Monthly Stays
Come Live Like A Local On Hilton Head!
As a leading property management company, we recommend extending your stay on Hilton Head Island to a month or longer during the fall, winter, or spring seasons. Hilton Head offers a unique blend of tranquil beauty and a mild climate, making it an ideal retreat for those looking to escape the harsher weather found elsewhere.
Staying on Hilton Head Island for an extended period allows you to fully immerse yourself in the local culture and lifestyle. During the off-peak seasons, you'll experience less crowded beaches, more intimate encounters with wildlife, and the true laid-back essence of island life. Golf enthusiasts will find pristine courses with fewer players, providing a more leisurely and enjoyable game. Likewise, tennis & pickleball lovers can take advantage of the cooler temperatures and excellent facilities.
Our vacation rentals offer all the comforts of home, with the luxury of resort living. You can choose from a variety of properties, from oceanfront condos to secluded homes. Each rental is equipped with full kitchens, comfortable living spaces, and often private amenities like pools and hot tubs.
Book your extended stay on Hilton Head Island with us and discover a perfect blend of relaxation, recreation, and rejuvenation during the serene months of fall, winter, and spring. It's not just a getaway; it's a transformative experience. And remember, stays for 90 days or longer are tax exempt!
93 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This fantastic 2nd row of the ocean is nestled in the palms of the Palmetto Dunes resort. With 6 bedrooms and 6.5 baths, this low-country home is the perfect getaway for family and friends!
A circular drive leads to a beautiful entrance way and wraparound p
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Modern comforts meet the classic styling of this traditional beach home. If you are looking for a house that has the look and feel of the beach house from your childhood memories, look no further. The home has gone through a complete renovation to restore it
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
6 Indigo Lane is a cozy beach home in a friendly neighborhood in the desirable Lawton Woods section of Sea Pines. A short walk or bike ride to the beach, Sea Pines Forest Preserve, and Lawton Stables. High-speed internet is available to accommodate remote wor
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This stunningly decorated 2-bedroom villa is just steps away from Harbourtown. The open-concept living space offers breathtaking views of the Calibogue Sound. Walking in on the first level, you are met with a spacious living room with comfy couches. Open to t
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home is spacious and relaxing 3-bedroom home in the charming, gated community of Sea Pines. Open the door to experience a serene view of a private lagoon shaded by palm trees and live oaks dripping with Spanish moss. An abundance of natural sunlight stre
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This oceanfront home offers unforgettable views and a private pool, spa, a game room and an open great room. The open floor plan is a must and is perfect for entertaining. The gourmet kitchen features updated appliances and is perfect for gathering together.
7 Guscio Way
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This property now offers an exciting new amenity with a free pickleball and tennis pass in Palmetto Dunes, which includes two free hours of court time every day of your stay!
Indulge in the tranquility of coastal living with this exquisite 3-bedroom, 3-bathr
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautifully updated 5-bedroom, 4-bath home with a 2-car garage, elevator, and private pool is located at Singleton By The Beach. This home is located by the beautiful Chaplin Park, which offers free tennis, pickleball, basketball courts, and walking trai
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2211 Seacrest has new LVT floors with walk-in showers, a garden tub, double vanities, and more!
This is a wonderful 2-bedroom, 2-bathroom villa located on the second floor of Building 2. Walk-in to the open-concept living space, perfect to spread out and rel
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This two-story Fazio villa boasts peaceful golf course views and is perfect for a family vacation. With close proximity to the spectacular beaches of Palmetto Dunes with new furnishings, flooring and remodeled baths, and an oversized covered deck overlooking
26 Fazio Villas
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Views, views, and more views! What better way to start your day than listening to the surf, enjoying the beautiful scenery of the marsh with active wildlife, and the ocean just beyond while sipping your coffee on the deck? An expansive, gorgeous beach is just
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Indulge in the epitome of coastal living at this meticulously maintained 1-bedroom, 1.5-bath renovated villa in the prestigious Barrington Villas. Every aspect of this retreat has been thoughtfully curated to offer a blend of elegance and comfort, promising a
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