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!
94 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautifully remodeled 3-bedroom home is very stylish, with a coastal cottage vibe throughout. The property features an open living, dining, and kitchen area that is fully equipped with top-of-the-line furnishings to provide all you need for a relaxing su
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This beautifully furnished and decorated home overlooks the Palmetto Dunes 11-mile lagoon and is just a 10-minute walk to the beach. With 4 bedrooms and 4.5 bathrooms, a gourmet kitchen, a private pool, and the beautiful Robert Trent Jones golf course, this i
39 Port Tack
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Thoughtfully refreshed and beautifully appointed, this 4-bedroom, 4.5-bath home in the heart of Sea Pines Plantation offers inviting coastal comfort with multiple gathering spaces, serene golf-course views, and a renovated pool deck perfect for relaxing days
2 Tupelo Drive
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
401 Windsor Place is a beautifully appointed villa in Palmetto Dunes with ocean views! Start your vacation memories today!
As you walk through the front door to be greeted with the ocean view, the light shines across the open-plan layout. An attractive livin
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Beautiful 3-bedroom villa with 3 full baths So close to the truly spectacular beaches of Palmetto Dunes Remodeled kitchen and baths Oversized covered deck overlooking the community pool.
Overlooking the Fazio Golf Course in Palmetto Dunes, this spacious, new
57 Fazio Villas
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Note: New photos of the backyards brand new fire pit and hot tub coming soon!
From the moment you arrive, the home welcomes you with its inviting façade featuring two balconies, a cozy front porch, and a secluded swing-bench nook tucked to the side, perfect
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This 2 bedroom, 2-bath Beachside Tennis villa has panoramic views of Calibogue Sound. Located in the South Beach area of Sea Pines on the first floor of a five-story building, just steps to the pool and beach,
When entering the villa, you will find the mast
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
1838 Beachside Tennis
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
253 Captain\'s Quarters, where amazing sunrises greet you in this contemporary one-bedroom villa. Coming this fall the kitchen will be renovated with new cabinets, counter tops and fixtures.
The villa is designed to offer a perfect blend of modern ameniti
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This home has been freshly updated with brand new exterior paint, kitchen countertops, renovated bedrooms and bathrooms, a new grill, and more exciting upgrades throughout! Photos have been updated to reflect these updates as of February 2026.
This pet-frien
36 Red Oak
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This charming Palmetto Dunes home offers expansive golf course views and features multiple living spaces to host large groups with ease.
On the main level, the living room offers comfortable seating around the flatscreen TV and fireplace, as well as direct v
176 Mooring Buoy
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
504 Barrington Arms is a lovely three-bedroom, three-bathroom direct oceanfront condo on the fifth floor. Enjoy panoramic ocean views and updated furnishings and décor throughout. The dining area is adjacent to both the living room and the well-equipped kitch
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