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
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 67
21 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 18 guests
Rating 4.9 (197)
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 50
6 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 23 guests
Rating 4.9 (146)
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
Hot HOT 32
4 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 18 guests
Rating 4.9 (78)
19 Singleton Beach Place, Hilton Head Island, is a 6 bedroom, 6.5 bathroom oceanfront home with a private pool and boardwalk, elevator, and chef's kitchen. This property offers a luxurious retreat for vacationers and includes up to $1000 in FREE activities with every reservation. The breathtaking ocean views, upscale finishes, and elegant d&eac
Hot HOT 34
19 Singleton Beach Place
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 16 guests
Rating 4.9 (99)
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 48
31 Singleton Beach Place
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths / 2 half baths
Guests 20 guests
Rating 4.9 (138)
20 Horvaths Peninsula, Hilton Head Island is a renovated oceanfront retreat, nestled in the desirable Burkes Beach Area, offers breathtaking views from every floor. With 6 bedrooms and 5 bathrooms, including five king bedrooms and a custom-built bunk area for the kids, it's perfect for families. The open-concept kitchen adds to the seamless flo
Hot HOT 66
20 Horvaths Peninsula
Burkes Beach Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (30)
6 Terra Bella Trace, Hilton Head Island is nestled between the salt marsh and the Atlantic Ocean, 6 Terra Bella Trace is a beach lover's paradise. This outstanding property features 6 bedrooms and 8 bathrooms. The chef's kitchen boasts top-of-the-line Wolf and Sub-Zero appliances and an oversized island with wrap-around seating. The open-co
Hot HOT 77
6 Terra Bella Trace
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 8 baths
Guests 20 guests
Rating 4.9 (133)
27 Singleton Beach, Hilton Head Island is a  direct oceanfront home that accommodates up to 18 guests and boasts an open-concept floor plan with breathtaking 360-degree views of the ocean and marsh. Enjoy a chef’s kitchen, 4 luxurious master suites with deep soaking tubs and oversized walk-in showers, dedicated work desks, and additional
Hot HOT 41
27 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 18 guests
Rating 4.9 (154)
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
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 45
14 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.9 (120)
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 72
9 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 20 guests
Rating 4.8 (26)
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 51
2 Collier Beach Road
Singleton Beach Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 14 guests
Rating 4.8 (95)

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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