​​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.

Browse Rentals by Community   See Rental Specials

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 43 properties available
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 39
5 Henry Lane
5 Henry Lane
Singleton Beach Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 4.8 (69)
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 63
3 Surf Watch Way
3 Surf Watch Way
Burkes Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 17 guests
Rating 4.9 (223)
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 32
10 Collier Beach Road
10 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 4.9 (63)
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 11
14 Collier Beach Road
14 Collier Beach Road
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.9 (118)
VIEW PROPERTY
Experience breathtaking views at 14 Singleton Shores Manor, where every level offers stunning marsh and ocean views. Step into the open and bright living area, complete with a wet bar and access to your private pool deck. On the second floor, an updated kitchen, second living area, and dining room await, with an ocean view balcony perfect for morni
Hot HOT 60
14 Singleton Shores Manor
14 Singleton Shores Manor
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.9 (83)
VIEW PROPERTY
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 40
133 Dune Lane
133 Dune Lane
Forest Beach
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.9 (38)
VIEW PROPERTY
3 Sutherland, Hilton Head Island. This updated 6-bedroom house, nestled within the prestigious private community of Palmetto Dunes, presents the perfect coastal retreat just moments from the beach! Boasting an open layout, it's ideally suited for accommodating large groups, ensuring everyone can gather comfortably. The spacious bedrooms offer a
Hot HOT 11
3 Sutherland Court
3 Sutherland Court
Palmetto Dunes
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.9 (64)
VIEW PROPERTY
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 32
20 Horvaths Peninsula
20 Horvaths Peninsula
Burkes Beach Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.9 (20)
VIEW PROPERTY
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 49
21 Singleton Beach Place
21 Singleton Beach Place
Singleton Beach
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 4.9 (180)
VIEW PROPERTY
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 48
2 Collier Beach Road
2 Collier Beach Road
Singleton Beach Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.8 (82)
VIEW PROPERTY
32 Corrine Lane is a beautifully decorated 6-bedroom, 6-bath open concept home that is truly a luxurious retreat for families or large groups. The presence of three primary king bedroom suites, private balconies and a private pool ensure that guests can enjoy both comfort and entertainment in their private spaces. The kitchen and living areas
Hot HOT 36
32 Corine Lane
32 Corine Lane
Singleton Beach
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 15 guests
Rating 4.9 (78)
VIEW PROPERTY
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 111
4 Brigantine
4 Brigantine
Palmetto Dunes
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Rating 4.9 (28)
VIEW PROPERTY

Tell us what you're looking for and someone will contact you with available options.

I agree

Copyright © 2025 • Vacation Homes of Hilton Head

All Rights Reserved.