
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 ﺩ.ﺇ 404 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

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

Wi-Fi availability
1,830 of Wailea vacation 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.

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

StunningReno*Palms in Wailea Condo-Beach*Golf*Pool
New 160K Renovation+Redecoration for a Hawaiian Beach Vibe.Wailea is one of the most sought after resort on Maui. Here you can relax in luxury of the beautiful grounds + refreshing swimming pool and spa. World Class Golf+Shopping. Ground floor condo with private lanai that overlooks the grass. King Master Bed with private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel+take long beach walks. EverythingProvidedBeach items+Yeti+ 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.

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 in Wailea Ekahi w/Direct Beach Access
Do you want direct and private access to probably the best beach (i.e. Keawakapu) on Maui? Then look no further than our unit in the Wailea Ekahi complex! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. You are also in walking distance to the stores and restaurants at the Shops at Wailea and also the Wailea Beach Path. This condo has everything you need to make your Maui experience memorable, luxurious, and convenient.

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.

*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

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 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

Oceanview Townhome • Modern • 2 Min Walk to Beach!

Condo in Kihei 2 BR - 2 bath Condo

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

Oceanview Home with Private pool and hot tub

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

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

South Maui • Pool • Hot Tubs• Beach • Ocean View
Condo rentals with a pool

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Ekahi 22C Toes in the Sand in Under 2 Minutes

Romantic, Luxury Condo with Spectacular Ocean View

Luxurious Condo in South Kihei

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

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

Mana Kai 608: Oceanfront Remod! Modern Surf Vibe
Other vacation rentals with a pool

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Luxurious Tropical Retreat with Oceanview

Maui Kamaole in Kihei | Ocean View, Pool, Hot Tub

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

Aloha Moon - The Honeymoon Hideaway

Beach Front Luxury in Makena

Wailea Ekolu – Oceanview in the Heart of Wailea

Stunning Wailea 2/2, AC, Upper Fl, walk to beach
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,392 | ﺩ.ﺇ 1,484 | ﺩ.ﺇ 1,326 | ﺩ.ﺇ 1,164 | ﺩ.ﺇ 1,058 | ﺩ.ﺇ 1,072 | ﺩ.ﺇ 1,028 | ﺩ.ﺇ 988 | ﺩ.ﺇ 955 | ﺩ.ﺇ 1,010 | ﺩ.ﺇ 1,157 | ﺩ.ﺇ 1,374 |
| 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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