Vacation Rentals


Properties Available 270 properties available
Welcome to 437 Plantation Club, a premier vacation rental villa with sweeping views of Atlantic Dunes golf! This property is new to Sunset's vacation rental program for December 2025! Enjoy your morning cup of coffee or mimosa while watching the sunrise on the beautiful private balcony overlooking hole number nine. This pristine 2 bedroom, 2 bathro
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 5 guests
Rating 5 (14)
Welcome to one of the island's most comfortable townhomes located in the tranquil Shipyard on Hilton Head Island. Tennismaster 1103 offers 2 bedrooms and 2.5 baths, a covered patio, and easy access to the beaches and amenities of Shipyard, Hilton Head.The tiled foyer leads to a convenient powder room and then on to the galley-style kitchen, which f
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths 1 half bath
Guests 6 guests
Rating 5 (8)
52 Lands End is a completely remodeled Hilton Head Sea Pines rental situated perfectly on the point where Braddock Cove meets the Calibogue Sound and Intracoastal Waterway. The screened-in porch and open deck are great vantage points for watching dolphins, pelicans, shrimp boats headed out for a fresh catch and so much more.Two of the four bedroom
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 4 bedrooms
Bathrooms 4 full baths
Guests 8 guests
Rating 5 (21)
5502 Island Club is a premier vacation rental with unparalleled views of the Atlantic Ocean. This 5th floor, oceanfront, 2 bedroom, 2 bathroom villa is completely renovated and beautifully furnished, making it the ideal location for your next beach getaway.The living area features comfortable furniture, a Smart TV and stunning ocean views. Guests c
Hot HOT 14
Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 5 guests
Rating 5 (10)
Welcome to Queens Grant 616, a stunning two-bedroom villa where coastal charm meets modern comfort. This beautifully appointed, dog-friendly, villa has been renovated top to bottom and offers the perfect retreat for families, couples, and small groups seeking an unforgettable Lowcountry escape. Throughout the villa, you'll discover thoughtful desig
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (1)
New to the vacation rental market for December 2025, this beautifully outfitted 2 bedroom, 2.5 bathroom townhome is the perfectly located vacation rental!The newly furnished living area features comfortable furnishings and a Smart TV, as well as access to the private patio. The dining area seats 4 comfortably and is open to the well-appointed kitch
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths 1 half bath
Guests 6 guests
Rating 5 (6)
Between boasting an incredible location within Sea Pines and having a beautiful remodel, Lighthouse Tennis 2413 is the perfect landing spot for your next Hilton Head vacation. Featuring 2 bedrooms, 2 bathrooms, and ample room to spread out, this villa is not to be missed.Upon entering the villa, you're immediately welcomed with coastal decor and co
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 4 guests
Rating 5 (27)
Welcome to Your New Favorite Shipyard Vacation Retreat!This beautifully renovated two-bedroom, two-bathroom villa is the perfect getaway for your family—and your furry friend! Thoughtfully designed with modern upgrades, including LVP and tile flooring, Smart TVs, and comfortable furnishings, this home offers both style and relaxation.The spacious l
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 7 guests
Rating 5 (16)
55 Night Heron is the perfect retreat for your next Hilton Head vacation. This 3 bedroom, 2 bathroom Sea Pines home is located in the historic Sea Pines community on Hilton Head Island with community pool access and just a short walk to the beach. Upon entry, you'll be greeted with natural light, vaulted ceilings, and an open floor plan. The spacio
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 7 guests
Rating 5 (12)
Step back into the charm of carefree summer days with all the conveniences of modern living at this 3-bedroom, 3.5-bath Beachwalk townhouse in Shipyard on Hilton Head Island. Styled with a cheerful beach cottage motif, this spacious villa offers comfort, value, and plenty of room for making memories.Upon entering the home, you'll find a cozy den to
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 3 full baths 1 half bath
Guests 8 guests
Rating 5 (4)
Your perfect island oasis awaits at 18 Ocean Club, Hilton Head! This second story, beautifully updated Forest Beach condo offers 3 bedrooms, 3 full bathrooms and easy access to the complex pool, beach and top attractions of Hilton Head Island.Wood and tile flooring span the property, and an open-concept living area offers plenty of space for your f
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Featured Properties Special

We’ve handpicked some of our favorite vacation rentals and made them even better with a discount! Browse our featured properties and find the perfect place for your next getaway. Availability is limited, so book your stay today and use promo code FEATURED10 to save today!


Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 10 guests
Rating 5 (9)
This stylish Shipyard villa boasts all the comforts of home. The open concept kitchen has all stainless steel appliances, an attached laundry room and a dining counter with 2 barstools.The formal dining area has a table for 6 and is open to the living area. The living area features comfortable seating and a wall mounted TV/DVD, as well as a large w
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 6 guests
Rating 5 (20)

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