​​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
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 27
4 Catboat
4 Catboat
Palmetto Dunes Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 18 guests
Rating 4.6 (69)
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Spring 2026 updates are currently underway including new dining room furniture, new kitchen table & chairs, new lights and new fans throughout. By April 2026, we will have new photos online but please call us with any questions. This property is now under new ownership and the owners are keen to make this already beautiful and spacious house li
Hot HOT 40
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 (112)
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133 Dune Lane, Hilton Head Island is a 4-bedroom, 4-bath oceanfront home epitomizes casual beach living at its finest. Wake up to breathtaking views of the ocean from every room, including the kitchen, living room, dining room, and all four bedrooms. The spacious and comfortable bathrooms ensure a relaxing stay. Recent renovations have revitalized
Hot HOT 23
133 Dune Lane
133 Dune Lane
Forest Beach
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.9 (48)
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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
3 Sutherland Court
3 Sutherland Court
Palmetto Dunes
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.9 (70)
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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
29 Singleton Beach Place
29 Singleton Beach Place
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.8 (150)
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4 Brigantine, Hilton Head Island is your perfect family vacation at this second-row home! With 6 bedrooms, each with a full bath, and ocean views from the second-floor living area, this home offers comfort and relaxation. Enjoy convenience with an elevator, oversized pool, and beach access just across the street. The large pool area boasts a table
Hot HOT 19
4 Brigantine
4 Brigantine
Palmetto Dunes
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 18 guests
Rating 4.9 (34)
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Welcome to 1 Barrier Beach Cove — your perfect Hilton Head getaway. Just a short stroll from the beach, this beautifully designed 6-bedroom, 6.5-bath coastal retreat was made for gathering, celebrating, and truly unwinding together.Start your mornings with coffee on the balcony as the coastal breeze rolls in, spend sun-soaked afternoons by th
Hot HOT 20
1 Barrier Beach Cove
1 Barrier Beach Cove
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 18 guests
Rating 5 (34)
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**WINTER/ SPRING 2026 UPDATES INCLUDE: adding 2 new bathrooms so that each bedroom will have its own ensuite! New pictures & floor plans coming April 2026!**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 span
Hot HOT 53
9 Singleton Beach Place
9 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths / 1 half bath
Guests 20 guests
Rating 4.8 (26)
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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
4 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 2 half baths
Guests 18 guests
Rating 4.9 (78)
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5 Shore Crest Lane is a newly constructed home that offers 6 bedrooms all with private bathrooms, a luxurious chef's kitchen, private heatable pool and heatable spa, and multiple entertaining areas. This property was built with renters in mind to ensure amazing memories are created and includes up to $1000 in FREE activities. 5 Shore Crest Lane
Hot HOT 26
5 Shore Crest Lane
5 Shore Crest Lane
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths / 1 half bath
Guests 20 guests
Rating 5 (21)
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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 33
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 (78)
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**FREE POOL & SPA HEAT FOR MARCH-MAY**47 Off Shore Dr is an incredible opportunity for a relaxing getaway! This 3-bedroom, 2.5-bath home is located in Palmetto Dunes and offers a perfect blend of privacy and convenience. Being nestled in a quiet area yet still close to Shelter Cove Towne Center & Harbour for various activities such as dinin
FREE Pool Heat FREE Pool Heat
FREE Pool Heat
September & October/ April & May
47 Off Shore Dr
47 Off Shore Dr
Palmetto Dunes Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths / 1 half bath
Guests 8 guests
Rating 4.7 (54)
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