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.

Guest favourite
Condo in Hilton Head Island
Luxe OceanView! KING BED BAR Tennis GYM PickleBall
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 2cd 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
Jan. 30 – Feb. 6
$294 CAD per night
4.98 out of 5 average rating, 217 reviews
Guest favourite
Condo in Hilton Head Island
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. 1 – 8
$244 CAD per night
4.97 out of 5 average rating, 205 reviews
Guest favourite
Condo in Hilton Head Island
Oceanfront Designer! KING BED 65"TV Bar Tennis GYM
PANORAMIC OCEANFRONT VIEWS THE MOMENT YOU OPEN THE DOOR! HGTV Featured Decorator! 100% Luxury Renovation Coastal Décor (2) 65" SmartTVs KING BED Expanded Bedroom Full Kitchen Oceanfront Balcony Beach Chairs, Umbrella, Boogie Boards , Ice Chest, Pool Noodles! Spa Bath RESORT: No Resort Fees Huge Oceanfront Pool Beachfront Bar & Grille Sports Bar FREE Tennis, Gym, Pickleball, Basketball, Volleyball & More Bike Rental 2cd Pool Gate w/24 Hour Security Trolley Stop Bradley Beach 4 Beach Boardwalks
Aug. 10 – 17
$806 CAD per night
4.97 out of 5 average rating, 216 reviews

Popular amenities for Hilton Head Island vacation rentals

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
Sonesta Resort Hilton Head Island3 locals recommend
The Westin Hilton Head Island Resort & Spa6 locals recommend
Omni Hilton Head Oceanfront Resort5 locals recommend

Other great vacation rentals in Hilton Head Island

Guest favourite
Guesthouse in Bluffton
Bluffton Casita
Aug. 31 – Sep. 7
$170 CAD per night
5.0 out of 5 average rating, 252 reviews
Guest favourite
Condo in Hilton Head Island
AWESOME Retreat! King bed! Ocean View! 2 Bikes 218
Dec. 14 – 21
$295 CAD per night
4.83 out of 5 average rating, 103 reviews
Guest favourite
Apartment in Hilton Head Island
Completely Renovated Duplex - 2 MIN WALK TO BEACH
Jan. 18 – 25
$794 CAD per night
4.97 out of 5 average rating, 34 reviews
Guest favourite
Apartment in Hilton Head Island
Poolside condo with ocean view and FREE BIKES
Oct. 11 – 18
$215 CAD per night
5.0 out of 5 average rating, 16 reviews
Guest favourite
Condo in Hilton Head Island
5 Star Location & Property: Harbour Town-Sea Pines
Nov. 17 – 24
$293 CAD per night
5.0 out of 5 average rating, 43 reviews
Guest favourite
Condo in Hilton Head Island
Hilton Head luxury direct oceanfront villa
Oct. 6 – 13
$416 CAD per night
5.0 out of 5 average rating, 54 reviews
Guest favourite
Condo in Hilton Head Island
Natural beach living with style
Oct. 19 – 26
$223 CAD per night
4.97 out of 5 average rating, 59 reviews
Guest favourite
Villa in Hilton Head Island
Oceanfront Scandi Oasis Amazing View & Heated Pool
May 7 – 14
$656 CAD per night
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Hilton Head Island
180º Ocean Views, Treehouse "Siren's Lookout"
Aug. 18 – 25
$979 CAD per night
5.0 out of 5 average rating, 53 reviews
Guest favourite
Apartment in Hilton Head Island
Palmetto Dunes Luxury Oceanfront Gem w/ View -King
Dec. 16 – 23
$636 CAD per night
5.0 out of 5 average rating, 8 reviews
Guest favourite
Condo in Hilton Head Island
New Ocean Front at Villamare!
May 14 – 21
$964 CAD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Condo in Hilton Head Island
Ocean Views at Villamare, New Pools and Hot Tubs!
Oct. 29 – Nov. 5
$652 CAD per night
4.96 out of 5 average rating, 46 reviews

Quick stats about vacation rentals in Hilton Head Island

Total rentals

5.6K properties

Rentals with a pool

4.9K properties have a pool

Pet-friendly rentals

730 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