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 146 properties available
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
Hot HOT 54
28 Corine Lane
House - Pet Friendly
$209.00 - $788.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 15 guests
Rating 4.8 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This Palmetto Dunes beach home features 4 bedrooms and is only a short walk to the beach—that is, if you ever want to leave this gem! 15 Sea Lane features a spacious open floor plan and plenty of natural sunlight! Unwind in the living room as you watch TV on
Hot HOT 100
15 Sea Lane Fairway Collection Icon
House -
$301.00 - $843.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (16)
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
Hot HOT 53
3322 Lake Forest
Villa -
$135.00 - $309.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.7 (11)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. There is no need to look any further than oceanfront Beachside Bliss for your next family reunion or friends’ getaway, as this one-of-a-kind, 8,000-square-foot luxury home will spoil everyone lucky enough to come along! As soon as the sun comes up, your days
Hot HOT 142
43 South Beach Lagoon Icone Collection Icon
House -
$1,992.00 - $5,724.00 / per night
Bedrooms 8 bedrooms
Bathrooms 10 baths
Half Bathrooms 2 half baths
Guests 24 guests
Rating 4.6 (6)
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. 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 a
7 Ginger Beer | Fairway Breeze Fairway Collection Icon
House - Pet Friendly
$256.00 - $796.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 4.9 (13)
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
Hot HOT 109
1690 Bluff Villas
Villa -
$128.00 - $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. 2517 Windsor Place is a beautifully decorated villa with 3 bedrooms and 3 baths! Perfect for a golf getaway, family vacations, and couple retreats! This villa offers bedroom separation from the living and dining areas, allowing peaceful rest for those who ret
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Recently Updated
2517 Windsor II Icone Collection Icon
Villa -
$267.00 - $747.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.7 (4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Step into the coastal charm and be met with the open planned living area and dining area with a nice open window into the fully equipped kitchen. From this floor you will be able to step into the cozy sunroom which is the perfect spot to sit back and enjoy th
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150 Otter Road Fairway Collection Icon
House - Pet Friendly
$114.00 - $1,771.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 4.9 (12)
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 -
$651.00 - $1,750.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 14 guests
Rating 5 (7)
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 -
$375.00 - $1,115.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (9)
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 Icone Collection Icon
Villa -
$157.00 - $525.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (6)

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