Hilton Head Rentals with Private Pool

Relaxing by the pool is a special part of visiting Hilton Head Island. Enjoy everything Hilton Head has to offer with our Hilton Head rentals with a private pool. Afternoons are hot, and when the sun is high in the sky, jumping into a refreshing pool feels like entering paradise. During your Hilton Head vacation, there’s no better place to hang out than your own private pool. Below you’ll find Hilton Head rentals with private pools. Our vacation rentals with private, heated pools place you in Hilton Head’s best communities. Hilton Head vacation homes with pools are perfect for families and groups. Plunge into an amazing vacation on Hilton Head Island with Vacation Homes of Hilton Head.


Properties Available 56 properties available
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 51
27 Singleton Beach Place
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Rating 4.8 (48)
This beautiful oceanfront home is located mid-island in the Singleton Beach community. It is conveniently located near the Shelter Cove Towne Centre, which offers tons of local shops, restaurants, and attractions. This home features six spacious bedrooms, private beach access, and amazing ocean views from all levels of the home. Vacationers are sur
Hot HOT 58
12 Collier Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 19 guests
Rating 4.6 (25)
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. Each bedroom comes with its own private bath, ensuring maximum comfort and convenience for all guests. The beautiful kitchen is perfect for culinary delights, while numerous balconies o
Hot HOT 63
2 Collier Beach Road
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.6 (35)
42 Bradley Beach, a 6 bedroom, 4.5 bath home with private pool, offers not only a great mid island location, but is among our most value attractive properties for families and groups. This property is also located next to Driessen Beach Town Park with playground equipment for the kids, comfort stations, and is just a four-minute walk to the beach o
Hot HOT 61
42 Bradley Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.7 (20)
This stunning, completely renovated oceanfront property will make all of your dreams come true! 7 Singleton Beach Place has direct, private beach access, a private pool, and furnishings that will make you feel right at home!Free Activities Included! Play a round of golf, explore Hilton Head on bicycle or even bring out your inner kid with a round o
Hot HOT 46
7 Singleton Beach Place
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 18 guests
Rating 5 (5)
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 101
3 Surf Watch Way
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 17 guests
Rating 4.7 (69)
***EV Car charging outlet (receptacle) in Garage (guest to bring their own charging station)***This beautifully decorated 6 bedroom, 6 bath open concept home has three master bedroom suites with king beds and flat screen TVs. The master bathrooms are simply exquisite, with spa tubs, dual sinks, and separate frameless showers with lavish stone floor
Hot HOT 138
32 Corine Lane
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 15 guests
Rating 4.7 (24)
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 26
3 Sutherland Court
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.7 (22)
1 Barrier Beach Cove, Hilton Head Island, is your ultimate vacation destination! Completed in 2023, this brand-new 6-bedroom, 6 1/2-bathroom residence offers a luxurious escape just moments from the beach. With a spacious private pool and spa, you can relax and unwind in style. Located adjacent to Chaplin Park, guests can enjoy easy access to ameni
Hot HOT 53
1 Barrier Beach Cove
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Rating 5 (4)
27 Corine Lane, Hilton Head Island is a luxurious 3-story home nestled in the picturesque Singleton Beach area. This stunning property features a private pool and elevator, adding to the convenience and comfort of your stay. With 7 bedrooms and 7 bathrooms, there's plenty of space for everyone to relax and unwind. The home's prime location
Hot HOT 50
27 Corine Lane
House
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 4.4 (21)
44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 13 and has a large 16' x 32' pool, and features an outdoor fire pit perfect for a night hosting around the pool or a cool day in the fall! There is plenty of seating and the home is conveniently located at the very end of Bradley Road with a fenced in patio givin
Hot HOT 54
44 Bradley Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 15 guests
Rating 4.6 (26)
7 Periwinkle Lane, Hilton Head Island. Come experience beachside bliss at this charming 5-bedroom, 4.5-bathroom home, just a short 5-minute walk from the sandy shores. Completely remodeled, it boasts a gorgeous private pool for relaxation. Inside, a top-floor loft and all-new appliances await. Conveniently situated near a local park, restaurants, a
Hot HOT 61
7 Periwinkle Lane
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 4.6 (16)

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