Hilton Head Island Spring Break

42 properties available

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 $152^.00 per night

Designed for simple, comfortable beach days, this condo accommodates up to 6 guests across two bedrooms and a sleeper sofa. The main living area gives you space to relax after the beach with WiFi and board games for low-key evenings. Step outside to an outdoor seating area for morning coffee or an afternoon breather. A private washer and dryer make

Beach Access, Pool & Tennis - Sleeps 6 2

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Beach Access, Pool & Tennis - Sleeps 6 6

Beach Access, Pool & Tennis - Sleeps 6

Condo | Hilton Head Island

As low as $91^.00 per night

Sleep up to 12 guests in this 4-bedroom, 4-bath single-family home located in Sea Pines, Hilton Head Island, SC. Designed on a single level for easy living, the home offers an open and comfortable layout that flows from the main living areas into the Carolina Room and outdoor spaces, making it easy to relax and enjoy time together throughout your s

Walk to Beach, Private Pool Onsite Sleeps 12

Walk to Beach, Private Pool Onsite Sleeps 12 2

Walk to Beach, Private Pool Onsite Sleeps 12 3

Walk to Beach, Private Pool Onsite Sleeps 12 4

Walk to Beach, Private Pool Onsite Sleeps 12 5

Walk to Beach, Private Pool Onsite Sleeps 12 6

Walk to Beach, Private Pool Onsite Sleeps 12

House | Hilton Head Island

As low as $289^.00 per night

4 bedrooms

4 baths

12 guests

Settle into a simple, comfortable 1-bedroom, 1-bath condo designed for easy beach days and relaxing evenings. The living area offers flexible seating and a sleeper sofa for extra guests, with WiFi and a laptop-friendly workspace if you need to check in with the office. A cozy hallway alcove holds twin bunks the kids will love, while the primary bed

Island Condo for 6 w Communal Pool - Perfect Spot!

Island Condo for 6 w Communal Pool - Perfect Spot! 2

Island Condo for 6 w Communal Pool - Perfect Spot! 3

Island Condo for 6 w Communal Pool - Perfect Spot! 4

Island Condo for 6 w Communal Pool - Perfect Spot! 5

Island Condo for 6 w Communal Pool - Perfect Spot! 6

Island Condo for 6 w Communal Pool - Perfect Spot!

Condo | Hilton Head Island

As low as $77^.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 $105^.00 per night

Settle into a comfortable, family-friendly condo designed for easy vacation living. The open living area offers plenty of seating for movie nights and includes a queen-size sleeper sofa to accommodate your group. Step out to two private balconies—one from each bedroom—to enjoy fresh breezes and water views.Each bedroom features a smart TV and an en

2 BDR Family with Water Views, Beach Access, & 0-Entry Pool!

2 BDR Family with Water Views, Beach Access, & 0-Entry Pool! 2

2 BDR Family with Water Views, Beach Access, & 0-Entry Pool! 3

2 BDR Family with Water Views, Beach Access, & 0-Entry Pool! 4

2 BDR Family with Water Views, Beach Access, & 0-Entry Pool! 5

2 BDR Family with Water Views, Beach Access, & 0-Entry Pool! 6

2 BDR Family with Water Views, Beach Access, & 0-Entry Pool!

Condo | Hilton Head Island

As low as $300^.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 $68^.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 offer

4BR for 6 w/ Shared Pool, Pickleball & Tennis!

4BR for 6 w/ Shared Pool, Pickleball & Tennis! 2

4BR for 6 w/ Shared Pool, Pickleball & Tennis! 3

4BR for 6 w/ Shared Pool, Pickleball & Tennis! 4

4BR for 6 w/ Shared Pool, Pickleball & Tennis! 5

4BR for 6 w/ Shared Pool, Pickleball & Tennis! 6

4BR for 6 w/ Shared Pool, Pickleball & Tennis!

House | Hilton Head Island

As low as $300^.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

Condo Near Harbour Town w/ Pool & Tennis! 5

Condo Near Harbour Town w/ Pool & Tennis! 6

Condo Near Harbour Town w/ Pool & Tennis!

Condo | Hilton Head Island

As low as $109^.00 per night

Designed for groups, this two-story home offers flexible sleeping options and simple comforts for an easy stay. You’ll have two living rooms to spread out, Smart TVs for movie nights, and high-speed Wi-Fi with a laptop-friendly workspace for those who need to check in at work. Central air and heating keep things comfortable year-round, and self che

Family-Friendly Hilton Head Home | 4BR, 3BA, Near Folly Field Beach, Sleeps 18

Family-Friendly Hilton Head Home | 4BR, 3BA, Near Folly Field Beach, Sleeps 18 2

Family-Friendly Hilton Head Home | 4BR, 3BA, Near Folly Field Beach, Sleeps 18 3

Family-Friendly Hilton Head Home | 4BR, 3BA, Near Folly Field Beach, Sleeps 18 4

Family-Friendly Hilton Head Home | 4BR, 3BA, Near Folly Field Beach, Sleeps 18 5

Family-Friendly Hilton Head Home | 4BR, 3BA, Near Folly Field Beach, Sleeps 18 6

Family-Friendly Hilton Head Home | 4BR, 3BA, Near Folly Field Beach, Sleeps 18

House | Hilton Head Island

As low as $163^.00 per night

Designed for easygoing coastal days, this villa is a relaxed home base for families or couples traveling together. It sleeps 6 guests across two private bedrooms and features one spa-like full bathroom with a walk-in glass shower.Unwind in the comfortable living area, stream your favorites on the smart TVs in each bedroom, and stay connected with W

HOT 149

Palmetto Dunes Villa - one level, beach, golf, tennis, pickleball, boating. Walkable area

Palmetto Dunes Villa - one level, beach, golf, tennis, pickleball, boating. Walkable area 2

Palmetto Dunes Villa - one level, beach, golf, tennis, pickleball, boating. Walkable area 3

Palmetto Dunes Villa - one level, beach, golf, tennis, pickleball, boating. Walkable area 4

Palmetto Dunes Villa - one level, beach, golf, tennis, pickleball, boating. Walkable area 5

Palmetto Dunes Villa - one level, beach, golf, tennis, pickleball, boating. Walkable area 6

Palmetto Dunes Villa - one level, beach, golf, tennis, pickleball, boating. Walkable area

Villa | Hilton Head Island

As low as $139^.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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