Book Holiday Homes in Islamorada
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Featured Holiday Homes in Islamorada

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Villa Largo Island Retreat

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

Beautifully remodeled Townhome in the Florida Keys

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Charming Home in Key Largo
Islamorada Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Islamorada vacation homes are the perfect way for you to wing it.
Holiday houses in Islamorada let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Islamorada in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Islamorada adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Islamorada with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Islamorada vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Islamorada Holiday Homes essential information
Accommodation | 687 Holiday Homes |
---|---|
Lowest Price | AU$693 |
Highest Price | AU$812 |
Popular accommodation | Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball, Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Villa Largo Island Retreat, WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!, Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly, New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities, Beautifully remodeled Townhome in the Florida Keys, Completely Remodeled 3/3 in the heart of Key Largo (Oceanside), Charming Home in Key Largo |
Holiday Homes in Islamorada
Top Locations for Holiday Homes in Islamorada
Top trending hotels in Islamorada

Cheeca Lodge & Spa

Islander Resort

Amara Cay Resort

Chesapeake Beach Resort
More ways to explore Islamorada
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.