Monthly Stays

Long-term stays with Island Time offer the perfect blend of comfort, convenience, and a home away from home, allowing guests to immerse themselves in the local culture and truly unwind. Enjoy lower rates for stays of 28 days or more and even tax exemption for 90 days or more.

83 properties available

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

This fully updated, high-quality villa exudes luxury and is just waiting for you to enjoy it. Featuring 2 bedrooms and 2.5 bathrooms, the spacious villa has plenty of room for the whole family to stretch out with over 1800 square feet of livable space. Walking into the villa, you are greeted with an abundance of natural light that floods the open f

Welcome to 669 Queens Grant! This picture-perfect 3-bedroom villa includes smooth ceilings, extensive stone flooring, updated kitchen and baths, stone tops, and just painted interiors. Featuring lagoon and poolside views, this villa is the perfect place to unwind. Bring the family out for a grillout on the large elevated composite deck. As you ent

This wonderfully comfortable 5th Row Ocean home is located in an ideal spot in Sea Pines. Close to the beach, about equal distance from South Beach and the Sea Pines Beach Club, and not much further up to Harbour Town. Once you take the steps to the front door, the living space is all on one floor, making this a perfect Hilton Head vacation rental

This beautiful home is only steps away from the beach! Simply a lovely second-row home that invites you to come inside and enjoy. After a walk on the beach only steps from the home, relax by the pool, enjoy lunch and a nap on the deck, or sit by the fire pit on a winter evening. Located on the first floor is one of the two living rooms. The first

Villamare will have a full pool and deck renovation, including the addition of a new adult-only serenity pool and hot tub, beginning September 15, 2023, with an expected completion date of April 30, 2024. The main pool will remain open until October 15th; however, there will be minor work on the deck during this time. The indoor pool and hot tub wi

Oceanfront

Please be advised that the Dune House Project is set to be updated between December 2023 and January 2024 and last up to 90 days. Dune House Lane and the parking lot will be reconfigured and repaved during this project to improve pedestrian safety and allow for a better flow of traffic. Moorings guests will have access to their respective parking a

Welcome to 7 Guscio Way! This oceanfront home offers unforgettable views and a private pool and spa. This home features a game room and an open great room. The open floor plan is a must and is perfect for entertaining. The gourmet kitchen features updated appliances and is perfect for gathering together. Upon entry, you walk into the home\'s livi

Oceanfront

Welcome to 2 Royal Tern! This charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably. The first floor features a very open floor plan that offers easy access between the multiple living spaces, kitchen and wet bar, and dining room. Guests can enjoy pl

2211 SeaCrest has new LVT floors with walk-in showers, a garden tub, double vanities, and more! This is a wonderful 2-bedroom, 2-bathroom villa located on the second floor of Building 2. Walk-in to the open-concept living space, perfect to spread out and relax after a long day at the beach and pool. The living room has new furniture and a brand ne

Oceanfront

Welcome to 7 Rum Row! This Palmetto Dunes home highlights coastal elegance with plenty of room for the whole family to spread out while all being together. The living room, dining area, and kitchen all make up the main great room, and the extremely open floor plan makes it easy for everyone to be together without feeling crowded! The living room i

401 Windsor Place is a beautifully appointed villa in Palmetto Dunes with ocean views! Start your vacation memories today! As you walk through the front door to be greeted with the ocean view, the light shines across the open-plan layout. An attractive living room provides a queen-sized sleeper sofa for additional guests and two swivel chairs. Amp

Oceanfront