Top 10 Luxurious Kiawah Island Oceanfront Rentals

This luxurious four-bedroom Kiawah Island rental offers beautiful views of the Jack Nicklaus-designed Turtle Point Golf Course and its sparkling lagoon. Guests can enjoy a private pool and spa with a wraparound porch, rocking chairs, and an outdoor shower. The interior of the home is surrounded by natural light, and the fully equipped kitchen features white cabinetry and high-end appliances. With a short five-minute walk to the beach and valuable credit towards beach gear rentals, this is the perfect location for a coastal getaway!

Guests can take advantage of nearby biking trails, golf courses, tennis courts, swimming, fishing, crabbing, and more. For a truly unique experience, explore the nearby city of Charleston with its incredible shopping, antique stores, museums, aquarium, and delicious dining.

2. Rare Eight Bedroom with a Private Pool

Filled with 6,000 square feet of space and eight bedrooms and eight full bathrooms, there is no shortage of room in this Kiawah Island rental. The expansive windows, open floor plan, and the centralized sitting room that opens to a lovely sunroom make this home exceptionally comfortable and inviting.

Enjoy wonderful marsh views from the large back deck or take a peaceful bike ride down to the stunning beach that is a mile-and-a-half away from this peaceful cul-de-sac. You and your group will also have access to five championship golf courses, the Kiawah Island Resort Tennis Center, and free wireless internet access.

3. 498 Old Dock: Oceanfront Vacation Rental

This spacious rental home is the perfect destination for your next beach vacation. With five bedrooms, a private pool and spa, a deep-water dock, captivating views of the Kiawah River, and a convenient location in Kiawah’s West Beach area, this home has something for everyone.

Enjoy biking, golfing, tennis, fishing, swimming, and boating, or take a short trip to explore Charleston. Take advantage of special beach gear and bike credit, and enjoy the beautiful sunsets and sunrises from the private dock. With plenty of space to entertain and relax, this is the perfect spot for your next family vacation.

4. 161 Flyway Drive

When you stay at this lovely vacation rental, you’ll get all the comforts of home and more. With five bedrooms, three master suites, and a fully-equipped kitchen, this spacious house is perfect for large groups. Enjoy the view of the 18th fairway of Osprey Point Golf Course from the back deck, or take a dip in the refreshing pool. Plus, guests receive valuable credit to use towards beach gear rentals during their stay!

With 30 miles of flat bike trails, five world-class golf courses, and a variety of other activities, Kiawah Island provides something for everyone. Guests will love 161 Flyway Drive’s comfortable beds, beautiful linens, and top-of-the-line appliances, and appreciate the smooth rental process.

5. Vanderhorst Home With Private Pool & Hot Tub

Located in the idyllic Vanderhorst Plantation residential neighborhood, this beautiful beachside escape features breathtaking views of the golf course and pond. The luxurious 5,200-square-foot home has been designed with the utmost sophistication and elegance. From the formal dining room to the gourmet kitchen with high-end cabinetry and stainless-steel appliances, every room is full of intricate detail.

The large infinity-edge pool and hot tub provide the perfect spot to unwind and take in the stunning views. With four bedrooms, each with its own bathroom, and two porches on the top floor, this property is perfect for families and groups of friends.

6. Grande Osprey Beach Home

Situated in the prestigious second-gated section of Kiawah Island, this coastal home offers the perfect retreat for your next beach getaway. Enjoy spectacular views of the 17th green of Osprey Point Golf Course and Kiawah’s largest canvas-backed pond, or take a few steps across the street to the pristine sands of Kiawah’s secluded Osprey Beach. You and your family can savor the best of Kiawah Island with convenient access to the Beach Club and the Ocean Course.

The home boasts exquisite interior designs, a vast amount of glassed-in spaces providing natural light and areas to accommodate the entire family — as well as a large private pool, gas grill, sun loungers, and plenty of outdoor seating. With a fully equipped kitchen, plenty of counter space and cookware, and entertaining areas like the billiard room and ping pong table, you’ll have everything you need for a memorable vacation for up to 14 people.

7. 136 Flyway

From its six bedrooms and spacious living areas to its private pool and spa, this stunning home has everything you need for an unforgettable stay with family or friends. Located on Kiawah’s most iconic street and just a two-minute walk from the beach, this rental offers easy access to the island’s endless activities — from biking on its 30 miles of cycling trails to golfing at its five world-class golf courses. Plus, guests receive a generous credit to use for beach gear rentals so you can maximize your fun in the sun.

Guests have nothing but positive reviews, raving about the easy access to the beach, the ample amenities, and the excellent customer service from the management company. With its stunning views of the Osprey Point Golf Course and its unbeatable location, this Kiawah Island rental is the perfect home away from home.

8. Ultimate Kiawah Luxury

With its gorgeous homesite on a quiet cul-de-sac, stunning golf course views, and abundant outdoor living space, this custom-designed home will provide unforgettable vacation memories. Staying here provides access to five championship golf courses, the Kiawah Island Resort Tennis Center, a luxurious spa, and many family-friendly activities. Inside, you’ll find a comfortable yet elegant interior that includes an oversized great room, a fully equipped kitchen and butler’s pantry, a dining room, a study, two bedrooms with en suite baths, and a master suite with spa-like bathroom.

There is also a media room, outdoor living area with a pool, waterfall spa, gazebo, screened-in porch, and multiple decks for even more relaxation. With all of the amenities and easy access to the beach, boardwalk, and resort activities, you won’t want to miss out on this amazing vacation rental.

9. Spectacular Oceanfront Kiawah Home

Experience the ultimate getaway at 140 Flyway Drive, a luxurious 9,300-square-foot oceanfront home on a private stretch of Kiawah Island. Enjoy the stunning views of the ocean from the 28-foot-high great room or one of the private balconies.

This home includes seven bedrooms with private bathrooms and a kitchen, a pool table, a wet bar, and an exercise area. As well as its own boardwalk to the beach, the property has a pool and covered patio for outdoor entertaining. With plenty of living space for up to 16 guests, you will have the freedom to do whatever you want as a group or independently. Unwind in an exquisite home that offers all the amenities and comforts you could desire for a luxurious beach vacation.

10. Stunning Kiawah Oceanfront Luxury Rental

This jaw-dropping vacation rental is the perfect place for your family vacation. Enjoy breathtaking views of the golf course and ocean from the rental’s multiple decks while lounging in the private pool and jacuzzi. Inside, you’ll find seven luxuriously appointed bedrooms, each with its own ensuite bathroom, as well as a gourmet kitchen and media room with an 80-inch TV.

The home is conveniently located behind the second gate of the exclusive Vanderhorst Plantation, within walking distance to the Sanctuary Hotel, Turtle Point Golf Course, and other amenities. With complimentary mid-week cleans, a Traeger smoker, outdoor beach games, toys, and more, this property offers all the comforts of home — and then some! You’ll love exploring Kiawah Island’s 30 miles of flat bike trails, five world-class golf courses, and many other outdoor activities.

Discover Kiawah Island’s Hidden Treasures

Ready to turn your dream vacation into a reality? Whether you’re longing for oceanfront rental properties or romantic villas, we’ve got you covered. Don’t miss out on the chance to experience Kiawah Island’s enchantment firsthand. Click below to start planning your unforgettable getaway!