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 115 properties available
Welcome to 253 Captain\'s Quarters, where amazing sunrises greet you in this contemporary one-bedroom villa. Coming this fall the kitchen will be renovated with new cabinets, counter tops and fixtures. The villa is designed to offer a perfect blend of modern amenities and a serene waterfront atmosphere. As you step inside, you\'re greeted by a sp
253 Captains Quarters
Villa -
$97.00 - $344.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 4.8 (7)
Looking for the perfect vacation retreat? You’ve come to the right spot! This home is completely renovated! The inside of the home has new floors, new light fixtures, a new stairway, a newly updated kitchen with stainless appliances, a new laundry room, and new bathrooms with updated tile and fixtures. It is bright and contemporary, with professi
57 North Sea Pines Icone Collection Icon
House -
$373.00 - $1,409.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 12 guests
Rating 5 (10)
This beautifully renovated 3-bedroom, 2.5-bath home has an open floor plan. The living room has ample room to relax and watch TV on the large flat screen; the dining area seats six people; and the kitchen has stainless steel appliances, granite counters, and everything you need. Attached to the great room, the Carolina room with a ping pong table i
26 Forest Drive
House -
$275.00 - $615.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 6 guests
Rating 5 (9)
This 3 bedroom, 3 bathroom, two story private condo is spacious and tastefully decorated. On the first floor there is a large living area with a 60" TV and entertainment center which looks out to a large sliding glass door and the private deck. The fully equipped kitchen including a Keurig coffee maker, has plenty of counter space and cabinets, and
52 Ocean Breeze
Villa -
$105.00 - $288.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (3)
435 Captain\'s Walk overlooks the pool out to the ocean! Lots of recent updates! 435 Captain’s Walk is a second-floor, 3-bedroom, 3-bathroom end unit that overlooks the pool and out to the ocean. A beautiful, updated villa with great views—you couldn\'t ask for more. The new owners have added great touches and updates to make this the perfect ocea
Oceanfront Oceanfront
Oceanfront
435 Captains Walk
Villa -
$218.00 - $858.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (16)
Take in the ocean views at this wonderful 1-bedroom villa. The open kitchen and living area are well-appointed to accommodate all your needs. The kitchen has been recently renovated. The dining table seats 2. The living room has a queen sleeper sofa. The primary bedroom has a queen-sized bed, and the bathroom has a walk-in shower. This villa off
212 Breakers
Villa -
$115.00 - $381.00 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Rating 5 (7)
Welcome to 101 Seacrest. This beautiful oceanfront property features three spacious bedrooms, providing ample space for a relaxing and enjoyable stay. A gorgeous foyer with a spiral staircase ascends to a massive open floor plan with open living, dining, and kitchen areas with high-end finishes and appliances. The living area is designed to be spa
Oceanfront Oceanfront
Oceanfront
101 Seacrest Icone Collection Icon
Villa -
$344.00 - $1,520.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half bath
Guests 8 guests
Rating 5 (9)
Welcome to the Salty Sixteen! This beautifully renovated 6-bedroom, 5.5-bath home has high-quality fixtures and unique southern features, including shiplap walls and coffered ceilings. Huge windows allow plenty of natural sunlight to shine through, creating a light and airy environment everyone will enjoy. The first-floor primary suite has a ki
16 East Garrison | Salty Sixteen Fairway Collection Icon
House - Pet Friendly
$384.00 - $1,319.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half Bathrooms 1 half bath
Guests 16 guests
Rating 4.9 (10)
Be Our Guest Beach Villa is proud to unveil a top-to-bottom remodel that makes it a showpiece of the Queens Grant Neighborhood. This end-unit villa offers an abundance of windows and sliding glass doors, allowing natural sunlight to flow in with views of the 11-mile lagoon system, a large stained wood deck, and a large, beautiful landscaped area n
672 Queens Grant
Villa - Pet Friendly
$165.00 - $516.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half bath
Guests 11 guests
Rating 5 (2)
Brand New Construction 3rd row home in Palmetto Dunes! 130 Mooring Buoy is a beautiful 5-bedroom, 4.5-bath luxury home nestled in the beautiful Palmetto Dunes Oceanfront Resort. Just three rows from the beach, this home is meticulously designed for your perfect vacation. With an open first-floor layout, the entire family can spread out without mi
Hot HOT 59
130 Mooring Buoy Icone Collection Icon
House -
$599.00 - $1,973.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half bath
Guests 14 guests
Rating 5 (8)
Welcome to Koi Cottage! This renovated oceanfront home features 3 bedrooms and 2 bathrooms to sleep up to 10 guests comfortably and is located in the quiet area of Folly Field, one of Hilton Head\'s finest beaches! Upon entry, you walk into the great room of the home- consisting of the kitchen, dining area, and living room, all newly updated! Many
22 Sand Dollar Road | Koi Cottage
House -
$289.00 - $1,137.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 5 (4)
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 - $804.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 4.9 (13)

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