
Vacation rentals in Wailea
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Top-rated vacation rentals in Wailea
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A.R.A Retreats: The Molokini
FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC
Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. 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 Not suitable for children or infants.

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi
Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The owner’s spared no expense in renovating this unit making it hand’s down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

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!

Luxurious Wailea Ocean Vistas
Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful lushness while enjoying a charming well-designed hideaway. We have considered every detail to provide the most effortlessly luxurious stay possible. With beaches nearby and two pools onsite, this island paradise has everything and more.

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.

Stunning ocean view, heated pool at home by Wailea
Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

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.

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.)
Popular amenities for Wailea, Wailea-Makena vacation rentals
Stay near Wailea's top sights
Wailea, Wailea-Makena apartment rentals

Ocean Front With Ocean View! AC, King Bed, 2 Bath!

Kamaole Sands 7-207-Stunning Remodel-Large Lanai

Wailea Ocean View Escape

Ocean Front Vibes Maui

High-end, On Beach, View Balcony, with Pool & BBQ!

Maui Oceanfront Penthouse at Nani Kai Hale (609)

Spring Special / One Bedroom- Closest to beach!

*Last Minute Deal! Beautiful by TOP Swimming Beach
Other great vacation rentals in Wailea

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

Wailea Elua 2007 – Oceanview Luxury Condo

Maui Full Oceanfront Paradise

Gorgeous Condo in Wailea Ekahi Village!

Stunning Ocean Views - Professionally Managed

Ekahi 22C Toes in the Sand in Under 2 Minutes

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

Tropical Wailea Retreat
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,374 | ﺩ.ﺇ1,451 | ﺩ.ﺇ1,300 | ﺩ.ﺇ1,138 | ﺩ.ﺇ1,025 | ﺩ.ﺇ1,058 | ﺩ.ﺇ1,010 | ﺩ.ﺇ973 | ﺩ.ﺇ933 | ﺩ.ﺇ995 | ﺩ.ﺇ1,138 | ﺩ.ﺇ1,340 |
| 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 |
Quick stats about vacation rentals in Wailea

Total vacation rentals
Explore 1,970 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

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

Family-friendly vacation rentals
1,100 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
1,870 properties feature pools

Rentals with dedicated workspaces
1,120 properties have a dedicated workspace

Wi-Fi availability
1,970 of Wailea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace 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
- Kapalua Bay Beach
- Polo Beach
- Old Lahaina Luau
- Black Rock Beach
- Whalers Village
- Big Beach
- Maui Vista Condominium
- Maui Ocean Center
- Kihei Kai Nani
- Black Sand Beach
- Hāmoa Beach
- Maui Arts & Cultural Center
- Haleakala National Park
- KOA Resort
- PacWhale Eco-Adventures
- Aston Mahana at Kaanapali
- Maui Tropical Plantation
- Waihe’e Ridge Trail





