Looking for a unique weekend getaway? Florida offers everything you could want in a tropical escape. We selected vacation rentals with something special to offer for the next time you have an itch to getaway to the Sunshine State for a long weekend, holiday weekend or really any weekend. These rentals are charming and some are a bit off the beaten path. The rental destinations are top notch and any of them would make a great retreat for your next escape!


Charming Stays: Uncover Hidden Gems

4-Story Home With Private Pool
Destin, FL

This charming Miramar Beach rental is spacious, newly renovated and only a 5 minute walk to the beach. It also boasts a private pool and other upscale amenities to make your next trip that much more special. With 4 floors and 6 bedrooms this house can accommodate up to 21 guests. This house is a hidden gem for a group, families or even if you just want to enjoy privacy and a lot of space. It has everything you will need, so pack a suitcase and book your next getaway!

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Seaside Palace
Destin, FL

This 8 bedroom home is perfect for an unforgettable family weekend vacation. One of Crystal Beach’s largest homes, this is truly a unique show-place. This house has a heated pool, hot tub and is only half a block from the beautiful white sand beaches of Destin. It also has beach view balconies and over 5000 ft of living space. It is also only a block from several dining options in Destin.

A Thousand Hidden Hemingways
Key West, FL

This rental has a farmhouse charm. It was built in the 1890s and has a porch off every bedroom. Indoor and outdoor living spaces make this the perfect warm weather getaway. There is also a private pool and huge roof deck with beautiful string lights to relax and have a nightcap. This house offers a true Key West experience.

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Luxurious Private Stays

“Oceans Blue” Luxury Living
Anna Maria Island, FL

This rental offers peace, tranquility and privacy on the beautiful Anna Maria Island. Anna Maria Island offers some of the quietest beaches and is off the beaten path from major cities. There are so many relaxing options with this house whether it is reading by the pool or visiting the beach nearby. Pine Avenue, which has shopping, restaurants and more is also only blocks away. The house has 4 bedrooms and a private heated pool/spa. This rental is the perfect retreat!

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“Endless Summer” Quiet Location
Anna Maria Island, FL

Endless summer is a perfect way to describe this beautiful and secluded rental. Located in a quiet neighborhood with a private heated pool. It is also a 2-minute walk from a gorgeous beach. Four bedrooms, 3 bathrooms and open concept living make this rental easy to get comfortable and is great for families. You will love this special property in this special location where you can really get away from it all!

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“Crystal Seashore” Beachfront
Naples, FL

This gorgeous beachfront home is right on Bonita Beach. You can not get more magical than these panoramic Gulf views. Direct access to the beach and a private pool. This house is luxurious and secluded. With 4 bedrooms and 4 baths it can accommodate up to 8. This rental allows a private location, while still being close to town and main amenities.

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Hi, I'm Jen and I love to travel, go to the beach and write about all the places I have visited. I also have a bucket list of places I can't wait to try! I've visited Cape Cod every summer since I was a kid and now enjoy traveling to all great beach destinations, including Florida! I have worked in the travel industry for all of my career. I love sharing my experiences of different restaurants and places and helping travelers find the best fit for them!

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