Kiawah Island Vacation Rentals

Condos and single family homes for rent in and around Kiawah, South Carolina

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Visit Kiawah Island

Fall in love with South Carolina’s Lowcountry when you rest and recharge on Kiawah Island. This barrier island brims with natural beauty, from miles of coastline featuring pristine beaches to inland waterways weaving their way through the landscape. Spy seabirds hard at work securing their next meal or watch turtles dive below the water. Take a break from nature and immerse yourself in world-class golfing, tennis, and biking as you wind along the 30-mile Kiawah Bike Trail. Enjoy shopping and dining, outdoor activities, natural beauty and the laid-back atmosphere that comes with island life.

Your Kiawah Island Vacation, Your Way.

Featured Kiawah Island Rentals

Your Local Team

Locally Owned and Operated In Kiawah Island

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.

With a passion for transforming vacation experiences and a sharp eye for emerging market opportunities, Matt leads the business development efforts at SkyRun Kiawah. Leveraging years of experience in hospitality and rental management. His forward-thinking strategies have optimized rental income for property owners!

Matthew Demirjian

Kiawah Island, SC

Owner of SkyRun Kiawah Island

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Kiawah Island

Kiawah Island offers 10 miles of oceanfront beach and plenty of space to play, relax or walk. Much of the beach access on Kiawah is private, but available to property owners and their vacationing guests. On the west end of Kiawah, Beachwalker Park (the only public beach access), offers oceanfront plus river views! Make your perfect beach day here with amenities that include boardwalk and handicap access, life guards, beach chair rentals, restroom and picnic areas.

Seabrook Island

Nearby Seabrook Island offers a  private community for homeowners and their guests. Pelican Beach’s picturesque sunsets leave sea lovers breathless with. The Atlantic Ocean and the Edisto River come together near here, offering light currents and easy waves. North Beach’s active lifestyle invites you to try horseback riding on the beach, walk your dog off  leash, and take in all that Mother Nature has to offer. 

Edisto Beach

With one and a half  miles of beach, seashells galore, and scenery to spare, Edisto Beach is the place to truly disconnect. Shell Island, a sandbar laden with seashells, is just across from Jeremy’s inlet. Word to the wise: Ask a local pro, like Botany Bay Ecotours, to take you on a private tour so you get there and back safely. The currents are strong! 

Don’t forget to check out Driftwood Beach, a local and remote paradise, for spectacular aged driftwood.

Folly Beach

One of America’s last true beach towns, Folly Beach lives by its own rules and the beach town vibe is alive and well. With six miles of beachfront, Folly Beach is ideal for sunbathing, relaxing, walking, biking, swimming or surfing. Folly Beach County Park, on the west end of the island, has beach access, dressing rooms, picnic areas, chair and umbrella rentals, and more. Skimmer Flats, a major Eastern Brown Pelican rookery, can be seen  from the west end of the park, as well. Walk the Folly Beach Pier and don’t forget your surfboard! 


The Kiawah Island Golf Resort is a premier destination for golf enthusiasts. Boasting world-class courses, revered for their impeccable design and challenging layouts, this resort hosts several prestigious tournaments. Seabrook Island is home to both Crooked Oaks and Ocean Winds courses. These courses both offer challenging play with undisturbed natural surroundings. With many championship courses to choose from, this is a golfer’s paradise.

Exploring on Bike or Foot

White-tailed deer,  loggerhead turtles, and of course the sea birds that make the Lowcountry home welcome you to explore the walking and biking adventures lining Kiawah Island. Scale to new heights when you take the boardwalk to Marsh Island Park’s lookout tower. Your payoff?  Panoramic views of the Kiawah River. While you’re at the park, take a quick loop along the one-mile walking and biking trail. Speaking of biking trails, March Island is only one destination along the 30-mile Kiawah Island Bike Trail. Simply put, there is no better way to breathe in the salt air and explore the tree-shaded stretches along this path that weaves its way along the coast and into Kiawah’s tree-lined enclaves. 


Thrill as you cast a line off the barrier islands of Kiawah. The waters teem with different kinds of fish, depending upon when you visit. As the waters warm in the spring, inshore fishing has the flounder and sea bass biting. The best time to reel in the heartiest catch is between April and December. Explore guided fishing charters and venture into deeper waters where mahi mahi, tuna, sailfish, grouper, and more big game fish can have you racking up serious bragging rights.


Dive into the crystal-clear waters or glide on the surface in a rented kayak or stand-up paddleboard.  Discover the art of riding the waves with private or group surfing lessons. For the more adventurous, jet skiing, parasailing, flyboarding, and wakeboarding await. Delve deeper into the maritime wonders with boat rentals and charters, ensuring an unforgettable exploration of these captivating islands. Unleash your inner adventurer and make a splash in an unforgettable aquatic playground.


Nestled in South Carolina’s Lowcountry, Charleston dazzles with Southern hospitality and history. Pristine beaches, national parks, history, shopping, and dining make this year-round destination special. In fact, Travel & Leisure Magazine voted Charleston the #1 Small City in America and the World. Find out why when strolling down King Street and through the Market. Splash in the beaches’ blue waters or spend the day touring, kayaking, or fishing the rich marshes and waterways then hit one of our locally-owned restaurants. Whatever your days and nights hold, come see why they say, “Once you visit, you’ll never want to leave!”. 


The esteemed Kiawah Island Golf Resort boasts an impressive collection of 22 tennis courts, nestled amidst breathtaking natural surroundings, earning accolades year after year. Seabrook Island presents professionally maintained clay courts, complemented by a well-equipped Tennis Pro Shop. 

Freshfields Village

Uncover a world of shopping and dining delights at Freshfields Village on Kiawah Island. Savor tantalizing lowcountry seafood or mouthwatering Mexican cuisine. Explore a diverse range of shops, offering stylish clothing, accessories, shoes, as well as groceries, pet supplies, and health and beauty products. Pamper yourself with rejuvenating spa services, adding a touch of relaxation to your island experience.

Fort Sumter Tours

Accessible only by tour boat concessioned by the National Park Service, Fort Sumter offers a walk back to the starting point of the Civil War. Multiple daily departure times from Liberty Square in downtown Charleston or Patriots Point in Mount Pleasant allow you to set off for the park where a National Park Ranger meets you to walk you through an hour-long tour. If you’re in Charleston on a summer Friday, dinner cruises allow you to take in the harbor’s beauty, history, and enjoy the region’s fare.

Beach Gear

Rent beach chairs and umbrellas on Kiawah at Island Beach Services or on Folly at Folly Beach Chair Company.

Beach Games

Don’t lug your beach games and baby gear. Rent them from Beach and Games to Go.

Bike Rentals

Want to explore Kiawah or Folly by bike? Visit Seaside Cycles on Kiawah or Folly Beach Adventures on Folly Beach.

Golf Carts

Get around Folly by golf cart. Rent one from Folly Beach Golf Carts.

Check-In Instructions

Check-In | Check-Out Times

Check-in is 4:00 p.m. Eastern and check-out is 10:00 a.m. Eastern.  A check-in instructions email will be distributed to guests 7 days prior to arrival date containing 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 usually only be confirmed on the day of arrival, but call or email us ahead of time. If we can provide an early check-in, we will.


Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with SkyRun Kiawah. Late check-outs must be coordinated directly with the SkyRun office 24 hours prior to check-out day and time. Please note that if we have an incoming guest on the same day as your departure we will not be able to accommodate a late check-out.  We ask that guests remove major trash from the unit, return the furniture to it’s original location, and load and run the dishwasher.


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.

What To Expect

Each of our Kiawah, Folly and surrounding area vacation rentals is a 2nd home to another family who have chosen to share their home with travelers like you! These owners enjoy their properties regularly for themselves, friends and family, and have lovingly outfitted and appointed their rental home!

These property owners have selected SkyRun Kiawah to professionally manage their home and care for you – their guests. SkyRun Kiawah is independently owned and operated by people that live in and are passionate about this area. Your SkyRun host will be glad to help you take care of any needs you have while staying with us. They can also share their favorite activities and local recommendations to make sure you have a wonderful experience. Hence our motto: Local Touch, Local Fun!

Since each rental home is unique, we recommend these tips:
TIP 1: Check the details and photos of the home you would like to rent to make sure it has everything you want and need. SkyRun tries very hard to show you what you’ll love and what you should be aware of with each rental property.
TIP 2: Most of SkyRun’s property listings feature virtual tours. Use the virtual tour to walk around in the home as if you were there! AND CHECK OUT OUR REVIEWS! There’s nothing like a previous guest’s testimonial to point a fellow traveler in the right direction.
TIP 3: Use the webchat feature to communicate in real-time with local SkyRun staff. We are intimately familiar with each rental home and will be glad to help you evaluate which rental home fits all of your wants and needs.


Property Damage Waiver

Enjoy peace-of-mind with our incidental damage protection.

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:

  1. Your intentional acts or gross negligence.
  2. 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).
  3. Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you.
  4. 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:

  1. Take all reasonable, necessary steps to protect the property and prevent further damage to it.
  2. Report the loss in writing (email ok) prior to check-out to the SkyRun staff.
  3. 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.

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 exceeded our expectations as a management company. They have brought great peace of mind over the care of our vacation rental home.

Vic & SusieKiawah Island, SC

“My property’s income has doubled in the last year! SkyRun is a great business partner to me and their willingness to listen and grow revenue has been stellar.”


Kay JohnsonDestin, FL

My relationship with Skyrun (Leidy) is great. The vibe we
have works well for the goals we have achieved.

MelvinFort Lauderdale, FL

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Kiawah Island 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% - 10.8% 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/or emailed to you shortly prior to your arrival, and our staff is always only a phone call away if any questions arise.

Although specific house rules may apply to each individual property, there is no smoking and no pets allowed in the rentals (unless specifically designated as a pet-friendly property and any associated pet fees paid).  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.

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