
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 $186 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, 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

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!

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

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!

*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!

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away
Welcome to Happy Everything! Wailea Ekolu Complex A fun, fully re-modeled, well appointed and comfortable townhome situated on hole 10 of the famous Wailea Blue Golf Course at beautiful Wailea, Maui. Comfortably sleeps 6. Spectacular views of the Ocean and Neighbor Islands. Close to beaches, shopping, restaurants, Wailea Resorts and just a chip shot away from the golf course and brand new Wailea Village shops.

*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

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.)

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

Stunning ocean view Villa, Heated pool, Wailea

Condo in Kihei 2 BR - 2 bath Condo

Go for an Ocean Swim From a Fun Beach Villa

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

Aloha Aku Bamboo Suite – Discover Beachfront Seren

Centrally located and steps to the beach!

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

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

Ekahi 22C Toes in the Sand in Under 2 Minutes

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

Grand Champions 169 Beautiful 3 BR on the Fairway!

Wailea Ekolu Village 2/2 with stunning ocean view!

Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Wailea Gem-Remodeled Ocean View

Coastal Dream Oceanfront Condo!
Other holiday rentals with a pool

Go Golfing from a Peaceful Apartment in a Beach Community

Romantic, Luxury Condo with Spectacular Ocean View

Fairway-front 2BR, pool, walk to Wailea Beach

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

Wailea Ocean View Escape

Luxurious Tropical Retreat with Oceanview

Aloha Moon - The Honeymoon Hideaway

Elua 1310 Oceanfront -Family Managed-Remodeled9/25
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $641 NZD | $683 NZD | $610 NZD | $536 NZD | $487 NZD | $494 NZD | $474 NZD | $455 NZD | $440 NZD | $465 NZD | $533 NZD | $632 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
- 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
- Rentals with beach access Wailea
- Condo rentals Wailea
- Beachfront rentals Wailea
- Serviced apartment rentals Wailea
- Rentals with a kayak Wailea
- Villa rentals Wailea
- Townhouse 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
- Outdoors Maui County
- Art workshops Maui County
- Wildlife Maui County
- Water sports Maui County
- Things to do Hawaii
- Food tours Hawaii
- Outdoors Hawaii
- Water sports Hawaii
- Wildlife Hawaii
- Workouts Hawaii
- Cultural tours Hawaii
- Wellness Hawaii
- Art workshops Hawaii
- Tastings Hawaii
- Landmarks Hawaii
- Things to do United States
- Shopping and fashion United States
- Dining United States
- Museums United States
- Cultural tours United States
- Architecture United States
- Workouts United States
- Art workshops United States
- Wellness United States
- Food tours United States
- Flying United States
- Wildlife United States
- Landmarks United States
- Water sports United States
- Performances United States
- Tastings United States
- Galleries United States
- Cooking United States
- Beauty United States
- Outdoors United States







