Hilton Head Island Spring Break

42 properties available

Set in the quiet, gated Carolina Place neighborhood within Sea Pines, this bright and comfortable home is ideal for families and groups. With four sleeping areas and three full bathrooms, everyone has space to relax.The primary suite features a king bed, private sitting area, and a spacious ensuite with a walk-in shower. A second guest suite offers

Sweet Carolina - 4BR Pools, Pickleball, Tennis

Sweet Carolina - 4BR Pools, Pickleball, Tennis 2

Sweet Carolina - 4BR Pools, Pickleball, Tennis 3

Sweet Carolina - 4BR Pools, Pickleball, Tennis 4

Sweet Carolina - 4BR Pools, Pickleball, Tennis 5

Sweet Carolina - 4BR Pools, Pickleball, Tennis 6

Sweet Carolina - 4BR Pools, Pickleball, Tennis

House | Hilton Head Island

As low as $300^.00 per night

Designed for easy, comfortable days between the beach and the pool, this 2BR/2BA condo is a welcoming home base for families and small groups. The living areas flow to an outdoor seating area for morning coffee or an evening wind-down, and a BBQ grill makes simple at-home meals a breeze.Stay connected with Wi-Fi and a laptop-friendly workspace. The

Beachy Vibe - 2 BDR In Desirable HHI Resort!

Beachy Vibe - 2 BDR In Desirable HHI Resort! 2

Beachy Vibe - 2 BDR In Desirable HHI Resort! 3

Beachy Vibe - 2 BDR In Desirable HHI Resort! 4

Beachy Vibe - 2 BDR In Desirable HHI Resort! 5

Beachy Vibe - 2 BDR In Desirable HHI Resort! 6

Beachy Vibe - 2 BDR In Desirable HHI Resort!

Condo | Hilton Head Island

As low as $100^.00 per night

Settle into a comfortable, easygoing villa designed for relaxed beach days and effortless evenings, perfectly located within Hilton Head Island’s most desirable communities: Palmetto Dunes Oceanfront Resort. Thoughtfully laid out for comfort and convenience, the bedroom features a king bed, while the living area includes a sleeper sofa with mattres

Lagoon and Links Escape

Apartment | Hilton Head Island

As low as $74^.00 per night

What You’ll Love:• About five minutes to the beach, Coligny Plaza, and Celebration Park• Complimentary golf cart to explore the island (waiver required; see Important Things to Note)• Hot tub relaxation• Beach access and near-ocean location• Streaming-capable smart TV for your apps• Board games for family-friendly fun• Laptop-friendly workspace• Gr

Lagoon Retreat - Pet-Friendly 4BR, Loft, Golf Cart Near Beach, Spa

Lagoon Retreat - Pet-Friendly 4BR, Loft, Golf Cart Near Beach, Spa 2

Lagoon Retreat - Pet-Friendly 4BR, Loft, Golf Cart Near Beach, Spa 3

Lagoon Retreat - Pet-Friendly 4BR, Loft, Golf Cart Near Beach, Spa 4

Lagoon Retreat - Pet-Friendly 4BR, Loft, Golf Cart Near Beach, Spa 5

Lagoon Retreat - Pet-Friendly 4BR, Loft, Golf Cart Near Beach, Spa 6

Lagoon Retreat - Pet-Friendly 4BR, Loft, Golf Cart Near Beach, Spa

House | Hilton Head Island

As low as $150^.00 per night

Settle into a comfortable 2-bedroom, 2-bath condo designed for easy vacation living. The open living area offers plenty of seating and a full-size sleeper sofa for extra guests, plus convenient WiFi and a laptop-friendly workspace if you need to check in with the office. Step outside to an outdoor seating area for fresh-air lounging. You’ll also ha

Condo Near Harbour Town w/ Pool & Tennis!

Condo Near Harbour Town w/ Pool & Tennis! 2

Condo Near Harbour Town w/ Pool & Tennis! 3

Condo Near Harbour Town w/ Pool & Tennis! 4

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Condo Near Harbour Town w/ Pool & Tennis! 6

Condo Near Harbour Town w/ Pool & Tennis!

Condo | Hilton Head Island

As low as $110^.00 per night

This comfortable second-floor condo is a simple, convenient home base for your Hilton Head stay. With two private bedrooms and two full bathrooms, it’s a great fit for families or couples traveling together.Unwind between outings with smart TVs in each bedroom and two shower/tub combo bathrooms for easy routines. Enjoy the resort setting with ameni

Ocean Breeze - Island Retreat for 6

Condo | Hilton Head Island

As low as $76^.00 per night

Settle into an open, inviting 3rd-floor villa with the largest 2-bedroom floor plan in Bluff Villas. The cathedral-ceiling living room offers a Smart TV, a full-size sleeper sofa, and sliding doors to a private balcony with outdoor seating and a slight peek of Calibogue Sound.The kitchen is fully equipped with newer appliances, granite counters, a

2BR Bluff Villa w Balcony, Walk to Salty Dog!

2BR Bluff Villa w Balcony, Walk to Salty Dog! 2

2BR Bluff Villa w Balcony, Walk to Salty Dog! 3

2BR Bluff Villa w Balcony, Walk to Salty Dog! 4

2BR Bluff Villa w Balcony, Walk to Salty Dog! 5

2BR Bluff Villa w Balcony, Walk to Salty Dog! 6

2BR Bluff Villa w Balcony, Walk to Salty Dog!

Villa | Hilton Head Island

As low as $110^.00 per night

Settle into a comfortable, family-friendly condo with space for up to 6 guests. Located on the 4th floor, the home includes two bedrooms, two full bathrooms, and a relaxed living setup that makes it easy to come back from the beach, refresh, and unwind.Head out to enjoy the resort’s indoor and outdoor pools, hot tub, tennis courts, sauna, fitness r

Aqua Vista Retreat - 2 BDR in Spectacular Resort!

Aqua Vista Retreat - 2 BDR in Spectacular Resort! 2

Aqua Vista Retreat - 2 BDR in Spectacular Resort! 3

Aqua Vista Retreat - 2 BDR in Spectacular Resort! 4

Aqua Vista Retreat - 2 BDR in Spectacular Resort! 5

Aqua Vista Retreat - 2 BDR in Spectacular Resort! 6

Aqua Vista Retreat - 2 BDR in Spectacular Resort!

Condo | Hilton Head Island

As low as $73^.00 per night

Perfect for families and groups, this spacious, kid-friendly house offers 9 private bedrooms and 6 full bathrooms. Relax and reconnect across easygoing indoor and outdoor gathering areas, then step outside to your private pool and furnished patio for sunny lounge time and BBQ dinners.Inside, you’ll find smart TVs in many bedrooms, a game console fo

Sandy Beach Retreat – Burkes Beach w/ Private Pool

Sandy Beach Retreat – Burkes Beach w/ Private Pool 2

Sandy Beach Retreat – Burkes Beach w/ Private Pool 3

Sandy Beach Retreat – Burkes Beach w/ Private Pool 4

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Sandy Beach Retreat – Burkes Beach w/ Private Pool 6

Sandy Beach Retreat – Burkes Beach w/ Private Pool

House | Hilton Head Island

As low as $300^.00 per night

Settle into a comfortable, beach-friendly condo designed for easy days by the shore and relaxed evenings in. The living area is a casual spot to unwind, and a small private balcony invites breezy morning coffee or sunset downtime. Two bedrooms plus a queen sleeper sofa sleep up to six, with two full bathrooms for convenient get-ready routines.You’l

Fiddler's Cove Retreat - Top-Floor Beach Condo, Pool, Walk to Shore

Fiddler's Cove Retreat - Top-Floor Beach Condo, Pool, Walk to Shore 2

Fiddler's Cove Retreat - Top-Floor Beach Condo, Pool, Walk to Shore 3

Fiddler's Cove Retreat - Top-Floor Beach Condo, Pool, Walk to Shore 4

Fiddler's Cove Retreat - Top-Floor Beach Condo, Pool, Walk to Shore 5

Fiddler's Cove Retreat - Top-Floor Beach Condo, Pool, Walk to Shore 6

Fiddler's Cove Retreat - Top-Floor Beach Condo, Pool, Walk to Shore

Condo | Hilton Head Island

As low as $81^.00 per night

This family-friendly condo offers a straightforward, comfortable base for your Hilton Head getaway. With two private bedrooms and two full bathrooms, it works well for a small family or two couples with kids.Both bedrooms have smart TVs for easy downtime. The primary suite includes an ensuite bath for added privacy. You’ll be in a resort community

Seashell Sanctuary - Overlooks pool, walk to beach!

Seashell Sanctuary - Overlooks pool, walk to beach! 2

Seashell Sanctuary - Overlooks pool, walk to beach! 3

Seashell Sanctuary - Overlooks pool, walk to beach! 4

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Seashell Sanctuary - Overlooks pool, walk to beach! 6

Seashell Sanctuary - Overlooks pool, walk to beach!

Condo | Hilton Head Island

As low as $83^.00 per night

Settle into a relaxed, family-friendly townhouse designed for easy coastal living. With two private bedrooms and two full bathrooms, the home comfortably sleeps four and gives everyone room to unwind.Enjoy a comfortable living area for gathering, Wi-Fi to stay connected, and a laptop-friendly workspace if you need to check in with the office. Step

Island Stay, Perfect for Adventure & Relaxation!

Island Stay, Perfect for Adventure & Relaxation! 2

Island Stay, Perfect for Adventure & Relaxation! 3

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Island Stay, Perfect for Adventure & Relaxation! 5

Island Stay, Perfect for Adventure & Relaxation! 6

Island Stay, Perfect for Adventure & Relaxation!

Townhouse | Hilton Head Island

As low as $94^.00 per night

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