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

Freewheeler Vacation Rentals

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United States
Islamorada, FL
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.

11/30/2024

It’s time for a little R&R. 🌴 The Florida Keys offer the perfect backdrop to hit pause, enjoy the quiet, and just breathe.

11/28/2024

Happy Thanksgiving from the Freewheeler team! 🦃

This year, we’re reflecting on how thankful we are for YOU and our incredible Islamorada community. It’s a privilege to help make your Florida Keys vacations your Florida Keys home away from home, and we’re so grateful to create unforgettable memories with you.

Wishing you and yours a tropical-filled day filled with friends, family, and delicious food!

11/22/2024

Swap the holiday chaos for ocean views and quiet moments. 🌊✨

Treat yourself to a peaceful getaway this season -your perfect escape is just a booking away!

wap the holiday chaos for ocean views and quiet moments. 🌊✨

Treat yourself to a peaceful getaway this season -your perfect escape is just a booking away!

11/18/2024

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!

10/23/2024

Make your way to Robert Is Here Fruit Stand & Farm—your ultimate pit stop on the way to the Florida Keys 🍉🌴

Open every day from 9am-6pm, this family-owned gem has been serving up local and exotic fruits, fresh veggies, and delicious groceries since 1959.

Don’t forget to treat yourself to a refreshing milkshake🥤✨ Swing by and taste the flavors of the sunshine state 🌞🍓

10/15/2024

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 ⚓️

10/13/2024

Hooked on the Florida Keys 🌊🐟

With vibrant marine life and endless fishing spots, there’s always something waiting to be caught.

Book your trip today and cast away your worries!

10/11/2024

A day trip to Key West is always a good idea 🌞

This colorful town has plenty of sights, sounds, and tastes to savor! From charming streets to vibrant local culture, every moment is worth the drive.

Make unforgettable memories in this island paradise!

10/09/2024

All good here at Freewheeler Vacation Rentals 🌧️ We are making the most out of a rainy day while keeping Florida in our thoughts. Stay safe, everyone!

10/07/2024

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

10/03/2024

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/

10/02/2024

Soaking up the sun and watching the world sail by—this is what paradise looks like 🌅✨

Book your getaway through Freewheeler and make this your reality!

09/29/2024

Give your pup the getaway they’ve been dreaming of 🌊🐾

Relaxing sunsets await in the beautiful Florida Keys.

09/27/2024

Who needs fall colors when you have sunsets like these? 🌅✨

Catch that endless summer vibe in the Florida Keys!

Address

85992 Overseas Highway
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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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

Who needs fall colors when you have sunsets like these? 🌅✨ Catch that endless summer vibe in the Florida Keys! #SeasideEscape #VacationGoals #BookNow #VisitFL #LoveFL #Florida #FloridaKeys #Vacation

While stormy weather may be upon us, we’re dreaming of clear days ahead in the Keys 🌊✨ Dive into island life with Freewheeler Vacation Rentals and get ready to soak up that sun-kissed serenity soon. Stay safe, everyone 🌴💙

Nothing heals like a dose of Florida therapy 🌺🌞 Sun, sand, and sea—just what you need for the perfect beach day in the Florida Keys! Spread the island love—nominate Freewheeler in the 2024 Best of Upper Keys Awards 🏝️✨ #Islamorada #Oasis #VacationGoals #VisitFL #LoveFL #Florida