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Check prices for these dates

In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Top Holiday Rentals in Islamorada

Our top choices for Islamorada holiday rentals

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

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (102)
"Unique House boat experience, friendly staff. "
The price is 2.371.982 ₫
6.375.074 ₫ total
includes taxes & fees
17 Sept - 18 Sept
Treasure Harbor
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (513)
"Best kept secret, love staying here,!"
The price is 2.032.390 ₫
3.656.453 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is 14.496.900 ₫
17.762.129 ₫ total
includes taxes & fees
6 Sept - 7 Sept
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

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Morning breakfast was great. Staff was very attentive and pleasant. Room view was amazing. Very convenient for a person in our party that is disabled. "
James 2-night trip
Posted 2 days ago
Chesapeake Beach Resort

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 575 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 Islamorada County Park and Anne's Beach, or simply take in cultural attractions like History of Diving Museum and MoradaWay Arts & Cultural District. Other places in town to visit include Bud n' Mary's Dive Center and Fiesta Key.

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.