
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 $128Â SGD per night before taxes and fees

Verified guest reviews
Over 49,550 verified reviews to help you choose

Family-friendly holiday rentals
1,050 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
1,040 properties have a dedicated workspace

Wifi availability
1,870 of Wailea holiday rentals include wifi 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 â 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.

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.

Spacious garden oasis near Maui's best beaches!
Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located next to Keawakapu Beach and minutes to Wailea. Our condo is perfectly suited for couples and small families wanting space with stylish comfort in a prime location. Relax on a luxurious king-sized bed, sectional sofa w/ a pull-out sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, with two full bathrooms. Soak in paradise on two lush garden patios!

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 âHoneymoon Houseâ 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!

Ekahi Ocean Studio: Wailea Paradise by the 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.

A.R.A Retreats: Garden Oasis
Nicknamed âGarden Oasisâ for its beautiful little garden walk out off the Lanai onto a beautiful field. While it also has a amazing view of the pacific ocean the beautiful private walkout really set the tone for a relaxing and private oasis. Wailea Ekolu Village is a three-minute drive or 18 minute walk to the beautiful golden sands of Wailea Beach. The Shops at Wailea, Monkeypod Kitchen and so much more just a short walk away!

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

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.

Rustic Upcountry retreat with breathtaking views!
Maui County Permits BBMP2019/0006 & SUP2 2019/0003 This is a BnB not a STRH Owners live on property At this time we are hosting to guests 12 or older. This property is terraced so not optimal for young children. This is a non smoking property. No smoking is allowed. Use of the pool, hot tub and dry sauna are private when reserved with our private calendar. Mahalo!

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

Newly Remodeled Cottage

Go for an Ocean Swim From a Fun Beach Villa

Oceanview Home with Private pool and hot tub

Luxe 3BR Pualei Beach House Retreat

Kula Jewel - Pool, Hot Tub & Awesome Views!

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

Aloha Aku Honu2 Suite â Relax by the Sea in Tranqu

Studio Kaanapali Beach, Sleeps 3, Beach Cabana, Ja
Apartment rentals with a pool

Tropical Escape to Wailea with Stunning Oceanview

Coastal Dream Oceanfront Condo!

Oceanfront Getaway, Brand New, Steps To Beach

Turtle Cove Oceanfront Views Island Sands Resort

Wailea Elua 2007 â Oceanview Luxury Condo

Whales Watch: Luxe Beachfront-180° Ocean views/AC!

Recently Renovated - Comfort with Ocean Views

Aloha Moon - The Honeymoon Hideaway
Other holiday rentals with a pool

Gem near Keawakapu Beach - Privacy and Ocean Views

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

Kihei Maui Getaway

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

Luxurious Wailea Ocean Vistas

Endless Ocean Views - 1bd/2 bath

Ekahi 22C Toes in the Sand in Under 2 Minutes

Wailea Elua: Huge Ocean Views, Pool, AC & Hot Tub
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $485 SGD | $517 SGD | $462 SGD | $410 SGD | $365 SGD | $378 SGD | $358 SGD | $344 SGD | $333 SGD | $352 SGD | $403 SGD | $479 SGD |
| 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
- Rentals with beach access Wailea
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- Luxury rentals Wailea
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- Rentals with a washing machine and dryer Wailea
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- Flat rentals Wailea
- Serviced apartment rentals Wailea
- Beachfront rentals Wailea
- Rentals with a hot tub Wailea
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- Rentals with a sauna Wailea
- Beach apartment rentals Wailea
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- Rentals with an EV charger Wailea
- Rentals with a patio Wailea
- Townhouse rentals Wailea
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- Pet-friendly rentals Wailea
- Rentals with pools Wailea
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Wailea Beach
- Kapalua Bay Beach
- Polo Beach
- Old Lahaina Luau
- Whalers Village
- Black Rock Beach
- Maui Ocean Center
- Big Beach
- Maui Vista Condominium
- HÄmoa Beach
- Black Sand Beach
- Kihei Kai Nani
- Maui Arts & Cultural Center
- Haleakala National Park
- KOA Resort
- PacWhale Eco-Adventures
- Aston Mahana at Kaanapali
- Maui Tropical Plantation
- Nakalele Blowhole





