Hilton Head, SC 2+ Bedroom Vacation Rentals

This condo has been charmingly refreshed throughout. As you enter, the Kitchen is on your left. The Kitchen features all stainless steel appliances, granite countertops and comes completely-equipped to meet your culinary needs. Beyond the open...

Beckenham 101Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beckenham 101 is a newly updated, two-bedroom, two-bathroom villa in Port Royal Village. It is...

*** Sanitation/Cleaning Update ***Over the next few months, when guests are in hotels within the Marriott portfolio, they will notice a number of additions to our cleaning regimen designed to set an even higher standard of cleanliness for the...

Enormous 3 bedroom/3 bathroom condo with nice kitchen, living and dining room, with a cavernous deck over looking the pool. Freshly refreshed bathrooms in January 2023.Ability to appreciate the amenities of the Westin Resort and Spa, which includes...

Kingston Dunes 68Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sophisticated, modern, cavernous, and private, the ideal Hilton Head Island hideaway exists...

Courtside, Unit #22Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the charming Forest Beach area, this downtown condo is close to the wide variety...

The villas at Beachwood Place are expertly managed by Vacation Time of Hilton Head and are best reserved directly through our website.This second-floor oceanfront villa on South Forest Beach Drive features two bedrooms, two bathrooms, and a roomy...

Island Club 5204Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With expansive ocean vistas and an oceanfront location, this freshly modernized...

Spa on Port Royal Sound 3231Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Stroll just across the property to the impressive beach on Port Royal Sound when...

One of the very best located properties in Palmetto Dunes. Walk everywhere. Ideal vacation location! Two min. walk to tennis and pickleball courts, eateries and Trent Jones golf course on award winning Palmetto Dunes Plantation. Fazio and Arthur...

This new, 5 bedroom, 5 ½ bath, home is a ideal fit for extended families, or as a multi-family vacation residence. Feel absolute luxury and convenience in this pretty professionally decorated coastal beach home. As a guest at Serenity Now you are...

This third floor gorgeous condominium, within the Captain's Walk community, has direct oceanfront vistas that will not disappoint.The kitchen to the left as you enter, comes entirely-supplied to meet all of your needs during your calming stay...

Island Club 4206Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Hilton Head, SC, this appealing condo offers a plethora of amenities...

*VILLAMARE PAINTING PROJECT TENTATIVELY SCHEDULED FOR SEPT 15, 2025 TO MARCH 30, 2026. Work will include stucco repair, balcony and ceiling enhancements, roof repairs, and painting. Guests can expect to see scaffolding in front of living room...

Treat your family to this handsomely refreshed home with four bedroom and three and half bathrooms! The kitchen will come entirely-equipped and features numerous updates like granite countertops and stainless steel appliances. A huge island makes...

Springwood Villas 51Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Updated with new paint, new fixtures, and new furnishings, this serene and very inviting...

Island Club 3105Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Walk to the beach, relax in the pool and hot tub, or play some tennis with your friends at...

Totally modernized in the fall of 2022, 7 Ocean Breeze will quickly become your new favorite Hilton Head vacation home. This end-unit is positioned at the front of the community, making it both private and an painless walk to the beach!As you enter...