
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 1,870 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

Verified guest reviews
Over 49,560 verified reviews to help you choose

Family-friendly vacation rentals
1,050 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,050 properties have a dedicated workspace

Wi-Fi availability
1,870 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.

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
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!

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.

Luxurious Condo in South Kihei
Beautiful fully renovated condo. Located in Maui Kamaole, the best resort complex in South Kihei. Walking distance to the beach, shops, restaurants and bars. This condo has everything a renter needs during vacation. Full kitchen, washer and dryer, beach gear, towels, bedding and more. The complex has two swimming pools, barbecues, tennis courts and outdoor picnic areas. This location is next to fun activities such as swimming, snorkeling, diving, surfing, kayaking, fishing, and more.

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.

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.

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.)
Popular amenities for Wailea rentals with a pool
House rentals with a pool

Kihei 533- OceanView, 20 min walk to stores/food

Hale Luana 4B House pool/spa/AC, STRH 2023/00001

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

Oceanview Townhome • Modern • 2 Min Walk to Beach!

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Stunning ocean view, heated pool at home by Wailea

Makena Surf B305 Beachfront Resort
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

Oceanview condo at Ulua Beach w/ lanai

Luxury Vacationing Modern Condo Aug Special $385

Last Minute Deal! Wailea Condo Oceanfront Complex

Grand Champions 169 Beautiful 3 BR on the Fairway!

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

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

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

Ocean View! Pool! Ho'okipa @ Wailea Ekolu Village!

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

Aloha Moon - The Honeymoon Hideaway

Luxe 2bed Wailea, 5-min walk to beach, ocean view,

Wailea Hidden Gem

Steps to Ocean View Pool, 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 1,175 | ﺩ.ﺇ 1,047 | ﺩ.ﺇ 1,083 | 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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