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Holiday rentals in Hilton Head

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Top-rated holiday rentals in Hilton Head

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Apartment in Hilton Head Island

4.88 out of 5 average rating, 161 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.)

15–22 Jan

$154 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.

7–14 Jan

$159 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.97 out of 5 average rating, 199 reviews

HHBT Resort-OceanView-Remodeled-Steps to beach!

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!

12–19 Dec

$209 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.

8–15 Nov

$206 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 132 reviews

"Beach Time" - a cozy HHI Condo, steps from beach

No price increase 2023 & 24! Low fees! New Solbello sail sunshade. HHI Beach & Tennis is a beachfront resort with many vacation amenities. Our condo is a first floor condo in Building B, close to the pool and beach activities but far away enough from noise of pool and restaurant. Our condo is 2-3 minutes from the beach. We provide a clean, safe, comfortable and affordable space for our guests. Our condo is cleaned, sanitized and ozonized. We have an air system, air purifier and dehumidifier.

30 Nov – 7 Dec

$136 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.88 out of 5 average rating, 196 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.

9–16 Nov

$165 SGD per night

Guest favourite

Guest house in Bluffton

5.0 out of 5 average rating, 446 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!

27 Sep – 4 Oct

$170 SGD per night

Apartment in Hilton Head Island

4.91 out of 5 average rating, 100 reviews

BEach HAPPY HHI Ocean view and steps to the Beach

Our Villa in South Forest Beach will make you BEach Happy! Our UPDATED 550 sqft 1-bedroom villa, located in historic Seaside Villas, can accommodate up to 4 beachgoers (1 bedroom with a queen bed, in the hall are captain bunk beds for the kids, or in the living room a pull-out queen sofa bed for 2). The private balcony has a view of the ocean! Our ocean view villa is only steps to the beautiful beaches of HHI, and within walking distance to Coligny shopping and dining. Choose BEach Happy!

7–14 Nov

$165 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**

18–25 Feb

$315 SGD per night

Guest favourite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 278 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.

9–16 Nov

$146 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.89 out of 5 average rating, 168 reviews

Hilton Head Island - Beach Retreat !!

Newly painted 3rd fl. 2 BR/2 Bath walk-up (2.5 short flights of stairs) unit, new kitchen floor & carpet. Sleeps 6. A total of 5 beds includes 1 king, 1 twin bed, twin over full/bunk beds & a sofa bed. Fully equip. kitchen w/new appliances. Unit has an open fl. plan w/view of lagoon & fountain. 5 min walk across the parking lot to the beach. Coconutz Sports Bar & Jamaica Joez Beach Bar on site. Gym & Laundry room on premises. Resort Parking Pass Fee is $35.00 per vehicle.

21–28 Mar

$157 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

$218 SGD per night

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Popular amenities for Hilton Head holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Hilton Head

Guest favourite

Guest house in Bluffton

4.98 out of 5 average rating, 357 reviews

Hickory Trace Carriage House

18–25 Jan

$179 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.87 out of 5 average rating, 55 reviews

Front Row to Beach and Pool - Upgrades! Location!

10–17 Dec

$178 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.95 out of 5 average rating, 21 reviews

Beach Front Resort - Ocean View King Bed

3–10 Mar

$216 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.96 out of 5 average rating, 92 reviews

Oceanfront Designer! KING BED 65"TV Bar Tennis GYM

13–20 Jan

$268 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.93 out of 5 average rating, 73 reviews

Turtle Cove w/ Lagoon, Golf Course & Ocean Views!

17–24 Jan

$172 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.95 out of 5 average rating, 63 reviews

Quick Walk to Beach- 2BR/1BA - South Forest Beach

12–19 Nov

$175 SGD per night

Flat in Hilton Head Island

5.0 out of 5 average rating, 5 reviews

Penthouse Bliss

23–30 Jan

$177 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.88 out of 5 average rating, 41 reviews

Beach side, pools, tennis/pickle ball, and more

21–28 Nov

$138 SGD per night

Destinations to explore