
Vacation rentals with a pool in Wailea
Find and book unique homes with a pool on Airbnb
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! Summer 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, right 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 Mgr. in Maui, Tracy O'Reilly to take amazing care of you!

Maui's Best - Wailea Ekahi 47A
Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

Oceanfront Mana Kai Penthouse..Heaven meets Earth!
Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and bi-coastal oceanfront views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (806) and includes two-bedroom suites on the world-famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent snorkeling, body surfing, whale watching, scuba diving, paddle boarding, and kayaking literally at your doorstep

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 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.

A.R.A Retreats: Big Blue Pacific
Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing 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 and when the sun goes down, watch your favorite shows on on our smart tvs!

Upscale and Elegant Vistas
Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled in September of 2021, 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!

Oceanfront Getaway, Brand New, Steps To Beach
Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.

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

*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
Popular amenities for Wailea rentals with a pool
House rentals with a pool

Kihei 533- A/C, Free Parking, and WiFi

Gorgeous Views! - Kihei Surfside #109

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

Walk to the Beach, Balcony w/ View, Communal Pool

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Kamaole Sands FRONT ROW OCEAN Unit 116

Aloha Aku Bamboo Suite – Discover Beachfront Seren
Condo rentals with a pool

Gorgeous Condo in Wailea Ekahi Village!

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

Stunning Ocean Views -November Specials $185

Sugar Beach Resort Beach / Ocean Front Unit 426

☀Very Desirable South Kihei | Enlivening Getaway ☀

Modern Renovated Palms at Wailea Condo!

Grand Champions 169 Beautiful 3 BR on the Fairway!

Beachfront Maui Oasis- Fully Remodeled, Beautiful
Other vacation rentals with a pool

Luxury Oceanview Wailea Retreat with Sunset Views

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

Fabulous Ocean Views - Ho'okipa at Wailea Ekolu!

Wailea Elua 1101 - Beachfront Section - Ocean View

Best Location, Panoramic Ocean View Remodel WE1508

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Modern and Luxurious Property at Polo Beach

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 | ﺩ.ﺇ1,311 | ﺩ.ﺇ1,326 | ﺩ.ﺇ1,322 | ﺩ.ﺇ1,175 | ﺩ.ﺇ1,047 | ﺩ.ﺇ1,083 | ﺩ.ﺇ1,083 | ﺩ.ﺇ1,003 | ﺩ.ﺇ955 | ﺩ.ﺇ973 | ﺩ.ﺇ1,054 | ﺩ.ﺇ1,238 | 
| 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 with a pool in Wailea
 - Total vacation rentals- Explore 1,580 vacation rentals in Wailea 
 - Nightly prices starting at- Wailea vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees 
 - Verified guest reviews- Over 46,890 verified reviews to help you choose 
 - Family-friendly vacation rentals- 900 properties offer extra space & kid-friendly amenities 
 - Pet-friendly vacation rentals- Find 10 rentals that welcome pets 
 - Rentals with dedicated workspaces- 850 properties have a dedicated workspace 
 - Wi-Fi availability- 1,570 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! 
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