Family-friendly holiday rentals in Harbor Island

Condo in Saint Helena Island

The open-concept kitchen and dining area are visible, featuring dark cabinetry and a granite countertop. A dining table for four is positioned nearby, and stairs lead to the upper level. Soft blue walls complement the space, creating a calm atmosphere.

Turtle Villa|Ocean Front/New DECK; B Building

Take in the lush, coastal beauty of the Carolina Lowcountry from our 2BR/2.5BA Cedar Reef Villas condo! Watch the glow of sunrise on the marsh & ocean without leaving your plush king bed. Play a game of tennis, then take a cool dip in one of the resort's pools within walking distance. Stroll to the beach via the Cedar Reef boardwalk access, or drive 3 miles to pristine Hunting Island State Park. Close out the day in nearby Beaufort with a date night dinner and a stunning sunset on the marina!

KitchenIndoor spacesWi-Fi

4.98 out of 5 average rating, 234 reviews

5.0 out of 5 average rating, 14 reviews

Home in Harbor Island

Blue Horizon - Oceanfront House on Harbor Island

Ocean views from every room, it is your ultimate Family Beach House! Escape to this beautiful 5-bedroom, 4-bath beachfront home designed for family to have the best vacation. Whether you’re relaxing at the beach or taking family for activities, the scenery is unmatched. Included with your stay: 🛺 Complimentary Golf Cart 🌊 Community pool 🏄 Paddleboards & Boogie boards 🎾 Pickleball & Tennis Gear 🏓 Ping-Pong, Air-hockey, & Beach Toys 🏝️ Hunting Isl pass Book your stay and start making memorie

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A two-story house features a light blue exterior with white trim and orange shutters. Two garages are visible on the ground level, while balconies adorned with white railings provide outdoor space. Lush palm trees and greenery surround the property, creating a tropical ambiance.

4.86 out of 5 average rating, 100 reviews

Big Golf Cart! Elevator! Views! Pets! Accessible!

WOW! Views, elevator, extended golf cart and 4 decks! Read on. Amazing long water views from this 3 bed 2.5 bath house on Harbor Island. 2000 sqft with spacious living area on a quiet lagoon. 3 min golf cart to beach. Master has private deck, double shower, jetted tub. Extended golf cart, elevator to all floors. 4 decks (2 screened), and game table. Organic cotton sheets and outdoor shower. 4 smart tvs! Coffee bar, kitchen essentials incl seasonings, sharp knives! Sat-sat only in summer

Indoor spacesKitchenParking

4.96 out of 5 average rating, 23 reviews

Home in Harbor Island

Private Home - Golf Cart, Gate Passes Included

If you’re looking for a comfortable, well-cared-for home near the beach where you can truly relax, this Harbor Island retreat is for you. Located in the quiet, lush section of the island, we offer peaceful privacy with easy access to the beach, pool, and fitness center just a short golf cart ride away. Thoughtfully designed and stocked with guests comfort in mind, this home is a welcoming space that feels easy from the moment you walk in. Hunting Island pass, golf cart and gate fees included.

Indoor spacesKitchenBeach

4.93 out of 5 average rating, 15 reviews

Home in Harbor Island

Oceanfront Restful Retreat-Pool •Sleeps 10 w/Bikes

Wake to quiet ocean sunrises, spend the day barefoot on sandy uncrowded beaches, & end your evenings w/ marsh sunset. Gated/private feel. Open floorplan perfect for entertaining, quiet front porch overlooking the peaceful marsh, & back porch facing the tranquil ocean. Walk to beach, ride 4 included beach cruisers, or cruise the island by golf cart-(rent) Enjoy the pool, pickleball/tennis courts, playgrounds & volleyball-short drive to historic Beaufort & free pass to Hunting Island State Park

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Cottage in Saint Helena Island

The living area features a comfortable sectional sofa, accented by decorative pillows. A wooden dining table is set nearby, surrounded by tasteful artwork on the walls. Exposed wooden beams enhance the ceiling, and natural light filters through multiple windows.

Harbor River Cottage

Romantic cottage on three-acres surrounded by gorgeous South Carolina waterways with endless views on all sides! Cottage is dog-friendly, has a fully-fenced front yard and screened-in porch. Full kitchen, private parking, washer & dryer, 55" TV with DirecTV. A short 10 minute drive from Hunting Island State Park, and 20 minutes to Downtown Beaufort and all the major attractions. Cottage is beautifully furnished with custom pieces to make this your ultimate low country luxury getaway!

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5.0 out of 5 average rating, 280 reviews

4.99 out of 5 average rating, 139 reviews

The Hampton House

CUSTOM BEACHFRONT HOME ON GORGEOUS LOW COUNTRY BEACH. Custom beachfront home with unparalleled views! Beautifully but comfortably decorated in low country beach style. All the comforts of home. Feels like your own private paradise. 4 bed 3 1/2 bath,Sleeps 12 with TWO King master en suites. Stainless Steel Kitchen, private boardwalk to the beach, Golf Cart, Kayaks, beach towels, chairs, umbrellas, 2 car passes... all included. Make memories that will last forever.

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Condo in Saint Helena Island

A serene view features palm trees framing a well-kept pool area, with bright blue lounge chairs arranged nearby. The scene is complemented by a sandy path leading to the ocean, under a soft pastel sky during dusk.

Island Retreat-Beautiful Condo w/ Ocean/Pool Views

September and October dates AVAILABLE! Pools are open until November 1. October 30-November 21 is OPEN with additional DISCOUNTS! Perfect time of year to explore the area! Enjoy a relaxing beach escape at the “Island Retreat" on Harbor Island! HUNTING ISLAND PASS & 2 bikes included! Guest Favorite with top reviews. We strive to be the best! Wake up to amazing sunrises & spectacular views overlooking the pool, dunes & ocean!

KitchenFamilyWalkability

5.0 out of 5 average rating, 15 reviews

Cottage in Saint Helena Island

Private Waterfront Retreat w/ Sauna

Escape to The Hideaway, a newly built modern 2BR/2BA waterfront retreat on St. Helena Island. Surrounded by live oaks and sweeping salt marsh views, this architecturally unique cottage blends luxury and nature with curated amenities, including a private indoor sauna. Peaceful and secluded, yet just minutes from beaches, outdoor adventures, local shops, and dining—designed for rest, reconnection, and renewal.

KitchenIndoor spacesBeach

4.98 out of 5 average rating, 144 reviews

4.97 out of 5 average rating, 32 reviews

3BR Home - 2 blocks to beach, golf cart, pool

Welcome to the Kick Back Shack, a designer decorated home with 3 BR/2BA and lots of room to spread out and relax. Catch the sunsets from the screened porch, breakfast overlooking the tidal creek full of wildlife, read a book in the hammock. Create your dream vacation in a luxury rental in the peaceful gated resort of Harbor Island. New to Market.

Indoor spacesKitchenAccuracy

4.88 out of 5 average rating, 8 reviews

Condo in Harbor Island

Coastal Comfort on Harbor Island - 2BR/2.5BA

Welcome to your perfect Harbor Island getaway! This beautifully updated two-story, second-floor condo offers 2 bedrooms, 2.5 bathrooms, and plenty of space for up to 6 guests. Thoughtfully designed and conveniently located, it’s the ideal spot for families, couples, or friends looking to unwind by the coast.

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The beach property features a two-story design with a light-colored exterior and a green metal roof. Palm trees surround the home, enhancing its coastal appeal. A welcoming front porch is accessed by a set of stairs, with a friendly American flag displayed. Parking and well-manicured landscaping complete the view.