Holiday rentals in Hilton Head

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Top-rated holiday rentals in Hilton Head

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Guest favourite
A spacious dining area showcases a light wood rectangular table surrounded by four upholstered chairs. A centerpiece bowl sits atop the table, and place settings with plates and cloth napkins are neatly arranged. A modern light fixture hangs above, illuminating the open layout shared with the kitchen.
Cottage in Hilton Head Island
4.92 out of 5 average rating, 148 reviews

A "WOW" factor-Palmetto Dunes Retreat in Turnberry

Come to enjoy a relaxing time in Palmetto Dunes Resort at Turnberry Village- located in the heart of Hilton Head overlooking the 9th & 10th hole of the Robert Trent golf course. This villa has it all- newly updated villa, deck with golf course view, secluded location, and fully equipped with modern decor, appliances, and linens to make your stay a memorable and enjoyable vacation. There are 3 miles of sun-kissed beaches, world-class golf, restaurants, shopping and 11 miles of lagoons to enjoy.

Top guest favourite
A wooden boardwalk leads through grassy dunes towards the beach. The path extends toward the calm ocean, under a gray sky. Soft sand is visible at the boardwalk's end, inviting guests to access the beachfront.
Apartment in Hilton Head Island
4.96 out of 5 average rating, 342 reviews

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!

Top guest favourite
A bright dining area offers a view of the ocean through open doors leading to a private beachfront balcony. Coastal décor is present on the round table, complemented by neutral tones and natural light streaming in from the outdoors.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 341 reviews

Oceanfront Luxury! KING BED 65"TV Pickleball & BAR

✨Top 1% Airbnb Home✨ PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! Beachfront Balcony - Watch Sunrise / Hear Waves! Beachfront Pool, Bar & Grille FREE Pickleball, Tennis, Gym, Volleyball & More HGTV Designer Renovation KING BED + Two 65" SmartTVs Spa Bath Expanded Bedroom w/Blackout Sleeping Coastal Décor Full Kitchen Beach Chairs, Boogie Boards, Ice Chest & More RESORT Bike Rentals on Site 4 Beach Boardwalks 3 Restaurants Sports Bar Gated 24/7 Security Seasonal Island Trolley Stop

Top guest favourite
A tranquil beach scene is captured, featuring soft sand leading toward shimmering ocean waves. A wooden fence guides the pathway, with grasses gently framing the foreground. The sky is illuminated with warm hues of orange and pink as the sun rises above the horizon.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 297 reviews

Ocean View! Remodeled! Steps to beach/Pool/Bar

FULLY REMODELED OCEAN VIEW VILLA Located in Hilton Head Beach & Tennis Resort, this beautiful 540 Square foot Villa is perfect for a small family or couple looking for a relaxing and fun getaway. The second floor balcony offers a view of both the ocean and pool, as well as, offering the soothing sounds of the ocean waves Located within a gated community and with access to the beach just steps away. The resort also features 2 private pools, 3 restaurants, bike rentals, a private gym & more!

Top guest favourite
A cozy sleeping area features a spacious bed with a decorative quilt, complemented by a patterned accent pillow. A ceiling fan hangs above, while adjacent wooden sliding doors lead to a closet. Light blue walls and dark wood flooring enhance the inviting atmosphere.
Villa in Hilton Head Island
4.93 out of 5 average rating, 101 reviews

Beach Awaits You! Weekly Discounts!

Located at the gated, ocean front Hilton Head Beach & Tennis Resort, this cozy condo is only a 4 minute walk to beach and pool. Enjoy the beach bar, sports bar, tennis/pickle ball courts, fitness room & bike rentals. Equipped with full kitchen, queen bed, futon sofa. Ideally suited for two adults (max occupancy 3). Starter set of toiletries/towels provided. Laundry room on-site. Resort is located close to all the fun the island has in store for you! *Additional cleaning fees for monthly stays.

Guest favourite
A sunlit living space features a navy blue sofa and an elegant dining table surrounded by four chairs. Large sliding glass doors provide access to the oceanfront balcony, where views of the beach and coastal landscape can be seen in the distance.
Apartment in Hilton Head Island
4.97 out of 5 average rating, 211 reviews

Oceanfront Luxury! KING BED Pickleball + Beach Bar

PANORAMIC OCEANFRONT VIEW THE MOMENT YOU OPEN THE DOOR! ✨See the Ocean Sunrise & Hear the Waves! ✨ Oceanfront Balcony FREE Tennis, Gym, Pickleball, Basketball, Volleyball HGTV Decorator Renovation KING BED + 75" & 65" SmartTV s Expanded Bedroom MARBLE BATHROOM Coastal Décor TOP FLOOR w/Elevator Beach Chairs, Boogie Boards, Ice Chest & More RESORT No Resort Fees! Beachfront Pool w/Bar & Grille Sports Bar 2nd Pool Bike Rental in Resort Gated 24/7 Security Free Island Trolley Stop (April-Sept)

Top guest favourite
Apartment in Hilton Head Island
4.95 out of 5 average rating, 116 reviews

Wide Ocean View! Beach Bar Pickleball Tennis 65"TV

✨ Top 1% Airbnb Guest Favorite ✨ Big Ocean View - Living Room & Balcony! Oceanfront Building Steps to Beach & Pool Hear the Waves Updated by HGTV Decorator FREE: Pickleball, Tennis, Gym, Volleyball Top Floor w/Elevator 2 XL SmartTVs Fast WiFi 652 mbps Beach Chairs, Ice Chest & More Couples Retreat / Small Families RESORT: Oceanfront Pool w/Tiki Bar & Grille Sports Bar w/Pool Table 3 Restaurants Bike Rentals 2nd Pool Huge ShadyPlayground 3 BBQ Areas Gated 24/7 Security 4 Beach Boardwalks

Top guest favourite
A light-filled living area features a white sofa complemented by a blue accent chair. A decorative table with a tray of flowers and a plush area rug enhances the space. Large glass doors open to a balcony, offering expansive views of the ocean.
Apartment in Hilton Head Island
4.98 out of 5 average rating, 161 reviews

My Blue Heaven, Direct Ocean Front View

Welcome to our ocean front rental, a haven for couples seeking a romantic and stylish getaway. With its breathtaking ocean view, five-star reviews, and recent remodel in 2023, this rental promises an unforgettable experience. Our guests have praised the attention to detail, the stunning view, and the overall ambiance of the space. Rest assured that your stay will be nothing short of extraordinary. Step out onto the balcony and take in the fresh sea breeze as you relax in the swinging chair.

Guest favourite
Apartment in Hilton Head Island
4.89 out of 5 average rating, 216 reviews

Easy Breezy at Hilton Head Beach & Tennis

Enjoy our wide ocean view from our 3rd floor 1 BR Ocean Villa - with all of the amenities needed to enjoy a relaxing stay at the Hilton Head Beach & Tennis resort. Our villa has been newly decorated, and is conveniently 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, 6 pickleball courts, & fitness center.

Top guest favourite
A modern kitchen features smooth white cabinetry and granite countertops, complemented by stainless steel appliances. A double basin sink is situated near the window, with a microwave and oven built into the cabinetry. Soft, recessed lighting illuminates the workspace.
Apartment in Hilton Head Island
4.95 out of 5 average rating, 226 reviews

Heron's Haven on Port Royal Sound, 2BR/2BA

Do you love nature? Walking on the beach? Birding? Photography? Tennis? Golf? Shopping? Wonderful restaurants? This is our beautiful Villa that is located in Port Royal Sound directly on the most unique and natural beach on the island. On both sides are public parklands and nature preserves to walk and view the wildlife. A perfect location to enjoy all that Hilton Head has to offer, yet it is quiet, serene and away from all the crowds. It's why we love it, and we're sure you will too.

Top guest favourite
A seagull walks along the shoreline, where gentle waves meet the sand. The tranquil ocean reflects soft pastel colors as daylight begins to fade, creating a serene atmosphere. The beach is vast, with a stretch of smooth sand visible in the foreground.
Flat in Hilton Head Island
4.99 out of 5 average rating, 341 reviews

Hilton Head Seaside Vacation Rental

Stay in a unique, quiet beachfront neighborhood for your vacation on HHI. Enjoy a 5 minute/2 block WALK TO THE BEACH, 2 FREE bikes, Roku with NETFLIX, and a mid-island location for easy access to local attractions. Step inside to a bright, super clean, well stocked place with all of the comforts of home. Outside, you are surrounded by Live Oaks and natural landscaping. The apt. features LR/kitchen combo, 1 bedroom w/ a queen bed, full bath, W/D in walk-in closet, and a deck w/ seating.

Top guest favourite
Apartment in Hilton Head Island
5 out of 5 average rating, 108 reviews

5 Star Location-Pool, Walk to Dining/Shops/Marina

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

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