Holiday rentals in Hilton Head

Sea Pines house ~ Golf Sim / Putting Green / Games

Town of Hilton Head Island STR Permit Number: 064406 Centrally located in Hilton Head Island just within the gates of Sea Pines, with golf simulator, outdoor putting green, 2 game rooms, and a backyard area with games, outdoor dining, fire table & seating, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 kings and 4 doubles), this luxurious space will offer unparalleled comfort, amenities, and the perfect location for you to use as your central base to enjoy the best of HHI.

*New* Easy Breezy at Hilton Head Beach & Tennis

Newly renovated in March ‘26 and brand new,from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa - with all of the amenities needed to enjoy a relaxing stay at the Hilton Head Beach & Tennis resort. Our villa is located just steps from the only elevator in the building. Our resort offers the largest pool on the island, several restaurants, a large playground & picnic area, on site bike rental, 24 hour gated security, 8 lighted tennis courts, and 6 pickleball courts.

Island Club Condo: Beach, Pool, Gym, Pickleball

Relax in this charming condo just a short stroll from the beach. Sip morning coffee on your private balcony overlooking the emerald lagoon. Spend sun-filled days by the shore or make the most of the resort-style perks—like the outdoor pool, sauna, and sports courts. Whether you're here to relax or explore, this is your perfect getaway Beach – 3 Min Walk Hilton Head Distillery – 5 Min Drive Coastal Discovery Museum – 11 Min drive Book for a Memorable Hilton Head Island Stay - Learn More Below!

98 Sandcastle Ct

98 Sandcastle Ct Brand New 6 Bedroom Home near Beach with Pool, Elevator/ (Sleeps Up To 22 Guests ) 20 in beds & 2 in Queen Sofa Sleeper. Over 3200 sq feet, 6 Bedrooms, Heated Pool, Elevator & about .3 miles from the beach = Tons of Fun!!! * 6 Bedrooms * 4 Full Baths * Walking Distance to Ocean. * Heated Private Pool. (Free pool Heat :) * Elevator Available: Free use Adults Only. * Free Parking: 4-6 reg cars/mini vans.. LRG SUV's or LRG Vans = 4 parking spots. Note: 2 = garage 4 =driveway.

Oceanfront KING BED 65"TV Beach Bar Pickleball GYM

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

Brand New Lux Condo - Ocean View! Steps to Beach!

Wake up to ocean views, catch the sound of the waves, and be just steps to the beach. The Carolina Condo is a newly remodeled coastal retreat inside the gated Hilton Head Beach & Tennis Resort, designed with a bright, stylish “boutique beach hotel” feel. Enjoy your private 2nd floor balcony, direct beach access, and resort-style amenities including two pools, tennis & pickleball courts, restaurants, and a seasonal beach bar—everything you want for an easy, relaxing Hilton Head getaway.

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**

BEACH PATH At Hilton Head Beach and Tennis Resort

🏖🏖🏖 Book your Summer trip with us!!!! Experience the ultimate beach getaway at our charming villa located within the gated Hilton Head Beach and Tennis. This oceanfront property boasts the largest oceanfront pool on the island, beach volley ball , tennis courts, pickle ball, bike rentals, a playground, grill/picnic area and three delightful restaurants. Nestled-mid island, our villa is conventiently located two miles from Shelter Cove/Palmetto Dunes. Trolley pickup onsite.

79 Fairway Ln Villa @ Sea Pines | Golf Views

Indulge in elevated coastal living at 79 Fairway Lane Villa, nestled within the tranquil ambience of Sea Pines Resort. Embrace captivating golf views across lush Lowcountry lagoon from every corner of this unique home. Recharge in 3 spacious King En-Suites or venture forth to explore the resort's myriad offerings—from pristine beaches just .2 miles away to world-class amenities like tennis and golf. Experience pure bliss on your Hilton Head Island getaway & Learn More Below!

HHB&T 3 min walk to the sand

Stylish Beach Condo | Walk to Ocean | Pool | Tennis | Sleeps 4 • Sleeps comfortably: Queen bed, bunk beds • Fully equipped kitchen – ready for family meals or romantic dinners • 3-minute walk to the beach or the largest oceanfront pool on the island • Tennis courts, pickleball, fitness center, and shuffleboard included • Beach chairs provided for your use • Private lanai • Smart locks with keyless entry and high-speed Wi-Fi for easy check-in and remote work

Walk to the Beach! Coastal Villa w Large Balcony!

Our newly renovated 2 BR/2 BA Fiddler's Cove villa is available for rent! Located on the quiet third floor, 24E is spacious and modern. The kitchen features new cabinets, quartz countertops, GE appliances, and floating shelves. Behind barn doors are the washer, dryer, and pantry. Updated bathrooms have new vanities and tile. The dining area includes a coffee/wine bar and seating for six. The living area has a queen sleeper sofa, side chairs, and a 65-inch TV.

Bluewater Resort & Marina - Large 3BR/3BA

Come delight in the beauty of the Intracoastal Waterway and savor stunning sunsets from the dock at Bluewater Resort & Marina located on Skull Creek. Bring your boat for free dockage or just relax and watch the boats and yachts go by. This resort has something for everyone, from water and nature lovers to golfers and loungers. This is also a great resort to enjoy the beauty of HHI without the crowds common to other areas of the island.