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.
121 properties available
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
Exceptional Oceanfront Penthouse Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8ATTENTION: Building Construction during the time period of Sept 11, 2027 until March 19, 2028 (Dates Subject to Change)Welcome to the luxurious vacation home of Villa 501 at Sea Cloisters in Hilton Head Island. This stunning penthouse villa offers a truly rema
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
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
Oceanfront Windsor Place II Villa in Palmetto Dunes3 Bedrooms | 3 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)Located just steps from the sand in the heart of Palmetto Dunes, 2117 Windsor Place 2 offers
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
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
Spacious Dog Friendly Home Located in Sea Pines4 Bedrooms | 3.5 Bathrooms | Sleeps 10 | Private Pool & SpaLooking for a prime location for your next vacation? Look no further than 16 Duck Hawk, located in the heart of Sea Pines on Hilton Head Island.Upon entering the home, you'll be greeted with an expansive living room that transitio
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.
Oceanfront Barrington Court 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)2 Bedrooms | 2 Bathrooms | Sleeps 5 | Complex Pool & Hot TubExperience the ultimate beach vacation in this stunning 2-bedroom, 2-bath
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
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.
Cozy Stones Throw Villa Ideal for Family Getaways3 Bedrooms | 2 Bathrooms | 1 Half Bathroom | Sleeps 8Welcome to this wonderful 3-bedroom, 2.5-bathroom villa in Hilton Head Island, offering the perfect setting for an unforgettable beach vacation. Situated just a short stroll away from the Atlantic Ocean and miles of pristine beach, this villa provi
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!
Coastal Getaway in Palmetto Dunes3 Bedrooms | 2.5 Bathrooms | Dog FriendlyWelcome to our beautifully remodeled villa, the perfect vacation home for families, golf groups, corporate retreats, or anyone looking for a peaceful getaway. This 3BR/2.5BA villa sleeps 8 guests and is located on the first floor of a two-story villa complex in Palmetto
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.
The Grouper Cottage – Moon River with a Private Dock3 Bedrooms | 3 Bathrooms | Sleeps 6 | Waterfront | Private DockRiverfront Cottage located within the Moon River compound on Daufuskie Island, Grouper Cottage offers direct waterfront views and a layout designed for relaxed, coastal living. This three-bedroom home provides a comfort
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.
