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
Extensive Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to our newly renovated villa, where no expense has been spared to provide you with the very best beach experience.The villa boasts a range of upgrades, including new granite countertops, crown moldings, baseboards, and fresh paint on walls and ceilin
High-End Inverness Golf Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 6 | Family GetawayWelcome to the jewel of the island, 924 Inverness! This stunning vacation home is located in the prime location of Hilton Head within Palmetto Dunes. This property offers first-class amenities and living arrangements that will exceed your expectations
Pet-Friendly Queens Grant Villa in Palmetto Dunes3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet FriendlyEscape to Hilton Head Island and experience the perfect family vacation or weekend getaway in this true three bedroom vacation home! With spacious living areas, big bedrooms, and a huge patio off the back of the villa, you'll love the space and lo
Cozy Cutter Court Villa in Sea Pines2 Bedrooms | 2 Bathrooms | Sleeps 5 | Serene RetreatWelcome to 911 Cutter Court, a second-floor villa that puts you right in the heart of Harbour Town. Overlooking the Harbour Town Golf Links Clubhouse, this two-bedroom, two-bathroom retreat offers a front-row seat to one of Hilton Head’s most iconic settin
Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 5 | Ocean ViewsWelcome to your dream vacation home in Hilton Head Island! Located in the picturesque Folly Field area, this oceanfront villa offers the perfect setting for your next beach getaway. Villa 312 Sea Cloisters is designed to accommodate five guests, making it
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
Light, Bright, and Beautiful Pet Friendly Stones Throw Villa2 Bedrooms | 1 Bathrooms | 1 Half Bathroom | Sleeps 7Welcome to this light, bright, and beautiful two-bedroom vacation home in Hilton Head Island, just a Stones Throw to the beach! The location of this home is truly incredible, offering you the opportunity to enjoy one of the most stunning
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
Dog Friendly Centrecourt Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 6 | Complex PoolWelcome to the Villa at 7830 Centrecourt, your perfect vacation home in Hilton Head Island! This villa offers a prime location where everything you need is right at your fingertips. Palmetto Dunes boasts some of the best golf courses on the i
Cozy Queens Grant Golf Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 6Indulge in the ultimate low country retreat at Queens Grant 649, a fully renovated 2-bedroom, 2-bath villa offering modern comfort and classic charm. With its spacious 1500 square feet and a queen sleeper sofa, this home comfortably accommodates up to 6 guests.The
Charming Pet-Friendly First-Floor Resort Villa at St. Andrews Common1 BED, 1.5 BATHSWelcome to this charming vacation home on Hilton Head Island! This first-floor villa offers a comfortable and versatile space for your stay.The fully equipped kitchen boasts full-sized appliances and has everything you need to prepare delicious meals during your vac
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
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