Welcome to the Raynor House so named after legendary pirate Captain George Raynor who owned and roamed Kiawah Island in the 17th Century. Captain Raynor anchored two ships on the island from which he would pillage and plunder the Carolina coast. Just as the pirates of yore commandeered priceless bounties from others, we hope you will get a steal on this fabulous vacation home aggressively priced to be the best deal in town in the luxury class. The Raynor House is located on arguably the most prestigious street in all of Kiawah behind what the locals term, “the second gate.” Many families enjoy the kids camp and nature programs at the Night Heron Park.
We are pleased to offer the Raynor House for vacation rentals and are confident that you will not find a better place to enjoy the charm, mysticism and natural delights of the Island while taking in the unique and indelible history dating back hundreds of years inclusive of a one-of-a-kind cast of characters ranging from Native Americans, British settlors and occupiers, Pirates (lots of Pirates), owners and even Union invaders to modern day host of the PGA Championship. This house has been completely remodeled inside and out/head-to-toe and we hope y’all will appreciate the work that has been done across the estate to capture the essence of an Antebellum southern home surrounded by island breeziness.
From the outside as you approach the elegant entrance to the home from an oak and palm lined driveway you will be instantly enamored with the southern charm, seaside colors and wide-swept front porch. Once inside, we hope you will enjoy the new hardwood flooring, vaulted ceilings and stunning windows which flow together from room to room like a symphony. The bright and open design was structured so as to let the island history surround and breathe through the home. When in this home we trust you will feel like you have been transported to another time and another place in the most glorious and relaxed of fashions. To help you soak it all in, please take some time to enjoy the loungers on the back porch and inhale the priceless view of the gorgeous and undeveloped, as the locals call it, Pirate Cove or Wally (think Gator) Pond. From the porch the genius of the understated elegance of the Raynor House is best understood as the home seemingly melts into the landscape of the incomparable low country vistas. Watch for the ripples on the water to let you know when your gator friends are in the neighborhood.
The Raynor House was professionally decorated with all new furniture and accoutrements from Restoration Hardware. The designer set out to form a collaboration of coastal pieces and modern day luxuries and convenience while staying true to the island heritage ensconced in the local environment. As a result, you will have all Viking appliances and sleep in comfort pillowtop beds. This is a large, comfortable home with privacy in all four of the bedrooms. This immaculate home comes with fresh paint, hardwood flooring, countertops, fixtures, furniture and five 50+ inch TVs. We trust your stay will be enhanced with the finest linens and a full complement of kitchen supplies and utensils. The estate also has something Captain Raynor could not have pillaged from all the ships on the all the seas…. Wi-Fi. The four bedrooms are classically acquainted to provide warmth, light and space; each of the four bedrooms has been professionally festooned including a room themed for the Buccaneer in each of us complete with a local treasure map. Step into the master suite and you will be greeted by flowing draperies and window dressings leading to a lovely balcony overlooking Pirate Cove. This room features not only luxury bedding, but also an ensuite bathroom, including a standalone bath and walk-in shower with relaxation comfort bench.
As much as we love the home, if you are on the Island, you need to experience all it has to offer and you will be centrally located to do that as the Raynor House lies in the heart of this coastal paradise. Perhaps the first thing you should do is walk to the beach. Don’t worry, it is a short walk, less than a thousand steps across a beautiful path straight to the sand. Or, you can bike across the island exploring all the wonderful natural beauty, boutiques and eateries. For sure you should explore Night Heron Park and take in one of the festivals or simply smile at the clowns and jugglers. Of course, we suspect you might be interested in golfing. Fret not, you are minutes away from the many world class courses that proudly call Kiawah home. We do no not need to go into detail as Kiawah is, quite simply, golf mecca.
Thank you for looking at the Raynor House. We would love to host you for a stay and please don’t worry…. except for the friendly variety, we guarantee the Villa is 100% Ghost Free.
Kiawah Island Business License #RBL 19-005654 2 Car Garage Maximum - Occupancy 10
Please see contract for additional details.
**SUBJECT TO SHORT TERM RENTAL LICENSE RENEWAL BY TOWN OF KIAWAH**
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RENTAL AGREEMENT - A valid Driver's License and signed Short-Term Rental Agreement are due after booking confirmation.
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a deadlock
About the area
Kiawah Island
Located near the beach, this holiday home is in Vanderhorst Plantation, a neighbourhood in Kiawah Island. Battery Number 5 Marker and McLeod Plantation Historic Site are local landmarks, and travellers looking to shop may want to visit Freshfields Village and Center Street. The Resort Shop and Splash Zone Waterpark are also worth visiting.
Charleston, SC (CHS-Charleston Intl.) - 58 min drive
Restaurants
Jasmine Porch - 10 min drive
Linnette’s - 35 min drive
The Nest Market - 11 min drive
FortyEight - Wine Bar & Kitchen - 22 min drive
River Room at The River Course At Kiawah Island Club - 12 min drive
Frequently asked questions
Is Hands-Down Best Deal in Kiawah! pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Hands-Down Best Deal in Kiawah!?
As of 12 Apr, 2026, prices found for a 1-night stay for 2 adults at Hands-Down Best Deal in Kiawah! on 3 May, 2026 start from S$630, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Hands-Down Best Deal in Kiawah!?
On-site parking is available at the property.
What time is check-in at Hands-Down Best Deal in Kiawah!?
Check-in begins at 3:00 PM.
What time is check-out at Hands-Down Best Deal in Kiawah!?
Checkout is at 10:00 AM.
Where is Hands-Down Best Deal in Kiawah! located?
Located in Vanderhorst Plantation, this holiday home is within 1 mile (2 km) of Kiawah Island Beach and Osprey Point Golf Course. Turtle Point Golf Course and Night Heron Park are also within 3 miles (5 km).
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
It was a great location! We had plenty of space for 4 couples, it was easy to get in and out of the area, an easy walk to the beach and a short drive to all the restaurants and the coffee shop. We had an awesome chef come cook at the house- highly recommend Chef Graham Calabria if you can book him. The whole weekend was top notch! We would love to book again soon!
This home is absolutely lovely and exactly as pictured in the photos! Stayed here with some family and had a small brunch gathering at the house Saturday morning then headed out to explore Kiawah! Both the home and the location were fantastic.
We stayed here 3 nights with 3 kids in tow and had plenty of room for everyone. Kitchen/living/dining area is very spacious and accommodating. Everything was as advertised.
We were attending a family wedding. The house was perfect for 3 generations. It was clean and very comfortable. In addition, it has multiple decks for relaxing outside with a beautiful view of the water. I would stay at this home again.
This home is absolutely spectacular. Has all the amenities you could possibly need very clean host responded extremely fast with any needs. Highly request this home for friends or family vacation about 45 minute drive to downtown. Charleston would definitely come again.
Loved our visit to Kiawah Island with this stunning home to stay in. Tons of space, clean, updated, great floor plan and a perfect deck. The kitchen was very well equipped. We love this house and hope to rent it again.
We booked the house for a wedding at Osprey point and a rehearsal dinner at oceans course. We had a couple issues and the property manager was very quick to address it. The layout of the house was wonderful. I loved the kitchen decorations. The view and the back and the alligators was amazing.
Everything we wanted. Beauty, quiet, accessibility to beach and wonderful golf courses. Biking is pure delight and a must activity to capture the habitat.
Wonderful location and Beautiful Home away from Home
We had a wonderful New Years Eve family celebration at this beautiful home. We wanted an intimate setting for our small family and this was more than we imagined. Comfortable beds, beautiful views, close to the beach, bike trails and a lot of space for us to stretch out and relax. We plan to return next year as well.
The property is in a great location, the back deck is fantastic. The owner worked with us to have an early check-in. The house itself needs some TLC, including new appliances and mattresses. But the price point for this property is lower, so expected it to be rather worn.
Overall we were very happy with the rental. Especially enjoyed the rear deck where we sat with our coffees in the a.m. while watching the gator cruise the canal. Kitchen was well equipped, beds were very comfortable and bathrooms spotless. One recommendation would be to replace the two couches in the living room as they were not easy to sit in. Overall, we were pleased.
Stephen M.
Stayed 2 nights in Nov 2024
About the host
Hosted by Jenny Blaylock
This home is managed by Simplicity Vacation Property Management. The owners have several rental properties from Key West to Catalina Island and their philosophy is to earn income through occupancy; Not Charging High Rates. Therefore, their properties are priced to be the BEST VALUE in their area…and are the nicest! This philosophy is reflected with this luxury home priced like a hotel room, but in a better location!
Why they chose this property
Five Championship Public Golf Courses with amazing club houses located on the island. Miles of uncrowded beaches with body surfing, snorkling kayaking, stand-up paddleboarding, nature preserves, lovely walking and bike paths, great restaurants and awesome and welcoming locals.
What makes this property unique
Close to Championship Golf Courses and uncrowded beaches