Best Vacation Homes in Wailea
New
Condo
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
1749 ft²
Oceanfront
Hot Tub
Parking
Pool
R58,936/Night
7 Nights - R412,559
Resort
10.0(5 Reviews)
1 Bath
24 Guests
3196.88 ft²
Private Beach- Oceanfront
- Hot Tub
Breakfast
R49,533/Night
7 Nights - R346,739
Condo
10.0(8 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Parking
- Pool
Ocean View
R18,925/Night
7 Nights - R132,477
Condo
10.0(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1259 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R14,031/Night
7 Nights - R98,211
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
3 Guests
796.53 ft²
- Pool
Internet
Child Friendly
Security/Safety
R9,391/Night
7 Nights - R65,737
New
Condo
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1564 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R22,779/Night
7 Nights - R159,459
New
Condo
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1363 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R17,032/Night
7 Nights - R119,225
Condo
10.0(1 Review)
1 Bedroom
2 Baths
6 Guests
Air Conditioner- Internet
- Child Friendly
Laundry
R6,525/Night
7 Nights - R45,677
Wailea Luxury Rentals
Apartment
3 Bedrooms
3 Baths
6 Guests
- Parking
- Pool
Balcony/Terrace
Kitchen
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Condo
8.0(1 Review)
1 Bedroom
1 Bath
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R155,733/Night
7 Nights - R1,090,138
Condo
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R151,247/Night
7 Nights - R1,058,733
Apartment
6 Bedrooms
6 Baths
12 Guests
4133.34 ft²
Spa- Balcony/Terrace
View- Air Conditioner
R118,165/Night
7 Nights - R827,156
Apartment
1.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1237.85 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R101,779/Night
7 Nights - R712,454
Condo
6 Bedrooms
6 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
R90,092/Night
7 Nights - R630,652
House
10.0(7 Reviews)
4 Bedrooms
5 Baths
8 Guests
4400 ft²
Private Pool- Oceanfront
- Hot Tub
- Parking
R87,715/Night
7 Nights - R613,996
New
House
4 Bedrooms
4 Baths
8 Guests
3417 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
R79,238/Night
7 Nights - R554,655
Wailea Pet Friendly Vacation Rentals
Condo
10.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R23,846/Night
7 Nights - R166,924
House
9.2(7 Reviews)
1 Bedroom
2 Baths
4 Guests
1022.57 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
R8,610/Night
7 Nights - R60,262
Condo
10.0(60 Reviews)
1 Bedroom
2 Baths
4 Guests
898 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R5,469/Night
7 Nights - R38,278
Resort
9.0(141 Reviews)
30 Baths
139 Guests
1073.16 ft²
- Oceanfront
- Hot Tub
- Breakfast
EV Charge Station
R25,217/Night
7 Nights - R176,510
Condo
5.0(4 Reviews)
3 Bedrooms
4 Baths
2718 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
R73,991/Night
7 Nights - R517,939
Condo
3 Bedrooms
2 Baths
5 Guests
1056 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R22,682/Night
7 Nights - R158,769
House
10.0(1 Review)
6 Bedrooms
6 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
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Condo
1 Bedroom
1 Bath
3 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
R12,114/Night
7 Nights - R84,794
Wailea Large Vacation Homes
Villa
10.0(135 Reviews)
1 Bedroom
2 Baths
2 Guests
906 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R7,065/Night
7 Nights - R49,459
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1905.21 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R22,566/Night
7 Nights - R157,963
Villa
10.0(100 Reviews)
1 Bedroom
2 Baths
4 Guests
908 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R7,899/Night
7 Nights - R55,296
Villa
10.0(1 Review)
3 Bedrooms
4 Baths
6 Guests
2615.63 ft²
- Hot Tub
- Parking
- Pool
- View
R29,558/Night
7 Nights - R206,896
Villa
10.0(66 Reviews)
2 Bedrooms
2 Baths
7 Guests
2000 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R19,845/Night
7 Nights - R138,906
Villa
10.0(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
1900 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R24,344/Night
7 Nights - R170,410
Villa
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1268 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R20,843/Night
7 Nights - R145,894
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
1978 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R21,767/Night
7 Nights - R152,373
Why Choose Rent By Owner for your Wailea 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 Wailea
When should you plan your Vacation Rentals stay?
Choosing the right time to visit ensures you enjoy the best weather and local experiences in this popular Hawaiian destination, making your stay here truly memorable.
Peak Season Highlights
December to March
During the winter months, you'll find this destination bustling with visitors seeking warm weather and exceptional beaches, making it an ideal time to explore the region's outdoor activities.
Average Temperature Daytime: 78°F - Nighttime: 65°F
June to August
Summer brings high demand due to vacationers enjoying the sunnier days and lively atmosphere, perfect for making the most of your stay here.
Average Temperature Daytime: 85°F - Nighttime: 72°F
Off-Season Highlights
April to May
The shoulder season offers a quieter experience with fewer crowds, allowing you to relax and enjoy the natural beauty of the area at a comfortable pace.
Average Temperature Daytime: 79°F - Nighttime: 66°F
September to November
Autumn provides a peaceful atmosphere with pleasant weather, making it a great time to find more affordable vacation rentals without sacrificing the warm island climate.
Average Temperature Daytime: 81°F - Nighttime: 68°F
Weekly Weather Forecast for Wailea
How to Book Your Wailea 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 Wailea
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
- Access to lush outdoor pools where you can relax and unwind under the sun.
- Private or shared barbecue grills perfect for enjoying local flavors outdoors.
- Well-maintained outdoor patios or lanais with scenic views of the surrounding area.
- Waterfront access or nearby beaches ideal for swimming, snorkeling, or sunbathing.
- Beautifully landscaped gardens and walking paths to explore the natural beauty of the region.
- Outdoor showers for rinsing off after a day at the beach or poolside.
- Community fitness areas or sports courts to stay active during your stay here.
Top Attractions Around Wailea
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of outdoor activities such as relaxing on beautiful beaches, exploring scenic hiking trails, and engaging in water sports like snorkeling and paddleboarding, all conveniently accessible from your vacation rental here.
Family Activities
- Snorkeling at Molokini Crater: Experience the vibrant marine life and clear waters just offshore, a must-do activity for families enjoying the natural beauty here.
- Exploring Kealia Pond National Wildlife Refuge: Discover a sanctuary for birdwatching and wildlife observation that offers educational and fun outdoor adventures for all ages.
- Family beach days at Wailea Beach: Relax and play on the soft sands and calm waters ideal for children, making it a perfect spot for memorable family picnics and sunbathing.
- Visiting the Maui Ocean Center: Engage with Hawaii’s marine ecosystems through interactive exhibits and aquariums that fascinate both kids and adults alike in this region.
Adult Activities
- Golfing at Wailea Emerald Course: Enjoy a round of world-class golf on this scenic course, renowned for its stunning ocean views and challenging layout.
- Spa and Wellness Treatments: Indulge in luxurious spa services available nearby, offering relaxation and rejuvenation amid the tranquil surroundings of this coastal region.
- Sunset Cruises: Experience breathtaking sunsets aboard a local cruise, providing a perfect way to unwind while taking in the stunning maritime scenery.
- Fine Dining Experiences: Savor exquisite cuisine at premier restaurants in the area, where fresh local ingredients enhance your culinary journey here.
Other Places to Stay in Wailea, HI
Keawakapu Beach
Mokapu Beach
Ulua Beach
Ulua Beach Park
Wailea Shopping Village Shopping Center
Shops at Wailea
Wailea Beach
South Maui
Polo Beach
Wailea Blue Golf Course
Palauea Beach
Makena
Wailea Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Beaches: Take advantage of the pristine beaches nearby to relax, swim, or enjoy water sports, making your stay truly memorable.
- Dine at Nearby Restaurants: Savor authentic regional flavors by dining at local eateries within walking distance or a short drive from your vacation rentals.
- Visit Cultural Sites: Immerse yourself in the area's rich heritage by exploring cultural attractions and events that showcase the region's unique history.
- Plan Outdoor Activities: Engage in outdoor adventures like snorkeling, golfing, or hiking to fully experience the natural beauty surrounding your accommodation.
Transportation Options
- Rental Car Services: You can easily explore the area at your own pace by renting a vehicle, with numerous rental agencies conveniently located nearby providing reliable transportation options.
- Public Transit: The local bus system offers affordable and accessible transportation throughout the region, making it simple to visit popular beaches and attractions without a car.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing apps like Uber and Lyft provide convenient, on-demand transportation for quick trips around the destination's scenic spots and amenities.
- Bicycle Rentals: For a more active way to experience the region, bicycle rentals are available, allowing you to enjoy the beautiful coastal scenery at a leisurely pace.
Local Customs Options
- Hula Dancing: Participating in or observing traditional hula performances is a heartfelt way to connect with the cultural heritage of this region.
- Respect for the Land and Sea: Showing reverence by practicing environmentally conscious behaviors reflects the deep aloha spirit that is central here.
- Local Greetings and Etiquette: Using friendly greetings like "Aloha" and demonstrating Hawaiian hospitality helps you honor local customs during your stay.
- Respect for Sacred Sites: Being mindful of and avoiding disturbances at spiritual locations shows respect for the area's cultural significance.
Frequently Asked Questions About Wailea?
1. What are the top vacation 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 Vacation Rentals in Wailea:
- Romantic, Luxury, Sensual Retreat - Couples Only
- Hawaiian Cottage and Personal Paradise/BBKM 2013/0004
- 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
- Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!
- Owner Direct - Check our 160 Reviews! - Elua Village 701, Luxury 2BR, Ocean View
- LOWEST Rates in Wailea right now! Spacious 5-STAR Wailea Retreat🏝Corner unit
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- NEW KITCHEN REMODEL! Amazing View!
- Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
2. How many vacation rentals have private pools in Wailea?
There are 71 vacation rentals with private pools near Wailea. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Wailea are best for families?
If you are looking for a family-friendly vacation home in Wailea, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wailea:
4. How many Rentbyowner vacation rentals are available in Wailea?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1827 in the Wailea 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 Wailea.
5. What is the cancellation policy for vacation rentals in Wailea, Kihei, Hawaii?
Cancellation policies vary by listing, so it's important to review the specific property's terms. Typically, you'll find details about refunds and deadlines on the listing page or by contacting the property owner directly.
6. How do I confirm the availability of a vacation rental in Wailea, Kihei, Hawaii?
Availability can be checked in real-time on the listing page. If you have specific dates in mind, it’s advisable to contact the owner to confirm availability and discuss any flexibility.
7. Are there any additional fees associated with booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes will be detailed in the listing. For precise information, review the detailed booking summary or reach out to the owner before confirming your reservation.
8. What amenities are typically included in vacation rentals in this destination?
Most properties include essentials like Wi-Fi, parking, and kitchen facilities. To find out about specific amenities, check the listing details or contact the property owner directly.
9. Is there a minimum stay requirement for vacation rentals in this region?
Many rentals have minimum stay requirements that vary depending on the property and season. It's best to verify the minimum stay length directly on the listing or by consulting the owner.
Wailea Top Rated Vacation Rentals
Condo
10.0(207 Reviews)
1 Bedroom
2 Baths
2 Guests
1012 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R9,670/Night
7 Nights - R67,694
Cottage
10.0(206 Reviews)
2 Bedrooms
2 Baths
4 Guests
700 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
R18,713/Night
7 Nights - R130,997
House
10.0(185 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
R12,238/Night
7 Nights - R85,665
Condo
10.0(182 Reviews)
3 Bedrooms
3 Baths
8 Guests
2500 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R25,787/Night
7 Nights - R180,506
Condo
10.0(165 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R7,995/Night
7 Nights - R55,970
Condo
10.0(164 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R20,081/Night
7 Nights - R140,567
Condo
10.0(162 Reviews)
1 Bedroom
2 Baths
4 Guests
908 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
R10,443/Night
7 Nights - R73,103
House
10.0(158 Reviews)
3 Bedrooms
3 Baths
8 Guests
2757 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
R20,746/Night
7 Nights - R145,220
