Holiday rentals in Calibogue Sound

Daufuskie Paradise: Oceanfront/3 Suites/Huge Porch

Daufuskie Paradise cottage blends luxury, wellness, and oceanfront living just steps from the Atlantic. Thoughtfully designed for comfort, it features three spacious suites with firm Purple® mattresses, 100% cotton bedding, feather pillows, down duvets, and Turkish cotton towels. A whole house NUVO H2O filtration system provides cleaner water for drinking, cooking, bathing, and laundry. Enjoy a gourmet kitchen, expansive screened porch with dining and relaxing amenities and stunning ocean views.

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Guest favourite

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.

Luxury Home All New, Dogs OK, Near beach, NEW POOL

It's time to relax & enjoy this newly renovated home on one of the more desirable streets in Sea Pines. NOW with a NEW POOL. Dog Friendly. (W/ APPROVAL & $200 Pet fee) 4 min bike - 7 min walk to one of the most premier SECLUDED beaches on the east coast. (Read reviews) This unique home offers the seclusion, privacy with plenty of space for your family to spread out and make memories. This house is in highly desired south end/ south beach area of Sea Pine. We are CLOSE TO THE BEACH.

1608 Port Villa @ Sea Pines | Water Views

Escape to this waterfront 3 bedroom townhome in the South Beach Marina area of Sea Pines Resort. Sleeping up to 8 guests, this three level retreat features two king primary suites, a twin suite, private ensuite bathrooms for every bedroom, and private balconies with water or resort views. Enjoy the fully equipped kitchen, updated 2026 living and dining room furniture, and easy access to beaches, biking trails, golf, tennis, dining, and marina activities throughout Sea Pines.

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Guest favourite

Daufuskie Island Beachside Escape • Birdsong Oasis

Accessible only by boat or ferry, Birdsong Oasis is a serene studio retreat with two queen beds featuring luxury Saatva mattresses, a kitchenette, spacious bath, and screened-in porch. Set between the salt marsh and beach in Daufuskie Island’s historic Melrose community, it overlooks the peaceful marsh beneath moss-draped oaks and is just steps from uncrowded white-sand beaches—perfect for swimming, beachcombing, birdwatching, or simply slowing down to island time.

Sea Forever - an iTrip Hilton Head Home

Welcome to Sea Forever! Located less than 50 yards away from the beach, this bright & airy end unit villa within the Beachside Tennis community in the South Beach area of Sea Pines Resort on Hilton Head Island is very well appointed and tastefully decorated. Situated on the third floor above the community pool and with spectacular views of the Calibogue Sound, this villa allows guests to relax and enjoy all of the peaceful tranquility of Hilton Head.

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Guest favourite

The Houseboat on Tybee Island

Located at the Tybee Island Marina on Lazaretto Creek, along the western boundary of Tybee Island, The Houseboat offers spectacular sunrise and sunset views nestled in a serene spot between the beach on Tybee or a day exploring Savannah. Due to its location on a floating dock in a tidal creek, with low tides making for a difficult/steep transition between the floating and stationary docks, The Houseboat is not ideal for guests with mobility issues.

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.

HHI South Beach at it's Best! Sea Pines

The two story floor plan has 4 bedrooms, 4.5 baths. The lower level has a garage, three bedrooms, three bathrooms and a covered porch. Upstairs you will find the main living area, gourmet kitchen, dining area, 2 decks, the master bedroom/bathroom, laundry room and half bath. There’s an open floor plan that flows from the kitchen to the dining room right out to the balcony overlooking Braddock Cove and the South Beach Marina.

Canopy House | Walk to Harbour Town | Marshfront

Canopy House is an artfully curated retreat in Sea Pines, nestled among live oaks and Spanish moss, where walls of floor-to-ceiling windows frame sweeping views of the tranquil salt marsh along the serpentine Heddy Gutter Creek. Walk or bike to Harbour Town for dining, live music, and shops, or spend the day at the beach. Return to a peaceful oasis where nature and design inspire meaningful moments together.

Top guest favourite

Guest favourite

Harbour Town Tree House | Private Office | HT Pool

Please see our almost 1000 5-star reviews at our other properties. Enjoy unbelievable tranquility high in the Sea Pines tucked away on Deer Island next to Harbour Town. Walk to the shops, restaurants, entertainment, and the Yacht Basin in just minutes. Feed the deer from your hand while you connect with nature. The Sea Loft is just one house away from the Turtle Trail that winds along the marshlands.

JonBie Tide's End

Melrose Cottage strategically located on the 2nd row with marsh side setting and ocean view from front of cottage. Private and family friendly cottage with its own tidal creek. Two bedroom/two bath with all the accoutrements of home. Enjoy sunsets over the marsh with your grilled dinner. Golf cart included with your booking. Paddle board & corn hole game for guests use.