Hilton Head, SC 2+ Bedroom Vacation Rentals

Welcome to your Hilton Head Retreat at 191 The Greens- Shipyard. Whether you’re here for a calming hideaway, a family vacation or a fun week of golf/tennis or pickleball, you will find this townhome to be a comfortable and inviting haven. Located...

Summary:Evian 104The Space:Impeccably decorated, this villa is laid out for a calming break along the Shipyard Golf Club. You'll adore sitting out on the furnished patio with a slight view of the golf course. Inside, recline and appreciate each...

This villa sits directly on the sand, you simply cannot get closer to the beach anywhere on Hilton Head Island.As you enter this single-level villa, you’ll be welcomed by an open-concept kitchen, dining, and living area. The kitchen features...

Welcome to your Mediterranean dream home! A gorgeous Tuscan-style getaway ideally located along the relaxing 11-mile lagoon. This chic residence features four cavernous bedrooms, a additional bunk room, and a completely air-conditioned private suite...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.Single-level home with 3 bedrooms and a short walk to the beach! Savor close access to the beach in this completely modernized coastal chic ranch home with a...

Escape to the beauty of Hilton Head Island in this striking 2-bed, 2-bath Palmetto Dunes’ Villamare Villa unit. This vacation rental offers access to 3 pools and hot tubs, including a serene adult-only pool area, pickleball courts, tennis courts...

Feel the best of beachfront living in this handsomely maintained, never before rented corner unit, offering striking expansive vistas of the Atlantic Ocean from every angle. Located on the 5th floor of the esteemed Villamare Community, this unique...

This charming Villamare condominium is directly oceanfront! The Kitchen contains bespoke cabinetry, granite countertops, bar seating for three and is entirely equipped to meet your family's cooking needs. Just beyond the Kitchen is the Dining Area...

Summary:Handsome LawtonThe Space:Welcome to your ideal hideaway in handsome Sea Pines, Hilton Head, SC! This striking home is charmingly located close to Lawton Stables, where you can embark on guided trail rides through the breathtaking Sea Pines...

Summary:Sealoft 2042The Space:Savor lush surroundings in a handsome treehouse that offers all of the amenities of modern life along with close by fishing areas, beaches, rivers, and the ocean. You'll be well-served by this Sea Pines treehouse called...

Summary:Hickory Cove 8The Space:Find yourself just steps from heaven at this elegant and roomy condo on Hilton Head Island. This vibrant, summery rental is located in a private corner of Palmetto Dunes and features a full, well-equipped kitchen with...

Welcome to this striking home, located in the heart of Palmetto Dunes Oceanfront Resort! With two cavernous living rooms and a charmingly refreshed Jack-and-Jill bathroom (completely updated in 2025 with a sleek tiled walk-in shower and modern...

Summary:Shorewood 219The Space:Whether you’re visiting sunny Hilton Head Island for boating, swimming, tanning, golf, or tennis, you’re certain to find everything and more that you seek at this Shorewood condo community. This ground-level condo...

Summary:Greens 152The Space:Treat yourself to an action-packed vacation when you stay at this striking condo on the island of Hilton Head. Tennis, golf, pools, and the beach are all within painless walking distance, making this an alluring...

Summary:Queens Grant 792The Space:Welcome to your serene hideaway in Hilton Head, SC! This roomy Palmetto Dunes condo offers a impressive lagoon view and a huge, sunny deck ideal for relaxation and outdoor dining. The additional-enormous, entirely...

Summary:Twin Oaks 207The Space:Adventure awaits you in this splendid condo which sits between the 9th and 10th fairways. You will appreciate sitting on the patio or balcony with your morning coffee or evening drink. Inside you will find everything...

Come savor this two bedroom and two bathroom condominium with outstanding ocean vistas! The Kitchen is on the right upon entering this penthouse-level condo and features granite countertops, new stainless steel appliances and bespoke cabinetry! The...

Summary:Beckenham 109The Space:Beckenham 109 is a beautiful end-unit villa in Port Royal Village with a impressive view of the 9th hole of the Barony Golf Course. It is bright and light with beachy coastal decor and new wood floor. The living room...