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

Total holiday rentals
Explore 1,840 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $186 NZD per night before taxes and fees

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

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

Pet-friendly accommodation
Find 10 rentals that welcome pets

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

Wi-Fi availability
1,830 of Wailea holiday rentals include Wi-Fi 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.

Mana Kai Palms Oceanfront Condo: Keawakapu Beach
Welcome to Mana Kai Palms Our luxurious, newly renovated condominium is located on Keawakapu Beach, named Maui's best for its pristine sand, clear waters, and abundant marine life. The Mana Kai Resort offers a wide range of amenities and with only 100 units, provides a warm, family feel. We are conveniently located minutes from all South Maui has to offer. Hosted by Tracy O'Reilly, a Superhost and #1 rated rental agent on Maui. Do as much as you want or as little as you desire at Mana Kai Palms

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

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.

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.

Mana Kai 608: Oceanfront Remod- Xmas Wk Now OPEN!
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!

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.

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!
This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

*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!

*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

Grand Champions 169 Beautiful 3 BR on the Fairway!
Prime Wailea location! Enjoy stunning ocean and fairway views from this rare 3-bedroom, ground-floor unit with Split System Air Conditioning in every room. Spacious 1,698 sq ft layout and wrap-around lanai. Walk to Wailea Tennis Club, Blue Golf Course, luxury hotels, Shops at Wailea, restaurants, and beaches just ¼ mile away. Experience luxury and comfort in the heart of Wailea!

Ocean/Golf Course Views, Tropical Resort in Wailea
Breathe in and exhale slowly while gazing at the beautiful ocean, 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.)

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

Stunning ocean view Villa, Heated pool, Wailea

Condo in Kihei 2 BR - 2 bath Condo

Go for an Ocean Swim From a Fun Beach Villa

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

Oceanview Home with Private pool and hot tub

Aloha Aku Bamboo Suite – Discover Beachfront Seren

Oceanfront Stunner w/ Cruiser Bikes & Pickleball

Centrally located and steps to the beach!
Condo rentals with a pool

Wailea Ekolu Village 2/2 with stunning ocean view!

Ekahi 22C Toes in the Sand in Under 2 Minutes

Luxury Condo w/wide Ocean View (Palms at Wailea)!

Wailea Gem-Remodeled Ocean View

Large 1BR, Palms at Wailea, Pool, Walk to Beach

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Groovy bright condo 2 bed / 2 bath South Kihei

3BR spacious Condo with Ocean View in top location
Other holiday rentals with a pool

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Go Golfing from a Peaceful Apartment in a Beach Community

Romantic, Luxury Condo with Spectacular Ocean View

Grand Champions - King Bed - Close to Wailea Beach

Wailea Ocean View Escape

Luxurious Tropical Retreat with Oceanview

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

* Wailea Elua 806 *
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $640 NZD | $682 NZD | $610 NZD | $535 NZD | $486 NZD | $493 NZD | $473 NZD | $454 NZD | $439 NZD | $464 NZD | $532 NZD | $632 NZD |
| 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
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