Top Hilton Head Island rentals with pool

Explore Hilton Head Island rentals with pools

⭐️⭐️⭐️⭐️⭐️ Exceptional Ocean Oriented Home!

Sleeps 16 · 5 bedrooms · 6 bathrooms

Beautiful 6 bedroom home near the beach!

37 Bradley Beach; Largest Pool & Deck on the block! Great rates & reviews!

Sleeps 15 · 6 bedrooms · 4+ bathrooms

Top rated rentals with pools - Hilton Head Island

Premier Host

Fabulous cottage. Great for a couple

Would highly recommend this property. Location ideal for exploring the low country. Walking distance to the downtown of beautiful Beaufort. Easy access to Savannah, Charleston, Bluffton, Port Royal. Cottage was perfect for our stay…extremely clean well equipped and thought out. Hosts Barbara and Steve have thought of everything to make sure your getaway is a great experience.

Bob K.

Stayed Apr 2025

Pool & Spa (Heated pool & spa additional fee) 3-6 ft

Premier Host

Hilton Head Family Vacation

We all had a wonderful time, very close to the beach. The house was awesome, plenty of space for 8 adults and two children. Really appreciated the bikes in the garage, the wagon and beach toys. The pool was fantastic for both adults and children. Great instructions posted on the fridge

Vera S.

Stayed Mar 2025

Morning sunrise walking out to the beach over private gated beach access

Premier Host

Incredible property!

This property has everything we needed for and amazing family vacation. The location and amenities were top notch and we always felt so welcome with Amy and Jeff.

Carla R.

Stayed Aug 2024

Premier Host

Perfect family vacation!

Our week at Mara's property at Captain's Cove was absolutely perfect. The location can't be beat - with the lagoon out back and the beach and pool across the road, grocery stores, patios, and parks within biking distance. The unit was clean, well supplied, and had everything we needed for an easy, relaxed vacation. We will definitely be back!

Heather H.

Stayed Apr 2023

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Frequently asked questions

How much does it cost to stay in a vacation rental with a pool in Hilton Head Island, SC (HHH)?

It doesn't get better than a vacation rental with a pool, and it doesn't have to be costly with Vrbo. While many factors will influence how much you'll pay for your getaway in Hilton Head Island, SC (HHH), our filters will help you find an amazing deal. Set your budget and use our "Discounts" filter to look for properties that offer savings if you stay longer. With an inviting pool waiting for you, you'll probably want to visit as long as you can.

When is the best time to book a vacation rental with a pool in Hilton Head Island, SC (HHH)?

First, consider if you prefer the energy of high season or the quieter vibe of the off-season. Also think about factors like the weather conditions and what you'd like to do in Hilton Head Island, SC (HHH). Whenever you visit, we'll help you find a vacation rental with a pool where you can kick-start your day with a refreshing dip.

What vacation rentals with a pool in Hilton Head Island, SC (HHH) have nice views?

Vrbo makes it simple to find a stay with stunning views and access to poolside relaxation. You can use the "Location" filter to narrow down the type of area you prefer to be in, and the scenery you want to stare out at, while searching for vacation rentals with a pool in Hilton Head Island, SC (HHH).

Are there vacation rentals with a private pool in Hilton Head Island, SC (HHH)?

Although there aren't any vacation rentals with a private pool in Hilton Head Island, SC (HHH), you will find options that have everything you need to be nice and comfortable. Picking a Vrbo property means you'll have more privacy, space and home comforts compared to a hotel. And with our filter tool, you can narrow your search by the exact amenities you're after, whether that's a fireplace or backyard.

What are the top things to do in Hilton Head Island, SC (HHH)?

Hilton Head Island, SC (HHH) has plenty of attractions and activities to keep you busy, so reach for a guidebook or download a travel app and start planning. Love the outdoors? Or are you more of a wellness enthusiast, art lover or foodie? However you spend your time, you can end your day kicking back by the water when you stay in one of our vacation home rentals with a pool.

Why should I book my vacation rental with a pool with Vrbo?

Whether you're getting away as a couple or with your besties, staying at a vacation rental with a pool offers a new level of fun and relaxation to your adventure. And finding the ideal pad is a breeze with our filter tool. Just fine-tune your search by budget, location, amenities and more, then lock in your favorite. Another awesome reason to book with us is our flexible cancellation policies. If you have to change plans, you'll get a complete refund as long as you cancel within the time frame stated by the property owner.