358,603 properties available

Located in Kiawah Island, South Carolina, United States. Kiawah Exclusives: 21 Surfsong 21 Surfsong is a single story 3 Bedroom, 3 Bathroom private vacation home in the Vanderhorst Plantation on Kiawah Island. This home offers 3,100 sq feet of classic interiors and an expansive private deck overlooking Canvasback Lagoon for sunning, entertaining or alfresco BBQ dining, only a short 2-minute stroll from the beach! The bright and elegant living room has ample seating for friends and family. The home has a formal dining room and a sunroom equipped with TV and is open to the deck. The library/den has two sofas and a 47" flat screen TV. The large, open kitchen is fully-equipped with modern appliances, an eat-in breakfast area and a TV for the chef in the family. 21 Surfsong comfortably sleeps up to 6 guests in 3 bedrooms. The serene master bedroom has a king sized bed, reading area, TV, large walk-in closet, private bath and opens privately to the deck. The lagoon bedroom has a queen sized bed, adjacent bath and private entrance to the deck. Sh

Located in Kiawah Island, South Carolina, United States. Spectacular Oceanfront Kiawah Home With Pool And Private Boardwalk To Beach This spectacular 9300 square foot oceanfront home is located at 140 Flyway Drive, the most sought after street on the island. The home offers 4 levels of indoor and outdoor living space, 7 bedrooms with private kitchen bathrooms, and it's own private boardwalk to the beach.As you enter the home's unique circular entry foyer, head downstairs to the first level complete with a pool table, tv, wet bar and powder room. This level also boasts four large bedrooms and four in suite-bathrooms. Two of the bedrooms offer king beds, and there is a bunk room with four bunks as well as an additional bedroom with 3 twin beds. A 2nd laundry room is on this level. Head outside from this level to access the covered patio and pool terrace. Upstairs, as you enter the spacious 28 foot high great room, framed by columns, your eyes are immediately drawn to the expansive ocean vistas. This is the main living area and it acts as

Located in Kiawah Island, South Carolina, United States. 65 Surfsong: Pool, Game Room, Easy Beach Access, Beach Gear/Bike Credit Take advantage of special beach gear and bike credit! This beautiful Kiawah vacation rental, located in Vanderhorst Plantation, features 6 bedrooms, a private pool, and a summer kitchen. The home is is a 3-minute walk from the beach.When you enter the home, to the right is a room offering leather seating, a game table, lots of shelving and TV, a bar equipped with all you'll need for preparing your favorite beverages, bar stools, glass backing and shelves behind the bar, a sink and ice maker. The kitchen is both functional and stylish. It provides seating for 6 at the table in addition to seating for 4 on bar stools as well as a small sitting area. The breakfast area leads to a screened porch and opens out to the deck. A formal dining room is perfect for entertaining a large group with seating for 12 or an intimate dinner for two. The first-floor master suite with king size bed is truly a tranquil retreat. This larg

Located in Kiawah Island, South Carolina, United States. NEW LISTING- Pool Coming soon! Gorgeous marsh views! Welcome to this incredible new home at 67 Otter Island Road on Kiawah Island! This 5 bedroom luxury beach vacation rental, located just off of the famed Ocean Course Drive, boasts lagoon and marsh views, a new private pool, and is just a short stroll or bike ride to the beach. It truly is an ideal island and golf getaway!A few highlights:- The porches! Southern-style wrap-around porch with rocking chairs allows one to relax, enjoy the scenic views, and take in the salty island air and a screened porch with conversational seating - ideal for enjoying your morning coffee!- The style! Spacious rooms and beautiful hardwood floors throughout the home, decorated in a comfortable, clean, neutral style. The large living room sectional is perfect for curling up with a book after a day at the beach.- The kitchen! With new appliances, large central island, an abundance of seating, and tons of prep & storage space, it will make cooking and e

Located in Johns Island, South Carolina, United States. NEW YEAR - NEW CRAZY LOW DEALS ON FANTASTIC HOME Kiawah Island Business License # RBL19-005654 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

Located in Kiawah Island, South Carolina, United States. New to the rental market, stunning views, all new furnishings! Renovations are complete, the 2nd floor kitchenette/bar has been removed and we added a 4th bedroom! New rental, like-new luxury home, close to the beach, with all new furnishings! This gorgeous marshfront home is situated within Otter Island, a private enclave on the eastern tip of Kiawah that backs onto the marshes of Bass Creek. Otter Island feels secluded and is just a short walk or bike ride to the beach via a path that leads you across the world famous host of the 2021 PGA Championship, The Ocean Course.Throughout the interior, an open floor plan flows easily between rooms with ample space for family activities, gathering with friends, or retreating for some quiet time. Floor-to-ceiling windows frame the marsh and creek views with an abundance of natural light. The living area, which spreads across two rooms, enjoys a wall of windows overlooking the marsh, a coffered ceiling, fireplace with stone and wood surround w

Located in Kiawah Island, South Carolina, United States. Luxury Oceanfront home, pool, hot tub You've found the most perfect, luxury vacation home on the island! There are too many pictures that won't fit on all websites, see our company site, ESPM Vacation Rentals, for more info and pics. The palatial palace at 38 Surfsong Road lies directly on the Atlantic Ocean, separated from the soft sands of the beach and the soothing sounds of the waves only by the graceful flow of sand dunes, access provided by a private boardwalk.In the front, this beautifully landscaped residence charms with pale shingle siding accented by round porch columns and gracefully curving dormer windows. From the rear, it is awe-inspiring. Three stories of balconies overlook the sea, flanked by two round turrets with wraparound windows. A brilliant blue pool invites private relaxation just steps down from a columned terrace, while a spa and wide, private deck rise beside its waters.Ascend the staircase to the second floor to find a spacious great room with even more spe

Located in Kiawah Island, South Carolina, United States. Oceanfront Surfsong Road: Pool, Oceanview, Boardwalk to Beach! Ideal Kiawah LUXURY! Located on the ocean side of sought-after Surfsong Road within the prestigious Vanderhorst Plantation on Kiawah Island, this enchanting 5-bedroom, 5.5-bath ocean-view home is a must-see for those seeking the pinnacle of a true luxury beach vacation. With a private pool and direct beach access via the home's semi-private boardwalk, this Southern-style gem is just what you've been looking for. Featuring a reverse open floorplan that maximizes the scenic island & ocean views, this home boasts an expansive 2,300 square feet of porches and over 5,000 square feet of tastefully designed interior space, seamlessly combining comfort and sophistication.First Level: - 3 bedrooms (king, queen, and twin + bunk), each with private bathrooms and porch or deck access. - Family sitting room, which can also be used as a game room, with large television. - Wet bar with granite countertops, sink and icemaker. - Ou

Located in Kiawah Island, South Carolina, United States. Spacious Waterfront Home with Lagoon & Golf Course Views - Near Beach 215 Glen AbbeyOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This spacious five-bedroom, five-and-a-half bath home is a haven for outdoor living with large decks, balconies, a huge screened porch, a gas grill, and outdoor enclosed showers. Just a short walk (about 500 yards) around the corner to the beach in Vanderhorst Plantation, this home offers lovely views of the fairway and lagoon behind the house. This home can accommodate up to 12 guests with two kings, three queens, two twins, a double sleeper sofa (in the two queen bedroom), and a single chair that folds out into a twin sleeper bed (in the bedroom with two twins). With seven televisions and free WiFi, you can stay connected during your visit. Although the garages are not used for vehicle parking the driveway will accommodate up to three cars.This non-smoking vacation re

Located in Kiawah Island, South Carolina, United States. SPACIOUS Kiawah Home, Pet Friendly and Private Pool! This exciting vacation home is perfectly located for enjoying the best of Kiawah Island. Golf, bike trails, tennis, restaurants, and beaches are easily accessible. The contemporary design uses skylights, vaulted ceilings, walls of windows, and local artwork to surround guests with the beauty of lowcountry. Step outside to the large screened porch, private pool with natural wood decking, and stunning views of the 8th fairway on the Turtle Point Golf Course. The home is perfectly situated on a large lot for privacy and extra parking.With 5 bedrooms and 5 baths, the floor plan offers multiple sitting areas and space to spread out. Wood floors connect the living areas with a modern kitchen and dining area seating eight. The custom designed gourmet kitchen is a chef's dream. On the large main level is a king master suite with modern en-suite bath and relaxing nature views. The first floor also features a bunk room and queen bedroom. Ea

Located in Kiawah Island, South Carolina, United States. Kiawah Island retreat- 5 mins from the beach-Large deck with pool Nestled within Kiawah Island The Porch House blends into the surrounding trees and marsh setting. Newly constructed in 2022- Designed with key Southern and European architectural features, the Porch house has all elements functional design and sophistication. Only one mile from the The Sanctuary Hotel and bike paths to beach access. The perfect retreat for families or couples. Gourmet chefs kitchen and scullery, open living space floor plan, guest ensuites, laundry room and large deck with plunge pool. Lets not forget the sweeping views out to the Kiawah River for amazing sunsets. Enjoy the peace and serenity of this private retreat.

Located in Kiawah Island, South Carolina, United States. Private Pool! Quiet Street! Lagoon Views! Great Space for Families! Ping Pong! This Kiawah classic features 4 large bedrooms, study, private pool and plenty of activities to entertain the whole group. Located at 50 Salt Cedar Lane, you’re going to love the beautiful heart pine, wide plank flooring and custom wooden trim throughout. Step inside to the welcoming two-story living room ahead. Two tiers of windows showcase the water views while glass doors lead to the outdoor living spaces. The living room opens to the dining room with its sideboard serving nook, tall windows framing the views, and a table that easilyseats ten. The kitchen features a Viking gas cooktop, stainless-steel appliances including a double oven, two dishwashers, and two refrigerators--one Sub-Zero. The center island includes a prep sink, breakfast bar, and granite countertop. Arched windows above the farmhouse sink invite sunlight inside. Also on this level is the master suite. The bedroom is spacious and sunny w

Located in Kiawah Island, South Carolina, United States. Gorgeous Kiawah House with Expansive Marsh and River Views! This house offers a true Kiawah Island retreat with some of the most expansive marsh and Kiawah River views on the island. Centrally located just six blocks past the second gate, guests can conveniently enjoy all that Kiawah has to offer. Upon entering the house, the living room includes a cathedral ceiling with huge windows showing off the expansive marsh and Kiawah River views and a large wall mounted TV. The dining room includes a dinner table that sits eight. The wrap around kitchen includes another table that sits six along with four bar stools for extra capacity. The kitchen is stocked with all necessities for eating, cooking, and cleaning, with a standard refrigerator/freezer, microwave, and wine cooler. An additional living room off the kitchen has another large wall mounted TV. The screened-in porch is the perfect place to begin the day with a cup of coffee or enjoy a cocktail at sunset. The outdoor deck in t

Located in Kiawah Island, South Carolina, United States. Updated island estate with serene lagoon views & 2 decks - bike to beach Trumpet Creeper 43Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled by the lagoon, this lovely home offers a serene retreat just minutes from the beach. At home, share alfresco meals on the large deck overlooking a peaceful pond. A game room and an impressive library of books and movies promise hours of fun. This two-story home boasts luxurious bedrooms and a newly updated kitchen. Island sunshine showers into the main living area through large windows. A sofa and two armchairs provide ample plush seating around the 43-inch TV. A festive tiki bar and a wood-burning fireplace add to the allure. Watch favorite TV shows in the second living area; a twin daybed with a twin trundle provides additional comfy sleeping space. The game room features a felt-top card table and well-stocked bookshelves. Chefs will appreciate the newl

Located in Kiawah Island, South Carolina, United States. Updates abound! Ultimate Kiawah Luxury house Ultimate Kiawah Property! 107 Goldeneye Dr is the quintessential Kiawah vacation house, with total luxury inside and amazing exterior space to enjoy. With seven spacious bedrooms there is plenty of room for everyone! Located on a gorgeous homesite on a quiet cul-de-sac that offers privacy while providing a beautiful golf course view. With windows across the back of the home and a second-floor sundeck, the home was designed to showcase superb views of Osprey Point’s 16th fairway. The outdoor living area, which include a pool, waterfall spa, gazebo with a full summer kitchen including plenty of seating at the bar or outdoor dining table, a screened porch, and multiple decks take full advantage of the stunning surroundings. There is also a screened porch that offers another dining area and overlooks the back patio. A circular brick entrance leads to the striking entry that welcome you inside this unique, one-of-a-kind custom designed hom

Located in Kiawah Island, South Carolina, United States. New home in popular Indigo Park New construction and stunning, this 4 bedroom is one of the newest additions to the Indigo Park family of homes. Perfect for family and friends to gather and entertain in an idyllic setting located next to the beautiful salt marsh on the fringes of Bass Creek. It is also located just steps away from Indigo Park’s private three-acre park. Designed with minimal maintenance and minimal impact on the environment on Kiawah Island, this environmentally sustainable home was built using the highest grade, earth-friendly, sustainable materials proved to reduce greenhouse emissions, lessen lasting effects on the environment, and provide durable, low-maintenance. Don't miss this opportunity to enjoy your vacation rental responsibly! Enter the home to a bright and airy kitchen, plenty of counter space and high end appliances perfect for entertaining your guests. Continue into the spacious dining and living room that take full advantage of the stunning views. Wi

Located in Kiawah Island, South Carolina, United States. Lowcountry Elegance, outstanding views Located on a quiet cul-de-sac behind Kiawah’s second security gate, in Vanderhorst Plantation, 761 Curlew Ct is an immaculately cared for Lowcountry home overlooking hole no. 2 of the Tom Fazio-designed Osprey Point golf course. This stunning home is within walking distance to the community crab and fishing dock or a short bike ride (7-8 min) to Osprey Beach, a private beach access point just for guests in the Vanderhorst Plantation. Private and centrally located, residents enjoy convenient access to all of Kiawah’s world-class amenities and distinctive venues, including fine dining, tennis and golf!This superb residence is adorned with professionally designed landscaping featuring native Lowcountry palmettos, royal palms, and crepe myrtles which attend the driveway and front lawn. An elegant staircase rises to a covered portico with a windowed front door and rich wood flooring where you can rest outside and enjoy the island breeze.Step inside to

Located in Kiawah Island, South Carolina, United States. NEW! 156 Bluebill: Stylish 5BR Home, Bike to Beach, Beach Gear/Bike Credit Take advantage of special beach gear and bike credit! This Kiawah Island vacation rental offers 5 bedrooms, a spacious screened porch, a deck, and a 4-minute bike ride to the beach. Settled in Vanderhorst Plantation, this one-story home creates a calm and contemporary feel. In the living area, you will find a cozy couch, two comfortable chairs, and a TV. The fully equipped kitchen offers beautiful white cabinetry, a spacious center island, barstool seating as well as additional kitchen seating perfect for your morning coffee. The dining area is sure to please as it is in close proximity to the kitchen area and provides ample seating for your whole party. The primary bedroom offers a king-sized bed, a TV, ample closet space, and a private primary bathroom. The full bathroom features a double sink vanity and a glass walk-in shower. The secondary bedroom also offers a king-sized bed, a TV, and deck access. The thi

Located in Kiawah Island, South Carolina, United States. 735 Virginia Rail: Pool w/ Stunning Lagoon Views, $300 Beach Gear/Bike Credit Take advantage of special beach gear and bike credit! This Kiawah Island vacation rental offers five bedrooms, a private pool and spa, and lovely lagoon views. The home is about a 15-minute bike ride to the beach. High ceilings and views of the lagoon through glass doors and windows welcome you into the home’s inviting living area. The main living area offers comfortable seating for the whole family around a large TV and opens to the kitchen and dining areas. Enjoy preparing meals and snacks in the gorgeous kitchen, featuring plenty of counter space, a breakfast bar with barstool seating for three, and updated appliances. The adjacent dining area overlooks the lagoon and a long wooden table with dining space for six. This home also has a den with a TV and bonus room with a pool table and ping pong table. Located on the first floor, the master suite offers a king-sized bed and luxurious private bathroom with a

Located in Kiawah Island, South Carolina, United States. Kiawah Exclusives: 12 Falcon Point Road Immerse yourself in the natural beauty of Kiawah Island from 12 Falcon Point Road, a 5 bedroom, 4.5 bathroom luxury Kiawah Island plantation style home with Lowcountry elegance amid a private setting. This home is quiet and peaceful and boasts plantation style porches, a private pool, classic interiors and easy access to Kiawah Island’s beautiful beaches. A scenic 12 minute bike ride or 3 minute hop in the car will get you to the beach. An ideal respite from the everyday hustle and bustle! 12 Falcon Point is meticulously maintained, furnished and boasts 4,554 sq ft of exceptional living space comfortably accommodating 10 guests. Highlights include high-end furnishings and wonderful outdoor spaces, a private pool, forever marsh views and expansive decks for year round al fresco enjoyment. The main living area is located on the 2nd level, with bedrooms on the first and third floors. 1st Floor: 3 bedrooms with private baths (1 king, 2 doubles, 2

Located in Kiawah Island, South Carolina, United States. Kiawah Exclusives: 23 Marsh Cottage Lane 23 Marsh Cottage Lane is a luxury 3 bedroom, 3.5 bathroom private Kiawah Island vacation home located in Vanderhorst Plantation This newly updated home features inspiring interiors, a beautifully furnished screened porch, a sun deck with a gas grill and tranquil marsh views, all just a short bike ride from Kiawah Islands scenic beaches and world-class golf courses. The beach is just a 7 minute walk or short bike-ride away! Enter the home to an open floor plan with a large upscale kitchen offering a free standing gas range, stainless appliances and plenty of counter space for food prep. Passing into the arched great room, you'll find a dining table with seating for 8 before flowing into the heart of the living room accented by a large stone fireplace with a mounted television. A cozy den with another TV and couch extends the living space offering plenty of room to spread out and relax after a day at the beach. This beautiful Vanderhorst Plantat

Located in Kiawah Island, South Carolina, United States. The Birdie - Luxury Kiawah Beach House The Birdie is tucked away on a serene culdesac, a hidden gem in the highly coveted Vanderhost Plantation area of Kiawah Island, South Carolina. The 5-bedroom house features a large backyard pool and hot tub—guests have the ability to heat or chill the pool for year-round enjoyment. The home underwent an extensive renovation in 2023-2024, with high-end finishes chosen to create an airy and comfortable beach home. Designed with luxurious beach-style living in mind, The Birdie comfortably accommodates large groups with its open floor plan and two expansive dining tables. Yet, it still offers abundant privacy to guests in each of the five bedrooms, ensuring a relaxing stay for everyone.This charming beach house is conveniently located just a half mile from the beach. Hop on one of the provided bikes and cruise down the shady bike path, Alle of the Oaks, to beach access No. 32; you may even spot one of the local alligators in a pond along the way!Every

Located in Kiawah Island, South Carolina, United States. Large home with extra common area for kids- 1 1/2 miles to beach Tyler Property ManagementRBL21-000362Parking- Four CarsOccupancy- 10 Adults ComfortablyNO PETSNO Pool AccessCustom home with beautiful architectural design. Located beyond the Vanderhorst Gate (The Second Gate), on Kiawah Island. Private corner lot, offering two driveways with parking for total of four cars. The Living Room offers plenty of seating with large T.V. The fire place is off limits and unavailable to guests. Open to Living Room is Formal Dining Room seating eight comfortably. The kitchen has plenty of storage and can accommodate all of your cooking needs with a small kitchen table seating four. The Master Suite is tucked away on the North side of home set in a quiet space with private balcony. The master suite offers a large smart T.V and does not have local cable channels. Please be prepared to use your own Roku remote or sign into your favorite account such as Netflix, Hulu, etc. Off the main entrance are thr

Located in Kiawah Island, South Carolina, United States. Spacious & Modern Home- Pond Views, Close to Beach *2024 Booking Special! Reserve for 7+ Nights in 2024 and get a $250 Reservation Credit! (Ask our team!)*Situated in the heart of the prestigious gated Vanderhorst neighborhood and only a short walk to the miles of sandy beaches of Kiawah Island, this lovely 4-bedroom home is an ideal escape for your next Charleston beach vacation. Highlighted by incredible panoramic views of Canvasback Pond which you can enjoy from both screened porch and spacious back deck, this is sure to be one of your new favorite properties on the island.The main living area features expansive windows and hardwood floors allowing for endless natural light to flow through the home. Unwind after a day on the beach on one of the comfortable sofas as you stream a favorite series on the large smart TV. There is a sound dock here as well. The open kitchen and dining area, with access to the screened porch and outdoor deck, is perfect for entertaining. The outdoors are