A beach with white lounge chairs, a covered pavilion, and palm trees.

Search Holiday Rentals in Islamorada

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Islamorada holiday rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (735 reviews)
"Good location"
United States
Orlando
The price is 2.384.833 ₫
4.034.788 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Breezy Palms Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

2. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (172 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
The price is 3.497.060 ₫
7.601.411 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Treasure Harbor
A beachside lounge with wooden lounge chairs and blue umbrellas, overlooking a calm sea and docked boats.

3. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
The price is 6.621.987 ₫
7.449.964 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Island Bay Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islamorada Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"we loved it !!!"
Ilyan 2-night trip
Posted 5 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Frequently asked questions

Can I find a holiday rental in Islamorada?

Yes, there are holiday rentals in Islamorada close to MoradaWay Arts & Cultural District, 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 403 Expedia holiday rentals, you're guaranteed to find just the right place for your Islamorada stay.

What can I see and do in Islamorada?

Islamorada County Park and Founders Park are a couple of scenic spots to enjoy the outdoors, whereas History of Diving Museum is one of the cultural attractions. Other places in town to visit include Bud n' Mary's Dive Center and Robbie’s of Islamorada.

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.