​​Hilton Head House Rentals with Pool

Discover true relaxation and luxury with our Hilton Head house rentals with pool. Surrounded by the beautiful shores of Hilton Head Island, our Hilton Head house rentals offer an unparalleled vacation experience. Each house rental is rigorously maintained and equipped with the best modern amenities to ensure your stay is comfortable and stress-free. Our selection of Hilton Head house rentals with pool caters to every need and preference. From cozy beachside cottages to expansive oceanfront estates, we have the perfect home for you. Enjoy the convenience of a private pool where you can swim, sunbathe, and relax in complete privacy. Many of our Hilton Head rentals are also within walking distance to the beach, allowing you to easily explore the pristine shores and indulge in water activities.

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About Hilton Head

Hilton Head Island is renowned for its stunning beaches and vibrant local culture. With over 12 miles of pristine coastline, the island offers numerous beach access points, including popular spots like Coligny Beach Park and Folly Field Beach Park. The beaches are perfect for sunbathing, swimming, and enjoying various water sports. Beyond the beaches, Hilton Head boasts world-class golf courses, scenic bike trails, and a rich culinary scene. The island's charming atmosphere and natural beauty make it a top destination for travelers seeking both relaxation and adventure. Explore the island's unique blend of serene landscapes and exciting activities, and make your next vacation one to remember. 

 Book your dream vacation today with Vacation Homes of Hilton Head and experience the best that Hilton Head has to offer.

Properties Available 40 properties available
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 41
3 Singleton Beach Place
3 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 26 guests
Rating 5 (35)
VIEW PROPERTY
3 Surf Watch Way, Hilton Head is a 4,450 square foot home, located just steps from Burke's Beach, boasts an open concept floor plan perfect for entertaining. Enjoy family movie nights in the media room on the 2nd floor, equipped with a large flat-screen TV and recliners. The garage features a putting green, foosball table, air hockey, and arcad
Hot HOT 86
3 Surf Watch Way
3 Surf Watch Way
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 17 guests
Rating 4.9 (230)
VIEW PROPERTY
Welcome to 15 Collier Beach Road. This three-level home offers ocean, marsh, and tidal creek views. The main level features a gourmet kitchen with a large island, a family room with an 82-inch smart TV, and a dining room, all with water views. The second level has three en suite bedrooms, including a master suite with a king bed, sitting area, pull
Hot HOT 27
15 Collier Beach Road
15 Collier Beach Road
Singleton Beach Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 26 guests
Rating 4.9 (52)
VIEW PROPERTY
This property is now under new ownership and the owners are keen to make this already beautiful and spacious house lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a magnificent 6-bedroom, 5.5-bathroom, pet friendly home accommodating up to 16 guests making it perfect for family reunions or large ga
Hot HOT 42
4 Surfwatch Way
4 Surfwatch Way
Burkes Beach Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 18 guests
Rating 4.9 (116)
VIEW PROPERTY
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
6 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 23 guests
Rating 4.9 (146)
VIEW PROPERTY
10 Collier Beach, Hilton Head Island is an escape to paradise in this stunning 6-bedroom, 7-bathroom oceanfront home, offering breathtaking ocean views and the ultimate in privacy. Relax by the private pool, enjoy direct access to the beach, and indulge in the luxury of a chef's kitchen. Entertain friends and family in the game room, or let tee
Hot HOT 45
10 Collier Beach Road
10 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 16 guests
Rating 4.9 (81)
VIEW PROPERTY
5 Henry Lane, Hilton Head Island is a home nestled in Singleton Beach, this stunning 4-bedroom, 4.5-bathroom home offers a perfect getaway. With a spacious patio area featuring a secondary fridge, ample seating, pool, private gas grill, and TV, it's ideal for hosting family gatherings on warm summer evenings. Plus, its proximity to the beach, s
Hot HOT 24
5 Henry Lane
5 Henry Lane
Singleton Beach Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 5 baths / 1 half bath
Guests 12 guests
Rating 4.8 (80)
VIEW PROPERTY
4 Catboat, Hilton Head Island is an open-concept floor plan with spacious bedrooms, each boasting its own bathroom, and an oversized private pool. Located just steps from the beach and close to all the amenities of Palmetto Dunes Oceanfront Resort, including tennis, golf, restaurants, and the renowned General Store, this vacation rental offers conv
Hot HOT 29
4 Catboat
4 Catboat
Palmetto Dunes Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 16 guests
Rating 4.6 (69)
VIEW PROPERTY
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 26
14 Collier Beach Road
14 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.9 (120)
VIEW PROPERTY
Welcome to 3 Sutherland, a six-bedroom retreat located in the heart of Palmetto Dunes — one of Hilton Head Island’s most sought-after private communities. Just moments from the beach, this home offers the perfect setting for a relaxed and memorable island getaway.The spacious living room features ample seating, making it the ideal place
Hot HOT 19
3 Sutherland Court
3 Sutherland Court
Palmetto Dunes
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 4.9 (70)
VIEW PROPERTY
35 Full Sweep, Hilton Head Island is a recently renovated 5-bedroom/5-bathroom home, located inside Palmetto Dunes Plantation, features a large private pool and new furniture throughout. With 3 King Primary bedrooms, each with private en-suite bathrooms, and a fourth bedroom with a pullout sofa and work space, it accommodates various needs. The lar
Hot HOT 41
35 Full Sweep
35 Full Sweep
Palmetto Dunes
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 20 guests
Rating 4.8 (46)
VIEW PROPERTY
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 40
29 Singleton Beach Place
29 Singleton Beach Place
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.8 (155)
VIEW PROPERTY

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