Unwind and explore along beautiful Hilton Head Island. Book a long-term rental along the coast and revel in ocean views, world-class golf courses, fresh seafood, scenic walking trails, and 12 miles of shoreline. Hilton Head Island is well-known as a favorite summer playground, but the fun doesn’t end when the season does. Snowbirds, couples, and families flock to these stunning shores for a change of scenery with remote work and schooling. Gather together in a fully furnished monthly rental and let your adventure begin.
Save your spot by the beach in this spacious and stunning crowd-pleaser. Located on a scenic oceanfront just two miles from Coligny Beach Park, this family home boasts two wraparound decks, an elevator, a luxurious outdoor pool, and a private boardwalk to the beach. Between boogie boarding at the beach or lounging by the pool, there’s something the whole family is sure to love.
For families looking to keep a focus on the beach, Forest Beach has two communities located on three miles of shoreline, with oceanfront homes and villas, as well as nearby shopping.
If you’re looking for a little bit of everything, Harbour Town is home to the island’s most frequented marinas, as well as the Harbour Town Lighthouse, a covered pier, shopping centers, dining, and a playground.
Shipyard is great for those looking to stay active during their trip, offering jogging and biking trails, a health spa, and a “mix and match” style of golfing, spanning three courses and 27 holes.
Stay connected with a long-term condo rental at Folly Field, centrally located to shopping plazas, restaurants, and live music.
Sea Pines Resort’s iconic three championship golf courses promise a getaway chock-full of practice, with a 605-acre forest preserve, swimming pools, and tennis courts to savor in between.
Make it a winter to remember with a treehouse vacation rental. Located just a short distance from nearby beaches, rivers, and fishing areas, you’ll have no trouble getting out to adventure or relax along the waves. Book this dog-friendly stay and bring the whole family out for some quality time by the ocean, whether playing fetch in the waves or hitting the nature trails.
Hilton Head Resort combines leisure and luxury for an unbeatable vacation experience. Boasting championship golf courses, rejuvenating spa experiences, tennis courts, swimming pools, and private beach access, your coastal getaway will want for nothing.
This beachfront resort offers a long list of on-site amenities to jumpstart your getaway. From the five private beach access points to the three-tiered pool area, you’ll slip into vacation mode with style.
Tranquil and scenic, Spa on Port Royal Sound provides a quiet atmosphere ideal for a romantic retreat, enjoying coastal wildlife, walking the waterfront, and fishing.
Resting on 14 miles of pristine beachfront, pick up a friendly game of tennis on any of the ten lit tennis courts, tee off on the private golf courses, or play with the kids in the resort’s Olympic-sized pool.
These beautiful French Quarter-style Evian Villas are part of the Shipyard Plantation resort community, featuring spacious villas, amenities like a fishing lake and swimming pool, as well as easy access to nearby beaches, golf courses, and island activities.
Surrounded by lush golf courses and meandering waterways, guests love Queens Grant Villas for its secluded feel and privacy while remaining close to the beach.
Split your time between the swimming pool and the sugar-white sand beach. Fit with a hot tub, private balconies, and ocean views, this gated community is sure to make your beach vacation a breeze.
Your four-legged friends want a vacation too. Book a pet-friendly monthly rental and bring your dog along for twice as much fun by the beach.
Your private slice of paradise awaits. Feel right at home in this family-sized pet-friendly retreat. Spend the day exploring all that HHI has to offer, then return to your vacation rental for more fun, between dinners on the outdoor patio, quality time on the screened porch, a dip in the swimming pool, and drinks at the pool bar.
The beach is nice, but sometimes there’s no substitute for poolside lounging. Float, swim, or play your way with access to a pool on your extended stay vacation.
If easy living is the name of the game, this beachfront home is your ace in the hole. Spacious and beautifully designed, you can come together with family for big breakfasts in the fully-equipped kitchen or lounge around across the outdoor deck, pool, hot tub, or the beach just a few steps away. Treat your loved ones to a new favorite tradition with a long-term vacation rental on Hilton Head Island all winter long.
Can’t get enough time on the greens? Spend your beach trip or snowbird vacation putting away on expertly-groomed fairways waiting just beyond your front door.
Make it easy to enjoy fishing, water sports, or a simple day on the water. The open sea (and waterways) await at these fully furnished long-term rentals on Hilton Head Island.
Vacation to the fullest with the ocean just beyond your front door. Grab a monthly beach house rental and savor a quick commute to fishing, kayaking, and water activities.
In many cases, yes. If your reservation is eligible for a discount, you’ll see that reflected in the price when you book. Our long-term reservation sales specialists can also help answer any questions about discounts. Call (888) 257-7970) or email email@example.com.
You don't have to pay all at once. In fact, you’ve got a couple of different options to pay in installments. First, you can make monthly payments (over 3, 6, or 12 months) on most reservations through our partnership with Affirm. It’s easy, too—just select “Pay later with Affirm” when completing your vacation purchase.
If you book at least 45 days before your trip, your other option is to split your trip into just two payments. If the cost of your reservation is between $2,000 and $9,999, 50% is due at the time of booking. If the cost of your reservation is over $10,000, 25% is due at the time of booking. If you choose to make two payments, you must make your second payment 30 days before the start of your trip.
Vacasa offers snowbird rentals across South Carolina’s coast, Hilton Head Island included. Find the perfect vacation rental for your trip when you add the snowbird-friendly filter to your search.
Find hundreds of long-term, snowbird, and monthly rentals on Hilton Head Island by adding the snowbird-friendly filter to your search.
Hilton Head Island makes for a great winter escape, with plenty of activities for all ages. With its year-round mild temperatures, beach activities, fishing, and water sports are always in season. Through the fall and winter, Hilton Head also enjoys several seafood festivals and holiday events, like the Hilton Head Island Seafood Festival. The island is a popular retreat for golfers who prefer to play year-round, as well as families and couples looking to spend time outdoors.