Hilton Head Island Spring Break

44 properties available

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! 6

Island Stay, Perfect for Adventure & Relaxation!

Townhouse | Hilton Head Island

As low as $86^.00 per night

The SpaceSet across two comfortable levels, this villa is a relaxed home base for families and small groups. Each bedroom has its own ensuite bath and private balcony, giving everyone a little extra space and privacy.Unwind after a day on the island, catch up on emails at the laptop-friendly workspace, and stay connected with WiFi. Step outside for

Fore Season Retreat - 2 BDR in Desirable Resort!

Fore Season Retreat - 2 BDR in Desirable Resort! 2

Fore Season Retreat - 2 BDR in Desirable Resort! 3

Fore Season Retreat - 2 BDR in Desirable Resort! 4

Fore Season Retreat - 2 BDR in Desirable Resort! 5

Fore Season Retreat - 2 BDR in Desirable Resort! 6

Fore Season Retreat - 2 BDR in Desirable Resort!

Villa | Hilton Head Island

As low as $89^.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 $61^.00 per night

Settle into a family-friendly condo designed for comfort and convenience. The living area offers room to relax and includes a full-size sleeper sofa for extra guests, plus a laptop-friendly workspace if you need to check in with the office. Both bedrooms feature smart TVs, and you’ll find board games on hand for low-key nights in.Head outside to en

Sunny Shores Retreat - Hilton Head Resort

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Sunny Shores Retreat - Hilton Head Resort 3

Sunny Shores Retreat - Hilton Head Resort 4

Sunny Shores Retreat - Hilton Head Resort 5

Sunny Shores Retreat - Hilton Head Resort 6

Sunny Shores Retreat - Hilton Head Resort

Condo | Hilton Head Island

As low as $80^.00 per night

Designed for easygoing island days, this family-friendly home offers three comfortable bedrooms and two full baths. You’ll have serene lagoon views and access to Sea Pines’ favorite perks—community pool, grills, tennis, pickleball, trails, and nearby beaches.A standout feature is the garage conversion into a polished, climate-controlled game room c

Stunning Lagoon View Rental Home in Sea Pines, HHI

Stunning Lagoon View Rental Home in Sea Pines, HHI 2

Stunning Lagoon View Rental Home in Sea Pines, HHI 3

Stunning Lagoon View Rental Home in Sea Pines, HHI 4

Stunning Lagoon View Rental Home in Sea Pines, HHI 5

Stunning Lagoon View Rental Home in Sea Pines, HHI 6

Stunning Lagoon View Rental Home in Sea Pines, HHI

House | Hilton Head Island

As low as $157^.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 $65^.00 per night

2 bedrooms

2 baths

6 guests

Designed for easygoing coastal getaways, this 2-bedroom, 2-bath condo offers a comfortable home base for families and small groups. Unwind after beach or pool time with Smart TVs in both bedrooms, a selection of board games, and a game console for low-key evenings in. Head outside to enjoy the fresh air with outdoor seating and make use of the on-s

2 BDR with Shared Pool & Tennis Courts, Walk to Beach

2 BDR with Shared Pool & Tennis Courts, Walk to Beach 2

2 BDR with Shared Pool & Tennis Courts, Walk to Beach 3

2 BDR with Shared Pool & Tennis Courts, Walk to Beach 4

2 BDR with Shared Pool & Tennis Courts, Walk to Beach 5

2 BDR with Shared Pool & Tennis Courts, Walk to Beach 6

2 BDR with Shared Pool & Tennis Courts, Walk to Beach

Condo | Hilton Head Island

As low as $67^.00 per night

Settle into a comfortable, family-friendly home designed for easy Lowcountry living. With 4 private bedrooms and 4 full bathrooms, everyone has space to spread out. The main living area flows to outdoor seating—perfect for morning coffee before a beach day or a relaxed evening barbecue. Smart TVs in select bedrooms make unwinding simple, while a la

Coastal 4 BDR for 8, Walk to Beach!

House | Hilton Head Island

As low as $300^.00 per night

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

4 bedrooms

3 baths

8 guests

Settle into a relaxed, group-friendly retreat designed for easy beach days and poolside evenings. The home sleeps 12 across four private bedrooms plus a studio-style suite above the garage, with four full bathrooms for added convenience.Gather indoors for game time at the foosball table, or head outside to your private swimming pool and hot tub. Fi

Beautiful 4BDR with Hot Tub & Pool, Shuttle to Beach!

Beautiful 4BDR with Hot Tub & Pool, Shuttle to Beach! 2

Beautiful 4BDR with Hot Tub & Pool, Shuttle to Beach! 3

Beautiful 4BDR with Hot Tub & Pool, Shuttle to Beach! 4

Beautiful 4BDR with Hot Tub & Pool, Shuttle to Beach! 5

Beautiful 4BDR with Hot Tub & Pool, Shuttle to Beach! 6

Beautiful 4BDR with Hot Tub & Pool, Shuttle to Beach!

House | Hilton Head Island

As low as $300^.00 per night

Perfect for families or a small group, this comfortable villa offers two private bedrooms, two full ensuite bathrooms, and an additional half bath. Settle into the living room for downtime, where a full-size sleeper sofa adds extra flexibility for your group.Both bedrooms include smart TVs, and there’s a laptop-friendly workspace if you need to che

Charming Condo Overlooking Pool, Minutes to Beach!

Charming Condo Overlooking Pool, Minutes to Beach! 2

Charming Condo Overlooking Pool, Minutes to Beach! 3

Charming Condo Overlooking Pool, Minutes to Beach! 4

Charming Condo Overlooking Pool, Minutes to Beach! 5

Charming Condo Overlooking Pool, Minutes to Beach! 6

Charming Condo Overlooking Pool, Minutes to Beach!

Villa | Hilton Head Island

As low as $89^.00 per night

Settle into a comfortable, family-friendly 2-bedroom, 2-bath condo designed for easy beach days and relaxed evenings. The living room offers a queen sleeper sofa for added flexibility, plus Wi-Fi, board games, and a DVD player for downtime. Both bedrooms feature smart TVs, and a laptop-friendly workspace makes it simple to check in with the office

Hilton Head Hangout - 2 BDR Resort Condo by Beach!

Hilton Head Hangout - 2 BDR Resort Condo by Beach! 2

Hilton Head Hangout - 2 BDR Resort Condo by Beach! 3

Hilton Head Hangout - 2 BDR Resort Condo by Beach! 4

Hilton Head Hangout - 2 BDR Resort Condo by Beach! 5

Hilton Head Hangout - 2 BDR Resort Condo by Beach! 6

Hilton Head Hangout - 2 BDR Resort Condo by Beach!

Condo | Hilton Head Island

As low as $79^.00 per night

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