Holiday rentals in Hilton Head Island

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Top-rated holiday rentals in Hilton Head Island

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Guest favourite

Guest house in Bluffton

4.97 out of 5 average rating, 689 reviews

Bluffton's Tropical Carriage House Getaway

Embrace the inviting atmosphere of this detached garage apartment. The guesthouse features an open-concept living/kitchen/sleeping area, a tropical design, a private entry, a luxury king mattress and blackout window treatments. Spacious carriage house apartment with king size Stearns&Foster mattress. This space offers a living area with sofa, chair, table with barstools and tv with Netflix as well as other apps that you access. *We do not have cable or local channels. The kitchenette has lots of utensils, plates, glasses, toaster, coffee pot, plug-in induction burner with pots and pans, and a panini press. There is also a ceiling fan for temperature control, or if you are like us and want to sleep with the fan on. In addition there is walk-in closet with hangers and luggage rack for you to hang your clothes and keep your luggage. Fresh towels and toiletries are available for your stay. Other amenities include a hair dryer, curling iron, iron and ironing board, beach towels and beach blanket. You have access to the carriage house apartment and all of its amenities. You are welcome to use our backyard as well, and our wonderful bed swing (thanks to Joey's craftmanship) that's on our front porch. We're also willing to run a load of laundry for you if the need should arise. Brittani works from home, so she will normally be able to assist you if you should need anything. We are both available by our cell phone. We are relatively new to the Bluffton/Hilton Head area, but would love to share our finds with you. This southern style hood offers ample sidewalks, ponds for fishing, a playground, and a park. Quaint Old Town Bluffton is a 3 minute drive or 20 minute walk to a number of shops and restaurants. Unfortunately public transportation is not readily available, so if you are not wishing to use your car then you can easily walk to a good bit of amenities or call for an Uber. Our puppy son, Gunner, is a lovable Labradoodle. He is very friendly and will most likely be barking at the door of our home when you arrive, but we promise it's all for show! You might encounter him in the backyard during your visit :)

23–30 Jun

$143 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.93 out of 5 average rating, 166 reviews

Hilton Head BIKE 'n BED - Perfect Couple's Getaway

Come relax and enjoy Hilton Head on South Forest Beach, the most popular section of the island. Ride our free bikes for a quick trip to Coligny Plaza where the quaint local shops and restaurants are. The beach is a quick 2 or less minute walk and the pool is just down the hall. Our condo is small, but perfect for a couple's getaway or a memorable trip with the kids. We have everything you need to help make yourselves at home with full size kitchen appliances and washer/dryer room just next door.

28 Dec – 4 Jan

$162 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 223 reviews

Ocean View Luxe! KING BED 65"TV Bar Pickleball GYM

Beachfront Building! Quiet Views of Coastal Marsh, Ocean & Trees - Not Parking Lot! HGTV Featured Decorator Coastal Decor KING BED Expanded Bedroom 2 SmartTVs Private Balcony Beach Chairs, Umbrella, Boogie Boards, Ice Chest, Pool Noodles Full Kitchen Top Floor Elevator RESORT: No Resort Fees Huge Oceanfront Pool 2nd Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rentals Gated/24 Hour Security Trolley Stop 4 Beach Boardwalks Bradley Beach

10–17 Nov

$233 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 239 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.

11–18 Nov

$211 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.85 out of 5 average rating, 157 reviews

Boardwalk to Beach, Hot Tub, 3 Pools and Tennis!

Welcome to our beautifully renovated family friendly villa within walking distance to the beach! The villa is located in a wonderful 24 hour gated community offering endless entertainment! The resort includes tennis courts, outdoor pools, pickleball, heated indoor pool, hot tub, sauna, fitness room, indoor track, volleyball, BBQ and picnic area, an onsite store and deli as well as easy access to Coco's Oceanfront Bar & Grill. There is so much to do on the resort you will never want to leave!

12–19 Jan

$197 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.88 out of 5 average rating, 195 reviews

Our Villa by the Sea

Enjoy our villa by the sea with a short board walk to one of the longest beaches in the US. Complementary beach accessories waiting for you. Relax on the balcony with the fresh ocean breeze and a peak of the ocean. Located on Hilton Head Beach & Tennis Resort, enjoy all of the amenities as our guest ... bar & grill on the beach, pool with ocean view, tennis courts, bike rentals, restaurant, and fitness center. Or just venture out and discover Hilton Head Island's beautiful attractions.

18–25 Jan

$167 SGD per night

Guest favourite

Guest house in Bluffton

5.0 out of 5 average rating, 443 reviews

Lowcountry Retreat Carriage House

Located in a quiet neighborhood, minutes from Old Town Bluffton, where you can find unique shops, art galleries, & great places to eat - many with live music! A stroll through the neighborhood will take you past a local park with playground, workout area, & walking paths. There are many ponds to enjoy the local wildlife, wetland areas, and beautiful oak trees. It's so peaceful! Convenient to Hilton Head, Beaufort, and Savannah, it's the perfect spot for exploring, shopping, or relaxing!

18–25 Oct

$173 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.97 out of 5 average rating, 121 reviews

Ocean Overlook - The Ultimate Vacation Experience

LUXURIOUS, 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! 3RD FLOOR! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM! WATCH EVERY SUNRISE & SUNSET! 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**

26 Dec – 2 Jan

$322 SGD per night

Guest favourite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 275 reviews

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

Location .. Location .. Location !!! Private guest suite 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, weekly fireworks during summer, bars, shops, outdoor pool and BBQ. Supermarkets and more restaurants in 10 minutes walking. Free shuttle from April till September, beach only 1.4 miles. Great golfing, biking, tennis, fishing and water sports.

8–15 Feb

$149 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.95 out of 5 average rating, 228 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo

Newly remodeled - just last year! Adorable beach front condo located in Hilton Head Beach and Tennis Resort. Watch and listen to the ocean waves right from your 2nd floor balcony! The condo is in a gated area within the resort where guests will have access to a private beach, 2 pools, resort restaurants, tennis, pickleball, beach volleyball, playgrounds, cookout areas, bike rentals, and a newly renovated gym. It's all here! 😊The 2024 getaway your been waiting for! 😎

8–15 Nov

$223 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.99 out of 5 average rating, 147 reviews

Reno’d 1st floor walk to beach, pools pickleball

Welcome to our lovely renovated 1st floor unit in Fiddler's Cove. Perfect for a tennis, golf, biking or beach holiday! A 6-7 min walk to Folly Field beach via private beach access. Use our beach gear. Great secure wifi. Surrounded by world class golf courses. Enjoy 5 star amenities including 2 pools, hot tub, racquetball, pickle ball courts and gym. Pools are open from march 1st-October 31st and hot tub remains open year round.

14–21 Dec

$189 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.96 out of 5 average rating, 115 reviews

Beach&Tennis, Stylish, Modern, Folly Field Beach!

Hilton Head Beach & Tennis, 1-bedroom, fully remodeled! New queen mattress, stainless appliances, Queen Sleeper Sofa. 5 units from the ocean, partial ocean view. Enjoy a glass of wine, and listen to the ocean on the private patio. Free Wi-Fi! Don't stay in a tiny hotel room with no kitchen. Hotels are cold and sterile, our home is warm and welcoming! 100 feet to our beautiful beach and oceanfront pool! 12 Pickleball courts!

7–14 Mar

$148 SGD per night