Wailea holiday lettings

We found 1,412 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Wailea by choosing from 52 houses, 29 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:2 Oct - 9 Oct

Image gallery for Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled

Indoor Dining Area
10 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)

Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled

Kihei

7% off
Price is £3,798
for 7 nights, 1 home
£543 per night
includes taxes & fees
Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled

Find spaces that suit your style

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    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, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Wailea

  • Pristine Beaches: Wailea boasts beautiful beaches like Wailea Beach and Keawakapu Beach, perfect for sunbathing and water activities.
  • Scenic Trails: Explore picturesque walking trails that offer peaceful strolls amidst lush landscapes and stunning ocean views.
  • Unique Shopping and Dining: Discover charming boutiques and delightful eateries in Wailea Village, offering a taste of local cuisine and culture.
  • Luxurious Accommodation: Enjoy a range of upscale vacation rentals, from elegant condos to private homes, ensuring a comfortable stay.
  • Outdoor Adventures: Engage in various outdoor activities, from snorkelling to hiking, making the most of Wailea's stunning natural surroundings.

Popular types of accommodation around Wailea

Welcome to Wailea, a stunning neighbourhood in Kihei, Hawaii, renowned for its breathtaking ocean views and luxurious atmosphere. Here, you'll find a variety of vacation rentals, from elegant condos to private homes and modern apartments. Enjoy the pristine beaches, explore lush landscapes, and indulge in world-class dining. With its rich cultural experiences and vibrant local attractions, Wailea promises an unforgettable getaway for every traveller seeking relaxation and adventure.

  • Condos: The most sought-after lodging option in Wailea, offering a blend of comfort and convenience.
  • Houses: A popular choice for those seeking a home-like atmosphere with added privacy during their stay.
  • Apartments: Ideal for travellers wanting self-catering facilities in a more compact setting.
  • Villas: Luxurious accommodations providing spacious living and stunning surroundings.
  • Cottages: Quaint and charming retreats perfect for a cosy getaway.**

Top attractions in and around Wailea

Wailea, located in Kihei, Hawaii, is a stunning destination perfect for beach lovers and outdoor enthusiasts. With beautiful beaches, lush parks, and scenic landscapes, it offers a variety of experiences for families and travellers alike. Visitors can enjoy sunbathing, water sports, and exploring local parks, making Wailea an ideal choice for a relaxing and adventurous holiday in paradise.

  • Wailea Beach: This stunning beach offers soft golden sands and crystal-clear waters, perfect for sunbathing and swimming. The tranquil atmosphere makes it ideal for relaxation, while nearby amenities enhance the experience.
  • Makena Beaches: Known for breathtaking natural beauty, Makena Beaches provide a sense of adventure with opportunities for snorkelling and exploring scenic landscapes, creating an unforgettable outdoor experience.
  • Kamaole Beach Park 3: A family-friendly urban park featuring lush green spaces, picnic areas, and gentle waves, perfect for swimming and enjoying a day out with loved ones.

Things to do recommended for couples

Discover the romantic charm of Wailea with sunset beach walks along the golden sands or a couples' massage at a luxurious spa. Enjoy a sunset dinner at a beachside restaurant, taking in breathtaking ocean views. Don't miss the chance to snorkel together at Molokini Crater for an unforgettable experience.

Things to do recommended for families

Families can explore the stunning beaches of Wailea, indulge in a snorkelling adventure at Molokini Crater, or visit the Maui Ocean Centre to learn about marine life. Don’t miss the scenic coastal walk along Wailea Beach Path for breathtaking views and family-friendly picnics.

Things to do recommended for groups

Groups visiting Wailea can enjoy a delightful luau experience, immerse themselves in traditional Hawaiian culture, and take a scenic hike along the breathtaking coastline. Snorkelling trips to Molokini Crater offer vibrant marine life, while leisurely beach days provide relaxation and stunning sunsets.

*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, family, pets, or seeking extended stays, it's important to filter your options based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Wailea with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Wailea with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with ensuring access to suitable amenities, such as a private swimming pool. Additionally, it’s wise to think about how close you are 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, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wailea: If you're in search of holiday rentals that offer great deals for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Wailea

Wailea, Kihei, Hawaii, is a picturesque neighbourhood ideal for sun-seekers and outdoor enthusiasts. With stunning spots like Wailea Beach and Keawakapu Beach, visitors can bask in the sun or partake in water activities. The charming Wailea Village offers unique shopping and dining experiences, while the scenic trails invite peaceful strolls. Whether you're after a romantic getaway or a relaxing family holiday, Wailea promises unforgettable moments amidst its breathtaking scenery.

  • Maui: Maui is an enchanting island located approximately 16km from Wailea, famed for its stunning beaches and breathtaking scenery. This tropical paradise is a haven for outdoor enthusiasts, offering a plethora of activities such as golfing on world-class courses and shopping in vibrant centres. Visitors can bask in the sun on family-friendly beaches or explore the picturesque bays that dot the coastline. With its diverse landscapes, from lush valleys to volcanic craters, Maui promises an unforgettable experience for travellers seeking both relaxation and adventure.
  • Kihei: Kihei is a lively city where Wailea is nestled, renowned for its beautiful beaches and outdoor activities. This coastal destination attracts visitors eager to enjoy the sun, surf, and stunning views. Kihei boasts excellent golfing facilities and shopping options, providing everything from boutique stores to local markets. The area is dotted with picturesque beaches and urban parks, making it an ideal spot for family outings or leisurely strolls along the shore. With its friendly atmosphere and vibrant community, Kihei offers a truly enjoyable Hawaiian experience.
  • South Maui: Located a mere 805m from Wailea, South Maui is a popular destination for those seeking beach fun and family-friendly activities. This area is characterised by its inviting beaches, charming urban parks, and convenient shopping centres, all of which contribute to its allure. Visitors can indulge in golf or relax on the beautiful shores while soaking up the local culture. With its close proximity to Wailea, South Maui serves as an excellent base for exploring the region and enjoying the best of Hawaii’s natural beauty.

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 Vrbo is a breeze

Are you eager to save on your next adventure? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you might enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday accommodation.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a convenient space to plan new trips, pick up from where you paused, or review and arrange your travel arrangements. You can easily access properties you've previously saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Wailea?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Wailea to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Wailea holiday house rentals?
You can find great discounts on house rentals in Wailea on Vrbo, 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.
Are there any Wailea holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
Can I find long-stay holiday rentals in Wailea?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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.
How early should I book a Wailea holiday rental?
Book your Wailea holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Wailea home rental booking on Vrbo?
To find Wailea holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Wailea holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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