Wailea holiday rentals

We found 1,409 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Wailea by choosing from 50 houses, 26 apartments and other holiday rentals. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Wailea

Showing deals for:11 Dec - 18 Dec

Private kitchen
Outdoor dining
Pool
Dining
Exceptional
(40 reviews)

Beachfront Condo E 303/ Incredible views/ Pickleball/Great Snorkeling

Kihei

6% off
AU$14,272
for 7 nights, 1 apartment
AU$2,039 per night
includes taxes & fees
Beachfront Condo E 303/ Incredible views/ Pickleball/Great Snorkeling
Guest room with XL twins or king—great for couples, kids, or friends.
Relax in oceanfront luxury with beach views, sunsets, and breezy lanai mornings.
Your expansive indoor outdoor lanai has a beautiful Maui view
Wake up to island beauty with local art and tropical Maui-inspired style.
Exceptional
(93 reviews)

Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles

Kihei

6% off
AU$11,331
for 7 nights, 1 apartment
AU$1,619 per night
includes taxes & fees
Makena Surf • Bright and Airy Retreat • Steps to the Beach: Swim w/Turtles
Lobby
View on the pool
Lobby
Spacious lanai with enough seating for the whole family.
Exceptional
(257 reviews)

Mana Kai Maui Condo - Right on the Beach!

Kihei

7% off
AU$6,303
for 7 nights, 1 apartment
AU$900 per night
includes taxes & fees
Mana Kai Maui Condo - Right on the Beach!
Welcome to Maui Kamaole, a premier, low rise, South Kihei resort
Tropical upper pool at Maui Kamaole
Includes two full bathrooms, AC in the bedroom and living area, and ceiling fans
Enjoy views of the private courtyard or close the blackout drapes for a nap
Exceptional
(34 reviews)

Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)

Kihei

7% off
AU$3,912
for 7 nights, 1 apartment
AU$559 per night
includes taxes & fees
Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)
Interior
Outdoor dining
View from Keawakapu Beach
Private kitchen
Exceptional
(79 reviews)

Newly Renovated 6th floor Panoramic Beachfront Condo Fully Air Conditioned

Kihei

8% off
AU$7,403
for 7 nights, 1 apartment
AU$1,058 per night
includes taxes & fees
Newly Renovated 6th floor Panoramic Beachfront Condo Fully Air Conditioned
Entrance to Pool Area
Oasis Pool with waterfall, Cabana, Kitchen, additional BBQs and Restrooms
Barbeque Area in Gazebo and near pool area
Beautiful Kitchen
Exceptional
(177 reviews)

Maui Kamaole CONDO M102 TOTALLY RENOVATED

Kihei

7% off
AU$2,986
for 7 nights, 1 apartment
AU$427 per night
includes taxes & fees
Maui Kamaole CONDO M102 TOTALLY RENOVATED
Living room
Close to the swimming pool with Jacuzzi and BBQs
View of the 2nd hole
Miscellaneous
Wonderful
(101 reviews)

Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.

Kihei

7% off
AU$3,040
for 7 nights, 1 apartment
AU$434 per night
includes taxes & fees
Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
Living Room
Living Room
Dining Area
Pool
Exceptional
(169 reviews)

Wailea 1 BR Condo, close to everything, good pricing

Kihei

7% off
AU$3,273
for 7 nights, 1 apartment
AU$468 per night
includes taxes & fees
Wailea 1 BR Condo, close to everything, good pricing
Dining
Pool
Interior
Dining
Exceptional
(28 reviews)

Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Kihei

8% off
AU$16,787
for 7 nights, 1 apartment
AU$2,398 per night
includes taxes & fees
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
Living Room
Lower Swimming Pool
Living Room from Master Bedroom Railing
Entry Sign by Kihei Rd
Exceptional
(95 reviews)

D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.

Kihei

5% off
AU$4,932
for 7 nights, 1 apartment
AU$705 per night
includes taxes & fees
D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
Pool
Grand Champions Entrance with Waterfall feature
Entrance to the condo
Renovated kitchen with built in bar
Exceptional
(110 reviews)

Escape to Paradise – Your Dream Wailea Getaway Awaits!

Kihei

7% off
AU$3,519
for 7 nights, 1 apartment
AU$503 per night
includes taxes & fees
Escape to Paradise – Your Dream Wailea Getaway Awaits!
Interior
Property grounds
Property grounds
Golf
Exceptional
(57 reviews)

Updated Designer Condo w/ Ocean Views within five minutes to the beach

Kihei

7% off
AU$3,719
for 7 nights, 1 apartment
AU$531 per night
includes taxes & fees
Updated Designer Condo w/ Ocean Views within five minutes to the beach
Dining
Property grounds
Interior
Living room
Exceptional
(88 reviews)

Ekahi 29C, Ocean View, Steps away from the pool

Kihei

7% off
AU$7,310
for 7 nights, 1 apartment
AU$1,044 per night
includes taxes & fees
Ekahi 29C, Ocean View, Steps away from the pool
The villa is nestled in the middle of world class golf courses
Outdoor dining
Private kitchen
Room
Exceptional
(71 reviews)

Immaculate and Chic - Come relax in our luxury villa…

Kihei

7% off
AU$5,309
for 7 nights, 1 apartment
AU$758 per night
includes taxes & fees
Immaculate and Chic - Come relax in our luxury villa…
Dining
Outdoor dining
Interior
Pool
Exceptional
(31 reviews)

Kihei Getaway in Paradise

Kihei

7% off
AU$4,341
for 7 nights, 1 apartment
AU$620 per night
includes taxes & fees
Kihei Getaway in Paradise
Kitchen bar view
Clubhouse pool and hot tub
Common Garden area
View from entryway
Exceptional
(10 reviews)

Fully Remodeled Modern Island Style!

Kihei

7% off
AU$7,269
for 7 nights, 1 apartment
AU$1,038 per night
includes taxes & fees
Fully Remodeled Modern Island Style!
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Wailea

  • Scenic coastal trails: Enjoy the breathtaking views along the Wailea Coastal Walk and beach promenades.
  • Pristine beaches: Relax on immaculate sandy shores ideal for sunbathing and water activities.
  • Outdoor adventures: Engage in various sports and leisurely strolls in a family-friendly environment.
  • Art and culture: Discover local art galleries that add a vibrant touch to the neighbourhood.
  • Upscale retreat: Experience a tranquil escape with luxurious amenities and natural beauty.

Popular types of accommodation around Wailea

Wailea, nestled in Kihei, Hawaii, is renowned for its stunning beaches and luxurious resorts. This upscale neighbourhood offers a tranquil escape with a range of attractions, including pristine golf courses, beautiful coastal trails, and vibrant art galleries. Whether you prefer a condo with ocean views or a private holiday home, Wailea holiday rentals provide the perfect base to explore the breathtaking scenery and indulge in a variety of outdoor experiences. Discover the charm of Wailea and enjoy a memorable Hawaiian getaway.

  • Condos: The top choice for holidaymakers in Wailea, condos offer a blend of comfort and convenience, ideal for enjoying the local scenery.
  • Private Holiday Homes: A popular option for those seeking more space and privacy, these homes provide a home-like atmosphere for families and groups.
  • Apartments: Perfect for shorter stays, apartments offer essential amenities in a compact setting, catering to solo travellers and couples alike.
  • Villas: Offering luxury and spaciousness, villas are an excellent choice for those desiring an upscale experience during their holiday.
  • Cottages: Quaint and charming, cottages provide a delightful retreat for those looking for a more intimate and cosy holiday experience.**

Top attractions in and around Wailea

Wailea, nestled in Kihei, Hawaii, is a stunning destination perfect for beach and outdoor enthusiasts. Visitors can enjoy the scenic Wailea Beach Walk, explore the picturesque Wailea Jewel, and partake in various sports activities. The Wailea Coastal Walk offers breathtaking views, making it an ideal spot for sightseeing. With its blend of natural beauty and family-friendly experiences, Wailea promises a memorable holiday for all travellers.

  • Wailea Beach: A pristine stretch with quintessential beach vibes, perfect for leisurely strolls and sunbathing in Wailea.
  • Makena Beaches: A national state park offering stunning outdoor scenery and adventurous experiences, ideal for exploring nature within Wailea.
  • Kamaole Beach Park 3: An urban park 3km from Wailea, blending family-friendly outdoor fun with a touch of city ambience.

Things to do recommended for couples

Wailea offers a perfect romantic getaway. Enjoy a sunset beach walk along the golden sands of Wailea Beach or indulge in a couples' massage at a luxurious spa. For a unique experience, take a scenic helicopter tour over the stunning Hawaiian coastline.

Things to do recommended for families

Families will love the stunning beaches of Wailea, perfect for building sandcastles and swimming. Visit the nearby Maui Ocean Centre to explore fascinating marine life, or enjoy a family-friendly hike at the scenic Makena State Park for breathtaking views and a chance to spot local wildlife.

Things to do recommended for groups

Explore the stunning beaches of Wailea, indulge in a delightful luau experience, or embark on a group snorkelling adventure at Molokini Crater. Enjoy a scenic hike through the lush landscapes of Haleakalā National Park, where breathtaking views await.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Wailea

If you're travelling with a group, as a family, bringing your pets, or seeking longer stays, it's important to filter according to your key preferences. Here are some helpful booking tips for Stayz.

  • Traveling to Wailea with a group: Think about how many bedrooms you will require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Fortunately, you can easily refine your search for these options and many more on Stayz.
  • Traveling to Wailea with young kids: Travelling with young children can present its challenges. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Wailea: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, consider exploring Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wailea: If you're seeking holiday lets offering long-stay deals, you've come to the right place. By using the appropriate filters, you can effortlessly locate and save on monthly rentals. You might also consider including amenities such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Wailea

Wailea offers a captivating retreat with pristine beaches and stunning coastal views. Ideal for a romantic and relaxing holiday, this neighbourhood boasts beautiful wailea beach and a vibrant wailea village. Stroll along the wailea cost and experience the charm of the local resort community. Enjoy an unforgettable maui holiday immersed in natural beauty and a family-friendly atmosphere, all within the serene embrace of Wailea.

  • Maui: Maui is a stunning island that beckons visitors with its breathtaking beaches and outdoor adventures. Located approximately 16km from Wailea, this tropical paradise offers a wealth of activities, from golfing on world-class courses to exploring vibrant shopping centres. The island is renowned for its picturesque landscapes, including family-friendly beaches and tranquil bays, making it an ideal spot for relaxation and exploration. Whether you're soaking up the sun or indulging in local cuisine, Maui promises a memorable experience for all travellers.
  • Kihei: As a vibrant city situated in close proximity to Wailea, Kihei is a hotspot for beach lovers and outdoor enthusiasts. The area is known for its stunning coastline, inviting visitors to engage in various water sports or simply bask in the sun. With numerous golf courses and well-equipped shopping centres, Kihei caters to both relaxation and recreation. Urban parks also add to the charm of this locale, providing green spaces for picnics and leisurely strolls. Kihei's lively atmosphere and beautiful scenery make it a must-visit destination.
  • South Maui: Located a mere 805m from Wailea, South Maui is a delightful area that offers a blend of family-friendly activities and natural beauty. This picturesque region is perfect for those seeking beach days and outdoor adventures, with an array of shopping centres and malls to explore. The local attractions, including scenic urban parks and stunning beaches, create an inviting environment for families and nature lovers alike. South Maui's charm and accessibility make it a fantastic addition to your holiday itinerary.

Best time to go to Wailea

If you're planning a trip to Wailea, it's a good idea to check both the weather and property rates. The warmest months are August and September. Peak season runs in January and March to April, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January72.7°F (22.6°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
February72.3°F (22.4°C)No Rain (Dry)Mostly SunnyAverageAverage
March72.7°F (22.6°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April74.1°F (23.4°C)No Rain (Dry)Mostly SunnySlightly HighAverage
May75.6°F (24.2°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
June76.8°F (24.9°C)No Rain (Dry)Mostly SunnyAverageAverage
July77.9°F (25.5°C)No Rain (Dry)Mostly SunnyAverageAverage
August78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverageAverage
September78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
October77.7°F (25.4°C)No Rain (Dry)Mostly SunnySlightly LowSlightly Low
November75.7°F (24.3°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December73.8°F (23.2°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Stayz is a breeze

Looking to save on your next holiday? Consider remaining flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay may offer significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday accommodation.

Stayz Trips: Planning as easy as it gets

Stayz's inventive Trip Board offers you a dedicated area to craft new journeys, pick up where you last left off, or review and organise your plans. Properties you have previously saved or booked are now categorised under Potential, Upcoming, or Current Trips. To access your Trip Boards, please visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

Frequently asked questions

When is the best time to visit Wailea for a holiday rental?
The best time to visit Wailea for a holiday rental is during the peak season from February to April, with March being particularly popular. This period attracts travellers seeking sun-soaked beaches and outdoor adventures, as the weather is pleasantly warm, typically ranging from 20 to 28 degrees Celsius. It's an excellent time for snorkelling, surfing, and exploring the stunning coastal scenery that Wailea is known for.During these months, you'll find a vibrant setting with numerous events and activities taking place, making it ideal for those looking to immerse themselves in the local culture while enjoying the natural beauty of Hawaii. The beaches are inviting, and the lush landscapes provide a great backdrop for relaxation and outdoor exploration.If you're considering a more budget-friendly option, October can be a lovely time to visit Wailea. This month often sees fewer tourists while still offering lovely weather, making it superb for enjoying the beaches and local attractions at a more leisurely pace. You can take advantage of lower rental rates and enjoy a quieter experience without sacrificing the beauty of the island.Ultimately, your choice of when to visit Wailea will depend on whether you prefer the lively option of peak season or the tranquil charm of the shoulder months.
What are the top attractions in Wailea, Hawaii, United States of America?
In Wailea, visitors can enjoy stunning attractions set against a backdrop of natural beauty. The picturesque Wailea Beach is a highlight, offering crystal-clear waters and soft sands, great for sunbathing and swimming. Close by, the luxurious Wailea Golf Club features three world-class courses with breathtaking ocean views, attracting golf enthusiasts from around the globe.For those interested in culture, the nearby Shops at Wailea provide a blend of upscale shopping and dining, with various boutiques and restaurants showcasing local cuisine. Additionally, the scenic Wailea Coastal Walk is a lovely pathway connecting several beaches and resorts, ideal for leisurely strolls and taking in the breathtaking views of the Pacific Ocean.Nature lovers will appreciate the proximity to the lush landscapes of Makena State Park, where you can explore beautiful hiking trails and enjoy the stunning views from Big Beach and Little Beach.
Are all fees included in the Wailea holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Wailea holiday homes with parking?
Stayz offers a wide selection of holiday homes in Wailea with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Wailea holiday homes?
You can find great discounts on holiday homes in Wailea on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Wailea holiday home booking on Stayz?
To find Wailea holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Wailea?
A long-stay holiday home in Wailea is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Wailea holiday home?
Book your Wailea holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Wailea?
Prices for holiday homes in Wailea vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Wailea to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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