Monthly Stays

Come Live Like A Local On Hilton Head!

As a leading property management company, we recommend extending your stay on Hilton Head Island to a month or longer during the fall, winter, or spring seasons. Hilton Head offers a unique blend of tranquil beauty and a mild climate, making it an ideal retreat for those looking to escape the harsher weather found elsewhere.

Staying on Hilton Head Island for an extended period allows you to fully immerse yourself in the local culture and lifestyle. During the off-peak seasons, you'll experience less crowded beaches, more intimate encounters with wildlife, and the true laid-back essence of island life. Golf enthusiasts will find pristine courses with fewer players, providing a more leisurely and enjoyable game. Likewise, tennis & pickleball lovers can take advantage of the cooler temperatures and excellent facilities.

Our vacation rentals offer all the comforts of home, with the luxury of resort living. You can choose from a variety of properties, from oceanfront condos to secluded homes. Each rental is equipped with full kitchens, comfortable living spaces, and often private amenities like pools and hot tubs.

Book your extended stay on Hilton Head Island with us and discover a perfect blend of relaxation, recreation, and rejuvenation during the serene months of fall, winter, and spring. It's not just a getaway; it's a transformative experience. And remember, stays for 90 days or longer are tax exempt!


Properties Available 75 properties available
"Fairway Palms" is a low-country gem. It is in a lovely private setting in Sea Pines, in the coveted Harbour Town neighborhood. The home is uniquely situated on the 8th fairway of Harbour Town Golf Links, surrounded by two beautiful lagoons. Expansive views wrap around the property of this gorgeous, totally remodeled 3 bedroom, 3.5 bath home. Walk
Hot HOT 215
21 Heritage | Fairway Palms Fairway Collection Icon
House -
$376.00 - $2,149.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 10 guests
Rating 5 (6)
Welcome to 6 Grey Widgeon! This breath-taking 4th-row home is one of a kind and has everything you need and more for your next Hilton Head vacation. The great room is spacious and is sure to keep guests feeling right at home with its stylish but cozy furnishings! Soaring ceilings and huge windows allow plenty of natural sunlight to shine through
6 Grey Widgeon Icone Collection Icon
House -
$450.00 - $1,190.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 4.8 (8)
Elegance is understated in this Lowcountry home, truly one of a kind. The setting could not get more perfect. This fabulous home offers 4 bedrooms, 2 master suites, 2 queen bedrooms, and a bunk room. The home boasts multiple living areas on the inside, a gourmet kitchen, and a massive backyard that includes a private pool, covered outdoor living ro
51 Haul Away Fairway Collection Icon
House -
$475.00 - $1,019.00 / per night
Bedrooms 4 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 (10)
This oceanfront stunner was built in 2019 and offers amazing views as well as direct access to the beach with a private boardwalk. Walk into an amazing great room to unwind from a day out in the sun. The living room has two couches and two comfy chairs that lead out to the first balcony to soak in the picture-perfect view of the ocean. The kitche
Hot HOT 75
103 Dune Lane Icone Collection Icon
House - Pet Friendly
$1,355.00 - $2,988.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half Bathrooms 1 half bath
Guests 20 guests
Rating 5 (7)
Welcome to 1838 Beachside Tennis! This Sea Pines villa is outfitted with elegance in every detail, offering guests complete coastal luxury. An alluring yet spacious layout offers guests plenty of room to spread out, all while being together. Upon entry, to the left, you will find the fully stocked kitchen. This kitchen is updated with top-of-the-
Hot HOT 89
1838 Beachside Tennis Icone Collection Icon
Villa -
$179.00 - $553.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (13)
Welcome to 2 Tupelo Drive! This 4-bedroom, 4.5-bathroom home is in the heart of Sea Pines Plantation. This cozy home features multiple living spaces throughout the home, making it perfect for large groups of friends and families. Relax and unwind by the pool and newly renovated deck or on the covered outside patio that has great views of the 3rd ho
2 Tupelo Drive Fairway Collection Icon
House -
$229.00 - $609.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 5 (8)
This spacious home embodies beach-centric vibes with its open layout and tastefully decorated interior! Soaring ceilings and lots of windows provide the great room with plenty of natural sunlight. In the living room, you will find plenty of plush seating around the brick fireplace (not for guest use), a flat-screen TV, and an array of board games t
31 Sand Dollar Road
House - Pet Friendly
$190.00 - $522.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 4.8 (5)
Welcome to The Sandbox! Newly renovated and outlined with elegance in every detail, this 3-story oceanfront home is truly perfect for your next Hilton Head Island family getaway. This home has an extremely open floor plan that allows an easy flow between the living room, kitchen, and dining area. The living room is well-appointed and spacious, an
Hot HOT 57
9 Guscio Way Icone Collection Icon
House -
$989.00 - $2,425.00 / per night
Bedrooms 8 bedrooms
Bathrooms 8 baths
Guests 20 guests
Rating 5 (9)
Welcome to Fairway Breeze! A beautifully renovated four-bedroom, three-bath golf course home in the gated oceanfront resort of Palmetto Dunes. Upon entry, be invited into the living room with a view of the pristine fairway of the George Fazio Golf Course. Separating the living room and dining room is a double-sided fireplace. Get a little work do
7 Ginger Beer | Fairway Breeze Fairway Collection Icon
House - Pet Friendly
$267.00 - $547.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 4.9 (12)
Welcome to 11 Junket! This oceanfront home is newly updated and offers direct access to the beach as well as an expansive outdoor entertainment area that is sure to be your favorite spot for summer days! Upon entry, you walk into the home\'s sitting room, which has a dining table for 4 and comfortable seating that is perfect to unwind on over your
Hot HOT 61
11 Junket Icone Collection Icon
House -
$999.00 - $2,701.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half Bathrooms 2 half baths
Guests 18 guests
Rating 4.8 (8)
Direct Oceanfront 3 bedrooms Villa with gorgeous renovations This 3-bedroom, 3-bath villa offers a comfortable vacation for friends or family groups. Enjoy ocean views with access to your private balcony through the living room or master bedroom. The living room is furnished with enough space to accommodate all your lazy beach bums after an exciti
Oceanfront Oceanfront
Oceanfront
404 Barrington Arms
Villa -
$265.00 - $602.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 (22)
Welcome to 26 Bradley Circle! Views, views, and more views! What better way to start your day than listening to the surf, enjoying the beautiful marsh with active wildlife, and the ocean just beyond while sipping your coffee on the deck? Gorgeous beach just a 1-minute walk away with secluded access! 26 Bradley is the perfect location on Hilton He
26 Bradley Circle
House - Pet Friendly
$333.00 - $942.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 (5)

Tell us what you're looking for and someone will contact you with available options.

I agree