Holiday rentals in Hilton Head Island

Oceanfront Condo w/ Balcony | Sea Side Villas HHI

Wake up to breathtaking ocean views at this Sea Side Villas condo in Hilton Head. Enjoy direct beach access, a private balcony overlooking the waves, and resort amenities including a pool, sun deck, and gated parking. This coastal retreat blends comfort and style with a fully equipped kitchen, fast Wi-Fi, and a cozy living area. Walk to Coligny Plaza for dining, coffee, and live music. Perfect for couples or small families seeking a relaxing oceanfront getaway in the heart of Hilton Head Island.

SeaPines - Walk to beach, Pet friendly, Pool, Golf

Overlooking the beautiful Atlantic Dunes Golf Course, this two story, 2 bedroom villa offers everything you need for your vacation getaway. With many updates in the kitchen and baths and lovely new flooring in 2023, this Wildwood villa is a great choice for a serene area that is still centrally located. Wildwood Spa is a short 12 minute walk to the Seapines Beach Club and has an on-site pool and tennis/pickleball courts. Pet friendly, spacious, and freshened with new linens, don't miss this gem!

*New* Easy Breezy at Hilton Head Beach & Tennis

Newly renovated in March ‘26 and brand new,from floor to ceilings, enjoy our wide ocean view from our 3rd floor Ocean Villa - with all of the amenities needed to enjoy a relaxing stay at the Hilton Head Beach & Tennis resort. Our villa is located just steps from the only elevator in the building. Our resort offers the largest pool on the island, several restaurants, a large playground & picnic area, on site bike rental, 24 hour gated security, 8 lighted tennis courts, and 6 pickleball courts.

Prime Waterview! Hilton Head Shelter Cove Marina

Permit 073816 Enjoy easy access to everything Hilton Head has to offer from this centrally located Condo in the heart of Shelter Cove Marina. Not only will you have breathtaking views of the sunset and the marina right from your balcony, but you also have many amenities right at your doorstep! Shelter Cove is one of the main attractions on Hilton Head Island with many shops, restaurants, weekly entertainment and water sports. You also have access to the private Palmetto Dunes Beach community.

Governor’s Quarters Pet Friendly, Fenced in Yard

Welcome to Governor's Quarters- your Luxury Hilton Head Getaway Stay Lowcountry in this stately-designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from the SeaPines Beach Club and HarbourTown Golf Links and the heated community pool! Located in famous, Sea Pines Resort. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, HarbourTown Lighthouse, & most importantly- the beach!

New Coastal 2 bed 2 ba villa - walk to the beach!

This Coastal Getaway will be your new home away from home at the beach in Hilton Head. First time on the rental market and as comfortable, clean and warm as your own home. This highly upgraded 2 bedroom condo is all n one level with no stairs in the unit. It is located on the second floor which provides for an open living area with vaulted ceilings. The living area features comfortable leather seating for all of your guests, a flat screen TV and a dining table that accommodates 6.

Available 6/7! King Bed/pools/3 blocks to beach

Stay just minutes from the beach and Coligny Plaza in this cozy, first-floor condo. Enjoy a renovated bathroom, a full kitchen with washer and dryer, and a Keurig for your morning coffee. The community has both an indoor and outdoor pools - updated in 2025. Our unit is the perfect home base to explore everything Hilton Head Island has to offer. This is the A unit of a lockout condo; the B unit may be occupied during your stay, but both are private and separately accessed.

Beautiful Couples Retreat Oceanview w/new bikes&Ch

Beautifully renovated oceanview retreat, perfect for a romantic getaway or small family escape. Enjoy a king bed, queen sleeper sofa, driftwood tile floors, stainless steel appliances, shiplap walls, and barn doors that add charm and privacy. Take in stunning views from your private balcony, relax with included beach chairs, or explore the island on two complimentary bikes. Walk to shops, restaurants, and entertainment—everything you need for a memorable Hilton Head stay.

KING BED!Ocean View, Free Bikes Poolside 3rd Floor

Pack your flip-flops and get ready for fun—this sunny poolside villa on Hilton Head Island is your ticket to the ultimate coastal escape! Just steps from the beach and the refreshing Atlantic breeze, this vibrant retreat serves up the perfect mix of relaxation, adventure, and ocean views. Start your day with coffee on the balcony, soak up the sun by the pool, then hop on one of our free bikes to cruise the island like a local! The perfect getaway starts right here!

5 Star Location-Harbourtown-Walkable Area

Escape to our luxury villa in Hilton Head's exclusive Harbour Town in the gated Sea Pines Resort! A short walk from Harbour Town Marina, which offers enertainment, dining, shopping, water sports, cruises, golf, tennis, and a pier. You will have access to The Sea Pines Beach Club, a short trolly, bike or car ride away. This private 3rd-floor impeccilbly appointed 'coastal chic' retreat does not share any walls and offers serene lagoon views from a private balcony.

Heron Hideaway: lovely updated near-beach 2bd/2ba

Beautiful, newly remodeled 2bd/2ba vacation home that's steps from the beach. Unwind on our private patio watching the birds frolic around the fountain in the pond below, relax in one of two pools, or kick it with a frozen beachy cocktail near the sea-grass with the ocean breeze tousling your hair while you watch the waves dance on the sand and the sun warmly kisses your skin. If this sounds great, our villa is the perfect choice for you.

Private Pool/Spa | Golf | Exq. Coffee | Seascape

Gourmet Coffee Lovers Paradise. And, over 1000 *5* star reviews! You found the perfect vacation home where you can enjoy a private pool with a spacious layout. Comfortably sleep 8 in 4 private bedrooms. The kitchen is fully equipped with everything needed to prepare a gourmet meal. You can enjoy dining in the large formal dining room, the sunroom adjacent to the kitchen, or outside. *The pool and spa can be heated for an additional fee.