
Holiday 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.

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.

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.

Coastal Dream Oceanfront Condo!
Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

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.

Wailea Couples Retreat, 300 FT To Keawakapu Beach
Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

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.

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.

Ocean Front Vibes Maui
Wake up to panoramic ocean views and end your day with sunsets from your private lanai in this top-floor corner condo at Haleakala Shores. Just steps to Kamaole Beach Park III with easy elevator access. Beautifully remodeled in 2020, fully stocked, and walkable to dining, shops & snorkeling. Light road noise possible. See more videos & details on social at oceanfrontvibesmaui Maui's airport code is OGG

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 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.)

Beach View! MODERN & SPACIOUS! 3 min to Downtown!
HAS CAL KING SIZE BED & BEAUTIFUL NEW KITCHEN AND APPLIANCES!! 3 mins from Downtown Kihei AND in front of the beach with an oceanfront view AND the view of the grand majestic crater Haleakala! This MODERN design suite is perfect for the dream vacation, enjoying the breeze and view of the world famous Kihei Hawaii beach from within the unit!
Popular amenities for Wailea rentals with a pool
House rentals with a pool

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

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

Centrally located and steps to the beach!

Maalaea Kai 307 - Maui Prime Oceanfront

Stunning ocean view, heated pool at home by Wailea

Condo in Kihei

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

CLOUD 9 BEACH HOUSE, Maui Family Owned and Managed
Condo rentals with a pool

Modern Kihei Studio Steps to Beach *Private Lanai*

Maui Banyan G-203 1 Bedroom, Highly Desirable G Bu

Renovated Condo | 3 Min Walk to Toes in the Sand!

Cozy Beach Condo Ocean & Mountain View’s

Romantic Beach Retreat, New King Bed & A+ Wi-fi

Stylish garden oasis nearby Maui's best beaches

As Seen on HGTV I Hale Kai O Kihei 307

“Paradise Views” Menehune Shores, Kihei, Maui
Other holiday rentals with a pool

Tropical Escape to Wailea with Stunning Oceanview

Gem near Keawakapu Beach - Privacy and Ocean Views

Location! Tropical King Suite: Steps to Beach

Kihei Maui Getaway

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

Gorgeous Condo in Wailea Ekahi Village!

Elua 1310 Oceanfront -Family Managed-Remodeled9/25

High-end, On Beach, View Balcony, with Pool & BBQ!
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $601 NZD | $607 NZD | $606 NZD | $538 NZD | $479 NZD | $496 NZD | $471 NZD | $453 NZD | $437 NZD | $444 NZD | $483 NZD | $567 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 |
Quick stats about holiday rentals with a pool in Wailea

Total holiday rentals
Explore 1,800 holiday rentals in Wailea

Nightly prices starting at
Wailea holiday rentals start at $185 NZD per night before taxes and fees

Verified guest reviews
Over 48,150 verified reviews to help you choose

Family-friendly holiday rentals
1,040 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,060 properties have a dedicated workspace

Wi-Fi availability
1,790 of Wailea holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Kapalua Bay Beach
- Wailea Beach
- Maui Ocean Center
- Polo Beach
- Hāmoa Beach
- Ka'anapali Golf Courses
- Old Lahaina Luau
- Big Beach
- Whalers Village
- Ulua Beach
- Maui Arts & Cultural Center
- Peahi
- Haleakala National Park
- Maui Vista Condominium
- Kihei Kai Nani
- Black Rock Beach
- Maui Sunset
- Kahana Beach
- PacWhale Eco-Adventures




