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Vacation rentals in Hilton Head

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Top-rated vacation rentals in Hilton Head

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Condo 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.)

Jan. 4 – 11

$201 CAD per night

Guest favourite

Condo in Hilton Head Island

4.93 out of 5 average rating, 165 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.

Oct. 14 – 21

$207 CAD per night

Guest favourite

Condo in Hilton Head Island

4.97 out of 5 average rating, 208 reviews

Cozy Oceanfront-Romantic Retreat-Mesmerizing Views

Villa is located on The Spa On Port Royal Sound complex on Hilton Head Island. Enjoy unobstructed sound & ocean views from your private balcony. Private beach access & observation pier. Beautiful landscaped grounds. 2 outdoor pools-opened Apr.-Oct. Indoor pool, hot tub, dry sauna & gym. Grills and picnic areas on premises, one near the villa, recently installed hammocks near the ocean pool. Tennis and basketball courts on site. Come enjoy the beautiful sandy beach with beautiful sunrises!

Dec. 8 – 15

$249 CAD per night

Condo in Hilton Head Island

4.81 out of 5 average rating, 112 reviews

HILTON HEAD RESORT CONDO - NEWLY RENOVATED

NEWLY RENOVATED condo near the beach! Ready for a relaxing time away? This newly renovated condo is tucked away in the lovely Hilton Head Resort - a gated community w/ 24 hr security, perfect for families who want to create lasting memories at the beach! The resort has everything you need - indoor/outdoor pools, sauna, spa, fitness room, tennis/pickle ball courts, and a private boardwalk to the beautiful beach. Within just a few miles are grocery stores, restaurants, shopping centers, and more!

Dec. 9 – 16

$209 CAD per night

Guest favourite

Condo 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!

Oct. 23 – 30

$184 CAD per night

Guest favourite

Condo 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.

Dec. 11 – 18

$225 CAD per night

Guest favourite

Guesthouse in Bluffton

5.0 out of 5 average rating, 441 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!

Oct. 10 – 17

$191 CAD per night

Guest favourite

Condo 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.

Feb. 1 – 8

$226 CAD 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.

Feb. 15 – 22

$172 CAD per night

Guest favourite

Condo in Hilton Head Island

4.89 out of 5 average rating, 167 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.

Jan. 23 – 30

$203 CAD per night

Guest favourite

Condo 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.

Jan. 21 – 28

$224 CAD per night

Guest favourite

Condo 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!

Dec. 18 – 25

$215 CAD per night

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Other great vacation rentals in Hilton Head

Guest favourite

Condo in Hilton Head Island

4.97 out of 5 average rating, 119 reviews

Ocean Overlook - The Ultimate Vacation Experience

Mar. 9 – 16

$397 CAD per night

Guest favourite

Condo in Hilton Head Island

4.95 out of 5 average rating, 201 reviews

Cozy Renovated Unit Great Location

Jan. 3 – 10

$210 CAD per night

Guest favourite

Condo in Hilton Head Island

4.88 out of 5 average rating, 182 reviews

Cozy Hilton Head Island Condo

Oct. 25 – Nov. 1

$203 CAD per night

Guest favourite

Apartment in Bluffton

4.99 out of 5 average rating, 117 reviews

Sunset on the May / Historic Old Town Bluffton

Feb. 11 – 18

$203 CAD per night

Guest favourite

Condo in Hilton Head Island

4.89 out of 5 average rating, 84 reviews

Beachfront Balcony | Walk Everywhere | Pool

Nov. 6 – 13

$174 CAD per night

Guest favourite

Condo in Hilton Head Island

4.87 out of 5 average rating, 55 reviews

Front Row to Beach and Pool - Upgrades! Location!

Oct. 23 – 30

$234 CAD per night

Guest favourite

Condo in Hilton Head Island

4.94 out of 5 average rating, 17 reviews

Beach Front Resort - Ocean View King Bed

Mar. 7 – 14

$267 CAD per night

Guest favourite

Condo in Hilton Head Island

4.97 out of 5 average rating, 77 reviews

Beach condo with pool and stunning nature views

Oct. 12 – 19

$232 CAD per night

Destinations to explore