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
Scenic Harbour Town Villa in Sea Pines2 Bedrooms | 2 Bathrooms | Sleeps 4Wake up to one of the most recognizable views on Hilton Head Island. From this two-bedroom, two-bath villa at 1030 Caravel Court, the iconic Harbour Town Lighthouse stands just beyond your window—framed by yachts, calm harbor waters, and the lively charm of Harbour Town
Oceanfront Modern Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean ViewsDiscover the ultimate in beachfront elegance with this stunning 2-bedroom villa in Hampton Place, Palmetto Dunes on Hilton Head Island. Designed with a coastal chic aesthetic, this villa seamlessly blends modern luxury with the serene beauty of the Atlantic Oc
Exceptional Oceanfront Penthouse Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8Welcome to the luxurious vacation home of Villa 501 at Sea Cloisters in Hilton Head Island. This stunning penthouse villa offers a truly remarkable oceanfront experience with breathtaking views from every room. With its three bedrooms and two baths, this spaci
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
Elegant Beachside Getaway Villa in Forest Beach2 Bedrooms | 2.5 Bathrooms | Sleeps 6 | Stunning ViewsWelcome to this beautiful Beachside Getaway, located in the perfect spot to enjoy all that Hilton Head Island has to offer! With all remodeled bathrooms, solid surface flooring, granite countertops throughout, smooth ceilings, and beautiful fur
Renovated Bluff Villa in Sea Pines2 Bedrooms | 2 Bathrooms | Sleeps 6 | Perfect For an Island GetawayA coastal haven nestled within the vibrant heart of Sea Pines Resort, specifically in the sought-after South Beach area, 1670 Bluff Villa offers an idyllic retreat for those seeking a blend of relaxation and adventure. This meticulously renovat
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
Cozy Inverness Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | Pickleball/Tennis Play PackageLocated in Inverness at Palmetto Dunes, 902 Inverness offers a relaxed Hilton Head Island stay with convenient access to beaches, golf, and the resort’s extensive bike path and lagoon system. This three-bedroom villa p
Family Friendly Villa in Palmetto Dunes4 Bedrooms | 3 Bathrooms | Sleeps 10Escape to your dream vacation home in Palmetto Dunes Resort, where luxury, comfort, and endless fun meet.This beautifully furnished, two-story townhouse at 975 Inverness Village Villas offers three bedrooms, three baths, and a loft that sleeps ten, making it perfect for
Dog Friendly Huntington Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | Lagoon ViewsThis lovely Huntington villa has the "feel of a home". Nature lover? Enjoy the tranquil views of the 11 mile lagoon and the wildlife on the lagoon.Beach lover-you're only a 3-5 minute walk across the quiet street to the beach! Spacious ope
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
Stylish Queens Grant Villa in Palmetto Dunes3 Bedrooms | 2.5 Bathrooms | Sleeps 8 | Pet FriendlyWelcome to 599 Queens Grant, a stylish and spacious Hilton Head vacation villa nestled in the heart of Palmetto Dunes Resort. This updated 3-bedroom, 3-bath villa rental is perfect for families, golf groups, or beach lovers seeking comfort and convenienc
Tell us what you're looking for and someone will contact you with available options.