Holiday rentals in Hilton Head

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Top-rated holiday rentals in Hilton Head

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Guest favourite

Apartment in Hilton Head Island

4.89 out of 5 average rating, 176 reviews

Hilton Head Hidden Gem

Comfy 3rd floor walk up retreat. Peaceful decor. Screened balcony. Furnished kitchen. Free use of WIFI, beach chairs/umbrella, gym, basketball & tennis courts, charcoal grills/picnic tables; pools. Steps from your door: explore our sandy beach, watch fish jump & dolphins swim; observe nature on a private pier. See the sunrise on the water. Grocery/restaurants w/in 1-5 miles. Make a meal or a reservation! Short drive to all island locales. Great island bike paths. (No pets or smoking.)

Guest favourite

Apartment in Hilton Head Island

4.96 out of 5 average rating, 107 reviews

OceanView Luxe KING BED 65"TV Bar Pickleball GYM

Oceanfront Building! BIG Ocean View from Balcony! 100% NEW HGTV Designer Renovation! KING BED! RARE Expanded Bedroom Two 65" SmartTVs Coastal Decor Beach Chairs, Boogie Boards, Ice Chest Designer Marble Kitchen & Bath Quiet Top Floor Elevator RESORT: No Resort Fees Huge Oceanfront Pool Beachfront Bar & Grille (Misc. Hours) Sports Bar FREE Gym, Pickleball, Tennis Basketball, Volleyball & More 2cd Pool Bike Rental Gated 24 Hour Security Free Seasonal Trolley Stop 4 Beach Boardwalks Bradley Beach!

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 262 reviews

Ocean Front Resort Villa

Freshly decorated in coastal cottage decor, this 540 sq ft one bedroom villa sleeps up to 6 and is located within the activity-filled Hilton Head Beach and Tennis Resort. The villa was recently remodeled with all new kitchen, bathroom and fixtures and is just 50 steps to gorgeous beach. The views from the living room include ocean, oceanfront pool , beach bar and grill, and pond with fountain. The villa is full of amenities including beach towels, beach chairs, beach umbrella and much more.

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 133 reviews

My Blue Heaven, Romantic, Fall and Winter Specials

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

4.96 out of 5 average rating, 123 reviews

Luxury Couples Retreat !

Welcome to Serenity by the Shore. Escape to this top floor unit which is steps away to the beautiful ocean. Our condo features a heavenly pillowtop mattress in the master bedroom, private ocean view balcony and fully equipped kitchen for all your cooking needs. The condo is perfectly located within the Hilton Head Beach and Tennis Resort, the island's largest ocean front pool, tennis courts, Pool Bar & Grill. This luxury condo is great for a solo getaway, family vacation or romantic escape!

Guest favourite

Rental unit in Hilton Head Island

5 out of 5 average rating, 297 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.

Guest favourite

Guest suite in Hilton Head Island

4.93 out of 5 average rating, 306 reviews

LOCATION! Harbour, Dining, Shops, Beach-1.4 mile

Location .. Location .. Location !!! Private guest suite (256 sq ft) with independent entrance from outside, total privacy, and complete amenities, queen bed and full bath (no kitchen). Just step outside - great water-front restaurants with live music, bars, shops and weekly fireworks during summer. Supermarkets and more restaurants in 10 minutes walking. Free shuttle to attractions in 2 miles radius from April till September, beach 1.4 miles away, biking, fishing and water sports.

Guest favourite

Apartment in Hilton Head Island

4.94 out of 5 average rating, 168 reviews

Ocean front condo with amazing ocean view!

Ocean front condo with amazing view of the ocean and beach from balcony. You are just steps to the beach. In addition, you will be within walking distance to Coligny Plaza with many great restaurants and shops. Guests get to enjoy the onsite pool, sun deck, and grilling area. Luggage carts are located by the pool and elevator to easily transport all your luggage to the condo. Fast upgraded wifi for streaming and work needs. No pets allowed. Preapproval required for service animals.

Guest favourite

Apartment in Hilton Head Island

4.97 out of 5 average rating, 180 reviews

Ocean Front Beach & Tennis Resort 2 BR 2 BA Villa

Welcome to our renovated 2BR 2BA Villa at Hilton Head Beach & Tennis Resort. It is a short walk to the Resort's beautiful Private Access Beach and largest outdoor pool on the Island Updated appliances, furniture & bathrooms. Villa has a fully equipped Kitchen, Coffee Bar with Keurig, Memory Foam Mattresses on all Beds 3 Wall Mounted Smart TV's Hi Speed Wifi. Sleeps 5 adults Comfortably contact us for info on add'l guests. Porta Crib supplied but guest must bring own linens for crib

Guest favourite

Apartment in Hilton Head Island

4.93 out of 5 average rating, 119 reviews

Spacious Two Bedroom Villa in Hilton Head Resort!

Spacious two bedroom/two bathroom villa includes its own washer and dryer! This recently updated villa will not disappoint as it's located in Hilton Head Resort with so many amenities: private access to Singleton Beach, two outdoor pools, seasonal onsite deli/bar/store, heated indoor pool, hot tub, kiddie pool, sauna, exercise room, and track. There are also tennis, pickleball, and badminton courts! Bike paths are plenty with many nearby stores, restaurants, and golf courses!

Guest favourite

Apartment in Hilton Head Island

4.99 out of 5 average rating, 121 reviews

Ocean Overlook II - The Penthouse Experience

LUXURIOUS, PENTHOUSE, 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! 4TH FLOOR (TOP FLOOR)! PRIVATE BALCONY! MILLION DOLLAR OCEAN VIEWS! SPA SHOWER! 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**

Guest favourite

Guest house in Hilton Head Island

4.89 out of 5 average rating, 122 reviews

Alli B's air B and B-great country access off 278

Your family will be close to everything when you stay at this centrally-located place. No gate fees or parking fees- right off of 278- central located between Bluffton and HHI under foot of bridge. Farm like experience -family owned 30 years . Quiet . Pet friendly . Beds-two twin -can pull together if wish -one couch(Not a sofa bed) and one mattress under a bed that can be moved out . Property has several buildings , Guest apt is above garage. NOTE: SEE Space info below