Family-friendly holiday rentals in Harbor Island

BIKE ‘n BED Hilton Head- Perfect Couple's Getaway

Come relax and enjoy Hilton Head on South Forest Beach, the most popular section of the island. Ride our free bikes for a quick trip to Coligny Plaza where the quaint local shops and restaurants are. The beach is a quick 2 or less minute walk and the pool is just down the hall. Our condo is small, but perfect for a couple's getaway or a memorable trip with the kids. We have everything you need to help make yourselves at home with full size kitchen appliances and washer/dryer room just next door.

Tranquility

Tranquility lives up to its name. Peace & quiet are the words guests use most to describe their visit. Less than 4 miles from the beach & 1 mile from the boat landing and hiking/bike trails, this is the place to unplug & reconnect with family & friends. To make sure you have a great vacation and know what to expect during your stay, it is important to read ALL information in our listing carefully. In addition to NOT being on the beach, several features make our home unique and not for everyone.

Lovely Cottage in Beaufort w/ State Park Beach Pas

This adorable but well-appointed farmhouse cottage is located just a few streets from the heart of DT Beaufort, in the desired neighborhood of Pigeon Point, with easy access to the boat launch. Just a few blocks from Bay Street and the Marina, where great shopping and outdoor dining with breathtaking views of the harbor await. A relaxed and inviting space, style, and beauty combine to make this special cottage a much sought-after resting space for a memorable vacation with your loved one(s).

Cara May Cottage

We love the laidback neighborhood, charming historic architecture, and the 5-block walk to the breezy waterfront along Bay Street. The cozy cottage is one bedroom, one bath, and a lovely living space on a postage stamp lot. The built-in breakfast nook is our favorite spot. Other features are the chic furnishings, 11’ ceilings, tall casement windows, and little front porch. Off-street private parking for one car and smart tv/wifi. The 400 SF cottage is named after the architect's daughter.

Stylish Renovated Chapel -Close to Everything!

We’ve renovated our mid-century chapel into a spacious , wonderfully outfitted vacation rental. The Chapel is exceptionally comfortable and very central-but still peaceful. Walk a mile along beautiful waterfront Bay Street and you're downtown amongst galleries, restaurants, bars, and shops and the 4 blocks in the other direction puts you on the Spanish Moss Trail, perfect for biking and running. For USMC graduations, Parris Island is an easy 6 mile drive- we are convenient to everything!

Bluffton Villa in the heart of the Promenade

Beautiful villa in the heart of the Promenade in the Historic District of Bluffton. Steps away are a wine bar, coffee shop, French bakery, 5 star and casual dining, & fabulous boutique shopping. Newly built in 2017, we offer our guests a fully equipped kitchen with an electric convection oven, microwave, dishwasher, ice maker in refrigerator. The bathroom offers a large walk in shower with a rain shower head, and the bedroom has a King size bed. You are a 15 minute ride to Hilton Head.

Fripp Island Dog Friendly Getaway OPEN ALL WINTER

325 sq. ft. studio efficiency offers a central island location just 1 min. from the beach! Bed arrangements: 2 TEMPURPEDIC mattresses, one queen size bed/one full size sleeper sofa. Ideal for 2 but will sleep 4 very snugly. *Our affordable rates are in part because "amenity cards" may not be purchased and are not available by any means with this unit Cards are necessary to use restaurants/bars/pools/tennis & golf. * **Check out our 2nd pet friendly unit at 530 Sunsuite!

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.

Cozy Sunsuite Fripp Island Resort- Steps to Beach!

Experience the perfect beach getaway on Fripp Island! This cozy 1st floor sunsuite is ideal for couples and families with young children, offering unparalleled convenience just steps away from the beach boardwalk. Enjoy easy close access to resort amenities like an Olympic pool, Arcade, Adults-Only pool with pool bar, tennis courts, and Beach Club restaurant for a memorable stay. Book now to receive up to Two Fripp Resort amenity cards included, a $110 value!