Vacation rentals in Hilton Head Island

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Top-rated vacation rentals in Hilton Head Island

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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. 29 – Feb. 5

$193 CAD per night

Superhost

Condo in Hilton Head Island

4.88 out of 5 average rating, 159 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

Guest favourite

Condo in Hilton Head Island

4.88 out of 5 average rating, 193 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. 22 – 29

$197 CAD per night

Guest favourite

Guesthouse in Bluffton

5.0 out of 5 average rating, 438 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!

Aug. 22 – 29

$191 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.

Oct. 15 – 22

$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. 7 – 14

$264 CAD per night

Guest favourite

Condo in Hilton Head Island

4.95 out of 5 average rating, 226 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!

Dec. 19 – 26

$294 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

$216 CAD per night

Guest favourite

Condo 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!

Dec. 3 – 10

$209 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!

Jan. 9 – 16

$204 CAD per night

Guest favourite

Condo in Hilton Head Island

4.95 out of 5 average rating, 201 reviews

Cozy Renovated Unit Great Location

Completely renovated, new everything! Easy access to beach, public restrooms and open bar / food / fire pits at beach access (see photo). High speed internet, 3 TV’s w/ YouTube TV included (70 channels, Golf, Tennis, ESPN family of channels, SportsSouth, Disney family of channels), local Cable through Spectrum included. The perfect location near Coligny Plaza, Sea Pines, the beach, miles of bike trails!

Oct. 25 – Nov. 1

$211 CAD per night

Guest favourite

Condo in Hilton Head Island

4.81 out of 5 average rating, 143 reviews

SeaForever-King Bed, Ocean Views w/ Beach Access

Enjoy ocean views from the balcony of this first floor villa in the heart of Hilton Head's main beach! The villa features a full kitchen, king bed in the bedroom, and a sleeper sofa in the living room. Flat screen TV's in both the bedroom and living room and WiFi. Just steps to the beach or pool, every thing needed for your beach vacation!

Nov. 30 – Dec. 7

$200 CAD per night