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!
107 properties available
Welcome to the 16 Ocean Club! Ocean Club is an oceanfront complex in South Forest Beach.
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. The living room has a small desk space, perfect for any last-minute work that needs to get done. T
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Beautifully updated 3-bedroom villa in Shelter Cove. Come in, take a seat, and relax in the living room. The living room, kitchen, and dining room have an open layout. The kitchen has granite countertops, new stainless steel appliances, and smooth ceilings.
Welcome to Fairway Breeze! A beautifully renovated four-bedroom, three-bath golf course home in the gated oceanfront resort of Palmetto Dunes.
Upon entry, be invited into the living room with a view of the pristine fairway of the George Fazio Golf Course. Separating the living room and dining room is a double-sided fireplace. Get a little work do
7 Ginger Beer | Fairway Breeze
Welcome to 12 Cassina Lane! This oceanfront stunner is located in South Forest Beach to offer panoramic ocean views and places you only minutes away from fun at Coligny Plaza.
Upon entry, you walk into the first-floor great room of the home, which consists of a living room, kitchenette, and dining area. The living room has plenty of seating around
12 Cassina Lane
Welcome to 40 Hickory Cove. Located in Palmetto Dunes, it is just steps away from the community pool and a short walk to the beach. The villa features two bedrooms and three bathrooms, providing ample space.
Upon entering, you find yourself in a bright and open living room, characterized by large windows that allow ample natural light to fill the
Welcome to 7 Guscio Way! This oceanfront home offers unforgettable views and a private pool and spa.
This home features 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.
Upon entry, you walk into the home\'s livi
7 Guscio Way
Welcome to 2334 Racquet Club! This renovated villa has 2 bedrooms and 2.5 baths and is located close to Harbour Town.
This cozy villa has two spacious bedrooms and large closets. When you first walk in, the kitchen is open to the dining area and living room. The living room offers plenty of seating to relax after a day out in the sun. Heading upst
Lots of natural light shines throughout this 2-bedroom, 2-bathroom villa, just steps away from the Salty Dog.
You’ll love the recently renovated kitchen, which is located just off the foyer. All overlooking the open-concept living and dining room and out to the Calibogue Sound.
The master bedroom consists of a king bed, a walk-in closet, and an
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 primary bedroom has a queen-sized bed, and the bathroom has a walk-in shower.
This villa off
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 views of and access to the private pool and deck. An open floor plan allows an easy flow to
176 Mooring Buoy
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 trails!
The coastal chic décor offers modern elegance that is perfect for a relaxing beach vac
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 porch. The grand foyer opens to a huge family room, a fully equipped chef-quality kitchen, a
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