Holiday houses in Calibogue Sound

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.

Marshfront gem with private dock; Adults only

Keep it simple at this peaceful and centrally-located place. See stunning sunsets over the marsh from this remodeled home, or from the private dock on a tidal creek. Halfway between Downtown and Tybee Island, on lovely Whitemarsh Island, you are close to shopping and nightlife, but feel miles away! Kayak off the dock, then refresh with the outdoor shower; or bike/walk the nearby Preserve. *Kayaks(2 single, 1 tandem) and bikes(3) supplied, but not beach gear. Chatham County Permit #22-23494

Harbour Town Marina Studio | Walk to Lighthouse

Cozy, bright penthouse studio with direct views of the Harbour Town Marina, just steps from the lighthouse, shops, dining, and golf. The space features a comfortable sleeping area with king bed, sitting space, kitchenette, and full bath with tub/shower combo. Enjoy the small private balcony, perfect for morning coffee or evening sunsets over the marina. Ideal for 1–2 guests looking to enjoy the Harbour Town lifestyle in Sea Pines. Located on the fourth floor with convenient elevator access.

Private Dock | FREE Golf Cart, Kayaks & Bikes

Welcome to Siren & Seafarer Cottage! Immerse yourself in all that Tybee Island offers with your own FREE GOLF CART, BIKES, & KAYAKS. Pamper yourself with this luxurious getaway and nature-lover's paradise. Relax on your PRIVATE DOCK on a cozy swing bed while surrounded by panoramic views of the tidal creek. Nestled amongst enchanting live oaks and marsh-side scenery, you'll soon discover something inherently romantic about this Tybee Island cottage, just 25 minutes to downtown Savannah.

Daufuskie Island Beachside Escape • Birdsong Oasis

Accessible only by boat or ferry, escape to the beauty of Daufuskie Island. Birdsong Oasis in the historic Melrose community is a serene 1BR retreat with two queen beds, kitchenette, spacious bath, and screened-in porch. Surrounded by moss-draped oaks and birdlife, it overlooks a peaceful salt marsh and is steps from uncrowded white-sand beaches—perfect for swimming, beachcombing, birdwatching, or soaking in the island’s quiet rhythms. Discover Daufuskie’s rich history and laid-back charm.

The Beachfield House on Daufuskie w/ Golf Cart

Listen to the waves, walk to the beach, and smell the salt air from this beautiful beach home located on Daufuskie Island, SC. Our home offers the ultimate private island experience as it's located in a small private community. House offers all modern amenities for a comfortable stay including a chef’s kitchen, play area/bikes, high ceilings, three balconies, and beautiful natural light. Four seater golf cart included. Feel like you are staying in the trees and enjoy the coastal outdoors.

Oceanfront Villa @ Sea Pines | Steps to Beach

Set off on your perfect island escape in this serene oceanfront villa tucked within Sea Pines’ South Beach Marina. Wake up to coastal breezes, unwind on your private deck at sunset, and enjoy direct beach access just steps away. Designed for easy, relaxed living, this spacious two-story retreat is ideal for families or groups. Walk to the iconic Salty Dog Café, enjoy the pool, and explore nearby tennis, pickleball, and scenic bike paths.

The Love Bird Suite

Located on the serene and historic Wilmington Island, this space was designed as a romantic couple’s getaway. Enjoy this spacious studio, equipped with a working indoor gas fireplace, a large soaking tub, floor to wall tiled shower, and an outdoor hot tub. Centrally located between Historic Savannah and Tybee Island, enjoy day trips to visit these amazing places and return to a relaxing and romantic retreat style stay.

Penthouse flat in Sea Pines | Harbour Town

Welcome to 681 Mariner’s Way, a beautifully renovated 2-bedroom, 2-bathroom penthouse flat, now available for rent! Formerly a private residence, the unit is situated on the 4th floor, this modern unit offers an open floor plan, flooded with natural light, and stylish, professionally designed interiors—perfect for your Sea Pines Harbour Town retreat. Town of Hilton Head, SC Short Term Rental Permit # 037692

Studio Sea - Free Cart & Grounds Transit!

Centrally located in beautiful Melrose area and just a short walk to the beach. First floor with private entrance, golf cart and grounds transport included with your booking. The whole group will enjoy easy access to everything from this centrally located place. Beach Chairs & Beach Towels are stocked. (no umbrella - bring your Bushimi or umbrella or rent from Daufuskie Waves once on island.

MyStay at 1027 Caravel Ct.-Lighthouse View & Pool!

Harbour Town villa with direct views of the iconic lighthouse and marina. This updated 2BR retreat features luxury vinyl flooring, stainless steel kitchen, private balcony, and elevator access. Walk to dining, shopping, golf, and the Harbour Town Pool. Located inside gated Sea Pines with two gate passes included. Premier views, unbeatable location, elevated MyStay hospitality. Sleeps 6.

4BR | Pool, Spa & Walk to Beach | 32 Baynard Cove

Beautiful 4BR/4BA Sea Pines retreat just 0.5 miles to the beach. Sleeps 10 and features a private pool & spa, two spacious living areas, and a peaceful backyard perfect for relaxing after a day in the sun. Ideal for families and groups, with easy bike access to Harbour Town, South Beach, and scenic trails. Enjoy elevated comfort and signature Beachside HHI hospitality.