Sleeps up to 6

Ideal vacation properties for couples, families & small groups!

Discover the perfect getaway with our vacation rentals on Hilton Head Island that comfortably sleep up to 6 guests. Ideal for couples, families or small groups, these rentals offer spacious living areas, fully-equipped kitchens, and cozy bedrooms. Enjoy easy access to Hilton Head's premier beaches, world-class golf courses, and vibrant local attractions. Our rental properties provide modern amenities, including high-speed Wi-Fi, flat-screen TVs, and private outdoor spaces.

Book your Hilton Head Island vacation rental today for an unforgettable stay in this beautiful coastal paradise, where comfort and convenience meet. Experience the ultimate blend of relaxation and adventure with us!

36 properties available

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 103 Seacrest is beautifully decorated and fully renovated for your comfort and convenience. Here, you will experience only the best. This charming property features two bedrooms, creating a cozy and inviting atmosphere for your stay. Allow me to paint a pictu

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Take in the ocean views at this wonderful 1-bedroom villa. The open kitchen and living area are well-appointed to accommodate all your needs. The kitchen has been recently renovated. The dining table seats 2. The living room has a queen sleeper sofa. The prim

Oceanfront

Where the beach is your backyard. Discover our luxury oceanfront collection.
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Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2538 Gleneagle Green is a pet-friendly Harbour Town villa with stunning views of Harbour Town Golf Course and is located just a short 5-minute walk to the shops and dining at Sea Pines Center, as well as the famed Harbour Town Marina! The open-concept floor

Booked for Heritage

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This gorgeous Sea Pines villa has been recently renovated and features golf and lagoon views. Walk into an open-concept kitchen, dining room, and living room. Relax on either of the comfortable couches in the living room and watch your favorite programs on th

Pet-Friendly

Your entire family deserves time away... even the family dog. Preview our selection of pet friendly properties.
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3 Lighthouse Road Villa

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2 bedroom, 3 bathroom Moorings villa close to the beach (650 feet from beach access; less than a two-minute walk) and the pool (located right outside the villa) in the sought-after Palmetto Dunes Oceanfront Resort on Hilton Head Island This Palmetto Dunes vil

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This Sea Pines villa is outfitted with elegance in every detail, offering guests complete coastal luxury. An alluring yet spacious layout offers guests plenty of room to spread out, all while being together. Upon entry, to the left, you will find the fully

Water View

Enjoy stunning water views from every room. Explore our water view properties.
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1838 Beachside Tennis

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This villa has been fully remodelled in a light coastal design, creating an inviting and serene retreat. This charming space is the perfect spot for a peaceful island getaway, combining modern comfort with classic coastal elegance. As you step inside, you\'l

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. A charming first-floor villa with a walkout balcony offering breathtaking views of the golf course. Nestled in the heart of Sea Pines, this delightful retreat combines comfort and convenience, making it the perfect getaway for golfers and vacationers alike.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This completely renovated (2024) 2 bedroom, 2 bathroom property is perfectly located within steps of South Beach Marina, a short five minute walk to South Beach, and a three minute walk to tennis, pickleball, The Salty Dog Café, restaurants, and shopping. T

Pool Access

Swim, lounge, and unwind. Explore our pool-access properties

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Notice: The Ocean Club parking lot is currently undergoing repaving, with work expected to be completed in April 2026. Discover your serene escape in the oceanfront complex of South Forest Beach! With direct beach access and a large on-site pool (heated in

Pool Towels Included

As a guest at this property, you receive one pool towel per person, perfect for lounging poolside.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This 3rd-floor villa is recently updated and places you just minutes outside of the world-famous Harbour Town. With 2 bedrooms and 2 bathrooms, this Sea Pines villa can sleep up to 4 people comfortably. The living room is illuminated with natural light and ha

Booked for Heritage

2380 Lighthouse Tennis

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This waterfront villa in Sea Pines offers a blend of coastal charm and relaxed sophistication, with sweeping views of the Calibogue Sound from nearly every angle. Designed to host family and friends, the stunning villa features three bedrooms, two and a half

New Property

New arrivals, just released. Explore our most recent properties.
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