
Holiday rentals with a pool in Maalaea
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Maalaea
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Maalaea rentals with a pool
House rentals with a pool

Oceanview Home with Private pool and hot tub
Excellent location, beautiful view, house was well stocked and the communication was terrific from both homeowner Steve alongside the property manager Walker. Speedy responses to any questions we had. Our family had a blast in Maui and would rent from Steve again. Steve also had great recommendations for local eating alongside a picturesque sunset spot. For our family of five, Steve's home was a winner.

Centrally located and steps to the beach!
Mike and Ashley were incredibly amazing and helpful. They really went above and beyond for us. Really appreciated the special touch they left us for our anniversary and will recommend them to and friends and family that visit Maui. Their place is beautiful and it looks even better in pictures. It is perfectly homey, private, and quiet, which was very nice but also close to the beach with a three minute walk couldn’t recommend staying with Mike and Ashley more. Thanks for helping make our anniversary trip special!

Maalaea Kai 307 - Maui Prime Oceanfront
We had the best time at this condo! It was quiet and clean and was exactly what we were hoping for! Don was incredibly responsive when I had questions or needed recommendations to rent baby gear! We had a great time and hope to Come back again

The Artists House
Jordanne's house was was perfect. Open and comfortable. Fully equipped kitchen. fenced in -making it feel private even out doors. good parking area. waking distance to restaurants or really anywhere in town.

Stunning ocean view, heated pool at home by Wailea
Sandra was very nice. The house was clean and exactly what we expected. She offered great suggestions when we asked for recommendations on places to visit. I would definitely recommend staying here.

Kula Jewel - Pool, Hot Tub & Awesome Views!
Pamela was a fantastic host. She was responsive and so friendly. She truly loved the area and making guests feel at home. The space itself was such a dream. It had everything we needed and then some. The location and views were stunning. we sat on the porch almost every night just to take it all in. We loved staying at the Kula Jewel and would stay here again!

#1 Kaanapali Beach Modern Condo C101 Maui Eldorado
Very beautiful location to stay at in Kaanapali! Has a gym with just enough equipment, grills and pools, and an included private golf cart upon request to the beautiful Kaanapali beaches. Also towel service available until 5:30pm! So wonderful! AC and other amenities were great, did not have a single issue or complaint my entire stay here. Had a great time here, will hopefully be back!!!

Waterfall House with Ocean Views in Haiku, Maui
Wow, what an amazing stay! The villa was absolutely stunning, with breathtaking views of the ocean, waterfall, and mountains. The private pool and hot tub were perfect spots to relax and soak in the scenery. We were delighted to discover a charming hidden nook upstairs overlooking the pool a delightful surprise! The bedroom was gorgeous, and while the outdoor shower took a moment to get used to, it turned out to be such a unique experience that we thoroughly enjoyed. Being nestled in a garden setting, we did encounter a few critters like cockroaches, spiders, lizards, and mosquito eaters, especially since we loved keeping the doors open to feel the refreshing breeze. It didn’t bother us much, though a quick sweep of some webs inside would have been appreciated. Now this is quite a drive from any towns/ restaurants so prepare in advance and stop somehwere before check in! Overall, the place was very clean, and our stay was incredibly peaceful. The tranquil garden and serene property mad
Condo rentals with a pool

Dolphin Penthouse at Milowai
We had a wonderful time staying here. The location is perfect if you plan on exploring the island. It's centrally located with easy access to the main road to other parts of the island. The location is beautiful with great views of the ocean and harbor. It is windier in that harbor so hold on to your hats. The unit was easy to access, thanks to a dedicated elevator, clean, had lots of towels, and full of useful beach items (i.e. coolers, chairs, ice packs in the freezer, etc.) Our family would definitely stay here again!

Cozy Beach Condo Ocean & Mountain View’s
Cheryl’s place was beautifully decorated and so very clean. We loved the view from the balcony and the sound of the waves. We saw some spectacular sunsets too. The furniture and bed was very comfortable. She supplied us with all you could need. We enjoyed the use of the washer and dryer too. The pool was very clean and we enjoyed walks on the beach several times a day. Everyone at the complex was very friendly and wonderful to talk too. Thank you for allowing us to stay in your lovely home. We will treasure the memories we made there.

Hot Deals! Limited Availability- Maui Getaway
Kalea’s was alway available to answer questions very quickly. The condo was very well taken care of and had everything we needed. Loved the location and area much different than Kanapali as it’s much closer to other areas of the Island to explore. The lights and fan can be tricky at times but remember your own Hawaiian time. Mahalo

Maalaea Kai 311 - Direct Ocean Front, Split AC
This is a great condo. It is centrally located making it perfect for first-time visitors to Maui who want to explore most of the island. You will need a car, as there are limited offerings within walking distance. We loved morning coffee on the Lanai while watching whales frolic in the bay. The unit was clean, comfortable, and well-stocked with necessities. We found beach chairs and snorkeling equipment in the closet and there were even a few spices and other extras in the kitchen. Vacation Maui was an excellent host. They always responded to emails within a few minutes and sent help within an hour of our reporting an issue with the TV. We'll be back!

Maalaea 5star Oceanfront Milowai- just remodeled
Great place to stay, beautiful view of the ocean and the heated pool is a great amenity. Had everything we needed to be able to cook breakfast. One small improvement could be the size of the hot water heater, because the hot water ran low after about 12 minutes. Other than that we loved the place and would definitely stay here next time we are in Maui. Highly recommended!!

Oceanfront Spectacular Condo, New Listing
Had a wonderful stay here. Has a beautiful view of the ocean and walkable distance to the beach. We will definitely be back!

Aloha Love! LUANA MOANA Signature Oceanfront Maui
The best condo I have ever stayed in. Top quality furnisher and decor. The beds were amazingly comfortable. The best part of our trip to Maui was waking up and drinking coffee while watching a beautiful sunrise and then coming home to a glass of wine while watching sea turtles constantly passing by. Love the stay. It is an amazing private place to just relax and forget about everything else. Denise responded to my questions within 20 mins. every time. Have nothing negative to say about this place nor about Denice. I truly doubt I can be lucky enough to find another listing like this one. Definitely recommend. Already planning on coming back. Thank you Denice! You are one of a kind!❤️

Oceanfront Panorama: Newly Refreshed 3rd Floor Gem
We enjoyed our stay at this condo. Wenqi was extremely responsive and helped answer any questions. The Airbnb itself was very clean upon arrival, the views were great, and it was in a good location for daily adventures. It was a great central point which made traveling to any area of Maui manageable. This particular area had consistently high winds which created a nice breeze on the lanai. We saw upwards of 20+ sea turtles swimming right in front of the condo during our stay. The A/C units and fan were strong. Overall, this was a great stay.
Quick stats about holiday rentals with a pool in Maalaea
Total rentals
520 properties
Nightly prices starting at
$134 NZD before taxes and fees
Total number of reviews
26K reviews
Family-friendly rentals
180 properties are a good fit for families
Rentals with dedicated workspaces
280 properties have a dedicated workspace
Wi-Fi availability
520 properties include access to Wi-Fi
Destinations to explore
- Fitness-friendly rentals Maalaea
- Rentals with an accessible height bed Maalaea
- Apartment rentals Maalaea
- Condo rentals Maalaea
- Rentals with a patio Maalaea
- Townhouse rentals Maalaea
- Family-friendly rentals Maalaea
- Rentals with a washing machine and dryer Maalaea
- Beachfront rentals Maalaea
- Rentals with beach access Maalaea
- Rentals with a sauna Maalaea
- Waterfront rentals Maalaea
- Rentals with outdoor seating Maalaea
- Rentals with a hot tub Maalaea
- Kid-friendly rentals Maalaea
- Rentals with pools Maui County
- Rentals with pools Hawaii
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Kaipukaihina
- Laie
- Honolua Bay
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Wailea Beach
- Manele Golf Course
- Hāmoa Beach
- Oneloa Beach
- Maui Ocean Center
- Mokulau Beach
- Wailea Golf Club
- Palauea Beach
- Old Lahaina Luau
- Kāhili
- Wailau Valley
- Papaloa Beach
- Kaulahao Beach