Memorial Day Vacation Rentals

Memorial Day Weekend marks the unofficial start of summer, and there are few better places to celebrate than Hilton Head Island. With warm sunshine, beautiful beaches, world-class golf, waterfront dining, and family-friendly activities, the island comes alive as visitors gather to honor our nation's heroes while enjoying one of the most anticipated holiday weekends of the year. 

Whether you're planning a long weekend with family, a golf getaway with friends, or a relaxing beach vacation, Memorial Day is the perfect time to experience everything Hilton Head Island has to offer. From sunrise walks along the Atlantic Ocean to sunset dinners overlooking the water, every day offers new opportunities to create lasting memories.

Memorial Day weekend is one of the first opportunities each year to fully enjoy Hilton Head's spectacular beaches. Miles of wide, hard-packed sand make it easy to walk, bike, or simply relax while listening to the waves. Families can spend the day building sandcastles, swimming, shell collecting, or playing beach games, while early risers are rewarded with breathtaking sunrises over the Atlantic. 

Popular beach areas such as Coligny Beach Park, Sea Pines Beach Club, Folly Field Beach Park, and Driessen Beach Park offer convenient access and amenities, making it easy to enjoy a full day by the ocean.


Properties Available 45 properties available
This two-story townhouse has been beautifully updated and is located within the gated community of Shipyard Resort, perfect for both beach and golf enthusiasts. With 3 bedrooms and 3.5 baths, this townhouse is ideal for families and groups of friends. The slightly elevated first floor features a spacious living room and flat screen TV. A half bath
Complex Pool Complex Pool
Complex Pool
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #045978
Beachwalk 145
Shipyard
Total Price: $3,090.99
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (6)
415 CAPTAINS WALK The Captains Walk Villas offer sensational oceanfront views plus an oceanfront pool and baby pool right on site for the guests of Captains Walk & Captains Cove. This villa provides an oceanfront view from the kitchen to the master bedroom and is just steps to the beach. 415 Captains Walk, located on the 3rd floor, has a panora
3rd Floor Oceanfront 3rd Floor Oceanfront
3rd Floor Oceanfront
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #071136
Captains Walk 415
Palmetto Dunes
Total Price: $4,302.38
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (35)
28 WAGON ROAD This lovely 3 Bedroom, 2 Bath, single level home offers an open living room with vaulted beamed ceilings, a spacious eat-in kitchen with Island, and Private Pool. 4 Flat Screen TV\'s and a fabulous floor plan. This home is ideal for avid golfers and beach lovers alike, with less than a 10 minute walk to the beach! Guests of 28 Wag
Private Pool Private Pool
Private Pool
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #033534
Wagon Road 28
Sea Pines Resort
Total Price: $5,930.93
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (5)
310 SHOREWOOD Ideal for beach lovers, this charming 3rd floor villa offers exceptional Oceanfront views and is within easy walking distance to Coligny Plaza with more than 60 shops & restaurants. The Oceanfront Master Bedroom offers a King bed & Private Bath and the Guest bedroom has a Queen & Twin bed plus a Private Bath. The villa offers an Ocea
3rd Floor Oceanfront 3rd Floor Oceanfront
3rd Floor Oceanfront
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #070674
Shorewood 310
Forest Beach
Total Price: $4,354.35
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.6 (54)
Welcome to The Greens! Your vacation will be special in this 1 bedroom, 1.5 bath townhouse style villa within the gated community of Shipyard Resort, perfect for both beach and golf enthusiasts. Upon entering The Greens 168 you will find a spacious open floor plan. To the right of the entrance is the dining area with seating for four, next to the
Complex Pool Complex Pool
Complex Pool
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #075804
Greens 168
Shipyard
Total Price: $2,043.74
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (8)
70 FULL SWEEP This unique home offers an open floor plan on one floor. Plenty of privacy, directly on a lagoon, with only one neighboring house. Exterior features include a Private Pool with a Spacious Deck to sit back and enjoy all of the wildlife in the area. Easy bike ride to the beach or a 10 minute leisurely walk. Free Wi-Fi. Limit 10. Gue
Private Pool Private Pool
Private Pool
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #029669
Full Sweep 70
Palmetto Dunes
Total Price: $7,270.73
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (11)
THE SPACE This updated ocean-view condo offers the perfect combination of comfort, location and costal style. The open-concept living and dining area is designed for relaxing after a day at the beach, with easy access to a private balcony overlooking the pool and ocean. The fully equipped kitchen has been upgraded with quartz countertops, stainl
Penthouse Oceanview Penthouse Oceanview
Penthouse Oceanview
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #077358
Shorewood 532
Forest Beach
Total Price: $3,545.85
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.7 (20)
1905 SOUTH BEACH CLUB VILLA This delightful first floor villa offers fabulous views of the Ocean, Beach, Sound and Beachfront Pool. This villa has been recently updated in 2025 and is sure to please every member of your family. It is within easy walking distance to the South Beach Marina Village and the ever popular Salty Dog Cafe. This unique v
1st Floor Oceanfront 1st Floor Oceanfront
1st Floor Oceanfront
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #025723
South Beach Club 1905
Sea Pines Resort
Total Price: $5,815.43
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (19)
Colonnade Club 205 offers the convenience of a first-floor flat for guests to enjoy. The furnished villa is located in close proximity to the shared outdoor grilling area, the on-site pool, and poolside spa. Access to the beach is a short walk away through the adjacent beach path that leads directly to the Shipyard Beach Club. The villa includes
Complex Pool Complex Pool
Complex Pool
Professionally Managed By Hilton Head Rentals - Town of Hilton Head Island Vacation Rental Permit #074852
Colonnade Club 205
Shipyard
Total Price: $1,878.72
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 4.7 (7)
539 SHOREWOOD This recently updated villa offers beautiful views of the Atlantic Ocean. Walk easily to Coligny Plaza with more than 60 shops & restaurants, or spend each day at the Beach! Free Wi-Fi. The Pool is Heated March, April, October & November. FIFTH FLOOR SINGLE LEVEL POOL AND OCEAN VIEW VILLA ~ Living Room | Ocean View Living | F
Penthouse Oceanview Penthouse Oceanview
Penthouse Oceanview
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #026096
Shorewood 539
Forest Beach
Total Price: $3,545.85
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.5 (54)
1408 VILLAMARE Experience the soothing sounds of the ocean from this stunning, fully renovated fourth-floor oceanfront villa on Hilton Head Island. Featuring elegant Italian porcelain wood-look flooring and custom cabinetry, this villa offers a tranquil coastal ambiance with sweeping views of the Atlantic from every room. The open-concept kitchen
4th Floor Oceanfront 4th Floor Oceanfront
4th Floor Oceanfront
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #036386
Villamare 1408
Palmetto Dunes
Total Price: $4,533.38
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (7)
1043 CARAVEL COURT This tastefully decorated, 2 story, 4th & 5th floor Penthouse offers breathtaking views of Harbour Town Yacht Basin, the Lighthouse, and the gorgeous sunsets! Guests of 1043 Caravel Court can sit back & relax on the balcony, taking in the perfect views, or take a short walk and enjoy complimentary access to the Harbour Town Pool
Harbour Town Harbour Town
Harbour Town
Professionally Managed By Sea Turtle Getaways - Town of Hilton Head Island Vacation Rental Permit #026825
Caravel Court 1043
Sea Pines Resort
Total Price: $4,960.73
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.7 (9)

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