Wailea Oceanfront Vacation Rentals
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
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
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
1012 ft²
2 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $687/Night
For 7 Nights US $4,811
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
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $1,039/Night
For 7 Nights US $7,271
Why Choose Rent By Owner for your Wailea Oceanfront Vacation Rentals?
What makes our Oceanfront 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 Wailea
When should you plan your Oceanfront Vacation Rentals stay?
Choosing the ideal time to visit this destination can enhance your experience of the region’s stunning coastal views and ensure you enjoy the best oceanfront rentals available here, whether you're seeking vibrant seasons or quieter periods for a more relaxed getaway.
Peak Season Highlights
Winter (December to March)
During the winter months, you'll experience the peak season when visitors flock here for warm weather and scenic ocean views, making it an ideal time to enjoy your oceanfront rentals.
Average Temperature Daytime: 78°F - Nighttime: 65°F
Summer (June to August)
The summer months bring high demand as travelers seek the region's sunny beaches and vibrant atmosphere, perfect for booking oceanfront accommodations that offer breathtaking views.
Average Temperature Daytime: 85°F - Nighttime: 72°F
Off-Season Highlights
Spring (April to May)
In spring, the area sees fewer crowds, providing a more relaxed experience while you enjoy your oceanfront rental amid pleasant weather and blooming scenery.
Average Temperature Daytime: 77°F - Nighttime: 62°F
Fall (September to November)
Fall offers a quieter atmosphere, making it a great opportunity to explore the coastline while savouring the peaceful surroundings of your oceanfront rental.
Average Temperature Daytime: 81°F - Nighttime: 68°F
Weekly Weather Forecast for Wailea
How to Book Your Wailea Oceanfront Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of oceanfront 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 Wailea
Common Oceanfront Vacation Rentals Amenities
What amenities can you expect?
Our Oceanfront 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
- Enjoy access to private or community beachfront areas for sunbathing and swimming.
- Take advantage of outdoor grilling stations and picnic areas to dine al fresco with ocean views.
- Relax by the sparkling swimming pools that overlook the coastline, perfect for unwinding after a day of exploring.
- Discover well-maintained outdoor lounge spaces and patios ideal for enjoying breathtaking sunsets.
- Utilize outdoor showers and foot washes to refresh after beach trips along the region’s pristine shores.
- Preserve your active lifestyle with on-site tennis courts and fitness facilities set amidst scenic surroundings.
- Capitalize on direct beach access paths, allowing you to easily explore the stunning local shoreline and watersports opportunities.
Top Attractions Around Wailea
What attractions are nearby?
In this vibrant region, you can enjoy a variety of outdoor activities such as snorkeling, paddleboarding, and sunset cruises, all just minutes from your beachfront accommodation, allowing you to experience the true essence of Hawaii’s natural beauty and warm hospitality.
Family Activities
- Snorkeling at Molokini Crater: Experience the vibrant marine life just off the coast, offering families a memorable underwater adventure suitable for all ages.
- Relaxing on Wailea Beach: Spend the day soaking up the sun on this pristine stretch of sand, perfect for building sandcastles and enjoying gentle ocean waves.
- Whale Watching Tours: During the season, embark on a guided cruise to observe majestic whales breaching and spouting, creating unforgettable family memories.
- Visit the Shops at Wailea: Explore local boutiques and open-air markets, providing family-friendly shopping experiences amid scenic surroundings.
Adult Activities
- Spa Treatments and Wellness Centers: Indulge in luxurious spa experiences that utilize the region's natural elements, perfect for relaxation after exploring this tropical paradise.
- Golfing at Championship Courses: Enjoy a round of golf on world-class courses that offer stunning ocean views, making it a must-do activity in this scenic destination.
- Snorkeling and Sea Turtle Encounters: Discover vibrant marine life and graceful sea turtles just offshore, providing unforgettable snorkeling adventures in the area.
- Dining with Ocean Views: Savor exquisite meals at restaurants overlooking the ocean, where fresh local ingredients complement the spectacular scenery.
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 popular beaches and outdoor attractions by booking your activities in advance to secure the best times and options.
- Explore Local Dining Options: Savor authentic flavors at nearby restaurants or indulge in private dining experiences within your oceanfront rental for a true taste of the region.
- Utilize the Convenience of Oceanfront Rentals: Stay in a beachfront property to enjoy direct access to stunning views and easy access to the area's renowned beaches and outdoor pursuits.
- Respect the Environment: Preserve the natural beauty of this destination by practicing eco-friendly habits during your stay, ensuring the area remains pristine for future visitors.
Transportation Options
- Rental Car Services Renting a vehicle offers the flexibility to explore the scenic areas and beaches, making it an ideal transportation option in this region renowned for its stunning coastline.
- Taxi and Rideshare Services Convenient for quick trips and airport transfers, these services provide reliable transportation without the need for personal vehicle ownership.
- Public Transit The local bus system connects key destinations within the area, offering an affordable way to navigate around the region’s popular spots.
- Bicycle Rentals Biking is a popular eco-friendly choice, allowing you to enjoy the natural beauty of the surroundings at a leisurely pace.
Local Customs Options
- Respect for Aloha Ethics: In the region, embracing the spirit of Aloha means showing kindness, humility, and harmony in all interactions with locals and visitors alike.
- Traditional Hawaiian Blessings: Participating in or observing local ceremonies and blessings is a meaningful way to honor the native customs of this destination.
- Respect for Natural Resources: It is important to practice environmental stewardship by keeping beaches clean and avoiding damage to coral reefs and native flora.
- Proper Cultural Etiquette: When engaging with local traditions such as hula or lei exchanges, do so with genuine respect and appreciation for their cultural significance.
Wailea Oceanfront Vacation Rentals Frequently Asked Questions
1. What are the top Oceanfront 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 Oceanfront 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,
- Hula On In to Beach House Chic Style, Click the Video tour below!
- Maui Luxury with Island Serenity - Wailea Beach Villas Penthouse K107
- Amazing view, Close to the beach, Wailea Ekahi Unit 20i
2. How many Oceanfront Rentals are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 1464 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in Wailea.
3. What is the cancellation policy for oceanfront rentals in Wailea, Kihei?
Cancellation policies vary depending on the individual listing. It is recommended to review the specific property's cancellation terms listed on the booking page or contact the owner directly for detailed information.
4. Are there any additional fees associated with booking oceanfront accommodations in this area?
Additional fees such as cleaning fees, service charges, or taxes may apply. These details will be clearly outlined in the listing, and you should review them before completing your reservation.
5. How do I confirm the availability of an oceanfront rental in Kihei?
Availability is subject to change and is updated regularly. You can check real-time availability on the property’s listing page or reach out to the property owner for confirmation.
6. Can I make special requests for my oceanfront stay in Wailea, Kihei?
Special requests like late check-in, specific amenities, or unusual arrangements can often be accommodated. Contact the property owner directly through the listing to discuss your needs prior to booking.
7. What amenities are typically included with oceanfront rentals here?
Most listings include amenities such as Wi-Fi, fully equipped kitchens, parking, and access to outdoor spaces. For a complete list of features, refer to the specific property description or contact the owner directly.
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- Pool
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