Island Life in Islamorada
Islamorada, known as the “Sportfishing Capital of the World,” is one of the most sought-after communities in the Florida Keys. Whether you’re searching for a waterfront retreat, a vacation rental investment, or a forever home with island charm, Islamorada offers a unique mix of natural beauty, laid-back lifestyle, and strong real estate opportunities. At The Little Island Group, we specialize in helping buyers and sellers navigate the Islamorada real estate market with ease.
Islamorada Real Estate & Homes for Sale
Why Buy in Islamorada
Living in Islamorada is about more than owning property — it’s about embracing the Keys lifestyle. Homeowners enjoy:
Waterfront living with ocean or bay access and private docks.
Outdoor lifestyle built around boating, diving, snorkeling, and water sports.
Small-town charm with art galleries, boutique shops, and locally owned restaurants.
High-demand rental market that provides strong investment returns for vacation homeowners.
Additional insight: Islamorada is particularly appealing to buyers who want easy access to the mainland (90 minutes from Miami) while still experiencing island living. This balance makes it a popular choice for both full-time residents and second-home buyers.
📍 Islamorada Neighborhoods & Communities
The heart of Islamorada, Upper Matecumbe offers walkable streets filled with art galleries, shops, restaurants, and a lively community vibe. Homes here range from quaint cottages to upscale waterfront properties.
Known for privacy and expansive waterfront estates, Lower Matecumbe is quieter and more residential. Many homes feature deep-water access for larger boats, making it popular with serious anglers.
Plantation Key is family-friendly, offering schools, marinas, and convenient mainland access. Buyers will find a mix of single-family homes, condos, and canal-front properties.
Windley Key is home to natural parks, diving attractions, and a slower pace of life. It appeals to buyers looking for affordable entry points into Islamorada with access to outdoor activities.
Upper matecumbe key
Lower matecumbe key
Plantation key
Windley Key
🌴 Lifestyle in Islamorada
Residents of Islamorada enjoy a lifestyle centered around the water and community:
Fishing & Boating 🎣: World-class deep-sea and backcountry fishing attract anglers from around the globe.
Beaches & Parks 🏝: Popular spots include Anne’s Beach, Founders Park, and Indian Key Historic State Park.
Dining 🍴: From fresh-catch seafood shacks to upscale waterfront dining, Islamorada is a foodie’s paradise.
Community 🎶: Art walks, music festivals, and fishing tournaments create a year-round calendar of events.
Extra detail: Islamorada also has a strong conservation culture, with organizations working to protect coral reefs and marine life. This appeals to eco-minded buyers and adds long-term value to the community.
📊 Islamorada Real Estate Market Insights
The Islamorada real estate market continues to see strong demand:
Median home prices remain among the highest in the Keys due to limited supply and high demand.
Vacation rentals generate excellent returns, with year-round tourism driving consistent occupancy.
Property types include single-family homes, condos, waterfront estates, and investment-friendly vacation properties.
Considerations: Flood zones, hurricane insurance, and rental licensing are important factors buyers must evaluate — and where expert guidance is essential.
Ready to explore available listings? Browse our Islamorada Homes for Sale
🙋 Work with The Island Collective Realty
Buying or selling in Islamorada requires local knowledge. Our team understands everything from flood zones and insurance requirements to investment potential and rental regulations. Whether you’re relocating full-time, searching for a vacation property, or selling your home, we’ll guide you every step of the way.
📞 Contact Us- today to start your Islamorada real estate journey.
❓ FAQs About Islamorada Real Estate
Yes. Islamorada is one of the strongest vacation rental markets in the Keys. Homes with rental licenses and waterfront access often achieve top occupancy rates.
Islamorada is about 90 minutes from Miami, making it convenient for weekend getaways and easy access to major airports.
Absolutely. Many Islamorada properties offer direct ocean or bay access with private docks for boating and fishing.
Islamorada is quieter than Key West while offering more dining and entertainment options than Marathon. It’s the perfect balance for buyers who want activity without the bustle of downtown Key West.
Is Islamorada a good place to buy a vacation home?
How far is Islamorada from Miami?
Are there waterfront homes with private docks in Islamorada?
What makes Islamorada different from Key West or Marathon?
You're in the right place.
It's no mystery that we are in our own little island bubble down here in the Florida Keys. From island time to island life, we do things a bit differently. But, if you get it you get it and when you're ready we're here to help. Whether buying your own piece of paradise, selling some Keys real estate, restoring a historic property, or renting out your home as a vacation rental, we'd love to chat with you. Ready to make some real estate moves down here in the islands?
Owning a piece of the Florida Keys means owning a slice of paradise. The process of buying, selling, renovating, and renting on the island can come with challenges so we are here to help.
"What made me happiest is that Stephanie was ON it. I thought I was diligent about combing through listings. But, she was always a step ahead of me. In the past, we've attempted to make progress in moving to the island. But we were not able to get the traction that we needed to strike while the iron was hot. Without Stephanie, I would still be shivering up north."
is always of the essence
Time
"Stephanie and Greg treated us like we were not just clients, but old friends. They answered panicked emails and texts with a sweet sense of humor."
the secret sauce
levity
real results
Buying your perfect piece of paradise is such an exciting time. We are here to help make the process as fruitful, fun, and easy as possible.
Buying
Renting your property can be challenging. Our team is here to do the heavy lifting so you can enjoy the cash and skip the headaches.
VACATION RENTAL MANAGEMENT
When it's time to embark on your next adventure, we're here to help get your house sold. Our consultative process keeps you feeling supported from start to finish!
Selling
Ways to Work Together
“Key West? That's not a place it's a dream.”
— anonymous
Buying in the Florida Keys
From waterfront estates in Islamorada to historic Old Town Key West cottages, we guide buyers through every step of the process. Our team offers local insight, market strategy, and personalized tours to help you discover not just a property, but your perfect island home.
Owning a piece of the Florida Keys is a dream you're ready to realize. Say no more!
A GOOD FIT FOR YOU IF:
You're ready to own a little slice of paradise but you're a little overwhelmed and not sure where to start. The islands are calling but you aren't quite sure how to answer!
You want the vacation rental revenues but not the vacation rental headaches. Oh! And proactive, customized marketing for your property would be swell.
A GOOD FIT FOR YOU IF:
Yes, we take care of your property like it is our own. Yes, we represent it on the usual online rental platforms. Here's our real difference: Our social media reach is millions. We have a large devoted following who look to us for recommendations on where to stay on the island. We actively and innovatively promote your property to increase occupancy and thus revenue.
Rental Management in Key West
Your vacation rental can be a blessing and a headache. Keep the cash leave the headaches to us.
We're about as low-pressure as they come, but we'd love to chat when you're ready.
Ready to Talk About Working Together?
lets do this.