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.
118 properties available
Coastal-Themed 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, 2028 (Dates Subject to Change)Welcome to your dream vacation home in Hilton Head Island! Located in the beautiful Sea Cloisters building, this two-bedroom, tw
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Coastal Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Panoramic Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Indulge in the ultimate tropical getaway at this professionally decorated vacation home in Hilton Head Island. L
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
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
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
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
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
Pet-Friendly Villa at St. Andrews Commons2 Bedrooms | 2 Bathrooms | Sleeps 6Welcome to our St. Andrews Commons vacation home, located in the renowned Palmetto Dunes Resort on Hilton Head Island. This second-floor villa offers a comfortable and inviting atmosphere for your stay. As you step inside, you'll find a fully equipped kitchen with full-
Oceanfront Coastal Villa in Palmetto DunesATTENTION: Elevator inoperable during the time period of Jan. 1, 2027 until March 6, 2027, due to the elevator being replaced (Dates Subject to Change)1 Bedroom | 1.5 Bathrooms | Sleeps 4 | Pet FriendlyWelcome to the luxurious one bedroom Barrington Villa, located on the third floor with stunning ocea
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Oceanfront Coastal 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 lovely 1st floor villa in the exclusive gated complex of Sea Cloisters. Our villa boasts stairs leading directly to the b
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Stunning Golf-View Oasis in Palmetto Dunes4 Bedrooms | 4 Bathrooms | Sleeps 12 | Family Fun Game RoomExperience the ultimate beach vacation at this 4-bedroom getaway with an open layout and stunning golf course views.Just a few minutes bike or walk via bike pathways to the beautiful beaches in Palmetto Dunes. Recently upgraded with gorgeous fu
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.
Moon River at Daufuskie – 8, 9 & 10 Daufuskie Bluff Lane 3 Coastal Cottages | 9 Bedrooms Total | Riverfront Retreat with Private Dock Located on Daufuskie Island, Moon River is a private three-home compound designed for group stays, family gatherings, and special occasions. The property includes three individual cottages—e
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.
New Property
New Property
Discover this fantastic property - a new addition to our growing family of vacation rentals.
Stunning Second-Row Family Oasis in Palmetto Dunes6 Bedrooms | 6.5 BathroomsThis stunning new 2020 beach home is perfect for families looking for a memorable vacation. With six spacious bedrooms and top-of-the-line amenities, this home is sure to exceed your expectations. Featuring three master suites, it's ideal for multi-generational getaways
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.
Elegant Oceanfront Penthouse Villa at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 8 | Stunning Ocean ViewsATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to our elegant penthouse villa located in Hilton Head Island's renowned Sea Cloisters. This tastefully decorat
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
