Hilton Head Vacation Rentals

Browse Hilton Head vacation rentals offering the space, comfort and convenience you need for an unforgettable island getaway. Host2Coast features locally managed vacation homes, villas and condos for family beach trips, romantic escapes, golf vacations and group getaways.

Choose from rentals near the beach, community amenities, shopping, dining, golf courses and Hilton Head Island’s extensive bike paths. Options include oceanfront rentals, dog-friendly properties, private-pool homes and spacious accommodations for larger groups.


Why Book Your Hilton Head Vacation Rental with Host2Coast?

  • Locally managed properties with personalized guest service
  • Vacation homes, villas and condos for different group sizes and budgets
  • Prime locations near Hilton Head Island beaches, restaurants, shops, golf courses and bike paths
  • Direct access to the Host2Coast team before and during your stay
  • Convenient direct booking without relying on a third-party marketplace


Browse Hilton Head Rentals by Location and Amenities

Find vacation rentals in popular Hilton Head communities, including Sea Pines, Palmetto Dunes, Shipyard, North Forest Beach and South Forest Beach.

You can also browse oceanfront rentals, dog-friendly rentals and vacation rentals with private pools.

Use the search filters on this page to compare available Hilton Head rentals and find the right location, property type and amenities for your stay.

Hilton Head Island vacation rental managed by Host2Coast

Properties Available 268 properties available
Welcome to 36 Bradley Circle, a breathtaking third-row ocean home that captures the beauty, charm, and elegance of Hilton Head Island. This six-bedroom, six-bath retreat offers everything you need for an unforgettable coastal getaway. Perfect for families and groups of up to 19 guests, it delivers a seamless blend of comfort, sophistication, and co
36 Bradley Circle
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 19 guests
Rating 4.8 (75)
Discover the perfect blend of luxury and coastal charm at 24 Red Cardinal, a breathtaking second-row ocean retreat on Hilton Head Island! Just steps from the iconic Sea Pines Beach Club, this home welcomes you into a world of elegance and relaxation. Every detail, from the hand-selected furnishings to the curated design accents, has been thoughtful
24 Red Cardinal
House
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half baths
Guests 12 guests
Rating 5 (9)
Your Hilton Head Island vacation should be nothing less than spectacular and 8 Dewberry Lane nestled in the heart of Sea Pines Resort gives you that and more! Community pool and tennis court included! This beautiful vacation “home away from home” comfortably accommodates a family or group of 8 and is located just a short walk or bike ride to the
8 Dewberry Lane
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 4.9 (54)
NEW! Welcome to your dream getaway at this spacious, light-filled end-unit villa in Palmetto Dunes Oceanfront Resort. Overlooking the stunning Robert Trent Jones Golf Course, this 3-bedroom, 3-bath retreat combines luxury, comfort, and an unbeatable location for a memorable Hilton Head Island escape.Step inside to discover a beautifully updated vil
6 Water Oak Villas
Villa
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 5 (21)
"Immaculate and modern. Comfortable beds, beautiful baths, wonderfully relaxing furniture in front of the living room TV (plus a TV in each bedroom). Steady wi-fi. A Keurig, a blender, and all the gadgets needed in the kitchen. The minute I walked in the door I could feel the stress of everything start to lift. I felt so welcome. I walked under tal
1657 Bluff Villas
Villa
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (63)
Welcome to 203 Beachwalk, a beautifully updated villa tucked within the lush, gated community of Shipyard Plantation on Hilton Head Island. Just a short walk from the beach and community pool, this inviting retreat places you close to the surf, sand, and scenic bike paths that make Hilton Head one of the East Coast’s most beloved vacation destinati
203 Beachwalk
Villa Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 7 guests
Rating 4.9 (54)
Live your best Sea Pines life when you choose Pedal and Paddle as your South Beach retreat! Waterfront with its own dock, 1603 Port Villa is a stunning 2-bedroom home on Braddock Cove just a short stroll from the Salty Dog Marina and HHI’s top-rated pickleball courts! Look no further - this beautiful coastal escape is now available for rent for the
1603 Port Villas
Villa
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 6 guests
Rating 5 (30)
Discover your ideal retreat at this charming, cottage-esque villa, where breathtaking views and a daily hour of complimentary tennis are just the beginning!This newly redecorated 2-bedroom villa offers stunning views from every angle, high ceilings, and private Adirondack chairs with serene lagoon views. Just steps from South Beach Marina and the b
Hot HOT 57
1601 Port Villas
Villa Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.9 (57)
Step into a world where azure walls meet warm wood textures, creating a bright sanctuary that feels like a permanent summer morning. The open living space welcomes you with plush velvet seating and woven bistro chairs that sit under the soft, golden glow of a patterned pendant lamp. Large glass doors invite the vibrant outdoors inside, filling ever
2404 Hilton Head Resort
Villa
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Ascend the grand staircase of this stately third row from the ocean, where mature oaks draped in silver Spanish moss frame a sanctuary of coastal refinement. Just a 1 minute stroll from the rhythmic pull of the Atlantic, this residence serves as a private bastion of luxury for those who appreciate the finer nuances of island living. Every architect
6 Kingfisher Street
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 1 half baths
Guests 16 guests
This just renovated villa is located in the Queen's Grant section of the Palmetto Dunes resort community and offers an ideal ground-floor locale with a private back patio and grill. The interior has vaulted ceilings, three smart TVs, and dual suites. Off of the living area two sliding glass doors open to the patio for outdoor grilling and relaxatio
558 Queen's Grant
Villa
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.9 (32)
The perfect place to start your island vacation is at this fabulous villa, stylishly designed for you by a professional interior designer. Also, strong Wi-Fi easily accommodates working/schooling remotely, so stay awhile and enjoy the beach and other amenities when you wish.This exquisite villa is truly a jewel in the SeaCrest crown. Experience dec
2402 Seacrest
Villa
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 (106)

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More Ways to Find Your Hilton Head Rental

Host2coast manages a wide selection of Hilton Head condo rentals and Hilton Head Island house rentals. Choose from comfortable condos, spacious villas and private vacation homes in some of the island’s most popular communities.

Our collection includes rentals in Sea Pines, Palmetto Dunes, Shipyard, North Forest Beach and South Forest Beach.

Browse Popular Hilton Head Rental Searches

Hilton Head Vacation Rental FAQs

What types of Hilton Head vacation rentals are available?

Host2coast offers vacation homes, villas and condos for couples, families and larger groups. Available properties range from convenient one- and two-bedroom condos to spacious homes with multiple bedrooms, outdoor living areas and private pools.

Which area of Hilton Head Island is best for my stay?

The best location depends on the kind of vacation you are planning. Sea Pines is known for Harbour Town, golf and resort amenities. Palmetto Dunes offers beaches, golf and lagoon activities. North Forest Beach and South Forest Beach provide convenient access to the beach and the Coligny area, while Shipyard offers a quieter resort setting with golf and beach access.

Can I rent an oceanfront property on Hilton Head Island?

Yes. Browse our Hilton Head oceanfront rentals to find available condos, villas and homes with convenient beach access. Location, views and amenities vary by property, so review each listing for complete details.

Are dog-friendly Hilton Head rentals available?

Yes. Host2coast offers a selection of dog-friendly Hilton Head vacation rentals. Pet policies, size restrictions and fees may vary, so check the individual property details before booking.

Do you offer Hilton Head rentals with private pools?

Yes. Our Hilton Head rentals with private pools include homes for families and groups seeking additional privacy and space. Pool availability, heating options and related fees vary by property.

What amenities are included with a vacation rental?

Amenities vary by property, but many rentals include equipped kitchens, Wi-Fi, laundry facilities, outdoor spaces and access to nearby beaches or community amenities. Use the search filters and review the individual property listing to confirm everything included with your rental.

When is the best time to visit Hilton Head Island?

Summer is popular for family beach vacations, while spring and fall offer comfortable weather for biking, golf and outdoor activities. Winter is typically quieter and can be a good choice for travelers looking for a more relaxed island stay.

Why should I book directly with host2coast?

Booking directly connects you with a local team that knows the properties and Hilton Head Island. Host2coast can help answer questions about locations, property features and availability before your trip and provide local support throughout your stay.

How can I get help choosing a rental?

Visit our general FAQ page for additional booking information or contact host2coast for personalized assistance finding the right vacation rental.