1449+ Private Villas and Holiday Rentals in Islamorada |
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Islamorada Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Islamorada

Discover more than 1449 vacation rentals available in Islamorada. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Islamorada.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Islamorada, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Islamorada. On average, places to stay near Islamorada offer 828.48 ft², with nightly prices averaging GB £531.

With Casai, finding and comparing holiday rentals in Islamorada is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Islamorada

Type Count
Vacation Homes 919
Villas 117
Holiday Apartments 105
Cottages 9

Use these Quick Filters to Find a Holiday Rental in Islamorada

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Islamorada.

Weather in Islamorada, FL

View the weather forecast for Islamorada before booking your Islamorada Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 56°F
March - May
High 87°F       Low 59°F
June - August
High 91°F       Low 74°F
September - November
High 90°F       Low 64°F

Top Attractions Around Islamorada, FL

Casai offers a large selection of top attractions around Islamorada . Research things to do on your vacation before you visit Islamorada.


Theater of the Sea
Bud n' Mary's Dive Center
Founders Park
Islamorada County Park
Hurricane Monument
Windley Key Fossil Reef Geological State Park
History of Diving Museum
Matecumbe United Methodist Church
Florida Keys Brewing Co.
John Pennekamp Coral Reef State Park
Jimmy Johnson's Big Chill
Dolphin Research Center
Key Largo Undersea Park
Dolphins Plus Bayside
Florida Keys Visitor Center
Dolphin Cove
Anne's Beach
Caribbean Club Bar
Dolphins Plus
Harry Harris Park

Other Places to Stay in Islamorada, FL


History of Diving Museum 811 Properties
Upper Matecumbe Key 784 Properties
Seabreeze Trailer Park 740 Properties
Theater of the Sea 738 Properties
Windley Key Fossil Reef Geological State Park 726 Properties
Plantation by the Sea 688 Properties
Islamorada County Park 650 Properties
Coral Cove 542 Properties
White Marlin Beach 347 Properties
Toll Gate Shores 335 Properties
Venetian Shores 43 Properties
Lower Matecumbe Beach 24 Properties

Frequently Asked Questions About Islamorada?

What are the top holiday rentals in Islamorada?

With numerous options available in Islamorada, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Islamorada:

How many holiday rentals have private pools in Islamorada?

Discover a selection of holiday rentals with private pools near Islamorada with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Islamorada are best for families?

If you're searching for a family-friendly holiday home in Islamorada, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Islamorada:

How many Casai.uk holiday rentals are available in Islamorada?

As of 2025, Casai boasts over 1449 properties listed in the Islamorada area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Islamorada.

Nearby Neighborhood (9) 
Neighborhood Property Count
Venetian Shores Vacation Rentals in Islamorada, Florida 43
Lower Matecumbe Beach Vacation Rentals in Islamorada, Florida 24
White Marlin Beach Vacation Rentals in Islamorada, Florida 347
Toll Gate Shores Vacation Rentals in Islamorada, Florida 335
Plantation by the Sea Vacation Rentals in Islamorada, Florida 688
Seabreeze Trailer Park Vacation Rentals in Islamorada, Florida 740
Coral Cove Vacation Rentals in Islamorada, Florida 542
Plantation Lake Estates Vacation Rentals in Islamorada, Florida 647
Bonefish Bay Vacation Rentals in Islamorada, Florida 350

People Also Ask

There are 1449 Islamorada, FL Holiday Rentals

Recently Booked Holiday Rentals in Islamorada