Family-friendly holiday rentals in Hilton Head Island

Ocean View KING BED 75"TV Beach Bar Pickleball GYM

✨Top Airbnb Guest Favorite Home✨ Ocean Views from Living Room & Balcony Oceanfront Building Steps to Beach Boardwalk, Pool & Tiki Bar FREE Pickleball, Tennis, Gym & More KING BED + 75" & 65" Smart TVs Expanded Bedroom HGTV Featured Decorator 100% NEW Luxury renovation Marble Kitchen & Bath Quiet Top Floor Well-designed 540 sq. ft. Elevator Beach Chairs + More RESORT: Oceanfront Pool & Bar & Grille Restaurants Sports Bar 4 Beach Boardwalks Bike Rental Gated 24/7 Security FREE Island Trolley Stop

Ocean View! Remodeled! Steps to beach/Pool/Bar

FULLY REMODELED OCEAN VIEW VILLA Located in Hilton Head Beach & Tennis Resort, this beautiful 540 Square foot Villa is perfect for a small family or couple looking for a relaxing and fun getaway. The second floor balcony offers a view of both the ocean and pool, as well as, offering the soothing sounds of the ocean waves Located within a gated community and with access to the beach just steps away. The resort also features 2 private pools, 3 restaurants, bike rentals, a private gym & more!

The Lookout - A Modern Beach Retreat (Oceanfront)

Welcome to The Lookout! The moment you step into this villa you will be greeted by an open floor plan, a fully stocked kitchen, & every amenity that you'll need for your stay. Take a seat on one of the high top adirondack chairs & enjoy your favorite beverage while overlooking the most popular beaches on the island. Truly - every square inch of this unit has been meticulously utilized to give you an unforgettable vacation. We look forward to hosting you at Seaside Villa's premier luxury villa!

Oceanfront Luxe KING BED 65TV Beach Bar Pickleball

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony Watch Sunrise/Hear Waves 1 min to Beach Boardwalk! Beachfront Pool, Tiki Bar & Grille KING BED FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs Expanded Bedroom Blackout Sleeping Marble Spa Bath Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Beach Bar/Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

Palmetto Dunes House: Private Pool, PDBeach, Golf

Magnolia & Maple is your upgraded resort destination. Sat to Sat rentals. Home includes a desk with hi-speed internet, surround sound in the living room and updated décor. This 3 BR, 2 BA home sits on a quite street and offers the opportunity to relax by the private heated pool, walk/bike the 3/4 of a mile to PD's famous beaches, or get some exercise with tennis, golf, or pickleball. Close to Shelter Cove shopping and dining. HHI is a pedestrian and bike friendly area with plenty to do.

Palmetto Dunes Beach House

Completely Renovated, designer decorated home with private pool/built in spa. One level EASY walk to the beach (15 mins) ...or call the Dunes Buggy, free of charge, to pick you up and bring you back! Open floor plan with large bedrooms (King, Queen, 3 Doubles). Plenty of space inside and out to relax. Situated on a body of water overlooking the the 9th hole of Robert Trent Jones Golf Course. pool/spa -extra fee Bring the whole family to this great place with lots of room for fun.

Beachfront Resort 2B Golf Beach Pickleball Tennis

✨Top 10% Guest Favorite✨ Gated Beachfront Resort Golf, Tennis, Pickleball, Pool, Restaurants & Bars Gorgeous Sunny Villa Panoramic Lagoon & Golf Views! Beautiful & Lush Scenery Huge Old Oaks dripping in Spanish Moss! Walk/Bike to Beach Abundant Wildlife! Walk to Shipyard Golf Club & Pub! Modern Coastal Sunny 1st Floor KING BED Master 3 XL SmartTVs WIFI 287 mps Fully Stocked Kitchen Walk-in Shower Washer/Dryer Beach Chairs, Boogie Boards & More! BBQ Bike & Walk Paths Close to Coligny!

Burkes Beach House - 2nd Row to Beach #023021

Our home is second row at Burkes Beach. Close to Palmetto Dunes Plantation Golf and Tennis , Port Royal Plantation Golf and Tennis. Convenient mid Island location. It is great for couples, solo adventurists, and families (not set up for toddlers and younger). Steps to the beach path and Chaplin Park, which has lit tennis courts, park and picnic areas. Walk or bike on beach to Coco's Beach Bar or Marriott Beach Bar. Open floor plan and under house parking. OWNER IS A LICENSED REALTOR.

Oceanfront Scandi Oasis Amazing View & Heated Pool

Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

5 Star Location-Harbourtown-Walkable Area

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

Waterfront Tree House | HT Pool | Private Office

One of our newest homes, see our over 1000 *5*-star reviews. Calibogue Escape-Harbour Town Treehouse in Sea Pines Sailboats, Dolphins, Sunsets, what else could you ask for? This treehouse offers floor-to-ceiling windows with unparalleled views and the perfect setting for a perfect escape. Located on a dead-end street on Deer Island, just steps from Hilton Head’s Harbour Town and the Yacht Basin, this hideaway could not be more perfect.

HHI South Forest beach/WLK TO BEACH, dining, pool

Pack up the whole crew—two-legged or four—and escape to this fully furnished, perfectly located cozy condo in Hilton Head’s popular Treetops complex. Enjoy three refreshing pools, tennis courts, and a laid-back vibe perfect for relaxing or playing. Just a 10-minute walk to the beach and steps from Coligny Plaza, you’ll be close to shopping, dining, and all the island fun. It’s your ideal home base for sun, sand, and good times!