Your Perfect Hilton Head Island Getaway Starts Here
Hilton Head Properties Realty & Rentals offers a diverse selection of Hilton Head vacation rentals to suit every type of traveler. From 1-bedroom villas for a quiet coastal escape to 7-bedroom vacation homes built for family reunions and group retreats, each property is thoughtfully furnished and ready for your stay. Guests can enjoy luxurious vacation amenities such as private pools, ocean views, and easy beach access in sought-after communities like Palmetto Dunes, Sea Pines, Forest Beach, and Folly Field.
These vacation homes and villas place you close to everything that makes Hilton Head Island special—championship golf courses, scenic bike paths, local dining, and Lowcountry charm around every corner. Each rental is backed by our experienced property management team, committed to delivering a seamless vacation experience from booking to check-out.
Spend your days relaxing by the pool, exploring the island, or enjoying the comforts of a professionally managed Hilton Head vacation home. With flexible options, top-rated amenities, and personalized service, Hilton Head Properties Realty & Rentals makes it easy to plan a stress-free Hilton Head Island vacation.
Start your search today and discover vacation rentals that bring comfort, style, and convenience together in one unforgettable island stay.
93 properties available
Coastal Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Panoramic Ocean ViewsIndulge in the ultimate tropical getaway at this professionally decorated vacation home in Hilton Head Island. Located on the fourth floor, this condo offers a luxurious and inviting atmosphere.As you step inside, you'll be captivate
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Villa with Panoramic Ocean Views at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontWelcome to Sea Cloisters Unit 206, a newly renovated vacation villa with stunning panoramic views of the ocean and the beach. The unit has a prime location on the second floor, with breathtaking views of the wide sandy beach and the ocean, and is so clo
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
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
Stunning Golfmaster Condo in Shipyard3 Bedrooms | 3 Bathrooms | Sleeps 8 | Community PoolWelcome to 102 Golfmaster, your dream vacation home nestled in the beautiful Shipyard community on Hilton Head Island. This stunning property offers a perfect blend of luxury, comfort, and convenience, making it the ideal destination for your next getaway. &nbs
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
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Beautiful Pet Friendly Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet FriendlyWelcome to this beautifully remodeled vacation home in Hilton Head Island! This newly remodeled villa awaits you in the esteemed St. Andrews Common community within the world-famous Palmetto Dunes resort. This second-floor villa is a true 2 bedroom-2 ful
Oceanfront Coastal Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontWelcome to our lovely 1st floor villa in the exclusive gated complex of Sea Cloisters. Our villa boasts stairs leading directly to the beach and pool, making it the perfect spot for a relaxing and comfortable family vacation. The conveniences of our villa are s
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Coastal Queens Grant Villa in Palmetto Dunes3 Bedrooms | 2.5 Bathrooms | Sleeps 9 | Pet FriendlyEscape to the beautiful Hilton Head Island and experience the perfect vacation in this spacious and charming 3-bedroom villa. With big bedrooms, living areas, and a huge deck off the back, this villa provides ample space for your family or group. You wil
Stunning Oceanfront Villa at Villamare2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontWelcome to 3230 Villamare, a stunning vacation home located in the beautiful Palmetto Dunes community of Hilton Head Island. This spacious 2-bedroom, 2-bathroom condo is situated in an oceanfront complex, offering a perfect retreat for your beach getaway.As you st
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Tastefully Decorated Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your tastefully decorated vacation home in Hilton Head Island. This two-bedroom, two-bathroom villa is the perfect destination for your beach retreat. With its well-equipped kitchen, spacious living and dining areas, and st
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Golf Inverness Villa in Palmetto Dunes2 Bedrooms | 2 Bathrooms | Sleeps 6Welcome to our newly remodeled Palmetto Dunes vacation home, a 2 bedroom, 2 bathroom villa that overlooks the beautiful fairway of the famous George Fazio Golf Course and lagoon. Step out onto the deck and take in the stunning views while relaxing on the comfortable patio furn
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
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
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
