Siesta Key Vacation Rentals

Explore the exhilarating water-sports scene in Sarasota and its neighboring beach towns. Glide through the enchanting mangrove forests on a kayak, embark on boat tours for high-speed thrills or tranquil cruises, soar above the barrier islands while parasailing, or find serenity by paddleboarding through Sarasota’s picturesque waters. The choices are endless for aquatic adventures and relaxation.

This village is the hub of Siesta Key. It spans about four blocks in the center of the island and is home to about a hundred shops, boutiques, restaurants, cafes and bars. Find souvenirs, jewelry, and handcrafted items with Caribbean influences. The bars and clubs provide fantastic nightlife with awesome DJs and drinks.

Every year, Siesta Key hosts its Crystal Classic Sand Sculpting Festival, where artists compete in a sand sculpting competition. During the competition, you can enjoy the sculptures and vote for your favorites. Other attractions at the festival include sand sculpting lessons, live bands, and an amateur competition.

Delve into Florida’s vibrant culture at the renowned Siesta Key drum circle. Join the free Sunday night gatherings at Siesta, Nokomis, and Englewood beaches. Witness mesmerizing performances by belly dancers, fire breathers, and more, creating an awe-inspiring live music spectacle. These family-friendly events are not to be missed for an unforgettable cultural immersion.

With shallow waters and numerous fish species, Siesta Key is the perfect place to try your hand at fishing. Whether you’re a novice or an experienced pro, you have the opportunity to catch grouper, bluefish, mackerel, flounder, snapper and more. Go on a deep-water fishing excursion for your chance to hook mahi-mahi, marlin, and tuna. Be sure to get the appropriate licensing before your trip.

Biking is a wonderful way to see the sights of Siesta Key. Whether you want to take an electric-bike tour or just rent bikes for a day, biking is a very popular way to get around. The whole island is extremely bike-friendly with bike lanes on the streets, and you can even ride directly on the beach. For a memorable low-key biking adventure, opt for a sunset bike tour.

Dining on Siesta Key offers a delightful array of culinary experiences amidst its laid-back beach atmosphere. Whether you’re craving fresh seafood, international flavors, or classic American fare, the island’s restaurants cater to a variety of tastes. Along Ocean Boulevard and in Siesta Key Village, you’ll find quaint cafes, seafood shacks, and upscale bistros serving everything from Gulf shrimp and grouper sandwiches to gourmet pizzas and sushi. Many eateries feature outdoor seating, allowing diners to enjoy their meals with views of the Gulf or under the shade of swaying palm trees, enhancing the relaxed coastal dining experience.

Julie Wilson comes to SkyRun Siesta Key with an abundance of experience and success in vacation rental management. From sales and marketing to managing a large local vacation rental management company, Julie has extensive working knowledge of every aspect of the business. According to Julie, “SkyRun Siesta Key is a perfect fit for me because we share the same values of outstanding customer service and maximizing the income potential for every one of our homeowners.”

“Our emphasis is on local” according to Julie, “meaning a homeowner will never get lost in the shuffle or be passed off from one person to the next. We offer a concierge quality service to both the homeowner and guest at a very competitive rate.”

Julie is a full-time Sarasota resident and is continually monitoring the vacation rental market. One high profile Real Estate Broker calls Julie “the most knowledgeable person in the area who understands the vacation rental management space. She is so helpful to my clients, and is an important resource for myself and our organization.”

When Julie is not working, she is enjoying this small slice of paradise playing on the beach, sailing at the Squadron, catching some fresh gulf snapper, and dining at all the locally owned restaurants!

Hans is an experienced entrepreneur with 15 years of business ownership experience, in addition to a successful career in sales, management & finance. Under his leadership, his previous company experienced tremendous growth through organic means and several strategic acquisitions.

After brokering a successful sale of that company in 2021, Hans turned his attention to vacation rental management and started SkyRun out of a desire to help homeowners and guests achieve their vacation dreams. Hans and his wife, Ellen, have enjoyed visiting Sarasota and the Keys for more than 15 years and have been homeowners and renters in the area for over 3 years. They have one core value – Good Karma. To them, that means they help first, they do the right thing, they have an abundance mindset, they have fun under pressure, and they always achieve a 5-star review.

The SkyRun Siesta Key Team is local and are a quick phone call or visit away.

Kali Quinn, a Sarasota native, is a vacation professional with a passion for helping others create unforgettable memories. With extensive travel experience, she brings a wealth of knowledge and enthusiasm to her role- although Sarasota’s beaches are still her favorite. Her career highlights include customer service and leadership positions at renowned organizations such as Marriott Vacation Club and Walt Disney World. Kali’s dedication to excellence and her warm, friendly approach ensure that every guest feels special, making their vacation experiences truly magical.