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Vacation rentals in Hilton Head Island

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Top-rated vacation rentals in Hilton Head Island

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

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Condo in Hilton Head Island

4.85 out of 5 average rating, 211 reviews

End unit w lovely ocean view @ HHBT

*4/22/2021 Brand new bath & kitchen with convection microwave, LVP flooring, lighting, fixtures, furniture, mattress, everything from curtains to bedding & Samsung smartTV. Our end unit offers amazing 360 views of the ocean & resort from our front & rear balconies! We're so proud to share our new space with you. We wanted to keep the vintage vibe of the villa while adding all the luxury and modern comforts you expect while traveling and relaxing in style. *2-3 guest max. No pets. 25 age minimum*

Apr. 29 – May 6

$213 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.

Jan. 22 – 29

$194 CAD per night

Condo in Hilton Head Island

4.88 out of 5 average rating, 158 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

$202 CAD per night

Condo in Hilton Head Island

4.82 out of 5 average rating, 109 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. 10 – 17

$217 CAD per night

Guest favourite

Condo in Hilton Head Island

4.89 out of 5 average rating, 102 reviews

Casa del Sol

You will be close to everything when you stay at this centrally located beachfront resort Villa. Enjoy on-site Tennis, Pickle-ball, indoor and outdoor swimming, track, workouts, sauna, hot-tub, and of course private beach access and Coco's snack shack at the dunes. 🏖️Bike rentals available on-site. On the Island nearby you'll find shopping, grocery, dinning, entertainment, fishing, boating, water sports, many public golf courses, walking, endless bike trails, miles of beach, ocean fun, etc.

Nov. 15 – 22

$217 CAD per night

Guest favourite

Condo in Hilton Head Island

4.88 out of 5 average rating, 192 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.

Jan. 25 – Feb. 1

$197 CAD per night

Guest favourite

Guesthouse in Bluffton

5.0 out of 5 average rating, 436 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!

Sep. 7 – 14

$192 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.

Jan. 1 – 8

$173 CAD per night

Guest favourite

Condo in Hilton Head Island

4.99 out of 5 average rating, 311 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.

Oct. 13 – 20

$264 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!

Jan. 17 – 24

$216 CAD per night

Guest favourite

Condo in Hilton Head Island

4.99 out of 5 average rating, 144 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.

Dec. 15 – 22

$235 CAD per night

Guest favourite

Condo in Hilton Head Island

4.88 out of 5 average rating, 180 reviews

Cozy Hilton Head Island Condo

Newly renovated unit is only foot steps from the beach! Conveniently situated near shopping, and dining at Coligny Plaza. Accommodates 5 people with two parking spaces. Fully equipped unit with two bedrooms. TVs, wireless internet, fully equipped kitchen. Guest have access to pool, picnic area w/ grills and tables. Feel free to reach out with any questions and how we can make your time at the beach the best that it can be!

Oct. 22 – 29

$204 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Houses

A space that's all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Hilton Head Island vacation 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 vacation rentals in Hilton Head Island

Guest favourite

Condo in Hilton Head Island

4.85 out of 5 average rating, 233 reviews

Charming Sea Pines Villa with View on Hilton Head

Oct. 31 – Nov. 7

$240 CAD per night

Guest favourite

Condo in Hilton Head Island

4.95 out of 5 average rating, 225 reviews

Ocean View! Steps to beach! Remodeled HHBT Condo

Dec. 19 – 26

$296 CAD per night

Guest favourite

Condo in Hilton Head Island

4.97 out of 5 average rating, 118 reviews

Ocean Overlook - The Ultimate Vacation Experience

Jan. 15 – 22

$399 CAD per night

Guest favourite

Condo in Hilton Head Island

4.95 out of 5 average rating, 201 reviews

Cozy Renovated Unit Great Location

Nov. 12 – 19

$211 CAD per night

Guest favourite

Condo in Hilton Head Island

5.0 out of 5 average rating, 45 reviews

5 Star Location & Property: Harbour Town-Sea Pines

Nov. 11 – 18

$289 CAD per night

Guest favourite

Condo in Hilton Head Island

4.94 out of 5 average rating, 16 reviews

Beach Front Resort - Ocean View King Bed

Feb. 7 – 14

$251 CAD per night

Guest favourite

Apartment in Hilton Head Island

4.78 out of 5 average rating, 9 reviews

Suite Life at 417 Forest Beach Villas - Location!

Feb. 23 – Mar. 2

$184 CAD per night

Guest favourite

Guesthouse in Hilton Head Island

4.86 out of 5 average rating, 85 reviews

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

Feb. 25 – Mar. 4

$181 CAD per night

Quick stats about vacation 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 CAD before taxes and fees

Destinations to explore