Monthly Stays on Hilton Head Island

Escape from routine and get away from it all with Hilton Head long-term rental homes! Available to book for 28 days or more, Hilton Head monthly rentals let you experience all the island has to offer, from adventurous outdoor activities to relaxing afternoons on pristine stretches of sand. Extend your vacation to really live like a local when you choose one of these long-term vacation rentals set in the beauty of Hilton Head! Hilton Head Island offers convenience, comfort, fantastic monthly rates and tropical days filled with sunshine. Give yourself the gift of time away in the island setting known as one of the most relaxing destinations in the world.
When you come in the offseason, you get to enjoy less crowded roads, restaurants and beaches; as well as big discounts and the freshest seafood.  We have offseason rates from September through April, with special festivities and festivals happening each month. Some more of the benefits of visiting during the offseason:
  • Stay for 28 days or more and receive heavily discounted rates
  • Less crowded roads, restaurants, bike paths and beaches
  • Very pleasant temperatures and weather 
  • Start annual holiday traditions at the beach
  • Friends and family have a place to come and visit you
  • Festival season is in the spring and the fall
  • The freshest seafood in these months 
  • Big discounts at local restaurants, golf courses and tennis courts
  • Let your pup be a local too, stay at one of our pet friendly properties

Just 45 minutes from Hilton Head Island, the Savannah/Hilton Head International Airport offers 21 non-stop destinations, including Atlanta, Boston, Cincinnati, Charlotte, Chicago, Columbus, Dallas, Detroit, Houston, Indianapolis, Newark, New York, Maine, Philadelphia and Washington, DC.  
An extended stay allows you to take some memorable day trips!

Come live like a local and opt for our monthly rentals in Hilton Head/ You get your pick of one- to seven-bedroom rentals on or near the beach. These villas and homes are wonderfully unique, and they’re professionally managed so you know you’re in good hands. 

  • Charleston, SC:      1 hour, 45 minutes 
  • Savannah, GA:       1 hour
  • Beaufort, SC:          45 minutes
  • Bluffton, SC:           30 minutes
  • Amelia Island, FL:   2 hours, 30 minutes
September:  Bluffton Beer & Brats Festival
October:      Historic Arts & Seafood Festival
November:   Concours d'Elegance
December:   Old Town Christmas Parade
January:       HH Symphony Concert Series
February:     Annual Historic Gullah Celebration
March:         Wine & Food Festival
April:            RBC Heritage PGA Tour



Any time on Hilton Head is a pleasure, but monthly vacation rentals are the ultimate in relaxing getaways. Whether you book a holiday vacation to remember or a fall getaway to make the most of the area, you’ll love your time away in Hilton Head. There’s so much to enjoy on Hilton Head Island, from kayaking to yoga on the beach. When you’re staying here, take your pick of the following exciting activities:

  • Heritage and Gullah Tours
  • Kayaking
  • Dolphin Boat Tours
  • Zip Lining & Rope Courses
  • See a Show at the Arts Center of Coastal Carolina
  • Spa Retreats
  • Attend an Oyster and Shrimp Roast
  • Fishing and Boat Charters
  • Take a Tennis Lesson
  • Yoga on the Beach
  • Paddle Boarding
  • Set Sail on a Dinner Cruise
  • Visit the Coastal Discovery Museum
  • Hike Pinckney Island
  • Bike Ride Throughout the Island
  • Dine on Fresh Seafood
  • Play a Few Rounds of Golf
  • Take a Cooking Class
  • Explore the Beautiful Surrounding Lowcountry