Holiday rentals in Hilton Head Island

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.

“Sea La Vie” 3BR, Sea Pines, Walk to Dining, Shops

Privately-owned 2000 SF one-level home sits on a wooded corner lot conveniently located inside the entrance of Sea Pines Resort. This 3 BR, 2BA home was extensively renovated in August 2020, with inviting French-inspired coastal decor for a relaxing cozy feel. "Sea La Vie" chalet is within walking distance to grocery stores, shops, and restaurants. A short drive or bike ride takes you to the private Beach Club, housing oceanfront dining and bar, upscale facilities, and wide beaches. Bienvenue!

Beach House, Elevator, Sleeps 12

Stroll just a few steps from Fish Haul Beach to discover our haven of relaxation.This newly built beach house boasts 3 bedrooms and 2.5 baths complete with complimentary linens and bath towel sets.Enjoy a fully equipped kitchen, ample dining space,and 2 expansive balconies to soak in the coastal ambiance.Enhance your beach stay with included amenities such as boogie boards,backpack beach chairs and wagons.We've anticipated every need and are dedicated to ensuring your stay exceeds expectations!

Fully Renovated 2 Bedroom Villa - Walk to Beach

Make yourself at home in this comfortable 2 story, ground floor Condo. Easy walk to the beach. Open concept living, dining and fully equipped kitchen and 1/2 bath on main floor. Chose either the comfy King or Queen bedroom with walk-in shower or bathtub of your choice. Private courtyard with Grill and outside seating. All this, in a setting of azaleas, palms and 20 steps to pool with stores and restaurants just 2 blocks away. Please note there is only 1 parking space available for your stay.

Hilton Head Island Beach Cottage/House

Our house is located on the southern end of Hilton Head Island in the North Forest Beach neighborhood. The house is an easy 5 minute walk to Hilton Head's beautiful beach. Heron St offers its own private beach walk. It’s also a 10 minute walk to Coligny Plaza, offering local shopping, restaurants, and a grocery store. The house features a delightful outdoor shower, 2 bicycles and a shed loaded with 2 beach chairs, boogie boards, a frisbee and a surf fishing pole and tackle. STR Permit# 073978

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

Family Memories Are Made Better at Deer Run

Relax with the whole family at this private and adorable 3 Bedroom, one level home just a short bike ride to the beach! Nature surrounds you in the secluded fenced in backyard setting with heated walk-in pool, and spa. This spacious home includes large bedrooms, Open living room with fireplace, and bedrooms. Prepare your family meals in the fully equipped kitchen, dine in or walk out walk-out to the screened porch perfect for family gatherings and memories to last a lifetime. Permit # 32403

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.

*New* Easy Breezy at Hilton Head Beach & Tennis

Newly renovated in March 2026 and completely redesigned from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa. Wake up to sunrise over the Atlantic, grab coffee on your private balcony, and walk to the beach in under two minutes. Spend the afternoon at Hilton Head’s largest oceanfront pool before ending the day with dinner and live music just steps from your condo. Beach chairs, wagon, pickleball, tennis, free parking, & close to the building's only elevator.

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

Panoramic 180° Oceanfront views the Moment You Open the Door! Beachfront Balcony Watch Sunrise/Hear the Waves 1 min walk to Beach! Beachfront Pool, Tiki Bar/Grill KING BED FREE Pickleball, Tennis, Gym HGTV Designer Renovation Two 65" SmartTVs Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest RESORT Beach Bar/Sports Bar 3 Restaurants Bike Rentals on Site 4 Beach Boardwalks Gated 24/7 Security Seasonal Island Trolley Stop

Coastal Fairways

Welcome to Coastal Fairways with private beach access on Hilton Head Island, a 2BR/2BA condo in Shipyard with beautiful golf course views from the unit. Enjoy a bright living space, full kitchen, in-unit laundry, and a dedicated workstation. The community pool is steps away with a covered hot tub and playground. Bike paths, golf, and paved beach access with restrooms and outdoor showers via Shipyard Beach Club are all conveniently located just minutes away.

Upscale Retreat w Pool & Spa | Palmetto Dunes

Experience relaxed luxury in this Palmetto Dunes retreat overlooking the golf course. Designed for comfort and connection, this home offers a private pool and spa, plus an expansive outdoor space with a bar and grill perfect for gathering. Inside, enjoy a chef’s kitchen, multiple living areas, and a quiet office for added flexibility. Just minutes from the beach, golf, and dining, this home delivers an easy, elevated Hilton Head getaway.