
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 1,870 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $176 NZD per night before taxes and fees

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

Family-friendly holiday rentals
1,050 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

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

Wi-Fi availability
1,870 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 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.

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

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

Go for an Ocean Swim From a Fun Beach Villa

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

Oceanview Home with Private pool and hot tub

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Luxe 3BR Pualei Beach House Retreat
Condo rentals with a pool

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

Grand Champions - King Bed - Close to Wailea Beach

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

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Oceanfront Getaway, Brand New, Steps To Beach

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

Luxury Vacationing Modern Condo Aug Special $385

Last Minute Deal! Wailea Condo Oceanfront Complex
Other holiday rentals with a pool

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

Elevated Panoramic Ocean Views

Oceanview condo at Ulua Beach w/ lanai

Gorgeous Condo in Wailea Ekahi Village!

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

Aloha Moon - The Honeymoon Hideaway

Steps to Ocean View Pool, Walk to Beach

Amazing location! Chic Maui Getaway (ground floor)
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $668 NZD | $712 NZD | $636 NZD | $564 NZD | $502 NZD | $520 NZD | $493 NZD | $474 NZD | $458 NZD | $485 NZD | $555 NZD | $659 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
- Kaanapali Beach
- Lahaina Beach
- Whalers Village
- Wailea Beach
- Polo Beach
- Kapalua Bay Beach
- Honolua Bay
- Maui Vista Condominium
- Old Lahaina Luau
- Big Beach
- Black Rock Beach
- Ka'anapali Golf Courses
- Black Sand Beach
- Haleakala National Park
- Kihei Kai Nani
- Kamaole Beach Park II
- Maui Ocean Center
- Maui Arts & Cultural Center
- Hāmoa Beach
- KOA Resort
- PacWhale Eco-Adventures
- Peahi
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