Last-Minute Vacation to Hilton Head Island
Sometimes the best vacations are the ones you don’t overthink. Hilton Head Island is perfect for spontaneous getaways, offering a wide selection of Hilton Head vacation rentals—from luxurious homes with private pools to oceanfront rentals in Forest Beach, Palmetto Dunes, and Sea Pines.
Enjoy the convenience of a last-minute escape without sacrificing comfort or experience. Many of our rentals feature stunning ocean views, access to a community pool, or close proximity to championship golf courses. Families, couples, and solo travelers will find spaces designed to relax, recharge, and enjoy the best of island life.
At Hilton Head Properties R&R, our dedicated property management team delivers top-tier customer service, helping guests make the most of every Hilton Head Island vacation. From oceanfront resorts to private homes, we make it easy to slip into island time—no stress required.
118 properties available
Villa with Panoramic Ocean Views at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to Sea Cloisters Unit 206, a newly renovated vacation villa with stunning panoramic views of the ocean and the beach. Th
Stunning Lagoon-View Home in Palmetto Dunes7 Bedrooms | 6.5 Bathrooms | Sleeps 18 | Private Pool | Golf SimulatorLooking for a vacation home that offers something for everyone in the family? Look no further than 25 Starboard Tack in Palmetto Dunes.This stunning home boasts spacious living areas and multiple bedroom wings, perfect for families or mu
Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to our beautifully remodeled villa, located just steps away from the sand on Hilton Head Island. This tastefully designed home provides
Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 5 | Ocean ViewsATTENTION: Neighboring unit currently under renovation; possible minimum construction noise; November 2026 - Feb 2027 (Dates Subject to Change)ATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Da
Oceanfront First Floor Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8 | OceanfrontATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to 113 Sea Cloisters—an oceanfront villa where comfort, convenience, and coastal beauty come together seamlessly.Perch
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
The Turtle Cottage – Moon River Retreat with a private dock3-Bedroom Riverfront Cottage on Daufuskie IslandLocated at Moon River on Daufuskie Island, Turtle Cottage offers direct waterfront positioning with long views across the New River toward Savannah. This three-bedroom home delivers a front-row coastal setting designed for gues
Stunning Vacation Oasis on North Forest Beach7 Bedrooms | 5.5 Bathrooms | Sleeps 22 | Stunning BackyardLooking for a vacation home with a spectacular outdoor space? Look no further than 16 Mallard St in North Forest Beach! This stunning 7-bedroom, 5.5-bathroom home boasts the best backyard on the island, including a huge private pool and
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
Newly Remodeled Water Oak Villa in Palmetto Dunes3 Bedrooms | 3 Bathrooms | 1 Half Bathroom | Sleeps 10Welcome to 46 Water Oak Villa, a newly remodeled vacation home located in the heart of a charming sea-side village in Hilton Head Island. This two-story villa offers three oversized bedroom suites, making it an ideal choice for couples or families
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
Charming Pet-Friendly Villa at The Cottages2 Bedrooms | 2 Bathrooms | 1 Half Bathroom | Pet FriendlyWelcome to 35 The Cottages, an idyllic vacation townhome is located in a beach community with beach club and surrounded by 50 miles of scenic bicycle paths in Hilton Head Island. Whether you're planning a family vacation, a golf group outing, or
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