Hilton Head's foot-shaped barrier island sits just across the Georgia line. Gated plantation communities (Sea Pines, Palmetto Dunes, Shipyard) house most luxury rentals. Golf is everywhere, the beach is firm enough to bike, and October is the sweet spot for weather plus price.
Affiliate links. About our partners.
The entire place is yours with beachfront location and a private pool.
6 Terra Bella Trace in Hilton Head Island offers direct beachfront access with stunning ocean views.
7 bedrooms and 7 bathrooms with private pool and beachfront access.
The entire place is yours, featuring 6 bedrooms, 5 bathrooms, and private amenities.
Spacious holiday home with five bedrooms and four bathrooms.
Beachfront Location: Paradise in Hilton Head Island offers direct beachfront access with stunning sea views.
The holiday home offers direct beachfront access with Hilton Head Island Beach just a few steps away.
Spacious vacation home with four bedrooms and four bathrooms.
Filter by dates, bedrooms, price, and distance to water. These are the full Vrbo and Booking.com inventories for Hilton Head Island.
Spacious holiday home with three bedrooms, two bathrooms, and a private pool.
Ocean Escape in Hilton Head Island offers a spacious holiday home with three bedrooms and four bathrooms.
Spacious Holiday Home in Hilton Head Island.
Spacious holiday home with three bedrooms and three bathrooms at The Sea Pines Resort in Hilton Head Island.
Affiliate link.
Spacious Holiday Home with a fully equipped kitchen and outdoor amenities.
Beachwalk 167 in Hilton Head Island offers a spacious holiday home with three bedrooms and four bathrooms.
Alexander Beach House in Hilton Head Island offers spacious holiday home accommodations with three bedrooms and two bathrooms.
Stones Throw 30 in Hilton Head Island offers a spacious holiday home with three bedrooms and three bathrooms.
Bags made from recycled sails. Handcrafted in Maine.
Shop Sea Bags →Affiliate link.
Spacious holiday home with three bedrooms and two bathrooms, a short walk to the beach.
Spa on Port Royal Sound 1221 offers a spacious setting with two bedrooms and two bathrooms, with sea views and a private pool.
Beachfront location with beautiful sea views.
Beachfront Location with direct access and stunning sea views.
Spacious two-bedroom apartment with access to a shared pool and beach.
Beachfront Location: Shorewood 511 in Hilton Head Island offers direct beachfront access and stunning sea views.
Spacious holiday home with 2 bedrooms and 2 bathrooms located in Hilton Head Island, just a 2-minute walk from the beach.
Beach + Pool Access: Colorful Hilton Head Condo! in Hilton Head Island offers direct beachfront access and a spacious layout.
Design-led hotels and villas via Skylark Travel Group. Mr & Mrs Smith properties, exclusive deals, real human concierge.
Direct beachfront access with stunning sea views.
Beachfront location with direct access and stunning sea views.
Spacious Accommodations with beach access and multiple pools.
7451 Anchorage in Hilton Head Island offers a two-bedroom holiday home with sea views.
Hampton Place 6407 in Hilton Head Island offers direct beachfront access and stunning sea views.
The entire place is yours, located on Hilton Head Island, featuring views, a fully equipped kitchen, and pet-friendly accommodations.
Schooner Court 705 in Hilton Head Island offers a spacious setting with two bedrooms and three bathrooms.
Shorewood 311 in Hilton Head Island offers a spacious setting with two bedrooms and two bathrooms.
Our curated picks are just the start. Browse hundreds more rentals in Hilton Head Island by date, price, and size.
1611 Port Villa @ South Beach offers a spacious holiday home with two bedrooms and two bathrooms.
2 Bed 2 and one half Bath 34 Coligny Villa Near Beach & Plaza in Hilton Head Island offers comfortable accommodations with outdoor swimming pool and free Wi-Fi.
Comfortable Accommodations: Hilton Head Cabana 52 in Hilton Head Island offers a two-bedroom holiday home with a living room.
The Hilton Head Resort features a private beach area and two swimming pools.
Bags made from recycled sails. Handcrafted in Maine.
Shop Sea Bags →Affiliate link.
Spacious Accommodations with direct access to the beach.
A charming 1-bedroom villa located steps from Harbour Town Marina in Hilton Head Island.
Breakers 215 in Hilton Head Island offers direct beachfront access and stunning sea views.
The entire place is yours with sea view and balcony.
Hotels, beach houses & apartments in Hilton Head Island.
Browse on Booking.com →Affiliate link.
Beachfront location with direct access and a private pool.
Seaside 211 in Hilton Head Island offers a holiday home with one bedroom and a living room.
The Village Palmetto Dunes offers a serene holiday home experience in Hilton Head Island with a private beach and outdoor swimming pool.
Oceanfront vacation home just steps from the beach.
Beachfront location with direct access to the beach.
Hampton Place 5501 in Hilton Head Island offers direct beachfront access and stunning sea views.
205 Windsor Place in Hilton Head Island offers a holiday home with one bedroom and two bathrooms.
Comfortable Living: Seaside 382 in Hilton Head Island offers a holiday home with one bedroom and a living room.
The holiday home features a beachfront location and stunning sea views.
Oceanfront, Sea Pines, Pool & Private Beach Access is a recently renovated vacation home in Hilton Head Island where guests can make the most of its outdoor swimming pool, garden, and terrace.
Oceanfront Condo - Hilton Head Island offers accommodations in Hilton Head Island, a few steps from Hilton Head Island Beach South.
Omni Hilton Head Oceanfront Resort is located in the exclusive Palmetto Dunes community.
Browse hundreds more waterfront rentals on Vrbo.
Browse on Vrbo →Affiliate link.
Pool Access! Oceanfront Hilton Head Island Condo offers accommodations in Hilton Head Island, a few steps from Hilton Head Island Beach South.
Oceanfront Hilton Head Villa Salt & Sunrise offers accommodations in Hilton Head Island, a 3-minute walk from Driessen Beach Park.
Oceanfront Hilton Head Island Condo with Pool! offers accommodations in Hilton Head Island, a few steps from Hilton Head Island Beach South.
If a hand-picked, design-led hotel sounds better than a vacation rental, Skylark Travel Group covers the same destinations with curated boutique stays, Mr & Mrs Smith, exclusive deals, real human concierge.
Sponsored.
Hand-picked for genuine waterfront. New finds and off-season picks, sent when there is something worth sending. No spam.
Join the newsletter. A short dispatch, zero spam, unsubscribe anytime.
