Stay Awhile This Fall
Settle into Island Time for a little longer and enjoy more of what makes Hilton Head so special. With fewer crowds, beautiful weather, and a slower coastal rhythm, fall is the perfect time to extend your stay and truly unwind.
Enjoy 10% off stays of 8 to 27 nights for stays between 9/14/26- 11/19/26.
Promo code: EIGHTPLUS
We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.
This offer cannot be combined with other offers. Valid for new stays only.
134 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.
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.
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.
This beautiful villa is perfect for relaxing and unwinding. The spacious great room features vaulted ceilings and unbelievable nature and water views.
Walk into this beautifully decorated villa and be greeted by lagoon views. The kitchen was recently update
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.
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
5303 Hampton Place
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.
103 Seacrest is beautifully decorated and fully renovated for your comfort and convenience. Here, you will experience only the best. This charming property features two bedrooms, creating a cozy and inviting atmosphere for your stay. Allow me to paint a pictu
103 Seacrest
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
Be Our Guest Beach Villa is proud to unveil a top-to-bottom remodel that makes it a showpiece of the Queens Grant Neighborhood.
This end-unit villa offers an abundance of windows and sliding glass doors, allowing natural sunlight to flow in with views of the
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.
2538 Gleneagle Green is a pet-friendly Harbour Town villa with stunning views of Harbour Town Golf Course and is located just a short 5-minute walk to the shops and dining at Sea Pines Center, as well as the famed Harbour Town Marina!
The open-concept floor
2538 Gleneagle Green
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 2-bedroom villa has been recently renovated and is the perfect oasis for a beach vacation. Nestled in the private oceanfront complex of Palmetto Dunes with perfect access to the beach and pool, the property features a complex pool, indoors and out! You w
1204 Villamare
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