Maybe it’s the salty air, the pastel porches, the wandering roosters, or the way time seems to stretch just a little differently here. Either way, one thing’s for sure: a weekend simply isn’t enough.
Key West isn’t the kind of place you visit once—it’s the kind of place that lingers with you long after your flip-flops have touched down back home. That’s why we’re sharing a curated list of Key West Airbnbs made for month-long stays—the kind of homes that invite you to unpack fully, sink into a slower pace, and live like you’ve always belonged on island time.
If you’re looking for creative inspiration, a remote work change of scenery, or just the luxury of staying somewhere long enough to learn your neighbors’ names, then these homes are the perfect excuse to take it easy for a while.
Let’s find your new favorite place that you will never want to leave, and things to do while in Key West.
First Breath
3 Bedrooms | Sleeps 6 guests
The name says it all—First Breath is the place you exhale, slow down, and remember how nice it feels to do absolutely nothing. This beautiful Conch-style retreat is tucked in the heart of Old Town, where tropical palms, a private saltwater pool, and shady decks create your own little slice of Key West calm.
Inside, you’ve got everything you need to live like a local: a fully stocked kitchen, comfy living room, and indoor-outdoor flow that practically begs you to spend afternoons poolside with a cold drink and zero agenda. And the best part? You’re just a bike ride away from Duval Street, the Seaport, and all the good island energy.
⭐ Best Features
- Private saltwater pool and furnished outdoor deck
- Fully equipped kitchen with modern appliances
- In-home laundry for long stays
- Dedicated indoor + outdoor dining areas
- Walkable Old Town location near shops, dining & Duval St
- Fenced-in yard for peace and privacy
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Lighthouse Villa
3 Bedrooms | Sleeps 8 guests
If your dream month in Key West includes sipping coffee on a balcony, lounging by the pool, and living in a postcard-worthy historic home, then Lighthouse Villa is your best choice. Just steps from some of the island’s most iconic spots, this elegant home makes it easy to fully settle into island life.
After a beach day or an afternoon of wandering Duval, this is where you’ll come home to unwind. A tropical retreat built for long stays, with multiple indoor and outdoor living spaces, allowing everyone in your group to spread out and have a bit of privacy.
⭐ Best Features
- Private pool, BBQ grill & multiple outdoor lounge spots
- Spacious 3-level home with flexible sleeping areas
- Full kitchen with a big dining table
- Washer and dryer available
- Located in the heart of Old Town, walkable to everything
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Spanish Lime Tree Cottage
1 Bedroom | Sleeps 2 guests
Stay at Spanish Lime Tree Cottage for a month and you’ll start living like a local by week two. Walk to the Key West beaches. Grab lunch on Petronia Street. Pick up fresh fish for the grill. After a few days here, the island rhythm takes over—and trust us, you won’t miss the rush.
Perfectly placed on historic Whitehead Street, right in the center of Old Town—but just far enough off Duval for peace and quiet when you want it. This cozy cottage is made for couples, solo travelers, or digital nomads looking to swap city noise for sunshine, Cuban coffee, and easy strolls to everything.
⭐ Best Features
- Private backyard patio with grill and dining area
- Full kitchen and in-home laundry for longer stays
- Pet-friendly for one small dog (with additional fee)
- Private parking spot!
- Central Old Town location, steps from local landmarks
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
La Casita
2 Bedrooms | Sleeps 4 guests
Tucked on a quiet little lane just steps from Duval Street, La Casita is your access to long, laid-back island living. It’s charming, colorful, and right in the middle of Old Town—which means you can go from your front porch to a slice of key lime pie in under 5 minutes (we timed it).
This hideaway has everything you need for a month of slow mornings, breezy sunsets, and feeling like a KW local. Whether you’re biking to the beach, walking to Hemingway’s house, or just enjoying the quiet rhythm of Key West life, La Casita makes you feel at home.
⭐ Best Features
- Fully equipped kitchen plus outdoor BBQ grill
- Tropical landscaped courtyard with dining and lounge space
- In-home washer/dryer available
- Workspace-friendly layout
- Unbeatable walkable location near Duval Street
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Ecco Domani
3 Bedrooms | Sleeps 6 guests
Settle in, unpack, and stay a while as Ecco Domani is made for the long haul and a cozy balance of luxury and livability. This three-story private home feels like a boutique stay where everything here is set up to help you slow down and enjoy every single day of your month in paradise.
Tucked just off Simonton Street, the house location puts you close to everything—restaurants, shops, beaches. And whether you’re sipping your morning espresso on the porch or floating in the pool after a day out, Ecco Domani is the kind of place that makes you want to extend your stay… indefinitely.
⭐ Best Features
- Saltwater pool with sunny private deck and loungers
- Gourmet kitchen with French doors to the patio
- Jetted soaking tub and luxe master bath
- TVs in every bedroom with strong WiFi for longer stays
- Walkable to Duval Street, South Beach & local favorites
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Paradise Palms
2 Bedrooms | Sleeps 4 guests
Paradise Palms is your perfect mix of easy, quiet, and close to everything. But what makes this place really special is how livable it feels! Located in a peaceful neighborhood, this renovated cigar-style cottage is where you settle in for the month and instantly feel like you belong.
You’ve got everything you need to make yourself at home where you can walk to yoga, bike to the beach, or pop over to the corner market for wine and snacks. Then enjoy a glass of something cold in your shady front courtyard. For 28 days of pure, unbothered Key West living—this is the move.
⭐ Best Features
- Renovated kitchen with stainless steel appliances
- Private side deck with outdoor shower and grill
- In-home washer and dryer
- Dedicated parking spot
- Quiet neighborhood, walkable to Old Town dining & shops
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Flagler’s Oasis
2 Bedrooms | Sleeps 4 guests
Looking for your private slice of paradise for a month? You just found it. Flagler’s Oasis is exactly the peaceful, palm-lined retreat with zero stress in sight. After a few weeks here, you’ll forget what rushing feels like as you are now used to easy living and quiet afternoons.
Imagine waking up each morning to birdsong and sunshine, taking your coffee out to the garden while the palm trees sway overhead. Life moves slower, the air feels warmer, and your only real decision is whether to swim before lunch or after. This isn’t just a vacation anymore—it’s your own slice of island life, stretched out over 28 perfect days.
⭐ Best Features
- Deep lagoon-style pool with waterfall and stone deck
- Covered gazebo with a TV for outdoor hangouts
- Fully renovated kitchen with everything you need
- Extra-long driveway for 2 cars
- Pet-friendly (additional fee) with a fenced-in yard for privacy or pups!
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Lazy Gecko
2 Bedrooms | Sleeps 4 guests
Where island time kicks in and every day starts with sunshine and ends with a nightcap in the courtyard. Rush to Lazy Gecko, a tucked-away, charming condo in Key West, made for simple pleasures, long walks, and even longer stays. One visit and you’ll see why this spot lives up to its name—you’ll never want to leave.
Here, mornings are for strolling to the seafood market or grabbing Cuban coffee down the street. Afternoons? They’re for reading on the front porch or exploring nearby galleries and historic sites. The light, airy, and thoughtfully designed space inside is just the perfect spot for breakfast or a breezy happy hour.
⭐ Best Features
- Private courtyard area with BBQ grill
- Fully equipped kitchen
- A washer and dryer are available for use
- Prime Old Town location near Seaport & Duval Street
- Walkable to shops, restaurants, and fresh seafood
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Casa de Rosalie
3 Bedrooms | Sleeps 8 guests
Not just a stay but a story. Welcome to Casa de Rosalie, with roots dating back to 1889. A historic Conch home that wraps you in breezy palms, quiet streets, and the kind of classic architecture that invites you to slow down. Mornings here start easily, and notice how life here just feels better.
A stroll through Bayview Park across the street, or coffee on the back porch while the pool sparkles in the sunshine. You’ll love how easy the flow is in this home. You’ve got a go-to sandwich spot. And that once-vacation rental? It feels like home.
⭐ Best Features
- Restored historic home with century-old Dade County pine tree
- Private backyard with pool, gazebo, and grill setup
- Spacious living and dining areas for group meals
- Full kitchen, in-home laundry, and flexible sleeping space
- Walkable to Bayview Park, local eats, and Duval Street
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Casita de Catherine
1 Bedroom | Sleeps 3 guests
Island life, perfected. That’s Casita de Catherine—a cottage where every moment feels just a little more intentional with simple comforts, soft colors, and just the right amount of cozy. Tucked just a block from Duval, this little gem is quiet and surprisingly peaceful given how close you are to everything.
A romantic getaway where you can escape this February and start to find your rhythm. Have a sunrise stroll to South Beach, lazy mornings in the hot tub, and spend afternoons with your feet up on the back deck as the breeze rolls through.
⭐ Best Features
- Private hot tub by the backyard deck
- Outdoor shaded lounge
- Full kitchen and in-home laundry
- One block from Duval, walkable to beaches, dining, nightlife
- Pet-friendly (with additional fee)
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Key Lime Pie
2 Bedrooms | Sleeps 4 guests
There’s something sweet about this place, and it’s not just the name. From the sunshine-yellow walls to the splash pool tucked under swaying palms, Key Lime Pie is your classic Key West bungalow brought to life. It’s bright, cheerful, and full of those little details that make it easy to settle in and stay awhile.
Spend your mornings wandering for fresh seafood and waterfront views, and your afternoons in the splash pool with a book and something cold in hand, or find your go-to coffee shop, get used to biking everywhere, and wonder how home ever felt this far away.
⭐ Best Features
- Private splash pool and lush fenced-in deck
- Full kitchen with washer and dryer
- Dedicated parking spot
- Pet-friendly (with additional fee)
- Walkable to the Seaport, restaurants, and Old Town hotspots
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Easy Livin’
3 Bedrooms | Sleeps 8 guests
Life really is easier at Easy Livin’. A quiet historic house at Truman Annex that brings all the comforts of home from the moment you walk in. It feels like someone hit the “relax” button on your life when you stay here, as it makes slowing down with the warm Key West breeze feel like second nature.
Built for families, friend groups, or anyone needing a long-overdue reset, this is the kind of home where brunch turns into happy hour, and one week turns into four. It’s called Easy Livin’ for a reason, and whether you’re staying here for a week or month-long, this house lives up to its name.
⭐ Best Features
- Private saltwater pool with pool towels
- Outdoor lounging and dining space
- Fully stocked kitchen and in-home laundry
- Private carport for 1 vehicle
- Located in gated Truman Annex, walkable to everything
👉 Book on Airbnb | Book on AvantStay Direct (Best Price!)
Why Staying in Key West for a Month Is Totally Worth It
Sure, a weekend in Key West is fun—but give yourself 28+ days here and you’ll unlock a whole new level of island living! Here’s why a longer stay isn’t just worth it—but it’s the move:
1. You actually get to slow down.
No rushing to cram it all in and make mistakes. You’ll have time to explore the beaches, brunch spots, galleries, and hidden gems without the pressure of a check-out clock ticking.
2. You’ll feel like a local.
After a few days, you’ll have your go-to coffee shop, your favorite bar stool on Duval, and a go-to order at the taco stand down the block.
3. Space to live, work, and recharge.
These homes are built for real life—cook in a full kitchen, catch up on remote work, and relax in your own private outdoor space. It’s comfort and freedom!
4. You can truly unplug (or not).
Want to disconnect and read three novels? Do it. Want to take a meeting by the pool and call it “work-life balance”? We love that for you.
5. The longer you stay, the more it feels like home.
By week two, the island will for sure feel familiar. By week four, you’ll be wondering how to extend your stay.
So yes—Key West is the perfect place to escape. But when you stay a little longer? It becomes the kind of place you’ll keep coming back to, year after year. Our loyal guests swear on that!
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The Longer You Stay, the Better It Gets
After a few days in Key West, you’ll fall in love. After a few weeks, you’ll wonder why you ever booked a return ticket! Slow down, stay a while, and discover what it really means to live on island time.
Whether you’re chasing sunshine, writing your next chapter, or just ready for a well-earned reset, a month here might be exactly what you didn’t know you needed.
Book your stay today and get ready to live a long, breezy day at a time.