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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Islamorada holiday rentals

25-inch flat-screen TV with digital channels, TV

Houseboat in Islamorada

Treasure Harbor
3.0 star property
9.0 out of 10, Wonderful, (124 reviews)
"Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !"
United States
Nick
Treasure Harbor
Exterior

Aparthotel in Matecumbe

Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (614 reviews)
"Friendly staff, beautiful peaceful beach, great room with a big comfy bed and all that you might need. "
United States
Alexander
The price is ฿5,562
฿7,878 total
includes taxes & fees
1 Feb - 2 Feb
Breezy Palms Resort
On the beach, sun-loungers, beach umbrellas, beach towels

Villa in Matecumbe

The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (70 reviews)
"Amazing stay, can’t wait to stay there again!"
United States
Anonymous traveller
The price is ฿19,033
฿23,135 total
includes taxes & fees
22 Jan - 23 Jan
The Islands of 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.
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Top Islamorada Hotel Reviews

Breezy Palms Resort

Breezy Palms Resort

10/10 Excellent
"Very clean and updated rooms as seen in the pictures. It is not a resort type of place with a lot of amenities. It is an old school type of Hotel from the keys as I call it, but it is all well kept we stayed in a room that has a kitchen and it was well stocked with a good size refrigerator and it was very roomy with more than plenty of storage space for your belongings it is a good area as long as you have some sort of transportation in my opinion it is towards the south end of Islamorada, which means you are about 3 to 5 miles away from where a lot of the restaurants and shops and boutiques and shopping is but there are restaurants scattered all through that area. There’s a couple that you could walk to from the hotel and even a breakfast café place that you can walk to, which is within less than a 10 mile walk. Would recommend this place and I would stay again."
Anneris 3-night trip
Posted 1 day ago
Breezy Palms Resort

Find out more about Islamorada

Search for holiday rentals in Islamorada on Expedia! You can easily find your home rentals, villas, holiday apartments in Islamorada using one of the methods below:

  • View our selection of featured holiday rentals in Islamorada
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  • Enter your travel dates to view the best deals on holiday rentals in Islamorada while they last

Look no further and take a look at our great range of rental properties in Islamorada!

Frequently asked questions

Can I find a holiday rental in Islamorada?

Yes, there are holiday rentals close to the most popular sights in Islamorada, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Islamorada like the scenic seaside and entertainment choices this destination is known for. While you're here, grab a bite or have a drink at the seafood restaurants.

How many holiday rentals are there in Islamorada?

With 478 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Enjoy the outdoors at Everglades National Park and Founders Park, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Florida Keys Brewing Co. and Bud n' Mary's Dive Center.

What’s a holiday rental in Islamorada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islamorada. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.