Luxury Vacation Rentals with a Private Pool in Hilton Head Island

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 121 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Hilton Head Island

Luxury

15 Collier Beach Road

6 bedrooms•6.5 baths

•

~$405 less than other sites

Luxury

9 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$440 less than other sites

Luxury

21 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$360 less than other sites

Luxury

71 Dune Lane

6 bedrooms•6.5 baths

•

New

~$385 less than other sites

Luxury

73 Dune Lane

5 bedrooms•5.5 baths

•

New

~$545 less than other sites

Luxury

3 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$415 less than other sites

Luxury

27 Singleton Beach Place

6 bedrooms•7 baths

•

~$430 less than other sites

4 Elderberry Lane

6 bedrooms•7 baths

•

~$365 less than other sites

Welcome to private poolside luxury in Hilton Head Island

Find your private-pool sanctuary on Hilton Head Island with Wander. Our collection of luxury vacation rentals in Hilton Head Island blends refined coastal style with the comfort of a private home, framed by ocean horizons and peaceful lagoons.

Expect sparkling pools with sunlit decks, generous outdoor lounges, chef-ready kitchens, ultra fast WiFi, and dedicated work nooks. Every home receives pristine, hotel-grade cleaning and is supported by 24/7 concierge, so your stay looks and feels exactly like the photos. Choose from oceanfront estates, lagoon-side retreats, and contemporary villas, each designed for effortless relaxation around your own pool.

Available soon in Hilton Head Island

Luxury

15 Collier Beach Road

6 bedrooms•6.5 baths

•

~$405 less than other sites

Luxury

9 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$440 less than other sites

Luxury

21 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$360 less than other sites

Luxury

71 Dune Lane

6 bedrooms•6.5 baths

•

New

~$385 less than other sites

Luxury

3 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$415 less than other sites

Luxury

27 Singleton Beach Place

6 bedrooms•7 baths

•

~$430 less than other sites

4 Elderberry Lane

6 bedrooms•7 baths

•

~$365 less than other sites

5 Shore Crest Lane

6 bedrooms•6.5 baths

•

~$290 less than other sites

Featured private pool vacation rentals in Hilton Head Island

Golf Sim Pickleball Theater Sauna Games

6 bedrooms•6.5 baths

•

New

~$225 less than other sites

Luxury

Beautiful New Beach Home with Private Pool, Spa & Stunning Beach Views

7 bedrooms•7.5 baths

•

~$780 less than other sites

Luxury

8 Sea Front Lane

10 bedrooms•11 baths

•

~$1,190 less than other sites

Luxury

Newly Built Oceanfront Stunner with private pool

7 bedrooms•7.5 baths

•

~$700 less than other sites

Luxury

Oceanfront stunner w/ private pool & spa, game rooms, outdoor kitchen & more

6 bedrooms•7 baths

•

~$530 less than other sites

Luxury

New Oceanfront Oasis in Palmetto Dunes with a private pool and EV plug

6 bedrooms•7 baths

•

~$1,750 less than other sites

Charming oceanfront home with brand new renovations and private pool & spa

8 bedrooms•8 baths

•

~$650 less than other sites

Luxury

Charming Oceanfront home with private pool

5 bedrooms•4.5 baths

•

~$765 less than other sites

Highlights in Hilton Head Island

Discover pristine beaches, world-class golf courses, and serene nature preserves on this idyllic South Carolina barrier island.

Coligny Beach Park

Harbour Town Lighthouse & Marina

Sea Pines Forest Preserve

Shelter Cove Harbour & Marina

Pinckney Island National Wildlife Refuge

Coastal Discovery Museum

Daufuskie Island

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Hilton Head Island

Luxury

15 Collier Beach Road

6 bedrooms•6.5 baths

•

~$405 less than other sites

Luxury

9 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$440 less than other sites

Luxury

21 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$360 less than other sites

Luxury

71 Dune Lane

6 bedrooms•6.5 baths

•

New

~$385 less than other sites

Luxury

73 Dune Lane

5 bedrooms•5.5 baths

•

New

~$545 less than other sites

Luxury

3 Singleton Beach Place

7 bedrooms•7.5 baths

•

~$415 less than other sites

Luxury

27 Singleton Beach Place

6 bedrooms•7 baths

•

~$430 less than other sites

4 Elderberry Lane

6 bedrooms•7 baths

•

~$365 less than other sites

View all homes

Most popular amenities for private pool vacation rentals in Hilton Head Island

Basketball court (16)

Beach essentials (16)

Beach umbrellas (13)

More popular private pool destinations near Hilton Head Island

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Other popular amenities & vacation types in Hilton Head Island

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Beachfront vacation rentals in Hilton Head Island

Hot tub vacation rentals in Hilton Head Island

Discover more beyond the pool in Hilton Head Island

Barrier-island beauty meets easygoing coastal rhythm. Hilton Head Island offers 12 miles of wide Atlantic shoreline, sweeping salt marsh vistas, and shaded maritime forests connected by more than 60 miles of bike paths.

Days can be as active or unhurried as you like. Kayak Broad Creek, watch for dolphins in Calibogue Sound, or tee off on championship courses framed by live oaks. As evening arrives, pastel sunsets wash over the water and sea breezes keep the tempo calm.

With restorative nature, family-forward energy, and year-round appeal, the island rewards every kind of traveler. This is why Wander’s luxury vacation rentals in Hilton Head Island are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Hilton Head Island

Why should I book a Wander in Hilton Head Island over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.

Every home in Hilton Head Island delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Hilton Head Island?

Some of our most popular private pool vacation rentals in Hilton Head Island include 15 Collier Beach Road, 9 Singleton Beach Place, and 21 Singleton Beach Place. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Hilton Head Island?

Wander offers 121 private pool vacation rentals in Hilton Head Island, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Hilton Head Island?

You can check-in to Wander private pool vacation rentals in Hilton Head Island after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Hilton Head Island have WiFi access?

Yes. Every Wander home in Hilton Head Island has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.