
South Shore long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Bookabach takes the hassle out of booking monthly rentals in South Shore. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Bookabach. Many long-term rentals in South Shore are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - South Shore
Showing deals for:28 Sept - 26 Oct
Image gallery for Wailua Hideaway - One Bedroom Stream-Side Apartment

Wailua Hideaway - One Bedroom Stream-Side Apartment
Kapaa
Image gallery for Poipu 3 Bd/4BA~ Pool~on Golf Course~Mt/Ocean View~Beach

Poipu 3 Bd/4BA~ Pool~on Golf Course~Mt/Ocean View~Beach
Koloa
Image gallery for 5 Star, Great for Families, 4BD w/AC, HTD Pool, Poipu Beach Athletic Club access

5 Star, Great for Families, 4BD w/AC, HTD Pool, Poipu Beach Athletic Club access
Koloa
Image gallery for ALOHA - ALOHA AUTHENTIC CONDO- C29, Comfy & Welcoming.

ALOHA - ALOHA AUTHENTIC CONDO- C29, Comfy & Welcoming.
Lihue
Image gallery for Luxury Hawaiian Modern Villa • Ocean Views • Huge Heated Pool • 3 Primary Suites

Luxury Hawaiian Modern Villa • Ocean Views • Huge Heated Pool • 3 Primary Suites
Koloa
Image gallery for AMAZING location steps from the beach - Ohia Lehua Suite - AC, & PBAC included!

AMAZING location steps from the beach - Ohia Lehua Suite - AC, & PBAC included!
Koloa
Image gallery for NEWLY Updated Kiahuna 1BR - AC + Pool

NEWLY Updated Kiahuna 1BR - AC + Pool
Koloa
Image gallery for Love Nest - Luxury Studio in tropical gardens with koi ponds, waterfalls

Love Nest - Luxury Studio in tropical gardens with koi ponds, waterfalls
Koloa
Image gallery for WOW-2BR@Beach Hear Waves-Value Best Location -Sept special 40 off a night SALE

WOW-2BR@Beach Hear Waves-Value Best Location -Sept special 40 off a night SALE
Lihue
Image gallery for Oceanview Kalapaki Beach Healthy / Non-toxic 2-bedroom condo with WiFi, AC

Oceanview Kalapaki Beach Healthy / Non-toxic 2-bedroom condo with WiFi, AC
Lihue
Image gallery for Amazing 3-bedroom house with AC in Bayview @ Poipu Kai - Ocean View

Amazing 3-bedroom house with AC in Bayview @ Poipu Kai - Ocean View
Koloa
Image gallery for PRIVATE HOME: 5 Min Walk to Beach, Pool & Tennis Courts

PRIVATE HOME: 5 Min Walk to Beach, Pool & Tennis Courts
Koloa
Image gallery for Poipu Pili Mai 4 Bedroom Condo with Ocean Views, Pool & Golf Course Access

Poipu Pili Mai 4 Bedroom Condo with Ocean Views, Pool & Golf Course Access
Koloa
Image gallery for Amazing Views in this 2 Bedrooms/2.5 Baths Condo

Amazing Views in this 2 Bedrooms/2.5 Baths Condo
Koloa
Image gallery for Updated ocean view retreat near Poipu Beach; A/C, pool, gym and restaurants.

Updated ocean view retreat near Poipu Beach; A/C, pool, gym and restaurants.
Koloa
Image gallery for Newly Upgraded 3 Bedroom Suite with AC, Pool, & Gym in Sunny Poipu!

Newly Upgraded 3 Bedroom Suite with AC, Pool, & Gym in Sunny Poipu!
Koloa
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in South Shore
You’ll often find discounted rates for long stays of over 28 days on Bookabach, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Bookabach, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
South Shore Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Bookabach with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in South Shore come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in South Shore
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Bookabach offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in South Shore with pool
Bookabach's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in South Shore
Plans change. We get that. With Bookabach, you can search, select 'free cancellation,' and see all rentals in South Shore with flexible cancellation policies.