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.
58 properties available
21 Horvath, Hilton Head Island. This stunning oceanfront home offers 5000 square feet of luxury living space, featuring 6 bedrooms and 6 bathrooms. The open-concept living area and chef’s kitchen provide the perfect space for gatherings, while the oversized oceanfront pool deck and propane grill are ideal for outdoor entertaining. Enjoy direc
Welcome to 12 Sea Front Lane, an exquisite oceanfront estate located in the prestigious Burkes Beach neighborhood of Hilton Head Island, SC. This expansive property boasts 7 bedrooms and 7 bathrooms, comfortably accommodating up to 22 guests. Each room is designed to offer a serene and sophisticated ambiance, perfect for relaxation and rejuvenation
Prepare to have your dreams come true at 7 Singleton Beach Place! This breathtaking oceanfront property has undergone a complete renovation, ensuring that every aspect of your stay is nothing short of extraordinary. With direct, private beach access just steps away from your door, you'll have the pristine sands and sparkling waters of Hilton He
**New Bonus Room Off of the Pool and Updated Bathrooms!!**44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 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
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
Welcome to 1 Surfwatch Way — a 2026 newly completed 6-bedroom 5.5-bath coastal retreat offering the very best of modern island living. Just a short 3–5 minute stroll to the beach, this exceptional home showcases all-new furnishings, appliances, and thoughtfully curated finishes throughout, creating a fresh and refined space for your Hil
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
37 Bradley Circle, Hilton Head Island, is a four bedroom, three bathroom home nestled in a quiet beach area of Burkes Beach. Step inside to the main level, where you'll find a cozy living room, large TV and access to the upper dining deck. The fully-equipped kitchen, complete with stainless steel appliances and granite counter
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
46 Folly Field is newly renovated house in the sought-after Folly Field area is a perfect blend of comfort and convenience for a Hilton Head vacation. With 4 bedrooms and 3 full bathrooms, it offers ample space for families or groups. The proximity to the open ocean, just a few rows away from Folly Field Beach, allows for easy access to the beautif
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
13 Moonshell Rd, Hilton Head is a perfect retreat for a coastal escape. With its five bedrooms and three bathrooms, it offers ample space for guests to relax and unwind. The spacious fenced backyard with a private pool and outdoor bar provides a wonderful setting for outdoor gatherings and leisurely days by the pool.Its convenient location, just a
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