Hilton Head Island rentals with pool

We found 8,621 rentals with pool — enter your dates for availability

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday rentals with a pool in Hilton Head Island?
Browse our 8,621 holiday rentals with a pool and start organising your Hilton Head Island trip. Whether you'd like to stay in South Forest Beach, North Forest Beach, Night Heron or another much-visited neighbourhood, you'll discover the ideal poolside retreat on Stayz.
How much does it cost to stay in a holiday rental with a pool in Hilton Head Island?
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 holiday 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.
When is the best time to book a holiday rental with a pool in Hilton Head Island?
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 12ºC to 19ºC, and when many guests unwind in a holiday 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.
What holiday rentals with a pool in Hilton Head Island have nice views?
If your perfect escape involves poolside activities and picturesque scenery, you'll discover Hilton Head Island holiday rentals with a pool that offer exactly that. Book one with golf course views and immerse yourself in a blissful holiday experience.
Are there holiday rentals with a private pool in Hilton Head Island?
From poolside get-togethers to midnight dips beneath the stars, a holiday rental with a private pool offers plenty of possibilities for relaxation and fun. If you're travelling to Hilton Head Island, use our "Private pool" filter to find accommodation that come with this luxurious feature.
What are the top things to do in Hilton Head Island?
There's always something cool to do with the family when you stay at a holiday 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.
Why should I book my holiday rental with a pool with Stayz?
No sharing your space, no awkward encounters with people you don't know. When you select a Stayz holiday rental with a pool, you get the entire place to yourself to have a splashing good time. Need to change or cancel your travel itinerary? Our flexible cancellation policies mean you're able to book your rental house with peace of mind.