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Freewheeler Vacation Rentals

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Islamorada, FL
Freewheeler Vacation Rentals

Freewheeler Vacation Rentals Freewheeler Vacations has been offering vacation rental homes and condos on the Upper Keys for more Just bring your toothbrush & bathing suit!

Freewheeler Vacations has been offering vacation rental homes and condos on the Upper Keys for more than 25 years. Our vacation properties, available for a week or longer, have all the amenities of home.

04/05/2025

Have you ever spent your Spring in the Florida Keys? 🌺

It’s everything sunny and serene with lots of ocean time in between. And in our opinion, there’s nothing like it! ☀️🌊🌴

At Freewheeler Vacations, we have plenty of oasis’s for you to enjoy the views + weather you’ve been dreaming of!

Hit the link in our bio 🔗 to see all of our gorgeous properties + find the perfect one for you. Questions? Just send us a DM! 🩵

03/24/2025

We 🩵 Islamorada with all our 🩵!!!

Shoutout to 151 Morada Way Gallery + Coffee Shop for this pretty picture and for keeping art alive in our island community. 🥥🌴

If you’re a lover of all things painting 🎨, jewelry, candles, coffee ☕️ , and more, check them out! They are always supporting local artists + makers as well as hosting art walks! 🩵

📸

03/17/2025

POV: You went on a color walk 💚 through 𝐈𝐬𝐥𝐚𝐦𝐨𝐫𝐚𝐝𝐚 …

and chose GREEN for 𝐒𝐭. 𝐏𝐚𝐭𝐭𝐲’𝐬 𝐃𝐚𝐲! ☘️

Wishing you all a 𝐥𝐮𝐜𝐤𝐲 holiday!

- Your friends at Freewheeler Vacations

03/15/2025

A vacation should clear the mind + provide a break away from the responsibilities and pace of daily life.

That’s why our accommodations at 𝐅𝐫𝐞𝐞𝐰𝐡𝐞𝐞𝐥𝐞𝐫 𝐕𝐚𝐜𝐚𝐭𝐢𝐨𝐧𝐬 are centered around creating spaces for leisure, ultimate relaxation, privacy, and views that give you that “𝐴ℎℎℎℎ, 𝑓𝑖𝑛𝑎𝑙𝑙𝑦“ moment. 🩵

We handle everything to make sure that you have everything you need and more upon arrival so that your stay provides all the comfort and serenity your heart desires — all in the beautiful island of 𝐈𝐬𝐥𝐚𝐦𝐨𝐫𝐚𝐝𝐚. 🏝️

Hit the link in our bio or head to www.freewheelervacations.com to use our free Area Guide and browse all of our stunning properties. 🩵

03/03/2025

Long before Freewheeler Vacations, there was a dream, and somewhere in between...

𝑻𝒉𝒆𝒓𝒆 𝒘𝒂𝒔 𝒂 𝒃𝒐𝒂𝒕! ⛵ Its name was Freewheeler, a play on our founder Alexa's last name. Alexa and her husband had always dreamt of sailing the Florida Keys and enjoying the beautiful simplicity and freedom found in island living.

Once their dreams came to fruition, Alexa wanted to share life in Islamorada with others, leading her to a passionate career in real estate and vacation rentals that has helped her give back to Islamorada for over 𝟑𝟎 𝐲𝐞𝐚𝐫𝐬 now! 💙

Today, Freewheeler Vacations is still the #𝟏 vacation rental company in the Upper Keys, and we pride ourselves on being under the same ownership and management since the beginning. 😊

02/25/2025

Our casa is your casa! Hit the link in our bio to access our FREE area guide + explore all the possibilities for your next stay. 🩵🐬🌞

As a local business who has had their roots in Islamorada for over 3 decades, we love sharing the beauty of the Florida Keys with our guests.

When you book with us, you can expect the highest level of hospitality and luxury.

🌟 Thank you, Josh, for this Google review! Your feedback means the world to us!

02/21/2025

Oh, to be laying in a hammock under swaying palms…Is it the weekend yet? 🌴

Almost! Happy Friday! ☀️

02/18/2025

What’s a home away from home?

A place that is just as cozy as (if not cozier than) your year round home BUT…

🏝️ Has a better view
☀️ Better weather
🧖‍♀️ No to do lists

If you’re dreaming of your next getaway, ask us about Turtle Cove, our oceanfront 🌊 gated estate with 4 charming cottages located in 📍Islamorada, FL.

Spend Spring in this gorgeous escape with access to our boat basin, tiki hut, oceanfront pool, outdoor showers, paddle boards, bikes, and kayaks! 🩵

02/05/2025

THIS is island life 🐚 🌴 🌺 ☀️ in Islamorada, one of the over 1,700 islands that make up the beautiful Florida Keys.

Each island is one-of-a-kind, with a magical element that's hard to find anywhere else. People come from all over the world just to soak it all up.

So how do you choose which island is right for your vacation? If you're looking to party, Key West is a great spot. But if you're looking to:

- relax and unwind
- enjoy a slower pace of island living
- have a more intimate experience with the Florida Keys' beautiful landscape (less crowded, quieter beaches + untouched mangroves)
- witness an abundance of island creatures and sea life in their natural habitat
- indulge in delicious food+bevs at the Keys' best waterfront restaurants and rooftop bars
- have access to the Florida Keys' most luxurious stays with Freewheeler Vacations
..then Islamorada 🌴 is the coconut to your palm tree. The next time you travel down to paradise, choose us for your relaxcation and let us guide you through your dream vacay. Hit the link below to see what's waiting for you!

https://www.freewheelervacations.com/

01/21/2025

A new year calls for new adventures. ✨ What’s on your adventure bucket list this year?

Here’s a peak at ours…

💦 Kayak through Islamorada’s crystal-clear waters
🪸 Snorkel in the world’s 3rd largest barrier reef
🌅 Experience a sunset sail with a local charter
🤿 Scuba dive with friendly sea life at the Florida Keys National Marine Sanctuary
☀️ See the sun rise at paddle board yoga (and hope for balance)

01/16/2025

Hi, winter. Leave a message after the beep.

We’re busy sunbathing ☀️, possibly a few cocktails deep, and living our best lives in the Florida Keys. 🏝️

01/14/2025

Here in the Florida Keys, we’re known for our rich history and preservation of iconic island gems like this one that remind us of our unique past.

Located in the heart of📍Old Town, the Key West Lighthouse offers 360-degree panoramic views of our beautiful turquoise waters, charming historic sites, and vibrant landscape. Originally built in 1825 and rebuilt in 1848 following the Great Havana Hurricane, this site is full of stories.

Once you arrive, check out the Keeper’s Quarters, climb the lighthouse steps for a stunning bird’s eye view of our little island 🌅, and head over to the Hemingway Home and Museum less than a minute’s walk away for another adventure down memory lane.

See you in paradise!

12/23/2024

Find your way to paradise! 🌍📍

Don’t just point to the destinations, make them your reality with Freewheeler Vacation Rentals! 🌴✨

If you’re new to the page, welcome! We’re the largest and most enduring vacation rental company in the Upper and Middle Keys. For over 30 years the same ownership and management at Freewheeler Vacations have provided first-class service to both guests and property owners in the Florida Keys.

We can’t wait to welcome you to your home away from home in the Florida Keys! Start planning your trip today with the link in our bio.

12/18/2024

Winter blues? Not when you’re in the Florida Keys with a paddleboard in hand! 🌊

In Islamorada, water activities are just steps from your vacation rental, making it easy to trade the cold for some warm, salty air and a little adventure on the water.

Book your last-minute winter getaway with Freewheeler Vacation Rentals and enjoy the perfect outdoor escape.

12/16/2024

🎣 Did you know the Florida Keys is a year-round fishing destination? And Islamorada isn’t just any fishing spot - it’s known as the Sportfishing Capital of the World. 🐟

It’s where backcountry sport fishing and saltwater fly fishing were born, making it the perfect place to reel in the catch of your dreams.

Book your stay and start planning your ultimate fishing adventure with some of our incredible local partners, including:

🌊 Fearless Fishing Charter -
🌊 Forever Young Charter Co. -
🌊 Lightly Salted Charters -

12/14/2024

There’s something special about spending the holidays in the Florida Keys.🌴🎄

In Key West, just a short trip from Islamorada, the transforms for Keysmas with lobster trap and buoy Christmas trees, a lighted boardwalk, and a packed calendar of holiday events.

One of the highlights (and a local favorite) is tonight’s Lighted Boat Parade. Between this, the Holiday Parade, Holiday Conch Tour Train, and so much more, it’s easy to see why is one of the most festive tropical destinations for the holiday season!

If you didn’t make it this year, now’s the perfect time to start planning your 2025 holiday getaway. Choose from hundreds of vacation homes with the link in bio.

📸:

12/09/2024

Greetings from Key West 🌴

Our rentals may be in the Upper Keys, but a day trip to Key West is always a good idea.

It’s only about an hour and a half drive - perfect for taking in some beautiful scenery along the way. 🚗💨

Whether you rent a car or hop on a bus, getting to Key West is easy and worth every mile. Spend the day exploring its iconic streets and colorful culture before heading back to your Freewheeler retreat in the Upper Keys. 🌞

📸: the_local_life_kw

Address

Islamorada, FL
33036

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm

Website

http://www.freewheelervacations.com/

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Videos

Come with us to the perfect romantic destination for you + your valentine! 💌 And yes, we’re still craving more banana bread. 🍞🤤 Find us while planning your romantic Florida Keys getaway? 🏝️ Choose us, Islamorada’s oldest and LOCAL vacation rental company .. Freewheeler Vacations to help you with your search! ☺️ #islamorada #islamoradaflorida #floridakeys #floridakeysvacation #romanticdestinations #thingstodoinflorida #floridavacation #floridavacationrentals #floridavacations #islamoradavacationrentals

🐚🌞 Islamorada Carry On Essentials 🐚🌞 🌺 Sunnies 🌺 Beach towel 🌺 Favorite Book 🌺 Sunscreen 🌺 And the perfect beachy tote to carry it all in Who’s booking their flight after watching this? 😎 #floridalife #floridaliving #floridatravel #islamorada #floridakeyslife #floridakeys #floridakeysvacation #floridaseastcoast #travel #traveldestination #tropicalvibes

💎 RARE FIND ALERT 💎 Would you stay in this luxurious dream home located in Islamorada, FL? ☀️🌊 The Pirate’s Chateau is a 5-bedroom, 4-bath retreat nestled in the pristine Venetian Shores on the open bay. 🏝️ It features a stunning backyard with all the amenities to make your getaway unforgettable: ⭐️ a resort-style pool ⭐️ hot tub ⭐️ outdoor kitchen ⭐️ hammock ⭐️ paddle boards ⭐️ kayaks ⭐️ and ample deep water dockage (150 ft.) and a double PWC jet dock perfect for boating enthusiasts! Nearby, you’ll have access to some of the world’s most beautiful beaches, Theater of the Sea, Founder’s Park (perfect for a family fun day), the Windley Key Fossil Reef Geological State Park, museums, dive centers, ecotours, and incredible oceanfront restaurants. Book your stay to experience the epitome of coastal luxury in the 📍Florida Keys! #visitislamorada #visitflorida #upperkeys #floridakeysrealestate #floridakeysvacation #floridakeysliving #islamorada #dreamhome #dreamstay #getawayhouse #secondhome #vacationtime

Why spend winter indoors when you could be living the dream at Pirate's Chateau? 🌴☀️ Cozy up to stunning bay views and save big with their exclusive winter special rate! Whether you're treating yourself or gifting the ultimate winter getaway, book now and give the gift of paradise this season! #SeasideEscape #VacationGoals #BookNow #VisitFL #LoveFL #Florida

Life on the water means community, connection, and sunsets that take your breath away 🌅✨ We’re so proud to be nominated for Best Vacation Rental Company in the Upper Keys. Your support means the world to us—please vote for us by this Sunday, 10/20! Click here to vote: https://keysweekly.com/buk24/#/gallery/?group=497176 Let’s keep making waves together ⚓️

Paradise found 🌅💦 Discover the magic of the Florida Keys with breathtaking views and island adventures waiting for you. Don’t forget to vote for us as Best Vacation Rental Company in the 2024 Best of Upper Keys Click here to vote: https://keysweekly.com/buk24/#/gallery/?group=497176 #Islamorada #Oasis #Expertise #VacationGoals #BookNow #VisitFL #LoveFL #Florida

Experience the Florida Keys from a whole new angle 🚁✨ With endless adventures waiting below, the view from above reveals just how spectacular this paradise truly is. We’re honored to be nominated for Best Vacation Rental Company in the Best of Upper Keys! This recognition reflects our deep love for our community and the stunning beauty of the Florida Keys. Now, we need your support! Vote for us and help us continue sharing the magic of this incredible place with everyone. Click here to vote starting at noon: https://keysweekly.com/buk24/ #SeasideEscape #VacationGoals #BookNow #VisitFL #LoveFL #Florida