Top Hilton Head Island oceanfront rentals with a pool

Swim, stay, and splash by staying at your new favorite beach home.
palm trees surround a pool with beach access and a dock
View from the pool towards a beach at a rental in Hilton Head Island

While Hilton Head offers a variety of beautiful vacation rental options, there’s something to be said for a beachfront house with a private pool. Imagine letting the kids pop in and out of the gate, enjoying the dunes and waves until they’re tired, all while you’re lounging poolside. Sound too good to be true? At these seven vacation homes, it’s reality.

The pool area at a Hilton Head Island rental

FOR A PET-FRIENDLY ESCAPE

1. Paradise

5 bedrooms | 4 bathrooms | 2 dogs

Located on the Island's Folly Field, this spacious, pet-friendly retreat delivers an unbeatable private pool party experience while keeping you steps away from the beach. Take a break from the sun in a poolside lounge chair underneath the beach umbrella while taking in the beauty of the island to discover why we call this oceanfront rental Paradise.

Oceanfront vacation rental in Hilton Head with pools.

FOR THOSE SEEKING LUXURY

2. Dune Lane 105

6 bedrooms | 5.5 bathrooms

This luxury beach house rental offers an unparalleled oceanfront experience. Boasting a private boardwalk with beach access, stunning ocean views, and a newly renovated pool, it's quite simply perfect. You'll find expansive wraparound decks overlooking the pool and a remodeled kitchen with top-of-the-line appliances, and six comfortable bedrooms inside. With its prime location near Coligny Beach Park and Plaza, this property delivers a truly elevated oceanfront stay on Hilton Head Island.

The pool area overlooking the beach at a hilton head island vacation rental.

FOR LARGE GROUPS

3. Singleton Beach

6 bedrooms | 6 bathrooms

This Hilton Head oceanfront home is perfect for large group getaways, comfortably accommodating up to 17 guests. The spacious living areas, including an elegant open kitchen and living space, allow for communal gathering. Outside, the spacious deck's private pool area offers stunning views of the Atlantic coastline while swimming.

The back pool area at a vacation rental on Hilton Head Island.

FOR A GOLF TRIP

4. Dune Lane 9

4 bedrooms | 4.5 bathrooms

Experience the ultimate golf getaway at this luxurious villa. Just minutes from several championship courses, this stunning property offers the perfect blend of comfort, convenience, and recreation. After hitting above 100, leave your scorecard at the clubhouse and let the opulence of the pool sink in after the game.

The pool area overlooking the beach at a hilton head island vacation rental.

FOR STUNNING VIEWS

5. Dunes House

5 bedrooms | 4 bathrooms

This gorgeous beachfront home gives you the best of both worlds. Leave your pool bag on a patio chair and spend some time out on the sand, just a few steps down the private boardwalk. Or, if you’re not feeling like taking a saltwater swim, enjoy direct beach views from the comfort of the pool area. With such easy access to the sun and sand, Dunes House is a winning choice for snowbirds, summer vacationers, and everyone in between.

The pool area designed in an exotic way of a luxury rental on Hilton Head Island.

FOR THOSE SEEKING SERENE SECLUSION

6. Royal Retreat

7 bedrooms | 6 bathrooms

This stunning Sea Pines retreat offers the perfect blend of privacy and entertainment. However, this rental home's centerpiece is the secluded pool area. It features a spa, multiple dining areas, and comfy lounge chairs, creating a resort-like atmosphere while delivering tranquility in an upscale coastal setting. And while technically three streets from the beach, this Hilton Head house rental is perfect for large groups and family getaways alike.

The patio area of a condo rental overlooking the resort pool at a rental in Hilton Head.

FOR A RESORT VACATION

7. Windsor Court North 4204

1 bedrooms | 2 bathrooms

Escape to this charming Hilton Head Island condo for the ultimate resort-style pool experience. Ideally located just steps from the beach and near popular attractions like Coligny Beach Plaza and Arthur Hills Golf Course, this condo provides the perfect blend of poolside relaxation and island adventure. Did we mention the patio overlooks the pool area?

Additional Hilton Head Island rentals with pools

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