5 Ideal Siesta Key Rentals For Your Winter Getaway!

Why Visit During Winter?

A wintertime beach vacation can sound a little contradictory at first, but there are a number of amazing benefits that come with visiting down South during the winter season. You might think that you’d be trapped in your Siesta Key condo rentals for the bulk of your trip, but you couldn’t be more wrong! The weather down in Siesta Key is actually quite pleasant during the majority of the winter months, with temperatures in the seventy-degree range. This is perfect if you want to avoid sweltering heat without sacrificing sunshine! Another great part about Siesta Key’s winter weather is that there’s typically very little rainfall. That means you can enjoy the area’s awesome outdoor activities without worrying about getting soaked!

Although the weather is favorable in the winter down in Siesta Key, there are far fewer people vacationing there over winter.

This means that if you’re someone who’s looking to avoid large crowds, wait times at restaurants, and backed-up traffic, there’s no better time of year to plan your trip!

Tower 304

Take in stunning views of Crescent Beach and the Gulf of Mexico from our third-floor condo on the world-famous Siesta Key Beach. With a private screened lanai, you can enjoy meals while taking in the sea views and sounds. This unit, much like many of our other Siesta Key oceanfront condos, has been professionally renovated with a coastal style, featuring a wood-look seaside tile throughout and ceiling fans in the living room and bedrooms to maximize the beach breeze.

The master suite boasts a king-sized bed, a 50″ smart TV, and a quartz double vanity with ample storage. The guest suite includes two queen-sized beds, a 50″ smart TV, and a bathroom with a tub-tile shower, granite countertops, and storage. Both bedrooms have independent access to the lanai. A stay in our Tower 304 unit guarantees a truly unforgettable experience with full views of the Gulf of Mexico and white sand Crescent Beach.

Balcony view of crystal blue water and white sands!

Tower 1202

Get ready to experience luxury living in our stunning two-bedroom, two-bath Gulf Front vacation rental. With convenient access to the resort’s private beach and two heated swimming pools, you’ll have plenty of opportunities to relax and soak up the sun. Tower 1202 boasts lanai access and stunning beachfront views from the living room and both bedrooms. Start your day with a fresh cup of coffee as you listen to the waves roll in and end it with a glass of wine as the sun sets over the Gulf of Mexico. Located just two miles from the popular Siesta Key Village, with shops, restaurants, bars, coffee shops, and more, you’ll never run out of things to do. Whether you’re planning a family vacation or a romantic getaway, our Tower 1202 unit could be the perfect choice for you. 

Extra long balcony overlooking views of The Gulf of Mexico.

Tower 1109

Experience luxury and relaxation at its finest in our unique four-bedroom unit, a fan-favorite of our Siesta Key oceanfront rentals. This highly desirable 11th-floor residence boasts stunning beach and sunset views from two screened-in balconies. Step inside to find a fully renovated space with brand-new stainless steel kitchen appliances and a full-size washer and dryer. The freshly painted walls, new durable flooring, and contemporary beach decor create a one-of-a-kind beach experience for the whole family. With three spacious bedrooms and a comfortable sleeping arrangement for up to 10 people, you’ll have plenty of room for everyone. 

Stunning modern kitchen overlooking living room with windows framing a crystal clear ocean view.

Villa 15

Our two-bedroom, two-bathroom villa will quickly become your new home away from home. The fully furnished, completely modern unit is spacious and cozy all at once. A perfect respite for the end of your exciting vacation days, you can take a warm shower in the beautiful, updated bathrooms before nestling down and heading to bed in the gigantic bedrooms within the unit. The villa has a very classic flair, with granite countertops and luxurious leather furniture. 

Though all of Siesta Key’s excitement is moments away from the villa, you don’t need to worry about finding parking because of the unit’s included garage. A perfect choice for those who don’t just look for convenience in their Siesta Key vacation rentals, but also comfort and a sense of hospitality.

Modern kitchen decorated with beautiful stone and red wood cabinets.

Villa 13

Our Villa 13 sets itself apart from the rest, mostly due to its completely modernized furnishings and central location. If you take a few short steps off of the property, you’ll find the beautiful beaches of Siesta Key practically right outside your back door. The two-bedroom, two-bathroom unit sits at the end of a sunny palm tree-lined boulevard, with its own private garage for convenience. 

Our unit’s many windows grant an amazing view of the paradise hiding outside, though you may never want to leave the luxury and comfort that comes with this impressive rental. We firmly believe that all of our Siesta Key vacation condo rentals are of the utmost quality, but this unit has many unique charms that allow it to shine and stand out among the other choices. 

Plan Your Visit!

Are you ready for sunshine and ocean waves without steamy summer temperatures? Plan your winter getaway to Siesta Key and discover the perfect climate this season offers! Browse our available rentals today!

Our Villa 13 is ideal for those who are planning a stylish getaway in a Siesta Key vacation rental, a vacation with friends, or simply a couple who wants an extra bit of legroom. You’ll be certain to get very comfortable very quickly, with an in-unit washer and dryer and wifi access that makes for a great home office setup. But don’t focus too much on work during your trip- be sure to soak in all of the beauty and excitement that Siesta Key has to offer during your stay.

Beautiful vacation rental dining room decorated with hints of teal and blue.