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.
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.
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.
435 Captain\'s Walk overlooks the pool out to the ocean! Lots of recent updates!
435 Captain\'s Walk is a second-floor, 3-bedroom, 3-bathroom end unit that overlooks the pool and out to the ocean. A beautiful, updated villa with great views—you couldn\'t ask
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
5 Jessamine Place is only a 10-minute walk to the best beach on Hilton Head Island!
This ranch-style cottage home is newly renovated and beautifully furnished. It offers four bedrooms and four bathrooms to comfortably host up to 13 guests. Nestled on a quie
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
You\'re going to love this Captain\'s Walk villa for one of the best panoramic ocean views on Hilton Head Island, for being centrally located within mid-island on new paved pathways, for having a golf course on the property, and for having conveniently locate
450 Captains Walk
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.
4 Junket sits 2nd row in Palmetto Dunes with Gorgeous Updates, Private Pool, Screened porch and Lowcountry luxury living
This second-row oceanfront, pet-friendly home is the epitome of Lowcountry luxury living on the beach. You are invited to this gorgeous m
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This recently updated Palmetto Dunes villa places you only minutes away from the beautiful sandy beaches of Hilton Head. Come in and relax on the comfy sectional. The living room is warm and inviting, with a pullout sofa bed. This villa has an open living roo
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
This oceanfront home is newly updated and offers direct beach access and an expansive outdoor entertainment area sure to be a favorite for summer days! Designed for gatherings large and small, it combines breathtaking Atlantic views with spacious, thoughtfull
11 Junket
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.
533 Shorewood is an amazing 2-bedroom, 2-bathroom oceanfront villa with a pool and ocean views! This stunning beach condo sleeps 7 and is on the 5th floor with elevator access, featuring all new furniture and décor, a community pool, beach access, and more!
533 Shorewood Place
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
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