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.
91 properties available
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
Coastal-Style Oceanfront Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8 | OceanfrontATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2027 (Dates Subject to Change)Welcome to your own piece of paradise at Sea Cloisters! This three-bedroom villa has been designed with your comfort and convenien
Oceanfront Penthouse Villa with Loft at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 8 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2027 (Dates Subject to Change)Welcome to our stunning two-story villa located in the beautiful Hilton Head Island. This spacious vacation home features a
942 Inverness Villas 3-Bedroom Inverness Villa in Palmetto Dunes Located in Inverness at Palmetto Dunes, 942 Inverness Villas offers a Hilton Head Island stay with access to beaches, golf, and the resort’s bike path and lagoon system. This three-bedroom villa provides added space for families and small groups looking to stay within
Beach-Themed Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2027 (Dates Subject to Change)Welcome to your perfect beach getaway in Hilton Head Island! This tastefully decorated oceanfront villa offers stunnin
Pet-Friendly Beach Villa in Stones Throw2 Bedrooms | 1 Bathroom | Sleeps 7 | Pet FriendlyWelcome to this beautiful beach-oriented villa in Hilton Head Island! Recently renovated to exceptional standards, this villa is sure to capture your heart. This 2-bedroom, 1-bath villa is the perfect vacation retreat, ready to provide you with an unforgettable
Charming Colonnade Club Villa in Shipyard2 Bedrooms | 2 Bathrooms | Sleeps 4 | Community PoolWelcome to your beautiful vacation home, nestled in the heart of Shipyard Plantation's Colonnade Club on Hilton Head Island. This charming property is just a short walk away from the beach, offering a perfect retreat for those seeking a relaxing beach g
Serene Huntington Villa in Palmetto Dunes4 Bedrooms | 4 Bathrooms | Sleeps 14 | Lagoon ViewsWelcome to our two-story, fully furnished Huntington villa located in the fantastic Palmetto Dunes Resort, just a short walk to the beach and pool.This villa offers 4 king bedrooms, each with an ensuite bathroom. The new mattresses and TV in each bedroom wil
Exquisite Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2027 (Dates Subject to Change)Welcome to our beautiful vacation home in Hilton Head, SC! This exquisite two-bedroom, two-bathroom condominium is the id
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
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
Newly Remodeled Villa Near Harbour Town at Stoney Creek1 Bedroom | 1 Bathroom | Sleeps 6Class, comfort, and a touch of prestige await at this beautifully remodeled one-bedroom, one-and-a-half-bath townhome in the sought-after Stoney Creek neighborhood of Sea Pines. This charming loft-style retreat features soaring cathedral ceilings, oversized wind
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