
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 $187 NZD 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, Wi-Fi 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
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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!
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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
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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.
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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, welcome to the beach! If you enjoy Wailea's 5 star resorts right down the beach, 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 PM in Maui, Tracy O'Reilly to take amazing care of you!
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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.
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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!
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*Last Minute Deal*Luxurious*2b/2b OceanView Wailea
This ground floor 1071 square foot unit is situated just above the 11th fairway of the Wailea Blue Course. The living room and master bedroom have private lanais that step out to a relaxing open lawn with sweeping ocean views. Features include AC throughout the property, bamboo floors throughout, brand new tile in the master bathroom, granite counter tops, and cherry cabinets. Tastefully decorated this spacious condo truly has everything you will need!
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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.
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*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
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Grand Champions 169 Beautiful 3 BR on the Fairway!
Prime Wailea location! Enjoy stunning ocean and fairway views from this rare 3-bedroom, ground-floor unit with Split System Air Conditioning in every room. Spacious 1,698 sq ft layout and wrap-around lanai. Walk to Wailea Tennis Club, Blue Golf Course, luxury hotels, Shops at Wailea, restaurants, and beaches just ¼ mile away. Experience luxury and comfort in the heart of Wailea!
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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.)
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Popular amenities for Wailea rentals with a pool
House rentals with a pool

Stunning ocean view Villa, Heated pool, Wailea
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Condo in Kihei 2 BR - 2 bath Condo
ValueFamilyComfort

Go for an Ocean Swim From a Fun Beach Villa
FamilyValueIndoor spaces

3B2B w/HotTub FamilyComfort HawaiianaCharm Central
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Oceanview Home with Private pool and hot tub
ValueLocationHospitality

Kihei 533- OceanView, 5 min drive to stores/food
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South Maui • Pool • Hot Tubs• Beach • Ocean View
LocationKitchenAccuracy

Oceanfront Stunner w/ Cruiser Bikes & Pickleball
LocationFamilyHospitality
Condo rentals with a pool

Spacious 3bd on Golf Course I Grand Champions 105
ValueFamilyCheckout

Wailea Gem-Remodeled Ocean View
LocationValueKitchen

Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool
LocationValueBarbecue

Ekahi 22C Toes in the Sand in Under 2 Minutes
LocationValueParking

3BR spacious Condo with Ocean View in top location
LocationValueLong stay

Luxury Vacationing Modern Condo Sept Specials $275
ValueFamilyNearby

Large 1BR, Palms at Wailea, Pool, Walk to Beach
LocationFamilyAccuracy

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC
LocationFamilyView
Other holiday rentals with a pool

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
FamilyValueBarbecue

Wailea Villa with Oceanfront Pool
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Go Golfing from a Peaceful Apartment in a Beach Community
ValueLocationOutdoor spaces

Luxurious Tropical Retreat with Oceanview
FamilyValueAccuracy

Beach Front Luxury in Makena
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Aloha Moon - The Honeymoon Hideaway
LocationComfortIndoor spaces

Wailea Ocean View Escape
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Elua 1310 Oceanfront -Family Managed-Remodeled9/25
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When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $645 NZD | $687 NZD | $614 NZD | $539 NZD | $490 NZD | $497 NZD | $476 NZD | $457 NZD | $442 NZD | $468 NZD | $536 NZD | $636 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 |
Destinations to explore
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- Rentals with pools Maui County
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- Maui
- Kaanapali Beach
- Lahaina Beach
- Whalers Village
- Maui Vista Condominium
- Wailea Beach
- 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 Ocean Center
- Maui Arts & Cultural Center
- PacWhale Eco-Adventures
- Hāmoa Beach
- Kahana Beach
- Things to do Wailea
- Water sports Wailea
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