Vacation rentals in Calibogue Sound

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.

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.

Water Oak 2BDR Luxury OF Stand-Alone w/ Golf Cart

Welcome to Water Oak Cottage, a stunning oceanfront retreat. - A 4-passenger golf cart is included for any reservation created on or after 12/31/25 - Luxuriously decorated with coastal artwork - Open floor plan with comfortable seating and a large flatscreen TV - Fully equipped kitchen and screened-in porch with ocean views - Master bedroom with king-size bed and ensuite bath - Second bedroom with two queen beds and ensuite bath - This property allows only electric golf carts.

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.

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 Oyster Cottage on Daufuskie w/ Golf Cart

A charming historic 3bd/1.5bath cottage that boasts authentic Daufuskie character with all the modern amenities. Located in the Historic district of the island, this cottage is nestled on a large piece of property next door to the Iron Fish Gallery, only a 5 minute walk to the Island Shack. Featured in Southern & Coastal Living, this retreat is perfect for a small group or family to escape and enjoy the serenity and quiet of the island.

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.

Historic Coastal Cottage on Isle of Hope

The Crooked Oak Cottage is a short walk to Historic Bluff drive which overlooks the intracoastal waterway. The Isle of Hope community has several crafts and art shows through out the year. The IOH Marina hosts monthly concerts, kayak rentals and local fishing charters. Crooked Oak is minutes from Wormsloe plantation, Tybee beach, Savannahs Downtown area and many other attractions.

Casula Solis

This is CASULA SOLIS!! Coming to you from the same owners as the CASITA :) Very unique stay with every amenity imaginable including a small 6' x 6' inground salt water dipping pool hot tub and fire pit! Very private 1 bedroom with king bed. I will even cook meals for an extra cost and plenty of heads up. I can send a breakfast/dinner menu upon request yum :)

Luxury Waterfront Tree House | Harbour Town | Pool

One of our newest homes, see our over 1000 *5*-star reviews. Nestled on a tranquil cul-de-sac on Deer Island - an island on an island - our enchanting Treehouse offers the ultimate getaway, surrounded by lush gardens and bamboo forests, stunning reclaimed wood floors, historic Savannah brickwork, and marvelous mid-century design and furnishings.