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Holiday rentals in Hilton Head Island

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Top-rated holiday rentals in Hilton Head Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Apartment in Hilton Head Island

4.88 out of 5 average rating, 160 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.)

26 Oct – 2 Nov

$158 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 222 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

$229 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.85 out of 5 average rating, 155 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!

16–23 Oct

$156 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.89 out of 5 average rating, 151 reviews

Beachfront property with ocean/sunrise view!

Ocean sunrises from your private balcony! Steps to the beach! Newly renovated 1 Bed/1 Bath villa in a gated ocean community. New flooring throughout with new central air/heat. Nicely appointed, fully equipped and immaculate. Perfect for up to 4 guests. Boardwalk to beach. Outdoor pool/showers. 2 beach cruiser bicycles included. Easy walk to Coligny Plaza for many restaurants, shops, grocery, etc. Great golf courses, tennis, biking/hiking trails, boating/fishing, parks in area.

12–19 Dec

$188 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.88 out of 5 average rating, 194 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.

27 Dec – 3 Jan

$165 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!

2–9 Aug

$171 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.97 out of 5 average rating, 120 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**

11–18 Mar

$316 SGD per night

Guest favourite

Guest suite in Hilton Head Island

4.94 out of 5 average rating, 274 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.

1–8 Feb

$147 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.99 out of 5 average rating, 312 reviews

Ocean Front Resort Condo

Enjoy Coastal Cottage Living in a lovely 540 sq ft one bedroom vacation villa within the activity-filled gated resort of Hilton Head Beach and Tennis. Completely remodeled from with all new fixtures, furnishings, housewares and accessories, this charming beach villa has just opened its doors for guests in March 2019. Amenities include coffee, popcorn, breakfast treats and bottled water to consume; and beach towels, chairs, umbrellas and other items to borrow while here.

29 Nov – 6 Dec

$212 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

$219 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.92 out of 5 average rating, 101 reviews

Secluded 1st Floor Beach Getaway

Newly Remodeled - 2 Bedroom/2 Bath First Floor Villa in a Gated Community - less than a five minute walk through our complex to a private, natural beach! Everything you need to enjoy a relaxing, peaceful getaway and all that Hilton Head Island is famous for. Located in a beautiful, quiet community that offers 2 outdoor pools and one indoor pool that can be enjoyed year round. Come discover why this island has been voted the #1 best island in the United States!

30 Oct – 6 Nov

$192 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.96 out of 5 average rating, 113 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!

13–20 Feb

$150 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Hilton Head Island holiday rentals

Free parking on premises

Air conditioning

Stay near Hilton Head Island's top sights

Coligny Beach Park116 locals recommend

Coligny Plaza Shopping Center179 locals recommend

Hilton Head Island Beach & Tennis Resort10 locals recommend

Omni Hilton Head Oceanfront Resort5 locals recommend

Sonesta Resort Hilton Head Island3 locals recommend

The Westin Hilton Head Island Resort & Spa6 locals recommend

Other great holiday rentals in Hilton Head Island

Guest favourite

Apartment in Hilton Head Island

4.99 out of 5 average rating, 145 reviews

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

11–18 Nov

$196 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.98 out of 5 average rating, 180 reviews

Lost Tiki Lounge TOP Floor Oceanfront 322 Breakers

10–17 Nov

$299 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.92 out of 5 average rating, 117 reviews

Book Now! 115B 2 Q Beds/Indoor Pools/Pickleball

8–15 Oct

$158 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.96 out of 5 average rating, 104 reviews

Luxury Couples Retreat !

11–18 Feb

$192 SGD per night

Guest favourite

Apartment in Hilton Head Island

4.87 out of 5 average rating, 448 reviews

(2) Renovated, beachfront complex w/3 restaurants!

8–15 May

$192 SGD per night

Guest favourite

Flat in Bluffton

4.99 out of 5 average rating, 117 reviews

Sunset on the May / Historic Old Town Bluffton

13–20 Mar

$170 SGD per night

Guest favourite

Guest house in Bluffton

4.93 out of 5 average rating, 166 reviews

Beautiful Carriage House! Your Home Away from Home

12–19 Jan

$162 SGD per night

Guest favourite

Guest house in Bluffton

4.96 out of 5 average rating, 322 reviews

Old Town Bluffton Carriage Apt.

10–17 Jan

$175 SGD per night

Quick stats about holiday rentals in Hilton Head Island

Total rentals
5.5K properties
Rentals with a pool
4.8K properties have a pool
Pet-friendly rentals
790 properties allow pets
Family-friendly rentals
4.6K properties are a good fit for families
Total number of reviews
110K reviews
Nightly prices starting at
$14 SGD before taxes and fees

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