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 265 properties available
Walk to the beach, Coligny Plaza, Celebration Park, and the community pool from this beautifully updated South Forest Beach villa. Forest Gardens 66 offers the perfect Hilton Head Island getaway for couples, small families, golfers, and friends looking to enjoy one of the island’s most convenient and desirable locations.This bright and inviting sec
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Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 1 full baths
Guests 4 guests
Rating 5 (21)
3299 Lake Forest is a beautifully renovated 2 bedroom, 2 bathroom Lake Forest villa that provides guests with a peaceful Hilton Head getaway!The open-concept floor plan features a comfortable living area with plenty of seating, a wall-mounted Smart TV and access to the private deck overlooking the lagoon. The deck space has seating for 4 around a d
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (44)
Evian 257 is a true home-away-from-home in the popular Evian community of Shipyard, Hilton Head Island. This immaculate 2 bedroom, 2 bathroom Hilton Head villa boasts designer touches and golf course views in a serene setting on Hilton Head. As you step into the foyer, you will be immediately aware of the updated designer's touch that begins with
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 7 guests
Rating 5 (20)
With thoughtful updates throughout and picturesque golf course views, this 3BR/3.5BA townhome will be your low country dream vacation spot!The open concept floor plan of the main level features coastal decor, a Smart TV and access to the screened in porch over looking the golf course. The dining area seats 6 comfortably with additional seating at t
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 7 guests
Rating 5 (13)
169 Mooring Buoy will easily become the island oasis your family has been searching for! This beautifully outfitted home is located just a 2 minute walk to the Atlantic Ocean! The homeowners completed exciting renovations for the 2023 rental season, including new bathrooms, paint and furnishings. As you ascend the stairs to the main level, you'll e
Hot HOT 58
Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (9)
826 Ocean Cove is a beautifully updated 3 bedroom, 3 bathroom townhome located just steps from the beach and commuity pool. This uniquely outfitted property features LVP flooring, an open-concept floor plan and a sunroom! The main level of the townhome offers plenty of space to spread out with a well-appointed living area and a large sunroom just b
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (1)
Nestled in the serene enclave of Sea Pines on Hilton Head Island, Otter Road 105 is your idyllic retreat for a memorable getaway. This charming 3-bedroom, 2-bathroom dog-friendly home exudes warmth and comfort, perfectly accommodating up to six guests. Upon entering, you'll be greeted by a spacious living area designed for relaxation and entertainm
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 6 guests
Rating 5 (4)
82 North Sea Pines, also known as "Sea Retreat" is a beautifully updated, single level home, located just a short walk to the beach! This 3 bedroom, 2 bathroom spacious vacation spot is dog-friendly and offers quintessential golf course views. As you walk through the front door, you're greeted with lots of natural light and an open-concept floor pl
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Featured Properties Special

We’ve handpicked some of our favorite vacation rentals and made them even better with a discount! Browse our featured properties and find the perfect place for your next getaway. Availability is limited, so book your stay today and use promo code FEATURED10 to save today!


Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 3 bedrooms
Bathrooms 2 full baths
Guests 8 guests
Rating 5 (4)
This charming 3 bedroom, 3 bath pet-friendly Shipyard home is located in Hilton Head Island’s Shipyard less than a mile from the beach with a private pool! The perfect Hilton Head home villa rental with the comforts and privacy of a home rather than a crowded Hilton Head hotel room. The living room features a sofa, and loveseat in an ocean blue, a
Specials Tag Special
Featured Properties Special

We’ve handpicked some of our favorite vacation rentals and made them even better with a discount! Browse our featured properties and find the perfect place for your next getaway. Availability is limited, so book your stay today and use promo code FEATURED10 to save today!

Bedrooms 3 bedrooms
Bathrooms 3 full baths
Guests 8 guests
Rating 5 (21)
Look no further for your next family vacation home! 36 Kingston is a stunning 4 bedroom, 3 bathroom Shipyard Hilton Head pet-friendly rental with a private pool! This spacious home with an open floor plan features 2 living areas and a fantastic kitchen. With separate wings of the home on either side of the living areas, this 36 Kingston is perfect
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 4 bedrooms
Bathrooms 3 full baths
Guests 9 guests
Rating 5 (28)
This 2nd floor, 2 bedroom, 2 bath Hilton Head vacation villa in St. Andrews Commons is a luxurious getaway in the middle of the beautiful Palmetto Dunes resort area. If you’re looking for pet-friendly Hilton Head vacation villas, St. Andrews 1880 welcomes the entire family, including your pooch.Step through the front door and down into the main liv
Specials Tag Special
Monthly Rentals

Hilton Head monthly rentals are available from October 1st- April 1st. Avoid the cold weather and live like a local at one of our fully furnished properties. Please call 800.276.8991 for availability & monthly quotes.

Bedrooms 2 bedrooms
Bathrooms 2 full baths
Guests 5 guests
Rating 5 (12)
Welcome to Tennismaster 703, your perfect island escape on beautiful Hilton Head Island. This charming, yet spacious two-bedroom, dog-friendly, townhome offers an ideal blend of comfort, convenience, and coastal living, making it the ultimate destination for families, couples, and friends seeking a memorable vacation. Located in the peaceful Shipya
Bedrooms 2 bedrooms
Bathrooms 2 full baths 1 half bath
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.