Wailea Family Rental
1978 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $1,345/Night
For 7 Nights US $9,414
3196.88 ft²
24 Guests
57 Bedrooms
1 Bathroom
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
US $3,013/Night
For 7 Nights US $21,088
US $1,151/Night
For 7 Nights US $8,057
1186 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $1,171/Night
For 7 Nights US $8,200
796.53 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Internet
- Child Friendly
US $571/Night
For 7 Nights US $3,998
960 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Condo
- Pool
- Kitchen
- Parking
US $560/Night
For 7 Nights US $3,922
1571.53 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Spa
- Pool
US $2,601/Night
For 7 Nights US $18,205
1056 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $392/Night
For 7 Nights US $2,741
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Pool
US $370/Night
For 7 Nights US $2,591
1948.27 ft²
5 Guests
2 Bedrooms
3 Bathrooms
Apartment
- Oceanfront
- Pool
- Ocean View
US $618/Night
For 7 Nights US $4,326
700 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Private Pool
- Oceanfront
- Hot Tub
US $1,012/Night
For 7 Nights US $7,087
Why Choose Rent By Owner for your Wailea Family Rental?
What makes our Family Rental 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 Wailea
When should you plan your Family Rental stay?
Choosing the optimal time to visit this destination ensures you enjoy ideal weather and fewer crowds, making your stay in family rentals here a memorable and comfortable experience throughout the year.
Peak Season Highlights
Winter (December to February)
During this time, you can enjoy the ideal weather with warm days and pleasant evenings, making it perfect for family stays in Hawaii. Expect higher demand as visitors seek to escape colder climates in the area.
Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F
Summer (June to August)
The summer months bring lively activity and extended daylight hours, attracting families looking to experience the region’s outdoor activities and sunny weather. Book early to secure your ideal family rental during this busy period.
Average Temperature Daytime: 85°F to 89°F - Nighttime: 72°F to 77°F
Off-Season Highlights
Spring (March to May)
This season offers a quieter atmosphere with mild temperatures, making it an excellent choice for families seeking a relaxed getaway in the region. Accommodation options tend to be more available and affordable.
Average Temperature Daytime: 78°F to 83°F - Nighttime: 64°F to 68°F
Fall (September to November)
As the crowds thin out, you can enjoy the area's natural beauty and pleasant weather at a more leisurely pace. It's an ideal time to visit for those wanting to avoid peak-season prices and busier beaches.
Average Temperature Daytime: 81°F to 85°F - Nighttime: 70°F to 74°F
Weekly Weather Forecast for Wailea
How to Book Your Wailea Family Rental
What's our booking process?
Our platform allows you to browse a curated selection of family rental. 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 Wailea
Common Family Rental Amenities
What amenities can you expect?
Our Family Rental 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
- Enjoy access to sparkling community swimming pools perfect for family fun in the sun.
- Relax in beautifully landscaped outdoor lounge areas designed for socializing and unwinding.
- Take advantage of outdoor barbecue grills to cook a family meal with a view of the surrounding scenery.
- Stroll through lush gardens or tropical landscapes that showcase the region’s natural beauty.
- Benefit from well-maintained walking paths ideal for exploring the area’s scenic surroundings.
- Make use of private patios or balconies to enjoy outdoor dining or peaceful mornings.
- Access nearby beaches or outdoor water activities, allowing you to experience the region’s coastal charm firsthand.
Top Attractions Around Wailea
What attractions are nearby?
In this vibrant destination, you can enjoy a variety of activities nearby, including relaxing on pristine beaches, exploring scenic nature trails, and discovering local cultural sites, all easily accessible from your family rentals in Wailea, Kihei.
Family Activities
- Molokini Crater Snorkeling Tour Experience the vibrant marine life at this protected volcanic caldera, perfect for family snorkeling adventures in the region.
- Wailea Beach Relaxation Spend a day unwinding on the pristine sands of Wailea Beach, where shallow waters and gentle waves make it ideal for family fun.
- Ulua Beach Park Enjoy picnicking and sandy playtime at this popular park known for its calm waters and family-friendly atmosphere in the area.
- Makena State Park Beaches Explore the expansive beaches offering safe swimming and scenic views, making it an excellent spot for family outings here.
Adult Activities
- Spa and Wellness Treatments: Indulge in rejuvenating spa services that offer relaxation amidst the scenic beauty of this tropical destination.
- Golfing Experiences: Play on world-renowned golf courses that provide stunning ocean views and challenge your skills in a picturesque setting.
- Snorkeling Adventures: Explore vibrant marine life through snorkeling excursions along the coast, perfect for immersing yourself in the region’s aquatic biodiversity.
- Fine Dining: Savor exquisite cuisine at upscale restaurants that showcase local flavors and fresh island ingredients, ideal for memorable evenings out.
Other Places to Stay in Wailea, HI
South Maui
Keawakapu Beach
Mokapu Beach
Ulua Beach
Ulua Beach Park
Wailea Shopping Village Shopping Center
Shops at Wailea
Wailea Beach
Polo Beach
Wailea Blue Golf Course
Palauea Beach
Makena
Wailea Travel Tips
How Can You Make the Most of Your Stay?
- Arrive early for sunrise: To enjoy the serene beauty of this destination's beaches and scenic views, start your day with an early morning visit to witness breathtaking sunrises over the region.
- Explore local dining options: Savor authentic flavors by exploring family-friendly restaurants that highlight the region’s fresh seafood and tropical cuisine.
- Plan outdoor activities ahead: Secure reservations or permits for popular outdoor adventures to make the most of your time in the area’s natural attractions.
- Utilize local transportation: Take advantage of convenient transportation options to easily access nearby beaches, parks, and entertainment venues within the region.
Transportation Options
- Rental Car Services: Renting a car offers you the flexibility to explore the area at your own pace and easily access all the scenic spots and family-friendly attractions nearby.
- Shuttle Services: Convenient shuttle options operate throughout the region, providing direct transfers between major hotels, airports, and popular destinations, ideal for families seeking stress-free travel.
- Public Transit: Local buses serve the area with reliable routes connecting key neighborhoods and beaches, making it easy for you to navigate without needing a personal vehicle.
- Taxis and Ridesharing: Taxis and rideshare services such as Uber and Lyft are readily available here, offering quick and comfortable transportation around this tropical destination for families on the move.
Local Customs Options
- Respect for Aloha Spirit: Embracing the local value of Aloha is essential, as it fosters warmth, kindness, and genuine hospitality in every interaction during your stay.
- Traditional Hawaiian Blessings: Participating in or observing traditional ceremonies like Oli (chant) and Pule (prayer) can deepen your connection to the area's cultural heritage.
- Local Etiquette on Beaches: When visiting the beaches here, it’s customary to show respect by avoiding loud noises and refraining from removing natural items like sand or shells.
- Celebration of Native Practices: Community events often honor native Hawaiian customs, so engaging respectfully and with an open mind enhances your experience here.
Wailea Family Rental Frequently Asked Questions
1. What are the top Family Rentals in Wailea?
There are a lot of options in Wailea. If you plan on staying in the Wailea area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Family Rentals in Wailea:
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
- Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA
- Walk to Beach, Ocean Views, Relax by the Pool
- The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- Maui Breeze Retreat at Ho'olei! Available April 9-17, April 24-May 1 & May 8-20!
- Paradise is calling, views, pool, hot tub,
- Amazing view, Close to the beach, Wailea Ekahi Unit 20i
- 1br/1ba Condo Steps From The Pavilion pool, Mokapu Beach with beautiful views.
- Ocean View, Double Lanai and a Quick Walk to the Beach
2. How many Family Rentals are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 1774 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Family Rentals in Wailea.
3. What is the cancellation policy for booking a family rental in Wailea, Kihei, Hawaii?
The cancellation policy varies by property, so it's important to review the specific terms listed on the property page. You can find detailed information about cancellations and any potential fees there or contact the owner directly for clarification.
4. Are there any age restrictions or requirements when booking a family rental in this region?
Age restrictions depend on the individual property’s policies. Some rentals may require guests to be a certain age or have specific rules for families and groups. To ensure compatibility, please check the listing details or reach out to the property owner before booking.
5. What amenities are typically included in family rentals here?
Most family rentals in the area offer essential amenities such as fully equipped kitchens, Wi-Fi, laundry facilities, and outdoor spaces. To confirm the availability of specific amenities, review the property listing or contact the owner directly.
6. How do I know if my booking will be accepted in this popular destination?
Booking acceptance depends on the availability and the property's booking criteria. It’s advisable to complete your reservation promptly once the property is available and communicate with the owner if you have special requests or questions.
7. What should I do if I need assistance during my stay in the region?
For any support or issues during your stay, contact the property owner or local management team listed on the rental page. They are experienced in providing reliable assistance to ensure your visit remains comfortable and enjoyable.
More Rentals You May Like Near Wailea
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1182 ft²
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Villa
- Oceanfront
- Hot Tub
- Pool
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- Oceanfront
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2 Bathrooms
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- Ocean View
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