ocean view.

Reviewed on 24 Apr. 2024

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
per person
16 Jun - 21 Jun
Return direct flight included
Toronto (YYZ) to Key West (EYW)
8.8/10 Excellent! (1,003 reviews)
Private Beach and the cleanliness

Reviewed on 22 Apr. 2024

Eden House

Eden House

3.5 out of 5
Key West Historic District
per person
16 Jun - 21 Jun
Return direct flight included
Toronto (YYZ) to Key West (EYW)
9/10 Wonderful! (1,008 reviews)
Very nice, friendly.

Reviewed on 24 Apr. 2024

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Key West Historic District
per person
16 Jun - 21 Jun
Return direct flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (1,001 reviews)
Wonderful hotel and staff! Location is perfect to walk to restaurants/shopping/excursions. We will be back!

Reviewed on 22 Apr. 2024

Our guide on 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 hotel + flight trips 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.

Our pick of the best Islamorada Hotel Deals

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 NZ$377 per night from 7 May to 8 May
NZ$377
per night
7 May - 8 May
8.8/10 Excellent! (1,303 reviews)
"The hotel is super convenient location and right on the beach. We were disappointed that We had to wait until 4 pm to get into our room. We called for early check in but they kept saying call back. We never got early check in. When my daughter was playing in the pool she scraped her knee on the broken ..."

Reviewed on 23 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
Fully refundableReserve now, pay when you stay
The price is NZ$510 per night from 23 May to 24 May
NZ$510
per night
23 May - 24 May
8.8/10 Excellent! (1,001 reviews)
"We loved the beach and all of the facilities! It was so easy to park under our room with the golf course view. The property is gorgeous and well maintained. Also, Spa Island was so pretty and relaxing as well as the waterfall grotto pool and jacuzzi near our room. Loved the adult pool too! Daydrian ..."

Reviewed on 16 Apr. 2024

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 NZ$515 per night from 8 May to 9 May
NZ$515
per night
8 May - 9 May
8.8/10 Excellent! (1,250 reviews)
Amazing
"Great"

Reviewed on 16 Apr. 2024

Amara Cay Resort
See all 2,114 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?
The cheapest Islamorada holiday package is NZ$1,899, so your dream holiday can become a reality — without breaking the bank. Combine flights, hotels, car rentals and more to tailor make a package suited to your travelling style.
How do I get a cheap travel package to Islamorada?
Combining your flight and hotel with Expedia won’t just save valuable time — it’ll save you cash too. An Islamorada holiday package makes it easy to create your dream adventure. With more than 550 airlines across the world to select from, finding convenient flights that suit your schedule won’t be a challenge. On top of that, we’ve got over 1 000 000 hotels globally to select from. Now that’s choice! No matter who you are, Expedia will help show you the world.
Where should I stay in Islamorada?
A getaway to Islamorada isn’t complete without checking out Theatre of the Sea, Bud n Marys Dive Centre and Annes Beach. Stay near these popular sights and make sightseeing a breeze.
What are the top hotels in Islamorada?
Travellers visiting Islamorada often make a reservation at Postcard Inn Beach Resort & Marina or Amara Cay Resort. These options are in Venetian Shores. Another interesting neighbourhood is Lower Matecumbe Beach. Chesapeake Beach Resort and Islander Resort are popular choices in this part of town.
How far in advance should I book my Islamorada holiday?
Travellers are usually able to browse international flights on Expedia up to a year in advance of departure. Booking late? With a little bit of luck, it’s still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Islamorada travel package include?
It comes down to what type of trip you’re planning. Islamorada travel deals can include hotels, car rentals and flights. You can mix and match to create the bundle that works for you! You can also add on experiences and activities after you’ve booked to score even bigger discounts.
What should I know before booking an Islamorada travel package?
Bundling your bookings into an Islamorada holiday package is the most convenient way to organise your trip. Not only that, you’ll save big just for combining your flights, hotels and car rentals. Once you’ve booked, why not add on an activity or a tour?
Can I choose my airline with an Islamorada Expedia holiday package?
Yes, you can. We have more than 550 airline partners across the globe, so fly with the carrier that matches your travel preferences.
If I'm not able to travel, can I cancel my Islamorada holiday package?
Plans can change suddenly, so yes, you can. You may be able to cancel or change your Islamorada holiday package for free within 24 hours of booking. For bookings older than that, you can still cancel or make changes, but your car rental company, hotel or airline may charge additional fees. Want more information? Look up our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.

Discover the most popular places to visit in Islamorada

Image for Theater of the Sea

Theater of the Sea

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

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

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

What to do in Islamorada

Image for Salty Keys Snorkel and Sandbar Activity

Salty Keys Snorkel and Sandbar Activity

NZ$260
Per adult
Salty Keys Snorkel and Sandbar Activity
Image for Half Day Private Boat Tour

Half Day Private Boat Tour

NZ$1,460
Per adult
Half Day Private Boat Tour
Image for Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours

Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours

NZ$608
Per adult
Islamorada Snorkel / Sandbar / Sunset / Fishing Charters & Tours
See all activities in Islamorada

More holiday ideas

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