Welcome to our collection of vacation rental properties in breathtaking Key West, Florida, where paradise awaits! Imagine waking up to the warm sunshine, gentle ocean breeze, and the sound of the ocean calling. Key West is renowned for its stunning natural beauty, vibrant culture, and crystal-clear waters. And when it comes to making your Key West vacation the best you’ve ever had, Fun in The Sun Key West is here to make it happen.

Our carefully curated selection of vacation rental properties offers a variety of options to suit your needs. Whether you’re seeking a Key West Penthouse, a beautiful oceanfront house with a pool, or a spacious family-friendly stay on a yacht, we have the perfect accommodation for you. Each property is handpicked for its comfort, amenities, and proximity to Key West.


Beautiful 43 ‘ sportfish yacht

Friendly Key West style marina. The boat is secure, won’t notice any movement! Just steps from the famous Hogfish Tiki Bar and Grill! Great community of artists and live aboard residents. The boat does not go out during the booking, but we can arrange a driver. There is an extra fee for leaving the dock. We also rent carts, bicycles, kayaks, paddleboards, smaller boats, and/or private backcountry charters. This rental requires a bareboat charter agreement. Come enjoy paradise on the Lisa Lynn!

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Your own private resort! Pool, tiki, RV Hookup

The grounds of this home will take your breath away. This is a unique opportunity to experience the Keys with your own private beach, resort-style tiki hut, pool, and 50ft dockage right on the gorgeous Florida Bay with a front-row seat for sunset every night. Just 15 min from Duval!

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Sophisticated Bright & Breezy Duval Street Apartment

This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, and Entertainment in the heart of Key West. Ones you enter the property through your private entrance, you would be captivated by its expansive space. The oversized living room has an abundance of natural light coming from the Cathedral Ceiling Skylights. Comfortable couches and flat-screen TV will help relax after all the fun playing. Tastefully decorated two bedrooms have a Queen and Full-size bed. Double sink vanity and a shower tub are in Master Bathroom. Plush towels and high -end linens are provided for our most discerning guests. 

Key West Boat Charters

But it’s not just about the accommodations. Fun in The Sun Key West goes the extra mile to ensure your vacation is truly unforgettable. Our dedicated team is committed to providing exceptional customer service, catering to your every need. Looking to explore the offshore island and wonderful sandbars? We can arrange day and sunset charters and backcountry adventures for you. Want to reel in the big fish? Our fishing charters will make it happen.

At Fun in The Sun Key West, we understand that your vacation is precious. That’s why we strive to create an experience that exceeds your expectations.

So pack your bags, leave your worries behind, and let Fun in The Sun Key West be your trusted partner in crafting the Key West vacation of your dreams. Book your stay with us today and get ready for an extraordinary adventure in this tropical paradise.