Siesta Key Vacation Rentals

A variety of single family homes, condos, and townhomes for rent on Siesta Key

USA > Florida > Sarasota > Siesta Key

Visit Siesta Key

Visit Siesta Key, Florida, for its pristine white quartz-sand beaches, clear turquoise waters, vibrant sunsets, and relaxed island atmosphere. This beautiful barrier island is also home to great fishing, watersports, biking, and the weekly Siesta Key drum circle, offering the perfect getaway for beach lovers and nature enthusiasts.

Your Siesta Key Vacation, Your Way.

Featured Siesta Key Vacation Rentals

Your Personal Vacation Planner

Locally Owned and Operated In Siesta Key

Remember, when you rent with SkyRun, you can expect superior, prompt, and personalized service that’s hard to find in a top-down rental corporation.

  • Enjoy a personal relationship with your property manager, who can answer any questions and address all concerns promptly.
  • Have a question about local activities, amenities, or services? Our local staff can provide recommendations for getting the most out of your stay.
  • Our property managers are just a stone’s throw away from most of our rentals. That means they’re available to step in to help with any situation.

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.


Kali Quinn

Siesta Key, FL

Guest Marketing and Vacation Planner

Let's Talk!

Turtle Beach

Turtle Beach is a serene and picturesque stretch of coastline nestled on Siesta Key, just south of Sarasota. Known for its soft, powdery white sand and clear, turquoise waters, Turtle Beach offers a more tranquil alternative to its bustling counterparts.

Visitors can enjoy leisurely walks along the shore, collecting shells or watching for dolphins playing in the surf. The beach is also a popular spot for picnics and family gatherings, with shaded picnic tables and grills available for use. Sunset views over the Gulf of Mexico are particularly breathtaking, casting a golden hue over the tranquil waters, making Turtle Beach a perfect retreat for those seeking relaxation and natural beauty.

Crescent Beach/Point Of Rocks

Crescent Beach, situated on Siesta Key near Sarasota, Florida, is renowned for its stunning shoreline and unique geographical features, notably Point of Rocks. This picturesque beach is characterized by its fine, powdery white sand that stays cool underfoot even in the heat of the day.
Point of Rocks, a cluster of ancient limestone formations, offers excellent snorkeling opportunities, with its shallow, clear waters teeming with colorful marine life and coral reefs. Visitors can explore these natural wonders right off the shore, making Crescent Beach a favorite destination for snorkelers and beachcombers alike.

Siesta Key Main Beach Access

The Siesta Key Main Beach Access is a gateway to one of Florida’s most beloved beaches, renowned for its powdery, quartz-crystal sand that remains cool to the touch. Located near Sarasota, this access point offers convenient parking, making it easily accessible for visitors looking to enjoy a day at the beach.
The Main Beach features expansive shores perfect for sunbathing, playing beach volleyball, or simply relaxing under swaying palm trees. Its amenities include picnic areas, playgrounds, and concession stands, catering to families and beachgoers seeking a comfortable day out by the Gulf of Mexico.

Siesta Key Village Access

The Siesta Key Village Access to the beach provides a lively and convenient entry point to the vibrant heart of Siesta Key. Situated just steps away from the charming Siesta Key Village, this access point offers visitors easy access to shops, restaurants, and amenities before or after a day on the beach.

Beyond its practical advantages, the Siesta Key Village Access area exudes a laid-back coastal vibe, inviting visitors to stroll along palm-lined streets or dine al fresco at beachside cafes. The village also hosts various events and festivals throughout the year, adding to its allure as a bustling yet relaxed beachside destination. Whether you’re looking to unwind on the sand, explore local shops, or savor fresh seafood, the Siesta Key Village Access offers a perfect blend of beachfront relaxation and coastal charm.


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.

Siesta Key Village

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.

Siesta Key Crystal Classic Sand Sculpting Festival

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.

Siesta Key Drum Circle

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.

What To Expect

As local residents, SkyRun staff are available to help you make the most of your trip to Florida.  We strive to have your property ready with everything you need and to provide you with all the information you will need even before you have to ask for it.

But if you DO need something, our staff are here to help daily (and on call 24/7 for emergencies).  We communicate with you the way YOU want to communicate.  That can be using our webchat or simply giving us a call. We’ll also be sending you a few emails before and during your stay with important information. You can also text us via our industry exclusive 2-way text messaging system.

Included Services:

  • Pre-arrival quality inspection
  • Hot tub maintenance (as applicable)
  • Most properties have free parking (check each property for possible charges)
  • Luxury linens and towels
  • Fully equipped kitchens
  • Wi-Fi and TV’s
  • Departure cleaning and trash removal

Starter Supplies:

  • Coffee and coffee filters (if applicable)
  • Salt and pepper and cooking oil
  • Garbage bags
  • Dish/Dishwasher and laundry detergent (as applicable)
  • Hand soap and lotion
  • Shampoo and conditioner
  • TP, paper towels and tissue
  • Hairdryer and ironing board

Property Damage Waiver

SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure.  It does not cover damage that is willful, the result of negligence, or damaged caused by the misuse of household items.  It also doesn’t cover unreported damage.  SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is non-refundable.

If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is provided to you and all travelling companions that are staying in the home overnight during your stay.

Coverage is not provided for loss due to:

  • Your intentional acts or gross negligence.
  • Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party).
  • Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you.
  • Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report.

Your Duties in the Event of Damage. You must:

  • Take all reasonable, necessary steps to protect the property and prevent further damage to it.
  • Report the loss in writing (email ok) prior to check-out to the SkyRun staff.
  • Provide us documentation such as pictures to substantiate the claim.

Travel Insurance

Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more.

Group coverage protects everyone in your traveling party for one low price.

Get a quote.

Check-In Instructions

Check-In | Check-Out

Check-in is 4:00pm ET and check-out is 10:00am ET.  A check-in instructions email will be distributed to guests day of arrival, and contain directions and access information for the property. In most cases guests will access a property via a lockbox or SMART lock using the given access code. Early check-ins can only be confirmed on the day of arrival.

Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with the SkyRun Sarasota office. Late check-outs must be coordinated directly with the SkyRun office no later than 9am on the day of departure; please note that if we have an incoming guest we will not be able to accommodate a late checkout.  We ask that guests remove all trash from the unit, return the furniture to it’s original location, load and run the dishwasher, set the thermostat to 78 degrees, turn off all lights and lock doors.


Parking may be limited. The check-in instructions email will contain information regarding parking at your property.   Any parking fines assessed to your vehicles during your stay will be billed to you if they are billed to us.  Parking fines can be significant.

Julie Wilson, Director Of Business Development

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 Kirkegaard, Owner Of SkyRun Siesta Key

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, Guest Marketing and Vacation Planner

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.

Property Management You Can Trust

Owning a vacation rental shouldn’t be stressful. Let SkyRun ease your worries and increase your revenue with our vacation rental management solutions.

Why choose SkyRun? As a locally owned & operated business, our homeowners are not just a number to us, they’re our neighbors. But as a franchise, we have access to tools and tech that help you stay ahead of the game. That’s why thousands of second homeowners trust us with their properties.

Learn More

SkyRun has done an amazing job with my beach condo. They pay attention to every detail and provide incredible service. They are super responsive and go way above and beyond. In just a very short time they have secured a large number of bookings for my unit. Exceptional company to work with and I highly recommend them.

Nan S.Sarasota, FL

SkyRun has been wonderful to work with. They are very forthcoming and professional. The team does an outstanding job taking care of both property owners and guests alike.

UliSarasota, FL
“This condo managed by SkyRun was amazing! Beautiful and in pristine condition! Short drive to beaches and walkable to Main St. Restaurants. The Hosts were wonderful to work with and great communicators. We loved our stay and amazing service by the hosts at Skyrun! I highly recommend this condo and SkyRun!”
TheresaStayed in Sarasota, FL

Frequently Asked Questions

SkyRun provides photos, virtual tours, maps, amenity details and reviews about the property you will be renting. Our staff has first-hand knowledge of each property, so don't hesitate to call us if you have any questions.

Our rentals come fully furnished including TVs, high-speed internet, linens and towels, a microwave, dishes, pots, pans, and other kitchen essentials.  We sweat the details and provide supplies like shampoo, conditioner, tissues, paper towels, dishwasher detergent, soaps, trash bags, etc.  We provide everything you expect from a fine hotel, and then some. Refer to individual listings to see more amenity information, and please contact us directly if you still have questions.

When you book direct with SkyRun you avoid paying service fees that traditional listing sites like Airbnb and Vrbo charge. Our prices are also competitive with rent-from-owner rates, but we offer professional service, optional travel insurance, and immediate on-site assistance should the need arise.  In addition, we offer exclusive discounts from local businesses, available only to SkyRun guests.  SkyRun can help you plan and save on your entire vacation experience, not only the rental itself.  We also offer a fantastic value on lodging booked within 30 - 60 days of arrival with our dynamically adjusted rates.

Travel insurance is an optional addition to your total rental charges. It is offered on our reservation form at the time of booking. It is also usually offered at the time of booking when you booked with a 3rd party booking site. You can also add travel insurance onto your reservation within 48 hours of booking with SkyRun. The cost of travel insurance varies and is usually between 7% - 9.5% of your total reservation cost depending on the coverage type.  If you do not have travel insurance, you can not cancel your reservation for any reason.  If you have travel insurance and need to cancel or make a claim refer to your specific policy. More information about the travel insurance policies SkyRun offers can be found here.

You can rent any of our properties by booking directly on this website using a credit card or you can call to book a reservation if you would like to speak with a vacation planner. When you book, 1/3 of your total reservation cost or a minimum of $300 is charged as a non-refundable deposit to secure your rental. 30 days before your arrival, the remaining amount is due and becomes non-refundable if you need to cancel for any reason (see travel insurance above for exceptions).  At this time, the credit card we have on file will be automatically charged for the balance.

For most properties, SkyRun utilizes a convenient keypad lock system which allows you to enter your vacation rental using a personalized access code, as opposed to having to pick up a key and worrying about keeping track of it during your stay. This also saves you the trouble of coming to a check-in center beforehand. Your welcome packet will be in your rental upon arrival, and our staff is always only a phone call away if any questions arise.

No smoking and no pets (unless specifically designated as a pet-friendly property) are allowed in the rentals.  House parties and exceeding the maximum occupancy at any time are prohibited. As in your own home, renters are of course subject to citations for noise violations, etc, handed down by public officials. Remember you are staying as a guest in someone's home, where much investment has been made to make your stay enjoyable; please treat all private property with the respect it deserves.

Sign up for emails

Trip inspiration, special offers, and vacation planning tips.

By submitting this form, I agree to SkyRun’s Privacy Policy