Skip the Crowds, Stay the Week
Looking to avoid the holiday traffic and crowds? Select properties have a rare six-night opening beginning July 5. Arrive after the holiday rush, enjoy quieter beaches and restaurants, and still experience everything that makes summer on Hilton Head so special. These limited six-night stays offer the perfect opportunity for a relaxing island escape with greater flexibility and availability.
32 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Welcome to a beautifully designed retreat where warm natural light, effortless flow, and thoughtful comforts create an unforgettable stay. From the moment you walk in, the home opens into a bright and spacious layout that invites relaxation.
To the left of t
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Discover your serene escape in the oceanfront complex of South Forest Beach! With direct beach access and a large on-site pool (heated in March & April and October & November), this villa combines relaxation and convenience, just steps from the ocean and a s
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Step inside to an impressive, oversized entryway that immediately sets the tone for this exceptional home. The grand entrance features a sweeping spiral staircase to the left, convenient elevator access, and direct entry to the garage, all thoughtfully design
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
510 Mainsail is a gorgeous two-bedroom, two-and-a-half-bath, top-floor villa with breathtaking panoramic views of Shelter Cove Harbour. Designer-decorated, this property is perfect for a Hilton Head vacation and comfortably accommodates up to four people. Th
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Our three-bedroom, three bath, ~2,000 square foot Guest Villa has recently undergone a stunning top-to-bottom renovation, creating the perfect coastal getaway in the highly desirable Queens Grant neighborhood within Palmetto Dunes Oceanfront Resort.
This spa
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
2538 Gleneagle Green
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This completely renovated Palmetto Dunes villa is sure to make you feel right at home! Welcome to 89 The Moorings, featuring 2 bedrooms and 3 bathrooms with enough room to host up to 8 guests very comfortably. Guests can enjoy the feel of brand new flooring,
Welcome to The Sandbox! Newly renovated and outlined with elegance in every detail, this 3-story oceanfront home is truly perfect for your next Hilton Head Island family getaway.
This home has an extremely open floor plan that allows an easy flow between the living room, kitchen, and dining area. The living room is well-appointed and spacious, an
9 Guscio Way
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Enjoy the unbeatable convenience of this home\'s location, offering effortless access to the very best of Hilton Head. Just minutes from the Sea Pines gates, you\'ll find it easy to explore iconic destinations like Harbour Town, Coligny Plaza, and the island\
150 Otter Road
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Notice: This property has recently undergone thoughtful updates, including a stunning new six-seat dining table, two stylish and cozy new chairs in the living room, and more! Brand new photos have been uploaded as of March 2026.
This stunning villa has been
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This villa has plenty of space to move around. Walk into the first floor, where you have the kitchen, dining room, and living room leading out to a small patio equipped with a new gas grill. The living room has a small desk space, perfect for any last-minute
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
A stunning retreat in the heart of Palmetto Dunes, designed for relaxation and entertaining. Step into the bright and inviting living room, where floor-to-ceiling windows flood the space with natural light and offer serene views of the golf course. Comfortab
6 High Water
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