Wailea Cottage Rentals
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
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Oceanfront
- Hot Tub
US $607/Night
For 7 Nights US $4,250
720 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Private Pool
- Oceanfront
- Pool
US $546/Night
For 7 Nights US $3,823
700 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Ocean View
- Balcony/Terrace
US $330/Night
For 7 Nights US $2,309
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Hot Tub
- Ocean View
- Balcony/Terrace
US $1,128/Night
For 7 Nights US $7,894
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $265/Night
For 7 Nights US $1,858
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
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Why Choose Rent By Owner for your Wailea Cottage Rentals?
What makes our Cottage 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 Cottage Rentals stay?
To make the most of your stay in this beautiful destination, consider planning your vacation during the off-peak seasons when the region's weather is still delightful and the area is less crowded, ensuring a more relaxing experience while exploring the many natural and cultural attractions nearby.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its peak tourist season as visitors seek warm-weather escapes and enjoy the region's ideal climate.
Average Temperature Daytime: around 78°F - Nighttime: about 65°F
Summer (June to August)
Summertime attracts many vacationers looking for sunny days and perfect conditions to relax by the beaches, making it another peak season in the area.
Average Temperature Daytime: approximately 85°F - Nighttime: roughly 72°F
Off-Season Highlights
Spring (March to May)
In spring, the area sees fewer visitors, offering a quieter atmosphere and excellent opportunities for affordable cottage stays while enjoying pleasant weather.
Average Temperature Daytime: around 77°F - Nighttime: near 62°F
Fall (September to November)
Autumn provides a more relaxed vibe with fewer crowds, ideal for those seeking an tranquil getaway and better value on cottages here.
Average Temperature Daytime: about 81°F - Nighttime: approximately 68°F
Weekly Weather Forecast for Wailea
How to Book Your Wailea Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage 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 Cottage Rentals Amenities
What amenities can you expect?
Our Cottage 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 outdoor swimming pools with stunning ocean views.
- Relax in beautifully maintained lush gardens and landscaped courtyards.
- Make the most of private or shared patios ideal for outdoor dining and lounging.
- Take advantage of barbecue grills for delightful cookouts under the Hawaiian sun.
- Stroll along walking paths that showcase the area's natural beauty and tropical flora.
- Utilize dedicated outdoor seating areas perfect for soaking up the warm island breeze.
- Participate in outdoor recreational activities like tennis or volleyball courts available on-site.
Top Attractions Around Wailea
What attractions are nearby?
In this vibrant region, you can indulge in a variety of activities such as exploring pristine beaches, enjoying water sports like snorkeling and paddleboarding, or discovering scenic hiking trails that showcase the area's natural beauty, all conveniently located near your chosen cottages for a memorable Hawaiian getaway.
Family Activities
- Snorkeling at Molokini Crater: Discover the vibrant marine life just off the coast, offering an unforgettable snorkeling experience for families in this tropical paradise.
- Beach Day at Wailea Beach: Relax and play on the pristine sands of Wailea Beach, perfect for building sandcastles and enjoying the calm, clear waters with your loved ones.
- Visit to The Shops at Wailea: Explore family-friendly shopping and dining options here, providing both entertainment and convenience during your stay in this region.
- Sunset at Makena Cove: Witness breathtaking sunsets over the ocean, creating a peaceful and scenic setting ideal for family photos and relaxation after a day of adventures.
Adult Activities
- Spa Treatments and Wellness Centers: Indulge in rejuvenating spa treatments that offer relaxation and luxury amidst the stunning scenery of Wailea.
- Golfing at Championship Courses: Play a round on world-class golf courses that provide breathtaking ocean views and challenging fairways here in this sought-after destination.
- Snorkeling Excursions: Discover vibrant marine life by embarking on snorkeling adventures along the coral reefs just off the coast, ideal for exploring the area's rich underwater ecosystem.
- Fine Dining Experiences: Savor exceptional cuisine at upscale restaurants that showcase local flavors and fresh ingredients, making every meal memorable during your stay.
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 area’s pleasant weather by booking outdoor activities and excursions well in advance to secure the best options during your stay.
- Explore Local Dining Options: While enjoying your cottage retreat, explore nearby restaurants and eateries that showcase authentic flavors of the region for a true taste of Hawaii.
- Make Use of the Beach Access: Stay close to the coast to maximize your time relaxing on the sandy beaches and experiencing the stunning ocean views right from your accommodation.
- Adapt to the Climate: Pack lightweight clothing and stay hydrated to comfortably enjoy the warm and tropical climate that defines this destination year-round.
Transportation Options
- Rental Car Services: Renting a vehicle allows you to explore the area at your own pace, offering convenience and flexibility when staying in this popular Hawaiian destination.
- Public Transportation: Local bus systems provide an affordable and eco-friendly way to get around here, connecting you to key attractions and neighboring communities with ease.
- Taxi and Rideshare Options: Taxis and rideshare services like Uber and Lyft are readily available, offering quick and reliable transportation for short trips or airport transfers in this region.
- Shuttle Services: Airport shuttles and private transportation providers offer convenient door-to-door service, making your arrival and departure stress-free in this island locale.
Local Customs Options
- Respect for the Aina: Showing reverence for the land is a fundamental aspect of local customs, encouraging visitors to leave no trace and honor the natural beauty of this destination.
- Ohana Spirit: Embracing the value of family and community, locals often greet visitors warmly and foster a welcoming atmosphere in the area.
- Kapu (Sacred) Practices: Understanding and respecting sacred sites and traditions ensures your visit aligns with the region's spiritual heritage.
- Traditional Luaus: Participating in or observing a luau offers insight into cultural festivities that highlight the area's rich history and customs.
Frequently Asked Questions About Wailea Rental Cottages
1. What are the top Cottages 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 Cottages in Wailea:
- Romantic, Luxury, Sensual Retreat - Couples Only
- Ekahi 34F - Best Panoramic Ocean View!
- 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
- Owner Direct - Check our 160 Reviews! - Elua Village 701, Luxury 2BR, Ocean View
- Walk to Beach, Ocean Views, Relax by the Pool
- Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!
- 🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
- nNEW KITCHEN REMODEL! Amazing View!
- The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
2. How many Cottages are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 6 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Wailea.
3. What is the cancellation policy for cottages in this destination?
The cancellation policies vary depending on the individual listing. You should review the specific terms listed on the property page or contact the owner directly to understand the cancellation and refund options available.
4. Are there any additional fees I should be aware of when booking a cottage here?
Additional fees such as cleaning charges, service fees, or local taxes may apply. Please check the detailed listing information or reach out to the property owner for clarity on any extra costs associated with your stay.
5. What amenities can I expect during my stay in this region's cottages?
The amenities offered are described in each listing and may include features like Wi-Fi, full kitchens, outdoor spaces, and parking. To ensure your needs are met, review the detailed amenities section on the property listing or contact the host directly.
6. How do I confirm the availability of a cottage in this area?
Availability is updated regularly on the booking platform. You can select your preferred dates and see real-time availability or contact the property owner for confirmation if needed.
7. Is it possible to get assistance if I encounter issues during my stay in this destination?
Support is available through the customer service team or directly through the property owner. For immediate assistance, refer to the contact information provided on the listing or the platform’s help resources.
More Rentals You May Like Near Wailea
1571.53 ft²
6 Guests
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Free Cancellation
Apartment
- Oceanfront
- Spa
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1250 ft²
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Ocean View
Condo
- Oceanfront
- Hot Tub
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US $954/Night
For 7 Nights US $6,679
1200 ft²
6 Guests
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2 Bathrooms
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Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $649/Night
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908 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $719/Night
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969 ft²
4 Guests
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US $522/Night
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