Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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 41 properties available
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2211 Seacrest has new LVT floors with walk-in showers, a garden tub, double vanities, and more! This is a wonderful 2-bedroom, 2-bathroom villa located on the second floor of Building 2. Walk-in to the open-concept living space, perfect to spread out and rel
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

2211 Seacrest
Villa -
$176.00 - $379.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 (20)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 253 Captain\'s Quarters, where amazing sunrises greet you in this contemporary one-bedroom villa. Coming this fall the kitchen will be renovated with new cabinets, counter tops and fixtures. The villa is designed to offer a perfect blend of modern ameniti
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

253 Captains Quarters
Villa -
$131.00 - $334.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 4.9 (11)
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
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

5303 Hampton Place
Villa -
$229.00 - $554.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (11)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Discover your serene escape in the oceanfront complex of South Forest Beach! With direct beach access and a large on-site pool (heated in March & April and October & November), this villa combines relaxation and convenience, just steps from the ocean and a s
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

24 Ocean Club
Villa -
$179.00 - $505.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 6 guests
Rating 5 (2)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Lots of natural light shines throughout this 2-bedroom, 2-bathroom villa, just steps away from the Salty Dog. You\'ll love the recently renovated kitchen, which is located just off the foyer. All overlooking the open-concept living and dining room and out t
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

1809 Bluff Villas
Villa -
$135.00 - $359.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (14)
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
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

767 Queens Grant
Villa - Pet Friendly
$135.00 - $259.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
Rating 5 (4)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This magnificently remodeled North Shore Place villa features two bedrooms. Walking into an open-concept floor plan. The master bedroom has a beautiful king bed and private ensuite bath. The ensuite bathroom features a walk-in shower. The guest bedroom has
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

103 North Shore Place
Villa -
$184.00 - $379.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (13)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 510 Mainsail is a gorgeous two-bedroom, two-and-a-half-bath, top-floor villa with breathtaking panoramic views of Shelter Cove Harbour. Designer-decorated, this property is perfect for a Hilton Head vacation and comfortably accommodates up to four people. Th
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

510 Mainsail
Villa -
$211.00 - $448.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 6 guests
Rating 5 (8)
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
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

1204 Villamare Icone Collection Icon
Villa -
$231.00 - $493.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (19)
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,
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

89 The Moorings
Villa -
$188.00 - $487.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (17)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 401 Windsor Place is a beautifully appointed villa in Palmetto Dunes with ocean views! Start your vacation memories today! As you walk through the front door to be greeted with the ocean view, the light shines across the open-plan layout. An attractive livin
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

401 Windsor Place
Villa -
$207.00 - $528.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (19)
Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This two-bedroom, two-bath ocean view condo features expansive ocean views from the patio, a variety of shared pools, and nearby beach access for the perfect island vacation. Walk into your oasis and find the kitchen, dining room, and living room with an ope
Specials Tag Special
Stay 2 Nights in Paradise

Escape to paradise with our exclusive 2-night minimum stay special in our luxurious 1 - 2 bedroom villas! Travelling here is effortless with easy access through Hilton Head Island Airport or the Savannah Airport. With beautiful weather year-round, stunning beaches, and breathtaking scenery, even a short getaway feels like a dream. Hilton Head is always worth the trip, even for just a couple of nights! Book now and make your Island escape unforgettable.

Valid for stays between 02/11/2025 - 05/16/2025This offer starts on 02/11/2025 and expires on 05/16/2025. Any arrival and departure date.

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.

4303 Island Club
Villa -
$168.00 - $392.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (18)

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

I agree