2923+ South Shore Monthly Rentals on Hawaii.Villas
Extended Stay Rental Homes By Owners South Shore
About South Shore Monthly Stay on Hawaii.Villas
HawaiiVillas monthly rentals simplify the process of finding, comparing, and booking vacation homes and condos for extended stays in South Shore. Whether you're seeking a weekly vacation rental, hotel suite, villa, cottage, or furnished apartment for extended stays, HawaiiVillas monthly holiday rentals offer a variety of options to suit your style and budget.
South Shore is renowned for its popularity with monthly stays. Our listings include rentals equipped with full kitchenettes, dryers, air conditioning, heating, indoor or private swimming pools, gyms, and hot tubs. Whether you're searching for a luxury villa, condo, pet-friendly cottage for a weekly or monthly stay in South Shore, with family, working remotely, or enjoying an extended honeymoon, HawaiiVillas offers a wide selection of monthly furnished accommodations with top amenities.
HawaiiVillas caters well to executive travelers or those relocating for work or school. We connect you with property owners offering longer-term, yet flexible rentals. Our website simplifies filtering options for guests seeking the best accommodations for groups, families, or solo travelers needing stays longer than just a few nights.
Frequently Asked Questions About South Shore Monthly Stays
There are a lot of options in South Shore. If you plan on staying in the South Shore area, consider making a reservation for a few nights at one of these properties as these have been rated the top Monthly Stays in South Shore:
- Poipu Bay Getaway - Poipu House - Saltwater pool, hot tub, AC!, Walk to Beach and Hyatt!
- Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai
- Ocean View 3BR at Makahuena | Lanai, Pool, AC
- Nihi Kai #602 - Save 20% in Sept/Oct 2026!
- MOST STUNNING Oceanfront Views, A/c, Washer/Dryer, Kitchen, Elevator, Beach 0.5m
- Alihi Lani 3 Beautiful Ocean View & Prime Location
- Spacious 2BR Poipu Retreat w/AC, Lanais & Resort Amenities
- Kiahuna Plantation Unit 53, Stunning View, Near Beach; AC; Free Pool, Gym
- Plantation Style Studio & Courtyard Garden In Koloa
- Spacious affordable 2br/2ba/3lanai remodeled condo, perfect location in Poipu!
There are 2923 monthly stays available for rent in South Shore.

















