The holidays are a time for gathering with family and friends and making new memories. This year, trade the snow for soft sands and celebrate in coastal luxury on Hilton Head Island. Its mild weather, sparkling shoreline, and festive spirit make it the perfect destination for a holiday escape that blends Southern charm with upscale comfort. Whether planning a family reunion, a friends’ getaway, or a quiet seaside retreat, Island Getaway Rentals offers beautiful holiday rentals on Hilton Head Island that make every gathering unforgettable.
Stay up to date with everything that Island Getaway Rentals has to offer!
7 Grey Widgeon
5 Bedrooms | 5.5 Bathrooms | Sleeps 14
True Southern living meets modern luxury at 7 Grey Widgeon, a stunning Sea Pines retreat. This home is designed for comfort, style, and togetherness, featuring an open floor plan filled with natural light and sophisticated coastal décor. The great room, anchored by a spacious kitchen island and top-of-the-line appliances, invites everyone to cook, dine, and relax together.
Step outside to a screened-in porch perfect for morning coffee or evening cocktails, where indoor and outdoor living flow seamlessly. Just steps from Hilton Head Island’s world-famous beaches, it’s easy to stroll down the beach path for sunset walks or spontaneous sandcastle building. A private office, luxurious primary suite, and four additional bedrooms—including a fun built-in bunk room—ensure plenty of space for everyone.
Featured Amenities
• 5 Bedrooms / 5.5 Bathrooms
• Screened Porch with Outdoor Living Space
• Private Office and Bunk Room
• Pool Membership Access
• Steps from the Beach
11 Cat Boat
6 Bedrooms | 6.5 Bathrooms | Sleeps 18
If your holiday wish list includes ocean views and plenty of room for loved ones, 11 Cat Boat delivers. This expansive 5,300-square-foot oceanfront home offers elegance, comfort, and endless gathering spaces. Two large living rooms, cathedral ceilings, and a kitchen create the perfect environment for hosting family dinners or festive celebrations.
Outside, the ocean takes center stage. A large heated pool with a waterfall feature and a hot tub are perfect for relaxing with friends and family. Meanwhile the private deck and grilling area make outdoor dining a daily event. Six bedrooms, each with en-suite baths, provide privacy for everyone—ideal for multiple families vacationing together. From sunrise on the balcony to evening dips under the stars, 11 Cat Boat makes every moment feel special.
Featured Amenities
• 6 Bedrooms / 6.5 Bathrooms
• Oceanfront Views and Private Beach Access
• Private Heated Pool with Waterfall
• Two Living Rooms with TVs and Wet Bar
• Expansive Outdoor Dining and Lounge Areas
121 Abbington Villa
4 Bedrooms | 3 Bathrooms | Sleeps 10
Gather your favorite people and experience coastal comfort at 121 Abbington Villa, a beautiful townhouse just steps from the beach. Large windows fill the open living space with natural light, highlighting serene lagoon views and modern coastal décor. The fully updated kitchen with high-end stainless appliances is ideal for cooking together after a day at the ocean.
This home offers two spacious king bedrooms on the main level and a kid-friendly upstairs with twin and double rooms—perfect for multigenerational families. Step out to the private back deck overlooking the lagoon or take a quick walk to the community’s heated oceanfront pools at Barrington and Hampton Place. Blending luxury with convenience, 121 Abbington Villa is the perfect home base for relaxed holiday gatherings.
Featured Amenities
• 4 Bedrooms / 3 Bathrooms
• Private Deck with Lagoon Views
• Access to Two Heated Oceanfront Community Pools and Hot Tub
• Fully Equipped Modern Kitchen
• Located in Palmetto Dunes Resort
14 Armada
5 Bedrooms | 5.5 Bathrooms | Sleeps 10
Elegant, timeless, and right on the ocean, 14 Armada embodies the best of HHI’s luxury. A grand marble entryway and dual staircases lead into a soaring two-story living room where sunlight pours in from floor-to-ceiling windows. This oceanfront home is built for unforgettable holidays, with spacious gathering areas, a designer kitchen, and multiple dining spaces that make entertaining effortless.
Five bedrooms, each with private baths, provide resort-style comfort, including two luxurious master suites with Jacuzzi tubs and balconies overlooking the Atlantic. Outside, enjoy the private pool and spa while taking in the ocean breeze. For groups seeking sophistication and space, 14 Armada is a true showpiece for your island holiday celebration.
Featured Amenities
• 5 Bedrooms / 5.5 Bathrooms
• Oceanfront Home with Stunning Views
• Private Heated Pool and Spa
• Multiple Balconies and Outdoor Seating
• Two Master Suites with Jacuzzi Tubs
5 Armada
6 Bedrooms | 6 Bathrooms | Sleeps 12
Blending coastal charm with Lowcountry luxury, 5 Armada offers the perfect setting for a festive Hilton Head getaway. Just one row from the ocean in Palmetto Dunes, this spacious home was designed for togetherness. Two inviting living rooms, a fully equipped kitchen, and two dining areas make it easy to share meals and celebrate with friends and family.
Six bedrooms, including a stunning primary suite with vaulted ceilings and a spa-inspired bathroom, offer plenty of comfort for large groups. Outside, enjoy the private backyard oasis complete with a sunny pool, loungers, and a shaded deck with a Weber grill—ideal for a relaxed holiday barbecue. Whether you’re watching a movie in the cozy living room or gathering around the pool, 5 Armada combines warmth, style, and sophistication in one unforgettable setting.
Featured Amenities
• 6 Bedrooms / 6 Bathrooms
• Private Heated Pool and Spacious Deck
• Two Living Rooms and Multiple Dining Areas
• Gourmet Kitchen with Stainless Steel Appliances
• Pickleball On Site
Book a Holiday Rental on Hilton Head Island Today
This holiday season, skip the crowded resorts and gift yourself the joy of a luxurious home-away-from-home. Book one of our holiday rentals on Hilton Head today! With Island Getaway Rentals, you can host your family and friends in stunning homes designed for togetherness and relaxation. Our homes provide the perfect backdrop for memories that last long after the season ends.
Start a new tradition this year and celebrate the holidays the Island Getaway way. Browse our Hilton Head vacation homes and plan your stay today!
Frequently Asked Questions about Holiday Rentals on Hilton Head
What’s the weather like on Hilton Head during the holidays?
Hilton Head enjoys mild, comfortable weather throughout the holiday season. December temperatures typically range from the mid-50s to mid-60s °F during the day and in the 40s to 50s in the evening. This makes it ideal for beach walks, golf, and exploring the local cuisine. While you may want a light jacket in the evenings, the sunny days and ocean breezes create a perfect winter escape.
What amenities can I expect in Island Getaway Rentals’ holiday homes?
Each home includes everything you need for a relaxing stay, fully equipped kitchens, private or heated pools, Wi-Fi, and outdoor spaces for dining or entertaining.