Longboat Key Vacation Rentals

A variety of single family homes, condos, and townhomes on Longboat Key

USA > Florida > Sarasota > Longboat Key

Visit Longboat Key

Escape to the serene and sophisticated ambiance of this tranquil community, nestled on a picturesque barrier island in Florida. With its breathtaking beaches and pristine, crystal-clear waters, relaxation is inevitable. Unwind on the shores or indulge in rejuvenating spa experiences. Dive into thrilling water activities or simply sit back, relax, and bask in the coastal charm.

Your Longboat Key Vacation, Your Way.

Featured Longboat Key Rentals

Your Personal Vacation Planner

Locally Owned and Operated In Longboat 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

Longboat Key, FL

Guest Marketing and Vacation Planner

Let's Talk!

Lido Key

Get ready for unbeatable sunsets and turquoise waters at Lido Key Beach, a lovely seaside paradise. This family-friendly beach is known for its natural beauty and more relaxed vibe.

Rich in ecology, Lido Key is the place to go for deep sea fishing, dolphin watching, or sunset sailing. After a day on the sand, don’t miss the shopping and dining at nearby St. Armands Circle.

Longboat Key

Looking to escape the crowds and enjoy a luxury beach experience? Longboat Key’s 10 miles of uninterrupted coastline offer elegance and exclusivity. Enjoy the many amenities of the area, including waterfront golf, fine dining, and cultural activities, all while taking in the breathtaking beach views.

Coquina Beach Florida

Coquina Beach, nestled on the southern end of Anna Maria Island in Florida, embodies the serene beauty of the Gulf Coast. Known for its powdery white sands and clear turquoise waters, Coquina Beach offers visitors a quintessential Florida beach experience. The beach stretches for miles along the coastline, providing ample space for sunbathing, picnicking, and leisurely strolls.
Shaded picnic areas and pavilions dot the landscape, offering respite from the sun and picturesque spots for gatherings. The beach is also equipped with amenities such as showers, restrooms, and ample parking, ensuring comfort and convenience for all who visit. 

Bradenton Beach

Bradenton Beach, located on the southern end of Anna Maria Island in Florida, offers a delightful blend of laid-back atmosphere and vibrant seaside activities. With its pristine sandy shores and stunning views of the Gulf of Mexico, Bradenton Beach attracts both locals and tourists seeking relaxation and recreation.

Bradenton Beach is renowned for its fishing pier, where visitors can cast a line or simply enjoy panoramic views of the coastline. Water enthusiasts can indulge in activities such as swimming, parasailing, and jet skiing in the clear waters. The beach also hosts events and festivals throughout the year, adding a festive vibe to its already lively atmosphere. .

Golf and Tennis

At The Longboat Key Golf Club, boasting two remarkable courses, you’ll find yourself immersed in top-tier golfing amidst picturesque landscapes. Tennis enthusiasts will also appreciate the Longboat Key Public Tennis Center, where you can enjoy thrilling matches while improving your backhand.

Spas and Wellness

Indulge in rejuvenating massages, soothing facials, and revitalizing body treatments amidst serene coastal surroundings. Experience the epitome of relaxation and self-care with expert therapists and luxurious spa amenities.

St. Armands Circle

St. Armands Circle is a vibrant shopping and dining district, offering a variety of boutiques, galleries, and specialty shops. With its cobblestone streets and diverse range of restaurants, it’s the perfect place to enjoy a delightful meal or leisurely evening stroll. Throughout the year, St. Armands Circle also hosts many events such as craft festivals, sidewalk sales, exotic car shows, and holiday-themed events.

Boat Trips

Embark on an unforgettable aquatic adventures as you immerse yourself in the beauty of Longboat Key’s surrounding waters. Opt for a thrilling dolphin sunset cruise or extend your adventure with a half-day fishing excursion or full-day island exploration trip. Some trips feature snorkeling and encounters with dolphins, manatees, and other marine life.


Longboat Key is renowned for its upscale dining scene, where fresh seafood takes center stage and outdoor dining thrives in the tropical ambiance. Indulge in the inventive, upscale menus that blend southern influences, locally-sourced ingredients, and innovative flavors. From upscale establishments to charming cafes, the culinary scene is vibrant and varied.


Embrace the adventurous spirit at Longboat Key as you dive into a world of exciting watersports. Explore stand-up paddleboarding, jet skiing, or kayaking while keeping an eye out for local wildlife, including dolphins, sea turtles, and diving seabirds. Enhance your experience by joining a guided adventure, led by experts who know exactly where to spot these amazing creatures.


Cast your line and reel in an impressive variety of species such as snook, flounder, ladyfish, pompano, and speckled sea trout. Explore pier fishing at Bayfront Park, the fishing pier behind Mote Marine, or the Longboat Key Public Pier. For a thrilling challenge, venture to the Longboat Key Pass Bascule Bridge where pompano, bluefish, sheepshead, snook, and snapper await your skilled angling.

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 Longboat 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 Longboat 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 Longboat Key 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 Longboat 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 Sarasota 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 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

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

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