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
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 40
19 Singleton Beach Place
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 4.8 (34)
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 22
5 Henry Lane
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 4.5 (22)
Wow! This AMAZING 3BR/2.5BA home is ready for your enjoyment! Nestled in a private, quiet areas of Palmetto Dunes, 47 Offshore Drive offers easy walking/biking access to Shelter Cove and Towne Center for dining, fishing, shopping, boating, etc. This home is also only 1 mile from door to sand. It has the desired open, updated, natural light concept
Hot HOT 55
47 Off Shore Dr
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 (15)
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, five-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 balco
Hot HOT 54
9 Singleton Beach Place
House
Bedrooms 7 bedrooms
Bathrooms 5 baths
Guests 20 guests
Rating 4.6 (8)
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 84
6 Collier Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 23 guests
Rating 4.7 (49)
8 Terra Bella Trace, Hilton Head Island. Indulge in the ultimate oceanfront experience at 8 Terra Bella Trace. This luxurious six-bedroom, eight-bathroom home, completed in late summer 2022, spares no expense. The chef's kitchen boasts top-of-the-line appliances and a spacious island with seating for all. The open-concept kitchen, living, and d
Hot HOT 73
8 Terra Bella Trace
House
Bedrooms 6 bedrooms
Bathrooms 8 baths
Guests 18 guests
Rating 5 (5)
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 16
3 Sutherland Court
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.7 (22)
You will feel very welcome at the home as it includes a partial view of the ocean from the front porch. Head into the main level of the house and you will enter a the great room, including stunning travertine tile floors, a fully-equipped kitchen with stainless steel appliances, and granite counter tops. This home also offers two decks, overlooking
Hot HOT 22
37 Bradley Circle
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 14 guests
Rating 4.5 (7)
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 69
2 Collier Beach Road
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.6 (36)
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 54
7 Periwinkle Lane
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 4.6 (16)
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 71
42 Bradley Beach Road
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.7 (20)
This house features 5 bedrooms and 6 bathrooms with space enough for 16.Please review our property photos and our available amenities to make sure this rental is a perfect fit for your needs. We strive to keep this information as up-to-date as possible so you can feel confident in knowing what you are renting.We will send you all necessary pre-arri
Hot HOT 74
7 Abalone Lane
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 16 guests
Rating 5 (1)

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