Hilton Head Vacation Rentals

Browse our HIlton Head vacation rentals. We offer homes and villas in all of the finest neighborhoods such as Sea Pines, Palmetto Dunes, Forest Beach, Port Royal, Shipyard, and many more. With a selection of properties ranging from from smaller villas to large homes. Learn about all of Hilton Head's best vacation spots in our Resort Area Guide Here.

Our local reservation agents are always happy to assist you in finding the perfect rental for your Hilton Head Island vacation at 843-785-6767.


Properties Available 256 properties available
Your vacation will be a breeze in this 2 bedroom, 2.5 bath, renovated townhouse style villa in the Greens community on Hilton Head Island’s scenic and serene Shipyard.As you enter Greens 151 you will immediately notice the renovated kitchen with granite countertops and new cabinets. The kitchen is fully equipped with all of your cooking essential
Hot HOT 16
Bedrooms 2 bedrooms
Bathrooms 2 full baths 1 half bath
Guests 6 guests
Rating 5 (1)
Anticipation is part of the Hilton Head Island vacation experience. Visitors come from all parts of the globe to spend a week or two here on this tropical paradise. Many have come to expect more upscale accommodations and elegance on this island. After all, you’re in Hilton Head.Prepare to be amazed at this “over the top”, incredible Shipyard villa
Hot HOT 26
Bedrooms 3 bedrooms
Bathrooms 3 full baths 1 half bath
Guests 6 guests
Rating 5 (7)
If beach strolling is one of your passions, look no further for the perfect island accommodations on Hilton Head Island. This 2 bedroom and 2 bath Hilton Head Captains Walk villa is located on the 3rd floor of building one with island-inspired interiors and breathtaking views of the Atlantic Ocean from inside and out. This Palmetto Dunes beach vill
Specials Tag Special
Beach Renourishment Project

A beach renourishment project is currently underway near this property and will continue through the summer. Please contact our Guest Services team at 843-785-6767 or follow this link for additional information. If this message is still active, the project in this area is expected or ongoing. Thank you for your understanding as we preserve our gorgeous beaches!

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (10)
40 Red Oak is a spacious, meticulously appointed 4-bedroom, 3.5-bathroom home, ideally located near Harbour Town and the famed 12th and 13th holes of the Harbour Town Golf Course. Completely renovated in 2024, this home has all the comforts you’d expect from a premier Hilton Head vacation rental. The main level of the home has an open-concept livin
Specials Tag Special
Beach Renourishment Project

A beach renourishment project is currently underway near this property and will continue through the summer. Please contact our Guest Services team at 843-785-6767 or follow this link for additional information. If this message is still active, the project in this area is expected or ongoing. Thank you for your understanding as we preserve our gorgeous beaches!

Bedrooms 4 bedrooms
Bathrooms 3 full baths 1 half bath
Guests 10 guests
Rating 5 (3)
14 Evergreen is a lovely single level Sea Pines Vacation rental home, dog-friendly located just inside the main gate of Sea Pines! This beautifully updated 3 bedroom, 2 bathroom stair-free property offers the perfect location for your next HHI trip!The open concept floor plan is perfect for entertaining. The living area is comfortably furnished wit
Hot HOT 18
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 6 guests
Rating 5 (1)
This 4-bedroom, 4-bathroom Hilton Head Island Sea Pines villa is located just outside of South Beach in Sea Pines. With stunning updates throughout, with a pool and jacuzzi located in the center of the home, this home provides guests with comfort and relaxation.The large living area, which is open to the dining room, features a large sectional sofa
Specials Tag Special
Beach Renourishment Project

A beach renourishment project is currently underway near this property and will continue through the summer. Please contact our Guest Services team at 843-785-6767 or follow this link for additional information. If this message is still active, the project in this area is expected or ongoing. Thank you for your understanding as we preserve our gorgeous beaches!

Bedrooms 4 bedrooms
Bathrooms 4 full baths
Guests 10 guests
Rating 5 (5)
1660 Bluff Villas is a beautifully renovated 2 bedroom, 2 bathroom Hilton Head Sea Pines vacation rental condo perfectly situated in South Beach Marina. This property features an open concept floor plan, tile and LVP flooring throughout and all new bathrooms.The living area features comfortable furnishings, including a sleeper sofa, Smart TV and ac
Specials Tag Special
Beach Renourishment Project

A beach renourishment project is currently underway near this property and will continue through the summer. Please contact our Guest Services team at 843-785-6767 or follow this link for additional information. If this message is still active, the project in this area is expected or ongoing. Thank you for your understanding as we preserve our gorgeous beaches!

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (25)
Comfort meets luxury when you vacation at 2405 Sea Crest. This stunning 4th floor ocean view condo is located within the gated Sea Crest community, featuring oceanfront pools, hot tubs, a fitness center, indoor pool and sundeck. 2405 Sea Crest features an open-concept floor plan with tile and LVP flooring throughout. The living area is comfortably
Hot HOT 23
Bedrooms 1 bedrooms
Bathrooms 1 full baths 1 half bath
Guests 4 guests
Rating 5 (3)
304 Shorewood is a beautifully updated 2 bedroom, 2 bathroom oceanfront flat with direct views of the Atlantic! This 3rd floor condo is located in one of the most coveted communities in Forest Beach and offers vacationers a relaxing and fun-filled stay. The open concept living area features comfortable furnishings, including a sleeper sofa and a Sm
Hot HOT 30
Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 6 guests
Rating 5 (6)
Years from now you'll still be talking about the view from this Palmetto Dunes Resort beachfront villa on Hilton Head Island. Just steps from the sand, this 3 level, 3 bedroom and 4-bath Palmetto Dunes villa will surely meet all of your expectations for the perfect Hilton Head Island vacation.The ground-level entry foyer shows off easy-care tile fl
Hot HOT 32
Bedrooms 3 bedrooms
Bathrooms 4 full baths
Guests 8 guests
Rating 4.6 (5)
1681 Bluff Villas is a beautifully appointed 2 bedroom, 2 bathroom ground floor property offers expansive landscaped views and easy access to the Calibogue Sound. The living area features comfortable seating, a flat screen TV and access to the private patio. The dining area is just beyond the living area, as is the kitchen which features new applia
Specials Tag Special
Beach Renourishment Project

A beach renourishment project is currently underway near this property and will continue through the summer. Please contact our Guest Services team at 843-785-6767 or follow this link for additional information. If this message is still active, the project in this area is expected or ongoing. Thank you for your understanding as we preserve our gorgeous beaches!

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 4 guests
Rating 5 (4)
1502 Island Club offers luxury vacationing with world-class amenities! This top floor, meticulously outfitted 2BR/2BA condo offers breathtaking ocean views!The open-concept floor plan features a comfortable living area with a Smart TV and access to a balcony overlooking the Atlantic Ocean and Island Club grounds. Enjoy your morning coffee or evenin
Hot HOT 17
Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 6 guests

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Hilton Head Vacation Rentals Frequently Asked Questions:

What are the top activities to enjoy on Hilton Head Island?

Hilton Head Island offers you plenty of ways to connect with the coast. With 12 miles of beaches, there’s plenty of room for swimming, kayaking, or dolphin watching just offshore. Golfers head to iconic spots like the Harbour Town Golf Links, while adventurers can explore over 60 miles of bike trails that wind through Hilton Head’s forests and marshes.

You’ll find tennis courts for a friendly match with new friends, as well as fishing charters and boat tours that take you into the island’s scenic backwaters. If you’re looking to dive deeper into the Lowcountry culture, you can sample the local cuisine, especially the fresh caught seafood from local waters. Another can’t miss experience is the Gullah Heritage Trail, which showcases the island’s deep-rooted history and unique cultural heritage of Hilton Head Island. 

So, whether you’re looking to explore or unwind, the island meets you where you want to go. 

 

When is the best time to visit Hilton Head Island?

Every season on Hilton Head Island brings something different. Spring (March to May) and fall (September to November) bring comfortable weather and lighter crowds. Summer (June to August) is centred around the beach and is the island’s busiest season, with hot sunny days and a livelier setting.

Winter (December to February) is when the island is at its calmest. The air is cooler and the vibe is more serene- great for leisurely walks, a few rounds of golf, or simply enjoying Hilton Head without all the hustle and bustle. Whether you’re chasing sunshine, savings, or just some time to yourself, there’s a season for every kind of traveler.

 

How do I get to Hilton Head Island and move around once there?

The majority of Hilton Head Island visitors arrive by way of the Savannah/Hilton Head International Airport, which is about 45 miles away. If you’re flying regional, the smaller Hilton Head Island Airport gets you even closer to the coast in less time.

When you get to Hilton Head, biking is one of the best ways to get around. Rentals are everywhere, and the island’s long, winding paths connect you to all the island’s top attractions. A car helps for longer journeys such as beach day trips, grocery runs, or dining out in restaurants.

Walking works well in spots like Harbour Town, but you’ll want wheels to cover Hilton Head Island as a whole.


What is the weather like on Hilton Head Island throughout the year?

Hilton Head Island is warm most of the year, owing to its subtropical climate, with summer (June to August) featuring humid days and highs in the 80s and 90s. It’s a great time for swimming, but the heat might encourage a slower pace. You can also expect the occasional afternoon storm, but don’t worry—they’re fast-moving and gone before you know it.  

Winters are more mild, with daytime temperatures hovering in the 50s and 60s. It’s cool enough to add an extra layer of clothing then you can comfortably enjoy a walk or a round of golf.

Spring and fall (March to May) is a perfect balance, still sunny but cooler and less humid. Temperatures reach highs of 70, creating the perfect conditions for a full day of outdoor adventures.

How you pack for your Hilton Head Island vacation shifts with the seasons, so be sure to plan accordingly.

 

Where should I stay on Hilton Head Island for the best experience?

Different areas of the island offer their own unique experiences, offering resorts, condos, and villas, each with its own slice of paradise. Forest Beach is known for being close to the beach, with oceanfront homes and beachside stays. If you prefer being closer to the shops, restaurants, and a quick round of golf, places around Harbour Town might be a better choice for you.

For more privacy, Sea Pines is a gated, secluded community with quieter streets, pools, and plenty of space that’s ideal for large groups. Most of these properties also have easy access to trails by bike.

Whatever your preference, from laid-back to luxury, it’s all available on Hilton Head Island.