Best Vacation Homes in South Shore
1443 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
CA $986/Night
For 7 Nights CA $6,903
1334.72 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Spa
CA $1,971/Night
For 7 Nights CA $13,796
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Balcony/Terrace
- Kitchen
CA $643/Night
For 7 Nights CA $4,501
12 Guests
6 Bedrooms
6 Bathrooms
Group Friendly
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
CA $2,209/Night
For 7 Nights CA $15,462
1033.34 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- View
- Child Friendly
- Wellness Facilities
CA $569/Night
For 7 Nights CA $3,985
2641 ft²
12 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
CA $1,783/Night
For 7 Nights CA $12,478
6 Guests
2 Bedrooms
2 Bathrooms
Condo
- Internet
- Child Friendly
- Laundry
CA $1,539/Night
For 7 Nights CA $10,776
1360 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $1,491/Night
For 7 Nights CA $10,436
South Shore Luxury Rentals
1041 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
CA $13,502/Night
For 7 Nights CA $94,510
1041 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
CA $13,502/Night
For 7 Nights CA $94,510
1041 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
CA $13,359/Night
For 7 Nights CA $93,509
1041 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Spa
- Fireplace/Heating
CA $10,353/Night
For 7 Nights CA $72,470
1041 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Spa
- Fireplace/Heating
CA $10,353/Night
For 7 Nights CA $72,470
1041 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Spa
- Fireplace/Heating
CA $9,601/Night
For 7 Nights CA $67,205
6997 ft²
22 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $9,154/Night
For 7 Nights CA $64,078
1041 ft²
8 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
CA $8,804/Night
For 7 Nights CA $61,629
South Shore Pet Friendly Vacation Rentals
900 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Hot Tub
- Pool
- Ocean View
CA $1,219/Night
For 7 Nights CA $8,533
139.93 ft²
7 Guests
2 Bedrooms
2 Bathrooms
House
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $707/Night
For 7 Nights CA $4,950
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $917/Night
For 7 Nights CA $6,417
1442.36 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Pool
- Balcony/Terrace
CA $460/Night
For 7 Nights CA $3,220
4300 ft²
14 Guests
5 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $3,711/Night
For 7 Nights CA $25,977
3400 ft²
20 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $3,714/Night
For 7 Nights CA $26,001
3000 ft²
10 Guests
4 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $4,466/Night
For 7 Nights CA $31,261
1443 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
CA $766/Night
For 7 Nights CA $5,365
South Shore Large Vacation Homes
1800 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Pool
- Ocean View
CA $1,138/Night
For 7 Nights CA $7,968
2615.63 ft²
11 Guests
5 Bedrooms
3 Bathrooms
House
- Oceanfront
- Ocean View
- View
CA $1,979/Night
For 7 Nights CA $13,855
CA $2,452/Night
For 7 Nights CA $17,161
4000 ft²
10 Guests
1 Bedroom
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $5,233/Night
For 7 Nights CA $36,630
2109.73 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Pool
- View
- Parking
CA $1,728/Night
For 7 Nights CA $12,097
1041 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $1,219/Night
For 7 Nights CA $8,530
4000 ft²
16 Guests
1 Bedroom
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $5,688/Night
For 7 Nights CA $39,820
1500 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
CA $1,450/Night
For 7 Nights CA $10,149
Why Choose Rent By Owner for your South Shore Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit South Shore
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation in South Shore, Hawaii, ensures you make the most of your stay in this beautiful region, allowing you to enjoy ideal weather and local activities while benefiting from the seamless booking options available here.
Peak Season Highlights
Winter (December to February)
During the winter months, the area experiences its peak season when travelers flock here to enjoy warm weather and ideal beach conditions.
Average Temperature Daytime: around 78°F (26°C) - Nighttime: approximately 65°F (18°C)
Summer (June to August)
Summertime attracts visitors seeking sunny days and vibrant coastal activities, making it a bustling period for this destination.
Average Temperature Daytime: about 85°F (29°C) - Nighttime: roughly 72°F (22°C)
Off-Season Highlights
Spring (March to May)
In spring, you'll find fewer crowds, offering a more relaxed experience as the region transitions into its busy season.
Average Temperature Daytime: around 80°F (27°C) - Nighttime: approximately 65°F (18°C)
Fall (September to November)
Autumn brings quieter beaches and lower prices, perfect for those seeking tranquility away from peak travel times.
Average Temperature Daytime: about 82°F (28°C) - Nighttime: roughly 68°F (20°C)
Weekly Weather Forecast for South Shore
How to Book Your South Shore Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in South Shore
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- You can enjoy a private outdoor pool, perfect for relaxing under the sun after exploring the area.
- Many properties feature lush, landscaped gardens that provide a serene outdoor setting.
- Covered or open patios offer ideal spots for outdoor dining and entertaining with scenic views.
- Grill stations or barbecue areas are commonly available for al fresco cooking experiences.
- Some rentals include tennis courts or other sports facilities to stay active during your stay.
- Outdoor showers are often provided for convenient rinsing after beach visits or outdoor activities.
- Many homes have spacious decks or lanais, allowing you to soak in the warm sunshine and ocean breezes.
Top Attractions Around South Shore
What attractions are nearby?
From your accommodation in the area, you can explore a variety of outdoor activities such as surfing, snorkeling, and hiking, all conveniently located near your stay in South Shore, Hawaii.
Family Activities
- Hawaii Water Park Adventure: Discover a fun-filled day at the water park, where you can enjoy slides, wave pools, and lazy rivers suited for all ages in this popular family destination.
- South Shore Beach Days: Relax on the sandy shores with your loved ones, building sandcastles and swimming in calm, clear waters just minutes from your vacation rental.
- Family snorkeling excursions: Explore vibrant coral reefs and marine life together on guided snorkeling tours that showcase the region’s rich underwater scenery.
- Local cultural experiences: Engage in authentic Hawaiian activities, such as luau shows and craft workshops, designed to create memorable family moments while immersing in the area's rich heritage.
Adult Activities
- Snorkeling at Hanauma Bay: Discover vibrant marine life and clear waters right here in this popular snorkeling destination on the island's south coast.
- Visit the South Shore Market: Enjoy a unique shopping experience featuring local artisans, delicious eateries, and cultural boutiques in the heart of the region.
- Sunset at Magic Island Beach Park: Unwind with spectacular sunset views along the scenic coastline, a perfect spot for evening relaxation after exploring locally.
- Hiking at Diamond Head State Monument: Embark on an exhilarating hike to panoramic viewpoints that showcase the breathtaking beauty of the area’s volcanic crater.
Other Places to Stay in South Shore, HI
Kipu Kai
Lawai Beach
Keiki Cove Beach
Koloa History Center
Prince Kuhio Park
Anne Knudsen Park
Bayview
Kukuiula
South Shore Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Beaches: Make the most of your stay by visiting the pristine beaches in the area for swimming, sunbathing, or simply relaxing to enjoy the region's natural beauty.
- Plan Outdoor Activities: Take advantage of outdoor adventures such as snorkeling, surfing, or hiking to immerse yourself in the diverse landscapes of this destination.
- Sample Regional Cuisine: Indulge in authentic local dishes at nearby eateries and food markets to experience the true flavors of here.
- Visit Cultural Sites: Discover the rich history and traditions of the region by exploring cultural landmarks and engaging with community events during your stay.
Transportation Options
- Rental Cars: Renting a car provides the flexibility to explore this region at your own pace, with numerous local agencies conveniently located nearby.
- Public Transit: The area's public transportation system offers an affordable and eco-friendly way to navigate between popular spots and local attractions.
- Taxi Services: Taxis and ride-sharing services are readily available, offering a quick and comfortable option for short trips around here.
- Bicycle Rentals: Biking is an excellent choice for enjoying the scenic views of this destination while traveling in an environmentally conscious manner.
Local Customs Options
- Respect for Aloha Spirit: Embrace the local custom of welcoming others with kindness and genuine hospitality, a key part of experiencing this region's warmth during your stay.
- Hula Dancing Etiquette: When participating in or observing hula performances, follow cultural norms by showing respect to the dancers and understanding the significance behind the movements.
- Traditional Hawaiian Blessings: Be mindful of sacred ceremonies and blessings, which are often performed at community events and gatherings here, reflecting the area's deep cultural roots.
- Environmental Respect: Practice sustainability by avoiding littering and respecting natural landmarks, ensuring that the beauty of this destination remains pristine for future visitors.
Frequently Asked Questions About South Shore?
1. What are the top vacation rentals in South Shore?
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 Vacation Rentals in South Shore:
- Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park
- Poipu Bay Getaway - Poipu House - Saltwater pool, hot tub, AC!, Walk to Beach and Hyatt!
- Coco Cottage at Poipu Beach - 2BR/2BA, Luxury Home
- Poipu Beach Plantation Style Cottage
- Delightful Historic Cottage Steps from Poipu/Brennecke's Beaches A/C
- OCEANFRONT Ground Floor 2bd/2ba Unit with Amazing Ocean Views & A/C
- New Custom Hawaiian Cottage - Poipu Beach- Koloa, Hi
- A/C throughout spacious clean comfortable main floor condo with lush garden view
- Sunny Poipu Beach House Near Grand Hyatt, Views, AC, Guest Favorite
- Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai
2. How many vacation rentals have private pools in South Shore?
There are 301 vacation rentals with private pools near South Shore. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in South Shore are best for families?
If you are looking for a family-friendly vacation home in South Shore, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in South Shore:
4. How many Rentbyowner vacation rentals are available in South Shore?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 3090 in the South Shore area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in South Shore.
5. What is the cancellation policy for vacation rentals in the South Shore area?
Each listing has its own cancellation policy outlined in the details. We recommend reviewing the specific property's policy before booking or contacting the owner directly for clarification.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or security deposits may apply and are specified in the listing's fee section. Confirm these costs during the booking process or by reaching out to the property owner.
7. How do I ensure my stay complies with local regulations and property rules?
Property listings include specific house rules and local regulations that you should review before booking. Contact the owner if you have questions about compliance or any special requirements for your stay.
8. What amenities are typically included in vacation rentals in this region?
Most properties offer amenities like Wi-Fi, kitchens, and parking; however, available features vary. Check the detailed listing description to confirm the amenities included with your chosen property.
9. How far in advance should I book a vacation rental in this popular destination?
To secure your preferred accommodation, especially during peak seasons, it's advisable to book several months ahead. Availability can vary, so early planning helps ensure you find the perfect spot here.
South Shore Top Rated Vacation Rentals
1650 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $993/Night
For 7 Nights CA $6,948
12 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $3,115/Night
For 7 Nights CA $21,804
1030 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Pool
- Ocean View
CA $959/Night
For 7 Nights CA $6,712
1000 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Private Pool
- Oceanfront
- Pool
CA $514/Night
For 7 Nights CA $3,597
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $1,387/Night
For 7 Nights CA $9,711
1343 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
CA $900/Night
For 7 Nights CA $6,302
1900 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Hot Tub
CA $1,118/Night
For 7 Nights CA $7,823
1260 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
CA $668/Night
For 7 Nights CA $4,674
