Shorter Stays
Find Hilton Head Island vacation rentals for shorter stays, including long weekends, midweek getaways, and flexible travel dates. Hilton Head Properties Realty & Rentals offers professionally managed homes and villas across Sea Pines, Palmetto Dunes, Shipyard, and Forest Beach. Expect clean, well-maintained properties, easy check-in, and local support—so you can book quickly and enjoy more time on the island.
93 properties available
3-Bedroom St. Andrews Commons Villa in Palmetto Dunes3 Bedroom | 2 Bathrooms | Sleeps 6 | Pet Friendly Located in Palmetto Dunes, 1779 St. Andrews Commons offers a Hilton Head Island stay with access to golf (paid additionally), beaches, and the resort’s bike path network. This three-bedroom villa provides a comfortable option for f
Immaculate Hickory Cove Villa in Palmetto Dunes2 Bedrooms | 3 Bathrooms | Sleeps 7 | Golf ViewsWelcome to Hickory Cove #24, your ultimate vacation home nestled in the prestigious Palmetto Dunes Resort on Hilton Head Island. This beautifully appointed villa offers a multitude of perks to ensure a memorable stay, including 2 beach chairs, 1 umbrella,
Spacious Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your spacious vacation home in Hilton Head Island, situated right on the oceanfront! This villa offers a prime location just steps away from the beach, allowing you to easily access the mesmerizing ocean. Whether you're whipping up a quick
Oceanfront Villa at Sea Cloisters with Breathtaking Views2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontWelcome to our stunning oceanfront villa, located on the second floor, offering breathtaking beach and ocean views. This spacious 2-bedroom, 2-bathroom villa is the perfect retreat for a memorable vacation.As you enter the villa, you'll noti
Oceanfront Windsor Place II Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | OceanfrontATTENTION: Elevator inoperable during the time period of Nov. 1, 2026 until March 20, 2027, due to the elevator being replaced (Dates Subject to Change)Located just steps from the sand in the heart of Palmetto Dunes, 2117 Windsor Place 2 offers
Coastal Windsor Place II Villa with Breathtaking Ocean Views2 Bedrooms | 2 Bathrooms | Sleeps 8 | OceanfrontATTENTION: Elevator inoperable during the time period of Nov. 1, 2026 until March 20, 2027, due to the elevator being replaced (Dates Subject to Change) Welcome to this professionally decorated vacation home located on the fifth fl
Beautiful Evian Golf Villa in Shipyard2 Bedroom | 2 Bathroom | Sleeps 8 | Golf GetawayWelcome to this beautiful second-floor condo located in the serene Shipyard Plantation area of Hilton Head Island! With its prime location, you'll have easy access to all the amenities the complex has to offer, ensuring a delightful and entertaining stay.Step
Oceanfront Penthouse Villa with Loft at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 8 | Ocean ViewsWelcome to our stunning two-story villa located in the beautiful Hilton Head Island. This spacious vacation home features a unique lofted sleeping space, adding an extra touch of charm and versatility to your stay.As you enter, you'll find two
Direct Oceanfront Second Floor Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to our absolutely cute and comfortable oceanfront villa, boasting 2 bedrooms and 2 baths within its spacious 1100 square feet. The villa offers a direct oceanfront location, allowing you to wake up to the breathtaking sunrise right from you
Oceanfront Beach Getaway in North Forest Beach1 Bedroom | 1 Bathroom | Sleeps 4 | Ocean ViewsWelcome to our beautiful one-bedroom, one-bathroom condo located in the North Forest Beach area of Hilton Head Island! This unit is perfect for a romantic getaway or a small family vacation. With panoramic ocean views from the oceanfront deck, you'll be
Upgraded Lagoon Villa by South Beach in Sea Pines3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet FriendlyWelcome to 1587 Lagoon Villa—an upgraded 3-bedroom, single-level retreat in the heart of Sea Pines, just a short stroll to the beach, Salty Dog Marina, and pickleball courts. Recently remodeled from top to bottom with high-end finishes, this vil
Updated Oceanfront Windsor Place Villa in Palmetto Dunes2Bedrooms | 2 Bathrooms | Sleeps 7 | Ocean ViewsATTENTION: Elevator inoperable during the time period of Nov. 1, 2026 until March 20, 2027, due to the elevator being replaced (Dates Subject to Change)Welcome to the spacious 2-bedroom, 2-bathroom condo located on the fourth floor of
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