
Holiday rentals in Wailea
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Quick stats about holiday rentals in Wailea

Total holiday rentals
Explore 1,930 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 55,470 verified reviews to help you choose

Family-friendly holiday rentals
1,150 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
1,840 properties feature pools

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

Wifi availability
1,930 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!
Top-rated holiday rentals in Wailea
Guests agree: these stays are highly rated for location, cleanliness and more.

The Pi Life: Ocean Views · 99 Steps from the Beach
We're Airbnb Superhosts w/ 100+ 5 Star Reviews. Welcome to The Pi Life! A cute and cozy condo, with gorgeous oceans views, that's 99 steps from the beach. We have everything you need for a perfect Maui vacation, including: ★ Ocean Views ★ Resort Amenities ★ Beach & Restaurant Access And, perhaps most importantly, we're deeply caring and responsive hosts ❤️ Our goal is to make your experience as fun, relaxing, and comfortable as possible. So please let us know how we can be helpful :)

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.

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!

Upscale and Elegant Vistas
Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled and freshly outfitted. No expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
Welcome to Happy Everything! Wailea Ekolu Complex A fun, fully re-modeled, well appointed and comfortable townhome situated on hole 10 of the famous Wailea Blue Golf Course at beautiful Wailea, Maui. Comfortably sleeps 6. Spectacular views of the Ocean and Neighbor Islands. Close to beaches, shopping, restaurants, Wailea Resorts and just a chip shot away from the golf course and brand new Wailea Village shops.

*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 : )

Ocean/Golf Course Views, Tropical Resort in Wailea
Breathe in and exhale slowly while gazing at serene greenery and misty mountaintops. Make the most of a country-club setting by lounging on sun decks and swimming in heated pools. Retreat to an updated condo to unwind and fall asleep in a comfy bed. (This unit is suitable for a maximum of four (4) guests. Infants of any age are counted as guests.)

Wailea Surf Shack: Beaches, Shops & Golf!
Welcome to Wailea Surf Shack, a beautifully renovated Maui retreat in the heart of Wailea. Book with confidence knowing that we live on the island, personally manage and care for the condo, and truly treat our guests like family. We go above and beyond to make sure your stay is comfortable, relaxing, and filled with wonderful Maui memories.
Popular amenities for Wailea holiday rentals
Stay near Wailea's top sights
Other great holiday rentals in Wailea

Oceanfront Makena Surf G202 - Professionally

Stunning Wailea 2/2, AC, Upper Fl, walk to beach

Beach Front Luxury in Makena

The BEST Condo in Wailea: Elua Resort 1002

Gorgeous Condo in Wailea Ekahi Village!

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

Aloha Moon - The Honeymoon Hideaway

Luxe 2bed Wailea, 5-min walk to beach, ocean view,
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $483 SGD | $510 SGD | $457 SGD | $400 SGD | $360 SGD | $372 SGD | $355 SGD | $342 SGD | $328 SGD | $350 SGD | $399 SGD | $471 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.
Destinations to explore
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- Maui
- Kaanapali Beach
- Lahaina Beach
- Wailea Beach
- Whalers Village
- Polo Beach
- Honolua Bay
- Kapalua Bay Beach
- Maui Vista Condominium
- Old Lahaina Luau
- Big Beach
- Ka'anapali Golf Courses
- Black Rock Beach
- Black Sand Beach
- Haleakala National Park
- Kihei Kai Nani
- Maui Ocean Center
- Kamaole Beach Park II
- Hāmoa Beach
- KOA Resort
- Maui Arts & Cultural Center
- PacWhale Eco-Adventures
- Peahi
- Kahana Beach
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