There’s something about the Florida Keys that always pulls me back in. Maybe it’s the soft ocean breeze that never seems to stop, or the way time slows down the moment you cross that first bridge.
Every time I plan a Keys getaway, I find myself obsessing over one thing more than anything else where I’m going to stay. Because in a place this magical, your Airbnb shouldn’t just be a place to sleep… it should be part of the experience.
I’ve stayed in the Keys enough times (and spent way too many late nights scrolling listings) to know that the right Airbnb can completely transform your trip.
Think sunrise coffee on a private dock, outdoor showers under palm trees, ocean views from your bed, and cozy coastal interiors that make you never want to leave.
So if you’re dreaming of a Florida Keys escape and want a stay that feels special, memorable, and totally worth it, these are 10 dreamy Airbnbs in the Florida Keys you truly can’t miss.
1. Overwater Bungalow-Style Retreat – Key Largo
If you’ve ever dreamed of staying in an overwater bungalow without flying halfway across the world, this Key Largo Airbnb is about as close as it gets in the U.S.
This stunning waterfront stay sits directly over clear, shallow water, with a private deck where you can literally watch fish swim beneath your feet.
Inside, it’s bright, airy, and coastal-chic white walls, soft blues, natural wood accents, and floor-to-ceiling windows that bring the outside in.
Why it’s dreamy:
- Direct water access for kayaking and paddleboarding
- Private deck perfect for sunrise coffee or sunset wine
- Peaceful, romantic atmosphere ideal for couples
Good to know:
This is best for couples or solo travelers looking for a quiet escape. It’s close to Key Largo’s best snorkeling spots, making it perfect if you love being on the water.
2. Tropical Canal-Front Cottage – Islamorada
Islamorada has a way of feeling both laid-back and luxurious, and this canal-front cottage fits that vibe perfectly.
This Airbnb feels like your own private tropical hideaway. Think pastel exterior, swaying palm trees, and a backyard dock where boats gently float by.
Inside, it’s cozy yet stylish beachy décor, comfortable furnishings, and thoughtful touches that make it feel like a real home.
Why it’s dreamy:
- Canal views with easy boating access
- Outdoor patio for evening dinners
- Walkable or short drive to local cafes and beaches
Good to know:
If you’re traveling as a couple or small family, this is an amazing middle-Keys base. Islamorada is known for great food, sunsets, and a slightly more relaxed pace.
3. Luxury Waterfront Villa with Infinity Pool – Marathon
This is one of those Airbnbs that makes you stop scrolling and say, “Okay… wow.”
Located in Marathon, this luxury villa offers uninterrupted ocean views, a private infinity pool, and expansive outdoor living space. It’s perfect if you want that upscale, resort-style feel but still want the privacy of a home.
Why it’s dreamy:
- Infinity pool overlooking the ocean
- Spacious layout ideal for groups or families
- High-end finishes and modern coastal design
Good to know:
This is a higher-end stay, but if you’re celebrating something special a birthday, anniversary, or girls’ getaway it’s absolutely worth it.
4. Colorful Conch-Style Home – Key West
Key West has its own personality, and staying in a traditional Conch-style home lets you experience it fully.
This Airbnb is full of charm, with a colorful exterior, wooden shutters, and a shaded porch that feels straight out of a postcard. Inside, you’ll find bright, cheerful décor, local artwork, and an easy, breezy layout.
Why it’s dreamy:
- Classic Key West architecture
- Central location near Duval Street
- Private outdoor seating area
Good to know:
If you want to walk or bike everywhere and soak up Key West’s lively energy, this is a perfect pick. You’re close to restaurants, bars, and historic sites.
5. Oceanfront Tiny Home – Big Pine Key
I have a soft spot for tiny homes, especially when they’re done right — and this one absolutely is.
Perched right along the water, this tiny home proves that small spaces can still feel luxurious. It’s thoughtfully designed with smart storage, a cozy sleeping loft, and a deck that feels bigger than the home itself.
Why it’s dreamy:
- Direct ocean views from the deck
- Minimalist, peaceful atmosphere
- Perfect for digital detoxing
Good to know:
This stay is best for travelers who value experience over space. Big Pine Key is quieter and less touristy, making it ideal if you crave solitude.
6. Boho-Chic Beach Bungalow – Islamorada
This boho-inspired bungalow is warm, inviting, and full of personality. From macramé accents to soft linen bedding, everything about this Airbnb feels intentional and calming.
The outdoor space is just as special, with string lights, tropical plants, and a seating area that practically begs for long, slow evenings.
Why it’s dreamy:
- Instagram-worthy interiors
- Cozy outdoor lounging space
- Short distance to beaches and shops
Good to know:
This is a great option for couples or friends who love stylish spaces and want a relaxed but polished vibe.
7. Private Island-Feel Home – Summerland Key
If privacy is your top priority, this Airbnb feels like your own mini island escape.
Surrounded by water and lush greenery, this home offers a true sense of seclusion. You’ll find spacious interiors, large windows, and outdoor areas that let you fully enjoy the natural surroundings.
Why it’s dreamy:
- Secluded, peaceful location
- Excellent for nature lovers
- Stunning sunsets
Good to know:
You’ll want a car here, as restaurants and shops are a short drive away. It’s perfect for travelers who want quiet evenings and slow mornings.
8. Sunset-Facing Houseboat – Key Largo
Staying on a houseboat in the Keys is a completely different experience — and one I highly recommend at least once.
This floating Airbnb offers unbeatable sunset views, gentle water movement that lulls you to sleep, and a truly unique perspective of the Keys lifestyle.
Why it’s dreamy:
- One-of-a-kind stay
- Incredible sunset views
- Romantic and adventurous
Good to know:
Houseboats are compact, so pack light. This is ideal for couples who want something memorable and different.
9. Modern Coastal Duplex with Private Pool – Marathon
This modern coastal duplex combines style, comfort, and functionality — making it perfect for longer stays.
Each unit has its own entrance, updated kitchen, and access to a shared or private pool (depending on the listing). It’s clean, bright, and designed for relaxation.
Why it’s dreamy:
- Pool access for hot afternoons
- Contemporary design
- Great value for families
Good to know:
Marathon is centrally located, making day trips to both Key West and Key Largo easy.
10. Beachfront Paradise with Private Dock – Lower Matecumbe Key
Saving one of the best for last this beachfront Airbnb is the kind of place you’ll talk about long after your trip ends.
With direct beach access, a private dock, and panoramic ocean views, this home delivers the full Florida Keys experience.
Mornings start with barefoot walks on the sand, and evenings end watching the sky change colors over the water.
Why it’s dreamy:
- Private beach access
- Dock for boating or fishing
- Spacious layout with stunning views
Good to know:
This is perfect for families or groups who want space, privacy, and direct access to the water.
Final Thoughts: Choosing the Right Airbnb in the Florida Keys
When it comes to the Florida Keys, where you stay matters just as much as what you do. Whether you’re dreaming of an overwater retreat, a boho beach bungalow, or a luxury waterfront villa, the right Airbnb can elevate your entire trip.
My biggest tip? Choose a stay that matches how you want to feel. Relaxed. Romantic. Adventurous. Completely unplugged. The Keys have something for every travel style you just have to pick the one that feels like you.
If you’re planning a Florida Keys getaway and want a stay that feels truly special, any of these dreamy Airbnbs would make your trip unforgettable.
