Hilton Head Vacation Rentals

Welcome to Hilton Head Island, where relaxation meets luxury, and unforgettable memories are waiting to be made. As your premier vacation rental company on this breathtaking island paradise, we invite you to experience the ultimate getaway in one of our exquisite properties.

Nestled amidst pristine beaches, lush greenery, and world-class amenities, our hand selected collection of vacation homes promises an unparalleled escape from the ordinary. From intimate beachfront villas to spacious oceanfront homes, each of our properties is meticulously designed to cater to your every need and desire.

Beyond the confines of your vacation home, Hilton Head Island beckons with a plethora of activities and attractions to delight every traveler. Tee off at world-renowned golf courses, embark on a thrilling dolphin cruise, or simply lounge by the pool and soak up the sun. With miles of pristine beaches, scenic nature trails, and vibrant cultural experiences awaiting you, there's never a dull moment on Hilton Head Island.

We are committed to providing unparalleled service and unforgettable experiences for our guests. From seamless booking processes to our signature Luxury Concierge services, we strive to exceed your expectations at every turn. So why wait? Book your stay with us today and discover the magic of Hilton Head Island in style. Your perfect getaway awaits.


Properties Available 147 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Nestled in the heart of Sea Pines, this coastal retreat offers the perfect blend of comfort and convenience for your next vacation. As you step into the villa, you\'ll find a welcoming dining area to your right, perfect for family meals or casual gatherings.
Hot HOT 184
892 Ketch Court
Villa -
$172.00 - $899.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (2)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Located in Palmetto Dunes, it is just steps away from the community pool and a 5 minute walk to the beach. The villa features two bedrooms and three bathrooms, providing ample space and is Pet Friendly! Upon entering, you find yourself in a bright and open l
Pet-Friendly Pet-Friendly
Pet-Friendly
40 Hickory Cove
Villa - Pet Friendly
$137.00 - $396.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Indulge in the tranquility of coastal living with this exquisite 3-bedroom, 3-bathroom condominium nestled on the 3rd floor of Windsor Place. Offering stunning oceanfront views, this unit features an open floor plan, tasteful decor, and a fully equipped kitch
Oceanfront Oceanfront
Oceanfront
308 Windsor Place
Villa -
$419.00 - $5,049.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (18)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This completely renovated Palmetto Dunes villa is sure to make you feel right at home! Welcome to 89 The Moorings, featuring 2 bedrooms and 3 bathrooms with enough room to host up to 8 guests very comfortably. Guests can enjoy the feel of brand new flooring,
89 The Moorings
Villa -
$196.00 - $427.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (36)
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, dining area and powder room. The living room featu
NEW PICTURES NEW PICTURES
NEW PICTURES
867 Ketch Court
Villa -
$129.00 - $1,735.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 4.8 (18)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This home is spacious and relaxing 3-bedroom home in the charming, gated community of Sea Pines. Open the door to experience a serene view of a private lagoon shaded by palm trees and live oaks dripping with Spanish moss. An abundance of natural sunlight stre
35 Shell Ring
House -
$149.00 - $3,089.00 / 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 stunningly decorated 2-bedroom villa is just steps away from Harbourtown. The open-concept living space offers breathtaking views of the Calibogue Sound. Walking in on the first level, you are met with a spacious living room with comfy couches. Open to t
Water View Water View
Water View
729 Schooner Court
Villa - Pet Friendly
$173.00 - $799.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 4 guests
Rating 4.9 (26)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This expansive property features five bedrooms and two separate entrances, providing ample space and privacy for larger groups. This property boasts multiple living areas, ensuring plenty of room for everyone to spread out and relax. This amazing villa featu
Oceanfront Oceanfront
Oceanfront
1013 Seacrest Icone Collection Icon
Villa -
$712.00 - $1,568.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 14 guests
Rating 5 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Indulge in the tranquil charm of a beach vacation at 25 Singleton Beach, a grand and luxurious 7-bedroom retreat designed for unforgettable seaside getaways. This stunning brand-new home boasts large glass doors and windows that flood the interior with natura
New Property New Property
New Property
25 Singleton Beach Icone Collection Icon
House -
$1,099.00 - $3,282.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 17 guests
Rating 5 (2)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. With beautiful craftsmanship throughout the well-appointed house. The ground level has a newly refinished pine floor and an open-plan design, with the large kitchen overlooking the cozy living room. There are lots of books to read; there is lots of seating on
Pet-Friendly Pet-Friendly
Pet-Friendly
30 Ruddy Turnstone | Ruddy Retreat
House - Pet Friendly
$477.00 - $1,713.00 / per night
Bedrooms 5 bedrooms
Bathrooms 6 baths
Guests 14 guests
Rating 4.9 (17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably. The first floor features a very open floor plan that offers easy access between the multiple living
2 Royal Tern Icone Collection Icon
House -
$679.00 - $3,033.00 / per night
Bedrooms 5 bedrooms
Bathrooms 6 baths
Half Bathrooms 2 half baths
Guests 14 guests
Rating 4.9 (21)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This home is a stunning haven nestled in the heart of Sea Pines, where luxury meets comfort in a beautiful retreat. Exciting updates are coming to the house, including the addition of a brand-new bunk room! Keep an eye on the website—updated photos will be av
18 Willow Oak Fairway Collection Icon
House -
$372.00 - $999.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 5 (3)

Tell us what you're looking for and someone will contact you with available options.

I agree