Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 


Properties Available 144 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This gorgeous Sea Pines villa has been recently renovated and features golf and lagoon views. Walk into an open-concept kitchen, dining room, and living room. Relax on either of the comfortable couches in the living room and watch your favorite programs on th
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

3 Lighthouse Road Villa Fairway Collection Icon
Villa - Pet Friendly
$170.00 - $455.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (11)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This beautiful, nine-bedroom Beachcomber house sports a private pool and spa and provides expansive living spaces, as well as fabulous views of the beach and the Atlantic Ocean from the sweeping picture windows. Situated on the most prestigious street in Sea
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

27 South Beach Lagoon
House -
$1,999.00 - $3,999.00 / per night
Bedrooms 9 bedrooms
Bathrooms 10 baths
Half Bathrooms 1 half bath
Guests 28 guests
Rating 5 (4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This oceanfront stunner is located in South Forest Beach to offer panoramic ocean views and places you only minutes away from fun at Coligny Plaza. Upon entry, you walk into the first-floor great room of the home, which consists of a living room, kitchenette
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

12 Cassina Lane Icone Collection Icon
House -
$867.00 - $2,134.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 4.8 (12)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 1206 Sea Crest is a spacious 2nd-floor corner villa in the Sea Crest complex where you can enjoy direct oceanfront views. As you enter the front door into a small foyer, you will notice the very nice plank-style flooring. To the left is a guest bedroom with
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

1206 Seacrest
Villa -
$259.00 - $649.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (8)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Nestled along the scenic fairways of the renowned Atlantic Dunes Golf Course, this brand new 6-bedroom, 6-bath home in Sea Pines captures the essence of upscale coastal living. 169 North Sea Pines welcomes you with a blend of contemporary design and Southern
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

169 North Sea Pines Drive Icone Collection Icon
House -
$686.00 - $2,224.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 5 (4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Step into coastal luxury with this beautiful second-row ocean home, where traditional Carolina charm meets modern elegance for an unforgettable beach getaway. Just steps from a serene semi-private beach, this spacious property is designed to maximize both com
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

19 Sand Dollar
House -
$607.00 - $1,854.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 18 guests
Rating 5 (1)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2390 Lighthouse Tennis Villa invites you to experience the Sea Pines Community on Hilton Head Island. In addition to its premier location surrounded by beautiful scenery, this well-appointed villa is an exceptional getaway retreat. From Harbour Town Marina to
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

2390 Lighthouse Tennis
Villa - Pet Friendly
$162.00 - $583.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 4.7 (9)
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
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

30 Ruddy Turnstone | Ruddy Retreat
House - Pet Friendly
$508.00 - $1,369.00 / per night
Bedrooms 5 bedrooms
Bathrooms 6 baths
Guests 14 guests
Rating 4.9 (11)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. A charming first-floor villa with a walkout balcony offering breathtaking views of the golf course. Nestled in the heart of Sea Pines, this delightful retreat combines comfort and convenience, making it the perfect getaway for golfers and vacationers alike.
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

426 Plantation Club
Villa
$139.00 - $334.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
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
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

1013 Seacrest Icone Collection Icon
Villa -
$698.00 - $1,575.00 / 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. 4 Ocean Club offers you the perfect beachfront getaway in South Forest Beach! With direct beach access and a private, heated pool, this villa offers the best of Hilton Head Island vacationing. Step into the inviting first floor, where you\'ll find a fully-eq
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

4 Ocean Club
Villa -
$195.00 - $483.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Beautifully updated 3-bedroom villa in Shelter Cove. Come in, take a seat, and relax in the living room. The living room, kitchen, and dining room have an open layout. The kitchen has granite countertops, new stainless steel appliances, and smooth ceilings.
Specials Tag Special
Earn 2,000 Bonus Points

Summer on Hilton Head Island is all about sun-soaked beach days, bike rides under the oaks, and evenings filled with ocean breezes and unforgettable memories. 

Book with our Voyager Club and earn an extra 2,000 points to make your getaway even more rewarding!

Valid for stays from 6/14/25 to 7/26/25 and 8/9/25 to 9/6/25.

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. 

7474 Anchorage Villas
Villa -
$138.00 - $332.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.6 (9)

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