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!


Properties Available 105 properties available
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
23 The Moorings
Villa -
$135.00 - $381.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (13)
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
504 Barrington Arms
Villa -
$266.00 - $722.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This Sea Pines home is nestled on a quiet street and places you only minutes away from Harbour Town and the sandy beaches! Upon entry, you walk into the sitting room, which has plenty of comfortable seating around the cozy brick fireplace (not for guest use)
11 Red Oak
House -
$305.00 - $679.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 4.8 (16)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This renovated 3-bedroom, 3-bath townhome features quartz countertops, soft-close cabinets, glass tile backsplash, LVP flooring, smooth ceilings, stunning tile showers, all new lighting, and new stainless steel appliances in the fully stocked gourmet kitchen.
283 Turnberry Villas Fairway Collection Icon
Villa -
$128.00 - $460.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (10)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This spacious 3-bedroom, 2-bathroom top-floor Bluff villa is perfect for a larger family, with an open floorplan and one of the largest living spaces found in any Sea Pines villa. With six beds and room for up to two children on the sleeper sofa, this unit ha
1690 Bluff Villas
Villa -
$97.00 - $399.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (11)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This beautiful 2-bedroom, 2-bath villa has amazing views of the ocean. The large balcony has a table, chairs, and sun loungers to soak up the view. The balcony can be accessed through the living room sliding doors and one of the bedrooms. The first bedroom h
Recently Updated Recently Updated
Recently Updated
5303 Hampton Place
Villa -
$185.00 - $644.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (10)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This 2-story Sea Pines villa has been recently renovated and places you only steps away from Harbour Town and a short bike ride to the Sea Pines Beach Club! On the first floor, find the living room, kitchen, and dining area. The living room features comforta
867 Ketch Court
Villa -
$129.00 - $619.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.6 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This 3-bedroom, 3-bathroom villa is an end unit located in the quiet Queens Grant neighborhood in the world-class Palmetto Dunes Resort. As you enter, you are met with a fully-stocked kitchen to your right that conveniently flows into the great room of the ho
591 Queens Grant | Palmetto Dunes
Villa -
$115.00 - $410.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 4.7 (9)
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
New Property New Property
New Property
26 Fazio Villas Fairway Collection Icon
Villa -
$136.00 - $348.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (9)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This spectacular villa has been renovated with new flooring, painting, and furniture. Walking into the villa welcomes you to an open-concept living area featuring high ceilings and large windows that bathe the space in natural light. The living room is elegan
New Property New Property
New Property
233 Turnberry Villas Fairway Collection Icon
Villa -
$122.00 - $354.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (2)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. No details were missed in this amazing 3-bedroom Palmetto Dunes home. Amazing golf course views greet you as soon as you walk in the door. The large living room\'s main sitting area has a sleeper sofa, a loveseat, and a desk. Heading further through this ho
Hot HOT 254
10 Troon Fairway Collection Icon
House - Pet Friendly
$199.00 - $550.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This stunning oceanfront 3-bedroom villa is situated within the highly sought-after Captain\'s Walk complex in Palmetto Dunes. Palmetto Dunes is a premier resort community known for its pristine beaches, lush golf courses, and picturesque surroundings. This v
Oceanfront Oceanfront
Oceanfront
401 Captains Walk Icone Collection Icon
Villa -
$194.00 - $845.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (9)

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