Holiday houses in Sea Pines

Sea Pines house ~ Golf Sim / Putting Green / Games

Town of Hilton Head Island STR Permit Number: 064406 Centrally located in Hilton Head Island just within the gates of Sea Pines, with golf simulator, outdoor putting green, 2 game rooms, and a backyard area with games, outdoor dining, fire table & seating, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 kings and 4 doubles), this luxurious space will offer unparalleled comfort, amenities, and the perfect location for you to use as your central base to enjoy the best of HHI.

Renovated 1BR HHI – Walk to Beach & Salty Dog Café

Welcome to your home away from home on Hilton Head Island! Stay steps from the beach in this newly renovated 1-bedroom villa with all new furnishings. It is the perfect blend of comfort, convenience, and coastal charm. Nestled just a short walk from the beach and the famous Salty Dog Café, you're in the heart of Sea Pines fun with dining, shopping, biking, pickleball and sun-soaked relaxation right at your doorstep, not to mention nearby access to some of the state’s most iconic golf courses.

Sea Pines Oasis | Pool + Golf Views | Sleeps 12

Escape to 7 Red Maple Road, a Sea Pines retreat managed by Host & Home, overlooking Heron Point by Pete Dye. This 4BR, 4BA home features upscale interiors, en suite bedrooms, and a private pool with sweeping golf views. Located minutes from Harbour Town, Sea Pines Beach Club, and top golf and tennis, it is ideal for families and groups seeking a seamless, high quality Hilton Head experience with comfort, space, privacy, and one of the most desirable locations in Sea Pines for your next stay.

2031 Deer Island Treehouse - Walk to Harbour Town

Take in the natural beauty of birds bouncing from moss drapped oaks to Carolina pines and the friendly deer roaming freely. 150 yards behind the Harbour Town Lighthouse and Marina with a variety of water sports, dinner cruises, shoppes & restaurants. Take a free seasonal Trolley Ride from the Harbour Town Stop to Sea Pines Beach Club or Salty Dog Marina & Pool. The Harbour Town Golf Links and Sea Pines Resort Tennis Club are a short walk. Easy beach access to 11 miles of sandy shoreline!

Luxury Penthouse in the Heart of Harbour Town

We offer a weekly a 10% off 7 nights or more. Discount is automatically applied. Plan your next vacation in this luxurious villa. It’s prime location is steps from Hilton Head’s iconic lighthouse, marina, shops and restaurants. There are only 9 villas in the this building. This unit is on the top floor on the end closest to the marina. If you are familiar with Harbour Town, Mariner’s Way is located between the live oak trees on the sandy playground and the Crazy Crab.

5 Star Location-Harbourtown-Walkable Area

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

CoCo's Island Treehouse

Unwind in a cozy, character-filled treehouse surrounded by nature, with seasonal access to a community pool. Tucked in a wooded setting just a short walk to the dog-friendly beach, shops, & restaurants of Harbortown, this retreat offers the perfect blend of privacy & convenience. Reach the wide shores of the Sea Pines Beach Club by car, bike trail, or trolley. After a day out, unwind with the 85-inch TV, cook in the fully equipped kitchen, or fire up the grill.

Harbour Town Lighthouse & Sunset Views | Sea Pines

Enjoy direct Harbour Town lighthouse, yacht basin, and Calibogue Sound views from our beautifully updated Sea Pines condo. Located in Ketch Court, this cozy coastal retreat puts you steps from Harbour Town dining, shopping, sunsets, bike paths, golf, and the marina. Perfect for couples, golfers, or a small family looking for one of Hilton Head’s most iconic locations. Come relax and unwind and take in all that Harbour Town has to offer!

Waterfront Tree House | HT Pool | Private Office

One of our newest homes, see our over 1000 *5*-star reviews. Calibogue Escape-Harbour Town Treehouse in Sea Pines Sailboats, Dolphins, Sunsets, what else could you ask for? This treehouse offers floor-to-ceiling windows with unparalleled views and the perfect setting for a perfect escape. Located on a dead-end street on Deer Island, just steps from Hilton Head’s Harbour Town and the Yacht Basin, this hideaway could not be more perfect.

Sea Pines Villa - Walk to Beach, Golf and Tennis

This pristine Sea Pines villa has undergone significant renovations and upgrades, enhancing your stay with modern comforts and amenities. Just a five-minute stroll to the beach, this property is perfect for beach vacations and golf trips. Enjoy views of the tree-lined lagoon and renowned Atlantic Dunes Golf Course. The villa offers a private, professionally maintained putting green, and private tennis courts are only steps away.

Seapines-2025 Remodel, Walk to Beach, End Unit

This newly remodeled, private end unit is located just 1/2 miles from the Sea Pines Beach Club. Stunning updates including fresh paint and furniture, updated baths and flooring. Pet friendly, yet pristine, crisp and tastefully coastal, your whole family will enjoy the thoughtful choices in #10 Lighthouse. This property's lovely, sunny exposure and open layout make it the perfect location for your relaxing Sea Pines getaway.

Evening Ember | Spa, Fire Pit, Pool Access, Pets

Evening Ember is a refreshed single-level Sea Pines retreat that sleeps 7 and features vaulted living spaces and a private patio with fire pit and complimentary year-round heated spa. Guests also enjoy Harbour Town pool access and a short bike ride to the beach. Pet friendly and close to Harbour Town and Lawton Stables, this cozy island escape blends comfort, relaxation, and convenience.