
Vacation rentals with a pool in Wailea
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Wailea

Total vacation rentals
Explore 1,840 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at $153 CAD per night before taxes and fees

Verified guest reviews
Over 50,970 verified reviews to help you choose

Family-friendly vacation rentals
1,080 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,030 properties have a dedicated workspace

Wifi availability
1,830 of Wailea vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Wailea
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
Stunning Full Renovation and Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the lanai.We are perfectly located just down from Money Pod+across from The Wailea Village popular with all the best restaurants. The Shops of Wailea with all of the exclusive brands is a short walk down the hill. Resort style amenities with 2 pools. Everything provided from Beach towels, Boogie Board, Yeti cooler and more.

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

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.

Spacious garden oasis next to Maui's best beaches!
Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located next to Keawakapu Beach and minutes to Wailea. Our condo is perfectly suited for couples and small families wanting space with stylish comfort in a prime location. Relax on a luxurious king-sized bed, sectional sofa w/ a pull-out sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, with two full bathrooms. Soak in paradise on two garden patios!

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.

*Last Minute Deal*Luxurious*2b/2b OceanView Wailea
This ground floor 1071 square foot unit is situated just above the 11th fairway of the Wailea Blue Course. The living room and master bedroom have private lanais that step out to a relaxing open lawn with sweeping ocean views. Features include AC throughout the property, bamboo floors throughout, brand new tile in the master bathroom, granite counter tops, and cherry cabinets. Tastefully decorated this spacious condo truly has everything you will need!

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.

*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

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 rentals with a pool
House rentals with a pool

Kihei 533- OceanView, 5 min drive to stores/food

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

Stunning One Bd Partial ocean, AC, wifi,Pool C209

Oceanview Townhome • Modern • 2 Min Walk to Beach!

Oceanview Home with Private pool and hot tub

Centrally located and steps to the beach!

Stunning ocean view Villa, Heated pool, Wailea

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet
Condo rentals with a pool

Grand Champions - King Bed - Close to Wailea Beach

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

Luxurious Condo in South Kihei

3BD Oceanfront Views I Menehune Shores 414

Ekahi 22C Toes in the Sand in Under 2 Minutes

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

Romantic One BR Condo (Remodeled)
Other vacation rentals with a pool

Beach Front Wailea, Full Ocean View A/C, ELUA102

Wailea Escape/Golf Views, Beaches & Family Comfort

Gem near Keawakapu Beach - Privacy and Ocean Views

Oceanfront Makena Surf G202 - Professionally

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

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Beach Front Luxury in Makena

Wailea Ocean View Escape
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $528 CAD | $562 CAD | $503 CAD | $441 CAD | $401 CAD | $406 CAD | $390 CAD | $374 CAD | $362 CAD | $383 CAD | $438 CAD | $521 CAD |
| 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 |
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- Maui
- Kaanapali Beach
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