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Buying a Vacation Rental Property in the Florida Keys: What to Know About Regulations
If you’ve been dreaming of owning a piece of paradise in the Florida Keys, chances are you’ve also thought about renting it out as a vacation rental when you’re not using it. After all, what could be better than a home that not only pays for itself but also welcomes you back to the island lifestyle whenever you want?
Before you start counting rental income, it’s important to understand how vacation rentals work in the Keys. Regulations, location, and property features all play a huge role in whether your home will be a successful rental—or sit empty waiting for guests.
Not All Properties Make Good Vacation Rentals
One of the first questions buyers often ask me is: “How much can I make by renting this home out?”
Here’s the reality: not every property in the Keys is a strong vacation rental.
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Dry lot homes (those not on the water) are typically harder to rent. Visitors come to the Keys for fishing, boating, and waterfront views, so they naturally gravitate toward properties with water access.
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Homes directly on the open water or on a canal with quick access to the ocean or bay are in much higher demand.
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A swimming pool is another must-have for most renters. After a day on the water, vacationers love having a pool to relax by.
Understanding Rental Regulations
Vacation rental rules vary by community, so it’s essential to know what applies to the property you’re considering.
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Most single-family neighborhoods in the Keys have a 28-day minimum rental period. This means you can’t simply rent your home out by the week (with one big exception below).
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Marathon is the exception to the rule. The City of Marathon has a much more relaxed approach, allowing shorter-term rentals. That’s why Marathon is such a hotspot for investors looking to maximize vacation rental income.
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Neighborhood and HOA rules may also restrict rentals. Some subdivisions don’t allow them at all, while others may have specific requirements.
What This Means for Buyers
If your goal is to generate rental income, focus on homes that:
✅ Are on the water (open water or quick canal access)
✅ Include a pool
✅ Fall within an area or municipality that allows short-term rentals (like Marathon)
✅ Don’t have restrictive HOA rules against vacation rentals
The good news is, once you find the right property, demand is strong! The Florida Keys remain one of the most desirable vacation destinations in the U.S., and renters are willing to pay top dollar for the right home.
Final Thoughts
Buying a home in the Keys can be both a lifestyle choice and an investment. The key (no pun intended!) is knowing the local rules and choosing a property that truly appeals to vacationers. With the right property and the right location, you can enjoy your own slice of paradise—and let it work for you when you’re not here.
Buying in the Florida Keys: Which Island Fits Your Lifestyle Best?
Buying a home in the Florida Keys isn’t just about the house. It’s about finding the island that matches your way of life. Each Key has its own personality, pace, and quirks. Let’s explore a few favorites so you can picture yourself living the dream.
Key Largo: The Commuter’s Paradise
Key Largo is the northernmost island, which makes it the easiest to reach from the mainland. Many people commute to Miami or Fort Lauderdale from here, yet still enjoy a laid-back island feel at the end of the day. If you want quick access to big-city amenities while still living in the Keys, Key Largo is your spot.
Tavernier: A Hidden Gem With Its Own Airstrip
Just south of Key Largo is Tavernier, a quieter community with a close-knit feel. It’s home to Tavernaero, a neighborhood with its own private airstrip — one of just a small handful in the entire island chain. For those who fly, it offers an incredible convenience that’s rare in the Keys.
Islamorada: The Fishing Capital
Islamorada is all about the water. Known worldwide as the “Sportfishing Capital of the World,” this Key draws serious anglers and anyone who loves boating. The island also has a lively arts and food scene, which makes it a great mix of fun, flavor, and fishing.
Marathon: Family-Friendly and Central
Right in the middle of the Keys, Marathon is known for being family-friendly. It has schools, shopping, and a community feel that’s a bit more year-round than tourist-heavy. It’s also a short drive to the famous Seven Mile Bridge, which connects the Middle Keys to the Lower Keys.
Big Pine Key: Nature’s Playground
Big Pine has a totally different vibe. It’s quiet, peaceful, and famous for the tiny and protected Key Deer that roam the neighborhoods. Nature lovers enjoy the National Key Deer Refuge, the freshwater Blue Hole, and the rustic feel of No Name Key just over the bridge. If you dream of living close to nature, Big Pine is your place.
Summerland Key: For Pilots and Boaters
Farther south, Summerland Key is a hidden gem. Not only does it have deep-water canals that attract serious boaters, but it also has its own private airstrip — one of the only others in the Keys besides Tavernaero. If you fly in and out often, Summerland gives you a lifestyle few places in the world can match.
Key West: Anything Goes
At the end of the road lies Key West. Colorful, historic, and known for its “anything goes” vibe, Key West is unlike anywhere else. Whether you love live music, art, or nightlife, there’s always something happening. But don’t forget, Key West also has quiet residential neighborhoods tucked away from the party scene.
Finding Your Key
Each island has its own heartbeat. The right Key for you depends on what you love most: fishing, nature, nightlife, flying, or family life. That’s why working with someone who knows the islands inside and out is so important.
If you’re ready to find your perfect fit in the Keys, let’s talk about your lifestyle and match you with the island that feels like home.
Florida Keys Market Update: What’s Selling?
No market update would be complete without looking at what’s closing across the Keys. Last week, 38 properties sold from Key Largo to Key West, showing just how active our market continues to be.
Here are the highlights:
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Average sold price: $1,348,632
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Average days on market: 114
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Average list-to-sale price ratio: 94%
At the top end, a Plantation Key oceanfront estate closed at $6,500,000. On the more affordable side, a camper with a deeded campsite in Key Largo sold for $330,000.
What does this mean for buyers and sellers?
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Buyers can see the Keys offer both luxury estates and more modest getaways.
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Sellers can take confidence in strong demand, with properties selling close to their asking price.
From multi-million-dollar homes to practical retreats, the Florida Keys continues to offer something for everyone.
Want to see all the details? 👉 Click here to view last week’s sold properties
Monday Market Update – Florida Keys New Listings
This past week, 44 new listings came on the market in the Keys. That’s a bit slower than earlier this summer, but there are still plenty of great options. Buyers can choose from waterfront homes, condos, dry lots, and vacant land. No matter what you’re looking for, there’s something out there.
✨ Spotlight Listing – Waterfront Paradise in Plantation Key
Welcome to Plantation Key, where this home makes the most of Florida Keys living. Step through the electric gate and into a tropical retreat.
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Outdoor Living: Enjoy a newer pool, a hot tub surrounded by lush greenery, and a large covered entertaining area with canal views. The dock has a boat lift, a private ramp, and a floating dock for a skiff, kayaks, or paddleboards. There’s also an outdoor shower and storage for your gear. With direct bay access and quick Atlantic access, it’s a true boater’s dream.
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Upstairs Living: The open-concept space has two bedrooms and one bath. The remodeled kitchen features a gas stove, stainless appliances, and a glass backsplash. The home also has updated plumbing, electric, A/C, and a newer roof. Warm wood ceilings and a big teak deck make it perfect for relaxing or dining outdoors.
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Guest Space: Downstairs you’ll find a separate one-bedroom, one-bath apartment. It’s ideal for guests, family, or in-laws.
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Extras: A spacious garage and workshop give you plenty of room for tools and toys.
This property comes fully furnished and ready for you to enjoy. A fantastic waterfront package at a great value—come see it for yourself!
Click here to see the full list of new properties
Living Aboard in the Florida Keys: Your Floating Paradise Awaits
Not everyone dreams of a white picket fence.
Some people dream of a gently rocking deck, the smell of salt air, and waking up to the sound of seagulls instead of an alarm clock.
In the Florida Keys, that dream is more than possible — it’s a real way to live.
Welcome to the liveaboard lifestyle.
Why Some People Trade Houses for Hulls
Living aboard your boat isn’t just for weekend sailors.
It’s a lifestyle choice that attracts retirees, remote workers, and adventure seekers.
Here’s why:
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It can be more affordable than a waterfront home. A slip fee is often less than a mortgage.
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No yard work. Your “lawn” is the ocean.
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Freedom to move. If you don’t like the view, change it.
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Built-in community. Marina neighbors often become friends for life.
For many, it’s not about saving money — it’s about living closer to the water, every single day.
How It Works
A liveaboard marina is a marina that allows you to stay on your boat full-time or for long periods.
Some slips are rented, while others are owned like a condo.
Marinas usually offer:
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Restrooms and showers
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Laundry rooms
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Wi-Fi
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Parking
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Social spaces and events
Rules vary from marina to marina. Some allow year-round living, while others limit the number of liveaboard slips to keep a balance between transient boaters and residents.
Why the Keys Are Perfect for Liveaboards
The Florida Keys offer year-round boating weather and some of the best access to coral reefs, sandbars, and fishing in the U.S.
From Key Largo to Key West, marinas cater to different lifestyles:
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Quiet and secluded — perfect for those who want privacy.
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Bustling and social — for people who love events, happy hours, and dockside chatter.
Many buyers see living aboard as a stepping stone.
It’s a great way to enjoy the Keys now while deciding if (or where) to buy a traditional home later.
Is It Right for You?
The liveaboard life isn’t for everyone.
Here’s how to tell if it might be for you:
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You like small, cozy spaces.
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You don’t mind boat maintenance.
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You love being outdoors and close to nature.
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You’re okay with occasional visits from curious pelicans.
Your Floating Home Is Waiting
Whether you’re looking to downsize, try a new adventure, or ease into Keys living before buying property, living aboard could be your ticket to paradise.
If you’re curious about marina slips, boat-friendly neighborhoods, or even the best way to transition to island life, I can help.
Let’s find you a place where the sun sets over your own bow every evening.
Click here to see a list of liveaboard boat slips available in the Keys
Dock Talk: Choosing the Right Waterfront for Your Florida Keys Lifestyle
In the Florida Keys, a dock isn’t just a place to park your boat — it’s the launch pad to your lifestyle. Whether you’re chasing mahi in the Atlantic, watching the sunset over the bay, or sipping coffee while the water ripples in your backyard, the view from your dock can define your days. But here’s something many newcomers don’t realize: the majority of waterfront homes here are on canals — and not all canals are created equal. Some give you a quick hop to open water, while others make you meander through a maze before you get there.
Ocean Side Living
When your dock is on the ocean side, you’re just minutes away from the Atlantic. It’s a straight shot to deep blue water, making it perfect for offshore fishing, diving, or heading to your favorite sandbar.
The ocean side is a boater’s paradise, but it can be more exposed to waves and wind. That means a little more boat prep — and sometimes higher seawall maintenance — but the reward is quick access to endless adventure.
Bay Side Living
Bay side docks give you calmer, often shallower waters on the Gulf side of the Keys. It’s an ideal setup if you love kayaking, paddleboarding, or cruising to waterfront restaurants without the chop of the open ocean.
From the bay, you can still reach the Atlantic — you’ll just pass under or through one of the bridges that connect the islands. That leads us to one very important point…
Why Bridge Access (and Canal Layout) Matters
Whether you’re on the ocean side or bay side, your boating time depends on how your canal is laid out.
Some homes are right on a main canal, meaning you can be in open water in minutes. Others are tucked deep in a canal system, where you’ll weave through smaller canals before reaching a main channel. Add in bridge or cut-through clearance limits, and your trip could be longer — or restricted at certain tides.
If quick access matters to you, look for a home that’s close to a main canal and near a bridge or cut that fits your boat. It can save you time, fuel, and frustration.
Plugged Canals: Peace Without Passage
Not every waterfront home in the Keys has direct boating access. Plugged canals are closed off from open water, creating a calm, mirror-like surface that’s perfect for those who want the water view without boat traffic.
These spots are quiet, scenic, and still let you enjoy the benefits of living right on the water — just without the maintenance and insurance costs that can come with having a boat lift or open water access.
The Bottom Line
When it comes to docks in the Florida Keys, the “best” setup depends on your lifestyle. If you live for offshore fishing, ocean side may be your match. If you prefer calm cruising and waterfront dining, bay side could be perfect. If you want peaceful views without boating, a plugged canal might be just right. And remember — the closer your home is to a main canal and a bridge, the faster you’ll get to open water.
Closing:
In the Keys, your dock isn’t just part of your home — it’s the gateway to your adventures. Whether you’re chasing fish, chasing sunsets, or chasing a little peace and quiet, there’s a perfect waterfront spot waiting for you. When you’re ready to find it, I’m here to help you dock your dreams right where they belong.
Discover Indigo Reef: Marathon’s Waterfront Gem
Indigo Reef is a beautiful, gated community on the Gulf of Mexico. It sits on more than 10 acres of private land, just minutes from the heart of Marathon. Here, you can enjoy the best of both worlds — close to shops, restaurants, and attractions, yet quiet and tucked away from the busy streets.
Room to Relax
The community feels like a private retreat. Lush landscaping, wide open spaces, and peaceful water views set the tone. You can walk the grounds, breathe in the salty air, and feel the stress melt away.
Amenities You’ll Love
Indigo Reef makes life easy and enjoyable with features designed for comfort:
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Heated Resort-Style Pool – Spacious, sparkling, and surrounded by cushioned lounge chairs for ultimate relaxation.
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Professional-Grade Fitness Center – Fully equipped so you can stay active without leaving the community.
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Kayak Storage – Easy access to explore the calm Gulf waters at your leisure.
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Ice Machine – Perfect for keeping your coolers ready for a day of fishing or boating.
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Temperature-Controlled Storage – Located in the HOA building, with plenty of room for bikes, fishing gear, and other essentials.
Close to Everything
When you’re ready for a night out, Marathon’s dining, shopping, and attractions are just a short drive away. Yet when you come home, you’re back in your quiet, private oasis.
A Place to Call Home
At Indigo Reef, neighbors quickly become friends. Days are filled with sunshine and sea breezes. Evenings end with stunning Gulf sunsets right outside your door. It’s not just a place to live — it’s a lifestyle.
8 Things You Won’t Find in a Florida Keys Neighborhood (and Why That’s Just Fine)
Life in the Florida Keys runs on island time. It’s warm, breezy, and just a little bit quirky. Our neighborhoods have charm to spare, but some things you see in most places are missing here — and we wouldn’t have it any other way.
1. Basements
The ground is too close to the water. Digging down would just make a saltwater swimming pool.
2. Big Grassy Lawns
The Keys are no friend to thick green grass. Sandy soil, salty air, and hot sun make it tough. Most people go for palms, gravel, or native plants.
3. Sidewalks on Every Street
Many streets go right from driveway to road. It’s part of the laid-back style — but keep an eye out for iguanas.
4. Fire Hydrants Everywhere
They’re not on every corner here. Many neighborhoods rely on other water sources, so hydrants can be far apart.
5. Bright Streetlights
The Keys like their night sky dark. Streetlights can be few, so the stars shine bright.
6. Garage Doors Facing the Street
Homes are often built on stilts. Instead of garages, you’ll see open carports under the house.
7. Tall Backyard Fences
The breeze is too good to block — and hurricanes can take tall fences down.
8. Neighborhood Watch Signs with Trench-Coated Figures
The “watchers” here are more likely to be herons peeking in your yard.
Bottom line? The Florida Keys skip some of the “usual” neighborhood features, but they give you sea views, salty breezes, and a style all their own.
Florida Keys Weekly Real Estate Update – New Listings
Good morning, Keys lovers! ☀️ It’s Monday morning, which means it’s time for your weekly look at the newest listings across the Florida Keys.
This week’s fresh finds range from a $395,000 condo at Plantation By The Sea in Tavernier to a spectacular $28,800,000 oceanfront estate in Islamorada.
🏡 Spotlight Listing – Tavernier, FL – $685,000
Charming 2 Bed, 2 Bath Sheffield Steel Home in Plantation Key
Nestled in a desirable subdivision, this well-maintained home offers:
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Excellent curb appeal with lush tropical landscaping
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Open-concept layout with soaring Dade County Pine ceilings
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Abundant natural light throughout
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Open upstairs balcony—perfect for soaking in the Florida Keys lifestyle
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Spacious front yard with ample parking
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Large ground-level storage room
Conveniently close to top-rated schools, shopping, restaurants, and the hospital, this home is ideal as a full-time residence or an investment opportunity.
📍 Location: Tavernier, FL
💲 Price: $685,000
📞 Contact me for details or to schedule a private showing.
Monday Market Buzz: New Listings in the Florida Keys!
Happy Monday, friends! You know what that means… it’s time to peek at the newest homes to hit the market in our island paradise. Whether you’re dreaming of a cozy hideaway or an oceanfront masterpiece, this week’s listings prove there’s truly something for every budget here in the Keys.
Let’s start small (but full of potential!):
🏝 1-Bedroom, 1-Bath Condo – Priced at just $290,000, this condo is ready for a makeover. Think of it as your blank canvas for island living. A little paint, a little love, and boom—your own Keys getaway.
And on the other end of the spectrum…
✨ Oceanfront Luxury Estate – Priced at $20,995,000, this home isn’t just on the ocean—it practically owns the view. From sparkling sunrise mornings to breezy sunset evenings, it’s the definition of living the dream.
In between those two extremes? Oh yes—plenty! We’ve got charming conch cottages, modern canal homes, and waterfront retreats with boat docks just waiting for their new owners.
So whether you’ve got $300K or $20M to spend, there’s a little slice of paradise here with your name on it. The only question is… which Keys lifestyle do you want to live?
🏡 Ready to explore? Let’s chat—I’ll help you find your perfect match. Click here to see the new listings
