
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 $154 AUD 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

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!

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- 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!

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.

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!

Wailea Ekolu Village 2/2 with stunning ocean view!
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

*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

Last Minute Deal! Wailea Condo Oceanfront Complex
Step into your own private tropical oasis in this fabulous Wailea condo! This adorable 792 square foot, ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This lavish condo boasts an open and airy living space you will love with AC throughout. Relax on the remarkable lanais with a table with seating for four.

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

Stunning ocean view Villa, Heated pool, Wailea

Go for an Ocean Swim From a Fun Beach Villa

Condo in Kihei 2 BR - 2 bath Condo

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

Aloha Aku Bamboo Suite – Discover Beachfront Seren

South Maui • Pool • Hot Tubs• Beach • Ocean View

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

Kihei 533- OceanView, 5 min drive to stores/food
Condo rentals with a pool

Modern Renovated Palms at Wailea Condo!

Ekahi Ocean Studio: Wailea Paradise by the Beach

Spacious 3bd on Golf Course I Grand Champions 105

Wailea Gem-Remodeled Ocean View

Ekahi 22C Toes in the Sand in Under 2 Minutes

Grand Champions 169 Beautiful 3 BR on the Fairway!

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Luxury Condo w/wide Ocean View (Palms at Wailea)!
Other holiday rentals with a pool

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Go Golfing from a Peaceful Apartment in a Beach Community

Luxurious Tropical Retreat with Oceanview

Wailea Ocean View Escape

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

Aloha Moon - The Honeymoon Hideaway

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

Beach Front Wailea, Full Ocean View A/C, ELUA102
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $529 AUD | $564 AUD | $504 AUD | $442 AUD | $402 AUD | $408 AUD | $391 AUD | $375 AUD | $363 AUD | $384 AUD | $440 AUD | $522 AUD |
| 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 |
Destinations to explore
- Apartment rentals Wailea
- Rentals with a hot tub Wailea
- Beach condo rentals Wailea
- Hotel rooms Wailea
- Pet-friendly rentals Wailea
- Family-friendly rentals Wailea
- Waterfront rentals Wailea
- Rentals with a sauna Wailea
- Luxury rentals Wailea
- House rentals Wailea
- Townhouse rentals Wailea
- Rentals with beach access Wailea
- Condo rentals Wailea
- Beachfront rentals Wailea
- Serviced apartment rentals Wailea
- Rentals with a kayak Wailea
- Villa rentals Wailea
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Maui
- Kaanapali Beach
- Lahaina Beach
- Whalers Village
- Wailea Beach
- Maui Vista Condominium
- Polo Beach
- Honolua Bay
- Kapalua Bay Beach
- Big Beach
- Black Rock Beach
- Black Sand Beach
- Haleakala National Park
- Old Lahaina Luau
- Ka'anapali Golf Courses
- Kihei Kai Nani
- KOA Resort
- Kamaole Beach Park II
- Aston Mahana at Kaanapali
- Maui Arts & Cultural Center
- Maui Ocean Center
- PacWhale Eco-Adventures
- Hāmoa Beach
- Kahana Beach
- Things to do Wailea
- Water sports Wailea
- Things to do Maui County
- Cultural tours Maui County
- Water sports Maui County
- Outdoors Maui County
- Art workshops Maui County
- Wildlife Maui County
- Things to do Hawaii
- Food tours Hawaii
- Outdoors Hawaii
- Water sports Hawaii
- Wildlife Hawaii
- Workouts Hawaii
- Cultural tours Hawaii
- Wellness Hawaii
- Landmarks Hawaii
- Art workshops Hawaii
- Tastings Hawaii
- Things to do United States
- Dining United States
- Museums United States
- Shopping and fashion United States
- Cultural tours United States
- Architecture United States
- Workouts United States
- Art workshops United States
- Flying United States
- Wellness United States
- Food tours United States
- Wildlife United States
- Water sports United States
- Landmarks United States
- Performances United States
- Tastings United States
- Galleries United States
- Cooking United States
- Beauty United States
- Outdoors United States







