Escape to Sea Cloisters, a hidden gem in Hilton Head’s Folly Field Beach. With direct oceanfront access, a private pool complex, and a gated community, this peaceful retreat is perfect for families, multi-generational vacations, and travelers looking for the ultimate beachside getaway.
Book Your Sea Cloisters Vacation Rental Below!
Unparalleled Oceanfront Access
Step outside and stroll across the private boardwalk over the dunes, leading directly to Hilton Head’s pristine shoreline. Wake up to breathtaking Atlantic Ocean views, enjoy morning beach walks, and unwind with the sound of crashing waves just steps from your door.
Resort-Style Amenities for Ultimate Relaxation
At Sea Cloisters, guests enjoy more than just a great location. Our rentals offer:
Gated, private oceanfront pool with a sundeck and lounge chairs
Spacious villas with private balconies or patios to take in coastal views
Secure private parking for a worry-free stay
Lush, beautifully landscaped grounds enhancing the island’s natural beauty
Perfect for Multi-Generational Gatherings
Planning a family reunion? Sea Cloisters makes it easy for each family to have their own space while staying close together. Spacious accommodations, ocean views, and shared resort amenities create the perfect setting for quality time and lasting memories.
Convenient Mid-Island Location
Nestled in the heart of Hilton Head, Sea Cloisters offers easy access to the island’s best attractions:
Minutes from dining and shopping at Shelter Cove Towne Centre
Nearby golf courses and tennis facilities for sports enthusiasts
Scenic bike trails connecting you to parks, marinas, and island landmarks
Why Choose Sea Cloisters?
With stunning oceanfront views, resort-style amenities, and a prime location, Sea Cloisters offers an unforgettable Hilton Head Island vacation experience. Whether you’re looking for relaxation, adventure, or quality time with loved ones, you’ll find it all at Sea Cloisters.
Start planning your Hilton Head getaway—book your Sea Cloisters vacation rental today!
***Please note that this community does not allow pets***
27 properties available
Exceptional Oceanfront Penthouse Villa at Sea Cloisters3 Bedrooms | 2 Bathrooms | Sleeps 8Welcome to the luxurious vacation home of Villa 501 at Sea Cloisters in Hilton Head Island. This stunning penthouse villa offers a truly remarkable oceanfront experience with breathtaking views from every room. With its three bedrooms and two baths, this spaci
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Direct Oceanfront Second Floor Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to our absolutely cute and comfortable oceanfront villa, boasting 2 bedrooms and 2 baths within its spacious 1100 square feet. The villa offers a direct oceanfront location, allowing you to wake up to the breathtaking sunrise right from you
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontWelcome to our beautifully remodeled villa, located just steps away from the sand on Hilton Head Island. This tastefully designed home provides convenient access to the beach, gated pool, and all the amenities you need to feel right at home. The coastal ambiance of the
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Villa with Panoramic Ocean Views at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontWelcome to Sea Cloisters Unit 206, a newly renovated vacation villa with stunning panoramic views of the ocean and the beach. The unit has a prime location on the second floor, with breathtaking views of the wide sandy beach and the ocean, and is so clo
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Newly Remodeled Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | OceanfrontWelcome to your dream vacation home at Sea Cloisters on Hilton Head Island! This newly-remodeled first floor villa offers convenient and easy access to the beach, pool, and all of the wonderful amenities that Sea Cloisters has to offer. With its tastefu
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Elegant Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your luxurious vacation home in Hilton Head Island! Each villa in Sea Cloisters is thoughtfully decorated to provide a tasteful and elegant atmosphere.As you step into your villa, you'll be greeted by spacious, open living and dining areas
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Top Floor Oceanfront Penthouse with Loft at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 10 | Panoramic Ocean ViewsWelcome to Sea Cloisters 509, a magnificent oceanfront penthouse villa located on the top floor (5th floor) of the building. This three-bedroom, three-bathroom villa offers unparalleled ocean views from the vaulted living room,
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Beach-Themed Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to your perfect beach getaway in Hilton Head Island! This tastefully decorated oceanfront villa offers stunning views of the ocean and provides a delightful ambiance. With two bedrooms and two bathrooms, this villa is the ideal vacatio
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Extensive Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to our newly renovated villa, where no expense has been spared to provide you with the very best beach experience.The villa boasts a range of upgrades, including new granite countertops, crown moldings, baseboards, and fresh paint on walls and ceilin
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Oceanfront Penthouse Villa with Loft at Sea Cloisters3 Bedrooms | 3 Bathrooms | Sleeps 8 | Ocean ViewsWelcome to our stunning two-story villa located in the beautiful Hilton Head Island. This spacious vacation home features a unique lofted sleeping space, adding an extra touch of charm and versatility to your stay.As you enter, you'll find two
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
HHP Luxury
HHP Luxury
Offers expert concierges that can assist with in-home services and local experiences to give you the most unforgettable memories with the ones you love most.
Coastal Fourth Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Panoramic Ocean ViewsIndulge in the ultimate tropical getaway at this professionally decorated vacation home in Hilton Head Island. Located on the fourth floor, this condo offers a luxurious and inviting atmosphere.As you step inside, you'll be captivate
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
Stylishly Furnished Third Floor Oceanfront Villa at Sea Cloisters2 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean ViewsWelcome to Villa 309, a recently renovated and updated vacation home in Hilton Head Island that exceeds expectations. This third-floor villa has undergone a complete transformation and now showcases quality craftsmanship throughout, fro
Oceanfront
Oceanfront
Enjoy this perfect oceanfront property for your beach getaway!
