Holiday rentals in Hilton Head Island

Prime Spot: Harbour, Dining, Shops & Beach

Stay in the heart of it all at this upscale, centrally located guest suite (256 sq ft) with independent entrance, total privacy, queen bed and full bath (no kitchen). Step outside to waterfront restaurants, live music, bars, shops, and summer weekly fireworks. Supermarkets and more dining are just a 10-minute walk away. Enjoy a free shuttle to attractions within 2-mile radius (April–September). Golfing, biking, fishing, and water sports all nearby, free access to Palmetto Dunes Beach community.

Ocean View! Steps to beach! Remodeled HHBT Condo!

Newly remodeled just last year! Adorable beach front condo located in HH Beach & Tennis Resort. Watch & listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rental, and a gym. We also provide beach chairs, coolers, boogie boards and coffee! It's all here! The getaway you've been waiting for and deserve!

SeaPines - Walk to Beach, On-Site Pool, Free Bikes

You'll love the location for this spacious pet friendly villa in Wildwood Spa, a private little neighborhood just ten minutes on foot to the Sea Pines Beach Club. This Premier Property features two bedrooms, two baths, and a loft area for reading and relaxing or extra sleeping arrangements. This quiet, secluded end unit affords privacy and serenity throughout your stay. Pet friendly, yet clean and updated, this centrally located villa is the prime home base for your next island getaway.

Oceanfront, 3rd floor, King Bed

Direct oceanfront! Perfect for a couples get away, week vacation or anything in between. Take a walk across the street to Coligny Square where there are more than 60+ shops and restaurants. Ride your bike on more than 100 miles of trails. Onsite parking, pool and free wifi. Just bring your bathing suit and a towel! We provide the rest for you to have a relaxing vacation; beach chairs, umbrella, cooler, all kitchen spices, a Coffee Bar, shampoo, conditions, body wash and tide pods!

Harbourside Haven

Harbourside Haven – Waterfront Luxury Villa in Shelter Cove, Hilton Head Island Welcome to Harbourside Haven, your upscale getaway on the water in the heart of prestigious Shelter Cove. This beautifully appointed 1-bedroom, 1.5-bath villa comfortably sleeps 2,(can add 2 more using available airbed), offering high-end finishes, designer furnishings, and all the comforts of home. It's the perfect retreat for couples or small families seeking a refined yet relaxing island experience.

Stunning Oceanview Luxury Remodel, Bikes Included!

With a view so stunning, you may never want to leave! Enjoy breathtaking beach sunrises from your private balcony and the sound of waves crashing just steps from the shore. Perfect for a romantic retreat or a small family getaway, this renovated villa features a Queen bed with a new mattress and a Queen sleeper sofa with a gel memory foam mattress for added comfort. Take morning walks, soak up the sun, or unwind with an evening stroll—your perfect beach escape awaits! 🌊☀️🏝️

Sea Pines house ~ Golf Sim / Putting Green / Games

Centrally located in HHI 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 & lounging areas, this home is a one-of-a-kind experience. Sleeping up to 10 guests (2 king beds and 4 double beds), 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 Hilton Head Island.

Spacious Harbor Town Condo!

Your perfect vacation begins when you walk out the door of this newly renovated condo into the Harbour Town marina with its boutique shops, gourmet restaurants, racquet club offering tennis and pickleball, famous PGA tournament golf course, and the iconic red and white lighthouse. The spacious 1-BR sleeps up to four guests. The master bedroom has a King-size bed and a large picture window that comes with blackout curtains for late sleepers.

💎Direct Oceanfront Villa - Heated Pool Ocean View

Welcome to the Ocean Gem! Relax and listen to the crashing waves on your private balcony of our newly renovated, newly furnished, direct oceanfront, one bedroom, one bathroom, beautiful beach villa. Ocean Gem is located in Ocean Dunes complex, a private gated community, on South Forest Beach and only steps from the popular Coligny Plaza. You will enjoy the wonderful accommodations, heated pool, picnic area and spectacular views! Thank you

Port Royal Village 302 - Walk to Beach

Spacious 2BR/2BA villa just a 5 minute walk to Hilton Head’s beach & Islanders Beach Park. Features a shaded balcony, community pool, full kitchen, washer/dryer, and elevator access. The master suite offers a king bed, balcony access, dressing area, and updated private bath. The guest bedroom also includes a king bed and ensuite bath. Enjoy peace and convenience in quiet Port Royal Village, perfect for couples, families, and beach lovers.

Port Tack - an iTrip Hilton Head Home

Welcome to Port Tack! This just-renovated 4 bedroom home features a gorgeous kitchen, spacious layout, private pool, private spa and serene lagoon views. This is the ideal rental for an active family that would like to spend time at the beach, riding bikes, relaxing in the pool and spa, or simply wanting to enjoy the best that Palmetto Dunes has to offer in a private & relaxing setting.

Direct Oceanfront View! Top Floor. Renovated.

Welcome to Vista del Mar! This stylish one bedroom beachfront villa is newly renovated and located within Hilton Head Beach and Tennis (HHB&T), a private gated oceanfront community with direct access to Folly Field Beach. This is a premium villa in HHB&T as it has a full ocean view, is one of the closest units to the beach and is located on the top (3rd) floor of the complex.