Holiday rentals in Hilton Head Island

Beachfront Resort 2b Golf Lagoon Pickleball Tennis

✨Top Airbnb Guest Favorite Home✨ Gated Beachfront Golf Resort! Beach, Golf, Pool, Spa, Restaurants & Bars FREE Pickleball & Tennis - across street HGTV Decorator designed Panoramic Golf & Lagoon Views XL Double Porch Lush Scenery - Tons of Wildlife! Coastal Décor Sunny 1st Floor End Unit KING BED + 2 QUEENS 3 XL SmartTVs FAST WIFI & CABLE Chef's Kitchen Washer/Dryer BBQ Beach Cart, Chairs, Boogie Boards, Ice Chest Walk/Bike to Beach Walk to Golf Club & Pub Close to Coligny Summer Beach Shuttle

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!

Luxury Oceanview King Villa + Steps to Sand

Ultimate Romantic Luxury for Couples. Recently renovated and perched on the top floor, our King Villa is the architectural “Sweet Spot” of the building. Situated at the unique Y-jut, it offers a Wider, more Expansive Oceanview panorama than any other Oceanview Villa! Being at the 'point' allows you to see further down the coast with total privacy and no neighbors above you. This is the ultimate coastal escape, combining high-end boutique finishes with the quiet serenity of the highest floor.

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 FREE Pickleball, Tennis & Gym HGTV Designer Renovation Two 65" SmartTVs KING BED 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

Prime Waterview! Hilton Head Shelter Cove Marina

Permit 073816 Enjoy easy access to everything Hilton Head has to offer from this centrally located Condo in the heart of Shelter Cove Marina. Not only will you have breathtaking views of the sunset and the marina right from your balcony, but you also have many amenities right at your doorstep! Shelter Cove is one of the main attractions on Hilton Head Island with many shops, restaurants, weekly entertainment and water sports. You also have access to the private Palmetto Dunes Beach community.

2 bed/2 bath, Oceanfront complex!

This beachside condo is just steps away from the ocean, and offers everything you need for the perfect vacation. Our complex has a private oceanfront heated pool. The unit itself is newly renovated with beach themed decor, and offers a peekaboo ocean view. It is fully equipped with beach chairs, toys, cooler and everything you need for a comfortable stay. The neighboring Hilton property offers a Starbucks and Poolside Bar and Grill ***ONLY accepting Sat-Sat booking June and July***

MyStay at 307 Forest Beach Villas - Prime Coligny!

Escape to 307 Forest Beach Villas, your ultimate Hilton Head getaway! This third-story corner villa is steps from Coligny Beach, dining, shops, and Lowcountry Celebration Park. Relax in a stylish space with a bright, airy vibe, a chef’s dream kitchen, and a private balcony perfect for your morning coffee or evening cocktail. With a king-size bedroom retreat, luxurious bathroom, on-site pool, and tennis courts, it’s a vacation dream. Book now with MyStay—your perfect beach escape awaits!

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, DIRECT, OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! KING BED! CAN SLEEP 4! THIS IS LUXURY LIVING WITH NO RESORT AMENITY CHARGES! SAVE THOUSANDS OF DOLLARS COMPARED TO OTHER NAMED RESORTS LUXURY HOTEL PROPERTIES! **UPGRADED INTERNET & HD TV PACKAGE + FREE AMENITIES**

Renters favorite!

This beautiful villa is a 1 bedroom, 2-bathroom villa that can accommodate up to 2 people and has beach access! This villa boasts a gorgeous kitchen with stainless steel appliances, and beautiful countertops and cabinetry. Walk out of the kitchen to the dining area. The master bedroom features a king size bed and a large sliding glass door for patio access! What a wonderful way to wake up!! The Master bed has a private bathroom with a walk-in shower, separate tub, and twin vanity.

100 Fairway Lane, Sea Pines: A Luxury Villa Stay

Welcome to all NEW BESTNEST/Luxe: An Elevated Experience in Vacationing, and our newest Luxe property at Unit 100 Fairway Lane Villas in Sea Pines. (200 Fairway Lane for mapping) Enjoy the ultimate in vacation rental accommodations on Hilton Head Island, featuring a carefully curated collection of homes and villas, chosen with the discerning traveler in mind, fabulously stocked, outfitted, and supported by your personal property concierge, available 24/7. STR Permit Number: 075152

Harbour Town Lighthouse & Sunset Views | Sea Pines

Enjoy direct Harbour Town lighthouse, yacht basin, and Calibogue Sound views from our beautifully updated Sea Pines condo. Located in Ketch Court, this cozy coastal retreat puts you steps from Harbour Town dining, shopping, sunsets, bike paths, golf, and the marina. Perfect for couples, golfers, or a small family looking for one of Hilton Head’s most iconic locations. Come relax and unwind and take in all that Harbour Town has to offer!

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.