Hilton Head Island rentals with pool

Browse our 8,219 vacation rentals with a pool and start organizing your Hilton Head Island trip. Whether you’d like to stay in South Forest Beach, North Forest Beach, Night Heron or another much-visited neighborhood, you’ll discover the ideal poolside retreat on Vrbo.

Indoor or outdoor pool, two bedrooms or five, high or low season — what you’ll pay for your stay in Hilton Head Island depends on many variables. But the one thing that stays the same? Our vacation rentals with a pool are where awesome family memories are made. To find a place that matches your budget, narrow your search results by price. You can also use our “Discounts” filter to find properties that offer savings on longer stays.

If you’d love to visit Hilton Head Island at a busy time, plan your trip for March. That’s when temperatures range from around 53ºF (12ºC) to 66ºF (19ºC), and when many guests unwind in a vacation rental with a pool in this destination. Of course, there are other great times to travel to this corner of South Carolina Lowcountry, so do some homework into which month or season is the best fit for your plans.

If your perfect escape involves poolside activities and picturesque scenery, you’ll discover Hilton Head Island vacation rentals with a pool that offer exactly that. Book one with golf course views and immerse yourself in a blissful vacation experience.

From poolside get-togethers to midnight dips beneath the stars, a vacation rental with a private pool offers plenty of possibilities for relaxation and fun. If you’re traveling to Hilton Head Island, use our “Private pool” filter to find accommodations that come with this luxurious feature.

There’s always something cool to do with the family when you stay at a vacation home rental with a pool in Hilton Head Island. Get out and explore well-known attractions like Tybee Island Beach, Coligny Beach and North Beach, then return to lounge and relax poolside.

When you book a vacation rental with a pool with Vrbo, you’ll get more than the basic hotel room experience — think a private pad with a place to relax by the water. You’re also covered by our Book with Confidence Guarantee. This means we’re here to guarantee a hassle-free stay throughout your entire break. Plus, when you join our free One Key™ rewards program, you can collect OneKeyCash™* and use it on all eligible bookings on Vrbo, Expedia and Hotels.com. Have an unexpected change of plans? Check out our cancellation policies to see if you are eligible for a complete refund. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.