Hilton Head Oceanfront Rentals with Pool

Hilton Head Oceanfront With A Pool

Discover the ultimate vacation experience with our Hilton Head oceanfront rentals, each featuring luxurious pools and breathtaking ocean views. Located along the pristine shores of Hilton Head Island, our Hilton Head oceanfront rentals provide a serene escape from the everyday chaos of life. Enjoy your morning coffee by the pool or spend your days on vacation basking in the sun on the beach. 


 Our Hilton Head oceanfront rentals with pools cater to all your needs, ensuring a comfortable and memorable stay. Each of our luxurious rentals are equipped with modern amenities, spacious living areas, and private pools that invite you to unwind and enjoy the beautiful surroundings. With easy access to the beach, you can spend your days swimming in the Atlantic, building sandcastles, or simply soaking up the sun. In the evenings, return to your rental to relax by the pool, dine al fresco, or take a leisurely stroll along the shoreline.


More About Hilton Head

Hilton Head Island is a paradise for beach lovers, known for its wide, sandy beaches and gentle waves. Popular beach access points include Coligny Beach Park, Driessen Beach Park, and Folly Field Beach Park, all offering amenities such as restrooms, showers, and picnic areas. Beyond the beach, Hilton Head boasts a vibrant community with excellent dining, shopping, and entertainment options. Explore the island’s numerous bike trails, visit the iconic Harbour Town Lighthouse, or enjoy a round of golf at one of the many world-class courses. With its natural beauty and endless activities, Hilton Head Island promises an unforgettable vacation. 

Book with Vacation Homes of Hilton Head today and start planning your unforgettable Hilton Head Island vacation!


Properties Available 21 properties available
4 Collier Beach Road, Hilton Head Island, is an oceanfront house with 6 bedrooms and 6.5 bathrooms, comfortably accommodating up to 18 guests. Its spacious layout is perfect for large groups, with two living areas for added convenience. The open concept kitchen offers top-of-the-line Wolf and Sub-Zero appliances. Enjoy the private pool and unbeatab
4 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 18 guests
Rating 4.9 (78)
31 Singleton Beach Place in Hilton Head Island, South Carolina epitomizes luxury living at its finest. With over 5,500 square feet of living space, this 6-bedroom, 9-bathroom residence offers an unparalleled level of comfort and sophistication. Upon entering, guests are greeted by a seamless open floor plan that effortlessly blends the chef's k
Hot HOT 49
31 Singleton Beach Place
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths / 2 half baths
Guests 20 guests
Rating 4.9 (138)
14 Collier Beach, Hilton Head Island is a stunning oceanfront estate that offers a state-of-the-art chef's kitchen, an open-concept living and dining area leading to an oceanfront pool, deck, and grill. The home features a luxurious master suite with breathtaking views of the Atlantic Ocean, a marble bathroom, and a free-form tub. With a privat
Hot HOT 24
14 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.9 (120)
29 Singleton Beach, Hilton Head Island is a modern home ideal for large groups, families with kids, or couples seeking a retreat! Its open-concept floor plan includes a sleek gourmet kitchen flowing into the dining room, perfect for meal preparation and socializing. After a day of adventures, unwind in the master suite with its oversized ensuite ba
Hot HOT 50
29 Singleton Beach Place
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.8 (153)
Prepare to have your dreams come true at 7 Singleton Beach Place! This breathtaking oceanfront property has undergone a complete renovation, ensuring that every aspect of your stay is nothing short of extraordinary. With direct, private beach access just steps away from your door, you'll have the pristine sands and sparkling waters of Hilton He
Hot HOT 39
7 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 18 guests
Rating 4.9 (18)
21 Singleton Beach Place is a luxurious 7-bedroom, 7.5-bathroom oceanfront home is truly a paradise for families or groups seeking an unforgettable retreat. Boasting stunning views of the ocean, its open concept floor plan seamlessly blends indoor and outdoor living, creating an inviting atmosphere for relaxation and entertainment. Each room i
Hot HOT 47
21 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 18 guests
Rating 4.9 (195)
This beautiful oceanfront 6-bedroom/ 6.75-bathroom home is everything you have been looking for! With 2 living areas there is plenty of room for your group to have fun, spread out, and relax. Play pool in the top floor media room or practice your swing on the ground floor putting green. Vacationers will enjoy their own private pool (with access to
Hot HOT 25
6 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 23 guests
Rating 4.9 (146)
21 Horvath, Hilton Head Island. This stunning oceanfront home offers 5000 square feet of luxury living space, featuring 6 bedrooms and 6 bathrooms. The open-concept living area and chef’s kitchen provide the perfect space for gatherings, while the oversized oceanfront pool deck and propane grill are ideal for outdoor entertaining. Enjoy direc
Hot HOT 37
21 Horvaths Peninsula
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 22 guests
Rating 4.9 (141)
9 Singleton Beach, Hilton Head Island. This oceanfront gem is a 10/10 with awe-inspiring views! Ideal for multiple families, this stunning seven-bedroom, seven-and-a-half-bathroom home spans three stories with an elevator. Professionally decorated, it boasts breathtaking panoramic views from most rooms. Four oceanfront bedrooms feature private balc
Hot HOT 39
9 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 20 guests
Rating 4.8 (26)
This remarkable oceanfront estate showcases 7 bedrooms and 7.5 bathrooms, exuding unmatched beauty and luxury. 3 Singleton Beach Place is positioned in the perfect location, granting effortless access to nearby local restaurants, and shopping centers. The focal point of this home is its splendid open kitchen, boasting a double oven and an expansive
Hot HOT 40
3 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 26 guests
Rating 5 (34)
2 Collier Beach, Hilton Head Island. Experience luxury living at its finest in this magnificent oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own private bath, ensuring maximum comfort and convenience for all guests. The beautiful kitchen is
Hot HOT 53
2 Collier Beach Road
Singleton Beach Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 14 guests
Rating 4.8 (95)
10 Sea Front Lane is a new 8 bedroom 9 bathroom property ready for summer 2026! Each room is designed to offer a serene and sophisticated ambiance, perfect for relaxation and rejuvenation. The estate features breathtaking views of both the marsh and the ocean, providing a picturesque backdrop for your stay. The home is equipped with top-of-the
New Construction! New Construction!
New Construction!
Ready for summer 2026! Call 843-715-2208 for more information.
10 Sea Front Lane
Burkes Beach Pet Friendly
Bedrooms 8 bedrooms
Bathrooms 9 baths
Guests 24 guests

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Frequently Asked Questions About Hilton Head Oceanfront Rentals

What are the best areas for Hilton Head oceanfront rentals?

The most popular areas for Hilton Head oceanfront rentals include Palmetto Dunes, Sea Pines, and Singleton Beach. These neighborhoods offer direct beach access, incredible ocean views, and easy proximity to dining, shopping, and golf. View Oceanfront Rentals

Do Hilton Head oceanfront rentals have private beach access?

Yes, many Hilton Head oceanfront homes feature private or semi-private beach walkways. Communities such as Palmetto Dunes and Sea Pines offer secure access directly to the shoreline. Browse Beach Access Homes

Are there pet-friendly oceanfront rentals in Hilton Head?

Absolutely! Several Hilton Head oceanfront homes welcome pets, allowing your four-legged family members to enjoy the beach too. Check each property’s listing for pet-friendly details and fees. Explore Pet-Friendly Rentals

Do Hilton Head oceanfront homes have pools or hot tubs?

Many oceanfront rentals in Hilton Head feature private pools, oceanview decks, and hot tubs overlooking the water. Pool heating options are also available during cooler months. View Pool Homes

What amenities can I expect in a Hilton Head oceanfront rental?

Hilton Head oceanfront rentals often include modern kitchens, outdoor living spaces, private pools, Wi-Fi, elevators, and direct beach access. Many homes are ideal for families, groups, or golf getaways. See All Amenities

What’s the difference between oceanfront and oceanside rentals in Hilton Head?

Oceanfront rentals are located directly on the beach with unobstructed ocean views, while oceanside rentals are nearby but may be separated by a dune, road, or path. Both options offer easy access to Hilton Head’s beaches. Compare Options

When is the best time to book a Hilton Head oceanfront rental?

To secure the best selection and rates, it’s recommended to book Hilton Head oceanfront rentals months in advance. Spring and summer months are most popular, while fall offers ideal weather with fewer crowds. Plan Your Stay