Family-friendly holiday rentals in Harbor Island

4.95 out of 5 average rating, 207 reviews

LOW Rates in May ~Sleeps 7~KING Bed~CLEAN~Big Pool

Fully Furnished, Renovated Non-Smoking Villa sleeps 7 - King bed in Master, 2 Single beds in Guest Room, Leather Queen Sofa Bed & Rollaway Bed. Built-in Bar, Fully-equipped Kitchen w/ small appliances. Beach Chairs, toys, games, cards. Flat Screen HDTV w/ hundreds of channels, DVD, Free Wi-Fi. Overhead Lighting & Ceiling fans in bdrms, extra blankets & pillows. Restaurants, Tennis, 2 Pools. Sip cold drinks on the wide sandy beach & watch Amazing Sunrises & Sunsets. Relax, You're in Paradise

Guest favourite

4.94 out of 5 average rating, 252 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Villa is located on The Spa On Port Royal Sound complex on Hilton Head Island. Enjoy unobstructed sound & ocean views from your private balcony. Private beach access & observation pier. Beautiful landscaped grounds. 2 outdoor pools-opened Apr.-Oct. Indoor pool, hot tub, dry sauna & gym. Grills and picnic areas on premises, one near the villa, recently installed hammocks near the ocean pool. Tennis and basketball courts on site. Come enjoy the beautiful sandy beach with beautiful sunrises!

Cottage in Hilton Head Island

4.86 out of 5 average rating, 372 reviews

Gypsy Sea Cottage - A Beachside Retreat

Welcome to The Gypsy Sea Cottage—a beautifully renovated standalone villa nestled in the prestigious Palmetto Dunes Resort, within the serene Queens Grant community. Just a short stroll to pristine beaches, championship golf courses, and world-class dining, this retreat offers perfect balance of relaxation and adventure. Inside, you'll find high-end furnishings, luxury linens, smart home features, and a fully stocked kitchen—every detail thoughtfully designed for a seamless, memorable stay.

4.91 out of 5 average rating, 203 reviews

2Bd/2.5 bth/Near Coligny Park/Few Blocks To Beach

Located within a short walking distance to the white beaches of Hilton Head, this beautiful vacation rental which sleeps up to 6 guests is ready to become your home away from home while you explore everything that the island has to offer. A relaxing beach getaway in this spacious second level townhome that boasts a fully equipped kitchen and two master suites and is within an easy walk/bike ride to the famous Coligny Circle shops and restaurants. Free hour at the Van der Meer Tennis Center.

4.93 out of 5 average rating, 253 reviews

Grand Views! Beautiful, Renovated, Walk to Beach!

Welcome to your perfect Hilton Head Island getaway! Modern, beautifully renovated two-bed bed/2 two-bath condo, top floor, walking distance to the beach with Panoramic Ocean Views! Ideal for families, couples, girls' weekends, and golf enthusiasts! Enjoy amazing sunrises from the patio. Located in a gated complex with access to the most beautiful beach in all of Hilton Head Island via a private boardwalk. Easy keyless entry, located in Building 2. Superhost where hospitality is #1!

4.76 out of 5 average rating, 172 reviews

Walk to Beach - 3 Pools - Central Location!

Recently updated 2 bedrooms, 2 baths, and a full kitchen! Located in the center of Hilton Head Island close to all the wonderful bike trails, restaurants, shopping, and famous golf! In a gated community full of amenities: - Boardwalk to the beach 🏖️ 🌊☀️🐚 - 2 outdoor pools (1 heated) 🤿 - Indoor pool (heated) ☔️ - Hot tub - 6 tennis & 2 pickleball courts 🎾 🏓 - Beachfront bar & grill 🍻 - Poolside bar & grill ⛱️ - Small fitness center 💪🏋️ - Sand Volleyball 🏐

Guest favourite

Apartment in Hilton Head Island

4.92 out of 5 average rating, 144 reviews

Relaxing Hilton Head Beach Getaway. 2 B/2 B

Great Vacation spot. Five minute walk to the Beach. Large 2 Bedroom and two new bathrooms & floors. Largest ocean front pool on the Island. 10 lit tennis courts with 12 pickle ball courts and a pro shop. Bar/Grill on the beach. Sports Bar/Restaurant & Pizza shop. On site Bike rental. Playground, grill stations, full gym. Laundry facilities. Convention Ctr. Chair and umbrella rentals, lifeguard on beach. Bike trails parallel roads on Island. Gated secure resort.

4.74 out of 5 average rating, 178 reviews

Hilton Head Resort, 3 Bed Room, 2 Bath

Welcome to Hilton Head Resort. You get total privacy in this 3-bedroom, 2 bath unit and free access to all the amenities in this beach front resort. Open kitchen / living room with large dining table for eating and game time. Full Kitchen with granite counter tops, pots, pans, blender, and spices. Bedrooms and living room have a flat screen TV with cable and Free Internet. We provide linens and towels for your stay plus there is an in-unit Washer/Dryer.

Guest favourite

4.75 out of 5 average rating, 138 reviews

Salty Sand-Close to the pool, steps to the beach!

Modern and cozy ocean-view villa with the pool view from the front door and ocean views from the patio! Recently renovated with plank flooring and shaker cabinets, this stylish retreat features a fully equipped kitchen, a queen bed in the bedroom, a queen sleeper sofa, and two child-sized bunks. Located in Seaside, an oceanfront complex, you're just a short walk from great shops, restaurants, and attractions—perfect for a relaxing beach getaway!

4.83 out of 5 average rating, 169 reviews

Mother's Day Month! Retro-Mod Family Beach Fun

Welcome to a Dwell-inspired midcentury decor. A minimalist condo designed to host your family in a bright and comfortable style. We have items for your travels with small children - High Chair, Pack-N-Play, Toys, books, and more so you can travel to the beach with less. Designed with care to host your small family. Sea, I Told You a trip to the beach is always a good idea.

Home in Hilton Head Island

4.89 out of 5 average rating, 102 reviews

(27) Boutique, Saltwater Pool, Baby Gear, Elevator

5 bedrooms PLUS Huge Kids Bedroom/Playroom, 3 Blocks to the Beach, Elevator, Heated Pool with waterfall and outdoor Shower. Outdoor grill area with marble counters. Modern Decor. Huge porches with large dining sectional, swing bed and rocking hammock for 2! This home boasts a gourmet Kitchen with double oven. The luxurious master has an enormous rain head shower.