Wailea Cabin Rentals
1978 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $1,370/Night
For 7 Nights US $9,590
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
958 ft²
5 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
US $445/Night
For 7 Nights US $3,113
1948.27 ft²
5 Guests
2 Bedrooms
3 Bathrooms
Apartment
- Oceanfront
- Pool
- Ocean View
US $618/Night
For 7 Nights US $4,326
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
Why Choose Rent By Owner for your Wailea Cabin Rentals?
What makes our Cabin 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 Wailea
When should you plan your Cabin Rentals stay?
Choosing the optimal time to visit here ensures you enjoy the region's beautiful weather and vibrant atmosphere, making your vacation in Wailea, Kihei, Hawaii, USA, a truly memorable experience while staying in one of the trustworthy cabins available for booking.
Peak Season Highlights
Winter (December to February)
During the winter months, this area experiences its peak season with ideal weather conditions that attract visitors seeking warm climates and outdoor activities.
Average Temperature Daytime: 75°F - Nighttime: 65°F
Summer (June to August)
Summer brings high travel demand due to school holidays and favorable weather, making it an optimal time for enjoying the region’s natural beauty.
Average Temperature Daytime: 85°F - Nighttime: 70°F
Off-Season Highlights
Spring (March to May)
The shoulder season offers fewer crowds and more affordable stays, while still providing pleasant temperatures perfect for exploring outdoors.
Average Temperature Daytime: 78°F - Nighttime: 66°F
Fall (September to November)
Autumn sees a slowdown in visitors, presenting an excellent opportunity to enjoy the tranquility of here with still comfortable weather conditions.
Average Temperature Daytime: 80°F - Nighttime: 64°F
Weekly Weather Forecast for Wailea
How to Book Your Wailea Cabin Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cabin 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 Wailea
Common Cabin Rentals Amenities
What amenities can you expect?
Our Cabin 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
- Enjoy access to beautifully maintained outdoor swimming pools with scenic views of the surrounding area.
- Relax in lush landscaped gardens that offer a tranquil environment for your outdoor leisure.
- Take advantage of spacious patios or lanai areas perfect for outdoor dining and entertaining.
- Make use of well-equipped BBQ grills for outdoor cooking amidst the tropical setting.
- Stroll through nearby walking trails that showcase the region’s natural beauty and coastal scenery.
- Unwind by outdoor fire pits, ideal for gathering with friends or family under the stars.
- Access to private or shared tennis courts to enjoy active outdoor recreation during your stay.
Top Attractions Around Wailea
What attractions are nearby?
In this beautiful region, you can enjoy a variety of outdoor activities such as snorkeling, whale watching, and exploring pristine beaches, all just minutes from your chosen cabins in Wailea, Kihei, Hawaii, where the warm climate and stunning scenery create the perfect backdrop for a memorable getaway.
Family Activities
- Snorkeling at Wailea Beach: Explore the vibrant marine life just offshore by snorkeling in the calm, clear waters of this popular beach.
- Visiting the Maui Ocean Center: Discover fascinating marine exhibits and interactive displays that offer an educational experience perfect for family outings.
- Enjoying a Luau Experience: Immerse your family in Hawaiian culture through traditional music, dance, and cuisine at a local luau event.
- Exploring Makena State Park: Spend quality time outdoors by relaxing on the pristine beaches or hiking along scenic coastal trails here in the region.
Adult Activities
- Sunset Sailing Tours: Experience an unforgettable sunset sail along the coast, offering breathtaking views of the Pacific and a chance to unwind in a serene setting.
- Snorkeling at Molokini Crater: Explore vibrant marine life and crystal-clear waters by takes a snorkeling trip to this renowned volcanic caldera just off the coast.
- Golfing at Wailea Golf Club: Play a round on world-class golf courses set amidst stunning ocean vistas, perfect for both beginners and seasoned players.
- Spa and Wellness Retreats: Indulge in luxurious spa treatments designed to rejuvenate your body and mind while enjoying the peaceful surroundings of the region.
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?
- Plan Your Activities Early: Take advantage of the region's beautiful weather by booking your outdoor excursions and attractions well in advance to ensure availability during your stay.
- Explore Local Dining Options: Savor authentic Hawaiian cuisine at nearby eateries or prepare meals in your cabin’s fully equipped kitchen for a relaxing, taste-filled experience.
- Make Use of the Beaches: Set aside time to enjoy the pristine beaches just steps from your accommodation, whether for sunbathing, swimming, or engaging in water sports unique to this area.
- Respect the Environment: Help preserve the natural beauty of this destination by practicing eco-friendly habits during your visit, ensuring it remains stunning for future travelers.
Transportation Options
- Rental Cars: Renting a car is a flexible way to explore the region at your own pace, offering easy access to local beaches and scenic spots from your cabins here.
- Public Transit: The area is serviced by reliable bus services that provide budget-friendly transportation options for sightseeing and daily errands during your stay.
- Taxi and Rideshare Services: Taxis and ride-hailing apps like Uber or Lyft offer convenient transportation for quick trips between your cabins and popular destinations in this destination.
- Bicycle Rentals: For eco-conscious travelers, bicycle rentals present an enjoyable way to traverse the region's picturesque streets and coastal pathways from your accommodations.
Local Customs Options
- Respect for Aloha Spirit: Embrace the local custom of showing genuine kindness and hospitality, which is deeply rooted in the area's welcoming atmosphere.
- Kapu Tradition: Be mindful of sacred sites and cultural practices by observing any posted signs or guidelines that honor traditional Hawaiian customs.
- Practicing Malama: Engage in the custom of caring for the land and environment, ensuring that your visit leaves a positive impact on this beautiful region.
- Celebrating Local Festivals: Participate in or observe traditional Hawaiian celebrations and events to gain a deeper appreciation of the area's rich cultural heritage.
Wailea Cabin Rentals Frequently Asked Questions
1. What are the top Cabins 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 Cabins 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
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
- Maui Breeze Retreat at Ho'olei! Available April 9-17, April 24-May 1 & May 8-20!
- Paradise is calling, views, pool, hot tub,
- Wailea Ekahi 40A - 5-Star South Maui Oasis
- ~ BOOK WITH WITH US AND WITH CONFIDENCE THOUGH 2031 ~
- BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!
2. How many Cabins are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 1867 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cabins in Wailea.
3. What is the cancellation policy for a cabin reservation in this region?
The cancellation policy varies depending on the specific listing you choose. It is recommended to review the property's cancellation terms carefully before booking, or contact the host directly for detailed information.
4. Are there any specific requirements or fees I should be aware of when booking a cabin here?
Additional fees such as cleaning or security deposits may apply, and certain requirements like age restrictions or minimum stay durations could be in place. Be sure to read the listing details thoroughly or reach out to the owner for clarification.
5. How do I find the best available dates and rates for cabins in this destination?
Utilize the search filters to specify your preferred travel dates and budget. Prices and availability are updated regularly, so checking frequently or contacting hosts directly can help you secure the best deal.
6. Is it possible to make special requests or customize my stay at a cabin in this area?
Many owners are open to accommodating special requests such as early check-in or additional amenities. To ensure your needs can be met, contact the host prior to booking.
7. What amenities and features can I expect from cabins in this part of Hawaii?
Cabins here typically offer features suited for a comfortable stay, including modern appliances, outdoor spaces, and scenic views. For specific amenities, review each listing carefully or ask the property owner directly.
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