
Holiday rentals in Wailea
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Top-rated holiday rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness and more.

Charming Art Studio on a Scenic Mountain Slope
Kula Jasmine studio is reached by a bridge pathway. The shared barbecue area just steps from your studio offers a place to prep your own meals. We provide reverse osmosis filtered water in the outdoor kitchen sink, so there is no need to buy bottled water. We also provide coffee, tea, oil, vinegar, salt, and pepper. You can either dine on the waterfall deck or the barbecue area while you watch the sunset. With years as AirBnb super hosts, we've got everything you need. Permit # BBMP20160004

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
Mana Kai 608 is a remodeled oceanfront condo DIRECTLY ON Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, on the border of Wailea and Kihei! Our condo is designed with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5 star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best Property Manager in Maui, Tracy O'Reilly to take amazing care of you!

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury accommodations in the heart of Wailea, Maui. Our condo has lovely ocean views, views of the lush tropical gardens and the pool. Sunset views from the lanai are stunning. Gourmet kitchen. 2 HD TVs, Bose sound system, AC, washer/dryer in unit, complimentary assigned parking. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Our condo is not suitable for children or infants.

Sweeping Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

Luxury condo • 180° Ocean Views • Steps to Beach
Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Modern Renovated Palms at Wailea Condo!
MODERN CONDO WITH ATTENTION TO DETAIL! Our bright, modern island condo awaits you! Breathe easy knowing that you have everything at your fingertips. Enjoy your morning coffee on the large lanai. Pack a beach bag and head to one of the best beaches just a 10 minute walk away. Explore the Shops at Wailea. You will feel right at home cooking in our fully equipped kitchen. Close out your day by watching the sunset from the pool area and then stargazing on the lanai. Then repeat!

Luxury Condo w/wide Ocean View (Palms at Wailea)!
There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

A.R.A Retreats: Garden Oasis
Nicknamed “Garden Oasis” for its beautiful little garden walk out off the Lanai onto a beautiful field. While it also has a amazing view of the pacific ocean the beautiful private walkout really set the tone for a relaxing and private oasis. Wailea Ekolu Village is a three-minute drive or 18 minute walk to the beautiful golden sands of Wailea Beach. The Shops at Wailea, Monkeypod Kitchen and so much more just a short walk away!

*Fully Remodeled* Modern Island Style*
I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini

130K Hawaiian Reno on Wailea Blue Golf *Ocean View
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of WaileaCheck out our other property #201 VRBO (2050379)+#1905 VRBO(1222713) in The Palms we are Super Host with 5 STAR reviews)!! BOOK UP TO 365 DAYS.

Wailea Gem-Remodeled Ocean View
Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.

Maui Wailea Brand New Modern Spacious Condo
Beautifully designed, modern, and brand new vacation condo is situated on the Wailea Blue golf course and the Wailea tennis club. Walk to Shops at Wailea and 3 min drive to Keawakapu Beach. Brand new kitchen, spa like bathroom with walk in shower, in-unit laundry. Relax with friends and families at this peaceful place to stay. Book your vacation today : )
Popular amenities for Wailea holiday rentals
Stay near Wailea's top sights
Other great holiday rentals in Wailea

Beautiful Beach Cottage: lush garden paradise

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Endless Ocean Views - 1bd/2 bath

Luxury Vacation at Special Summer 2026 Rates

Wailea Ocean View Escape

Wailea Elua: Huge Ocean Views, Pool, AC & Hot Tub

Stunning Sunsets & Ocean Views Every Day!
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $482 SGD | $509 SGD | $456 SGD | $399 SGD | $359 SGD | $371 SGD | $354 SGD | $341 SGD | $327 SGD | $349 SGD | $398 SGD | $470 SGD |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Wailea-Makena?
Wailea-Makena has a variety of vacation rentals, including oceanfront homes, condos, and properties near golf courses and beaches. Many neighborhoods provide easy access to local shops, restaurants, and outdoor activities.
What are the best things to do in Wailea-Makena with kids?
Children often enjoy swimming at sandy beaches, exploring tide pools, or joining marine life tours. Interactive cultural sites and family-friendly parks around Wailea-Makena are frequently suggested for a relaxed day out.
What are some of the best things to do in Wailea-Makena?
Wailea-Makena has sandy beaches, snorkeling opportunities, and scenic coastal walks. Visitors often explore local parks, enjoy golf courses, or join guided tours highlighting marine life and Hawaiian heritage.
How is the weather in Wailea-Makena?
Wailea-Makena has mild weather throughout the year, with winter temperatures averaging 53–68°F (12–20°C) and summer months reaching 59–76°F (15–24°C). Rain is more common in winter, while summers tend to be sunny and dry.
When is the best time to visit Wailea-Makena?
Late spring and summer are frequently suggested for warmer days near 75°F (24°C) and lower rainfall, making beach and outdoor activities popular. Winter, around 68°F (20°C), is also lively with more visitors, and brings occasional rain alongside mild temperatures.
What are the best places to visit in Wailea-Makena?
Visitors often explore sandy beaches, local parks, and scenic coastal paths in Wailea-Makena. Marine reserves and cultural centers highlight Hawaiian heritage, nature, and community events.
What are some hiking trails in Wailea-Makena?
Visitors can explore coastal trails, gentle walking paths through local parks, or routes winding near lava fields and scenic overlooks. Some areas have accessible hikes suitable for diverse abilities and interests.
What are some family activities we can do in Wailea-Makena?
Families can explore sandy beaches, try snorkeling in clear waters, or visit local parks with picnic spots. Cultural sites, marine life tours, and gentle hiking paths around the area are frequently suggested for visitors of all ages.
What are some of the best day trip ideas from Wailea-Makena?
Day trips can include exploring coastal hikes, visiting traditional markets, or discovering historic towns around the region. Nature reserves, scenic viewpoints, and cultural attractions frequently appeal to visitors seeking local experiences.
Are there any pet friendly accommodations available in Wailea-Makena?
Many vacation rentals in Wailea-Makena welcome pets, especially in neighborhoods near outdoor spaces or parks. Hosts often provide guidance on pet-friendly beaches and walking areas around town.
What are some local tips for visiting Wailea-Makena?
Respect beach etiquette, bring reef-safe sunscreen, and consider reusable shopping bags for local markets. Early mornings offer quieter outdoor experiences, and chatting with local hosts or vendors can reveal community traditions.
What is Wailea-Makena known for?
Wailea-Makena is known for its sandy beaches, distinct golf courses, and locally rooted hospitality. The area blends natural beauty, marine activities, and celebrated Hawaiian traditions throughout its neighborhoods.
What are the best hidden gems to explore in Wailea-Makena?
Wailea-Makena has secluded beaches, lesser-known lava rock pools, and small local markets. Off-the-beaten-path walking trails and traditional workshops offer quieter, locally rooted experiences.
What are the best foods to try in Wailea-Makena?
Local cuisine often features fresh seafood, poke bowls, and tropical fruits like papaya or mango. Try dishes rooted in Hawaiian traditions, including laulau, Loco Moco, or regional desserts made with coconut and taro.
What should I bring for a trip to Wailea-Makena?
Pack lightweight clothing, swimsuits, sun protection, and sturdy sandals for outdoor activities. Reusable water bottles, hats, and light rain jackets are useful for changing weather and exploring coastal or park areas.
What is the nightlife in Wailea-Makena like?
Wailea-Makena has a laid-back nightlife scene, with open-air lounges, live music at local venues, and casual beachside bars. Evening entertainment often blends local musicians, sunset views, and relaxed dining.
What are the most popular events or festivals in Wailea-Makena?
Annual events often include cultural celebrations, Hawaiian music festivals, and food gatherings during summer or late spring. Community events, arts fairs, and outrigger canoe races are frequently suggested for visitors seeking local traditions.
Are there family friendly vacation rentals in Wailea-Makena?
Wailea-Makena has a wide selection of family-friendly rentals, including spacious homes, condos with pools, and properties close to parks and beaches. Many hosts provide amenities like cribs, high chairs, and beach gear.
Quick stats about holiday rentals in Wailea

Total holiday rentals
Explore 1,970 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 53,930 verified reviews to help you choose

Family-friendly holiday rentals
1,100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
1,870 properties feature pools

Rentals with dedicated workspaces
1,130 properties have a dedicated workspace

Wifi availability
1,970 of Wailea holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests – averaging 4.8 out of 5!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Wailea Beach
- Honolua Bay
- Polo Beach
- Kapalua Bay Beach
- Old Lahaina Luau
- Whalers Village
- Ka'anapali Golf Courses
- Maui Vista Condominium
- Big Beach
- Black Rock Beach
- Black Sand Beach
- Maui Ocean Center
- Kihei Kai Nani
- Hāmoa Beach
- Maui Arts & Cultural Center
- Peahi
- KOA Resort
- Haleakala National Park
- PacWhale Eco-Adventures
- Kahana Beach
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