If you’re dreaming of owning a piece of paradise but aren’t quite ready for the maintenance of a single-family home, waterfront condos in Islamorada are one of the smartest ways to live the Florida Keys lifestyle- dockage, sunsets, and all.
As a third-generation real estate broker born and raised here in the Keys, I’ve walked every dock and toured just about every condo complex in town. Whether you’re relocating full-time, buying a vacation home, or looking for a flexible rental investment, here’s what to know—and where to look—when searching for Islamorada waterfront condos for sale.
Why Buy a Waterfront Condo in Islamorada?
Located in the heart of the Upper Keys, Islamorada offers some of the most sought-after boating, fishing, and dining experiences in all of Florida. You’ll get:
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Direct access to the Atlantic Ocean and Florida Bay
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Some of the best sportfishing and diving in the world
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A peaceful, small-town atmosphere with upscale flair
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Easy access to dining, art galleries, boutiques, and marinas
And with a waterfront condo, you enjoy it all without the maintenance of a house or the overhead of luxury estates. Many complexes even allow for short-term rentals, giving you the flexibility to generate income when you’re not using it.
Top Waterfront Condo Communities in Islamorada
Let’s break down a few of the most popular and well-appointed communities:
Beacon Reef
Right on the ocean in Upper Matecumbe, Beacon Reef offers:
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A private marina with dockage
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Heated oceanfront pool and hot tub
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Tiki huts and grills for waterfront gatherings
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Gated access with covered parking
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Strong rental demand for investors
It’s a great choice if you want both comfort and boating access.
Maison Residences
Maison is ultra-luxury condo living, with only a handful of elite units offering:
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Private elevators
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Expansive terraces
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Designer finishes and open ocean views
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Private beach access and heated pool
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Gated, boutique atmosphere with high-end touches throughout
Ideal for those looking for modern design + island luxury.
Port of Call
Located right off the bay side in Plantation Key, Port of Call features:
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Boat slips
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A quiet, residential feel
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Easy access to both schools and local restaurants
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Solid value for buyers seeking water access without breaking the bank
What to Consider When Shopping Waterfront Condos in Islamorada
Before falling in love with that water view, be sure to ask:
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Does the condo include dockage? Is it deeded or assigned?
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Are vacation rentals allowed? What are the minimum stay rules?
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What’s the monthly HOA? And what does it cover?
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What floor is the unit on? Are there elevators?
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Is it oceanfront, bayside, or canalfront? (Each has pros and cons depending on your lifestyle and boating needs)
Shane’s Tip: If boating is important to you, make sure the water access works for your boat. Not all “waterfront” condos offer easy navigation or deepwater canals. And don’t be shy—ask for a walkthrough of the dock, not just the unit.
Start Your Search for Islamorada Waterfront Condos for Sale
From Venetian Shores condos with direct Snake Creek access to boutique oceanfront properties in Lower Matecumbe, Islamorada offers something for every buyer.
📍 Browse Islamorada Waterfront Condo Listings
📞 Reach out to me to tour your favorites—by land or by water.
85960 Overseas Hwy Suite 4