Vacation rentals with a pool in Wailea, Wailea-Makena

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Popular amenities for Wailea, Wailea-Makena rentals with a pool

House rentals with a pool

Guest favorite
A clear view of the private pool is presented, surrounded by lush greenery and palm trees. An orange umbrella offers shade over poolside loungers, enhancing the outdoor relaxation space. The ocean and mountains create a scenic backdrop under a bright blue sky.
Home in Kihei
4.94 out of 5 average rating, 32 reviews

Oceanview Home with Private pool and hot tub

BlainRating, 5 stars4 weeks ago
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.
Guest favorite
A wooden dining table with eight chairs is set on a balcony that overlooks the ocean. Palm trees sway gently in the breeze, and the tranquil waters are visible in the distance, accompanied by a scenic backdrop of mountains and a colorful evening sky.
Home in Wailuku
4.97 out of 5 average rating, 30 reviews

Maalaea Kai 307 - Maui Prime Oceanfront

HayleyRating, 5 stars2 weeks ago
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
Top guest favorite
A refreshing swimming pool is surrounded by lounge chairs, set among tropical palm trees. The water's surface reflects the nearby buildings and sky, creating a serene atmosphere. The pool area is designed for relaxation and enjoyment.
Home in Kihei
4.98 out of 5 average rating, 57 reviews

Centrally located and steps to the beach!

DonnyRating, 5 stars1 week ago
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!
Guest favorite
An outdoor table features a decorative bowl of fresh fruit, including bananas and a pineapple, set against a breathtaking ocean view. Lush palms frame the scene, while the blue waters of the ocean stretch to the horizon with mountains visible in the distance.
Home in Lahaina
5 out of 5 average rating, 5 reviews

Best Studio Ocean Views at Honua Kai -Hokulani 719

TomRating, 5 stars1 month ago
We, a small family, recently stayed in Kaanapali Maui and couldn’t have been happier with the experience. From the moment we arrived, everything exceeded our expectations. The unit was spotless, beautifully decorated, and fully stocked with all the essentials — from kitchenware including a blender and all of the beach necessities. After going around the island and picking up some fresh fruit, it was a nice afternoon treat to be able to make our own smoothies! Highly recommend it. The view from the lanai (balcony) was absolutely stunning. Every morning we enjoyed our coffee while watching the sunrise over the ocean, and in the evenings we were treated to the most spectacular sunsets. The sound of the waves crashing was the perfect background to a truly relaxing vacation. The location was ideal just a short walk to the beach, shops, and great local restaurants. We loved being close to snorkeling spots and whale watching opportunities. The complex also had a pool, hot tub, and BBQ grill
Top guest favorite
A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.
Home in Kula
4.92 out of 5 average rating, 347 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pi'ikeaRating, 5 stars4 days ago
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!
Guest favorite
A patio area features a light-colored chair and a round table, overlooking a grassy lawn that leads to the ocean. A tree with twisted branches is visible in the background, along with several upright, leafy plants. The inviting blue water of a pool can be seen beneath the sunlit sky.
Home in Kihei
4.82 out of 5 average rating, 11 reviews

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

MichaelRating, 5 stars4 weeks ago
Absolutely incredible stay. The suite was everything we needed and more. The beachfront porch was peaceful and private. There was gear for every beach activity you could ever want to do and it was so fun. We cannot wait to come back!
Superhost
A panoramic view of a sandy beach is offered, with gentle waves lapping at the shore. Clear turquoise waters meet a bright blue sky, dotted with fluffy white clouds. Lush greenery fringes the beach, enhancing the natural beauty of the idyllic setting.
Home in Kaanapali
4.88 out of 5 average rating, 109 reviews

#1 Kaanapali Beach Modern Condo C101 Maui Eldorado

JesseRating, 5 stars9 months ago
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!!!
Top guest favorite
Home in Lahaina
4.94 out of 5 average rating, 581 reviews

Maui direct ocean front . Super private

JulietteRating, 5 stars1 week ago
We absolutely LOVED our stay here. Originally, we were only supposed to stay 4 nights, but we loved it so much that we extended our stay 2 more nights! Jay made it so easy to extend our stay and make us feel welcomed. The location was close to various beaches and restaurants, yet it still felt private. It was calm, peaceful, and exactly what we wanted. The view was absolutely breathtaking and every night we slept with the slider open to hear the waves. We even saw turtles from the balcony!

Condo rentals with a pool

Guest favorite
A modern kitchen is visible, featuring light cabinetry, stainless steel appliances, and a tile backsplash. A round dining table is surrounded by cushioned chairs, while bar stools are positioned at the countertop. The open layout reveals sliding glass doors leading to a covered lanai with tropical views.
Condo in Kihei
4.95 out of 5 average rating, 65 reviews

Gem near Keawakapu Beach - Privacy and Ocean Views

DrewRating, 5 stars1 month ago
Amazing spot and stay
Guest favorite
A scenic outdoor space features a table set for dining, overlooking a vibrant green lawn and an expansive ocean view. Nearby, comfortable seating invites relaxation. The kitchen area is equipped with modern appliances, while a stylish clock adorns the wall.
Condo in Wailuku
4.96 out of 5 average rating, 109 reviews

Oceanfront Getaway, Brand New, Steps To Beach

RikkaRating, 5 stars1 month ago
Gorgeous spot! The location is fabulous, close to fun restaurants and the harbor, but it still felt private. We would 100% stay here again!
Top guest favorite
Condo in Kihei
4.96 out of 5 average rating, 197 reviews

Spectacular Ocean Front 1bd at Menehune Shores

JasonRating, 5 stars2 weeks ago
A gem in Kihea High end remodeled kitchen and bathroom with thoughtful amenities / awesome host / beautiful full ocean view / easy parking and close to elevator. Winner!!
Guest favorite
A spacious bedroom features a comfortable bed with a light-colored, art-inspired bedspread. A wooden dresser stands opposite a corner television. Large windows provide views of the surrounding tropical landscape, while soft lighting enhances the serene atmosphere.
Condo in Wailea
4.92 out of 5 average rating, 77 reviews

Wailea Elua 1101 - Beachfront Section - Ocean View

LisaRating, 5 stars2 months ago
Beautiful location and setting. Very well organized and equipped. Especially nice bathroom and kitchen. She was also very thoughtful on the smaller details too, such as hooks to hang towels, clothes line in tub, non scented cleaning products . Also Very nice setup on the lanai
Top guest favorite
A dining setting is displayed on a balcony with a platter of fresh fruit, accompanied by glasses and a bottle of olive oil. Lush greenery and tropical plants surround the view, complemented by a bright blue sky and scattered clouds.
Condo in Kihei
4.95 out of 5 average rating, 155 reviews

Newly Renovated Corner Unit w/ View at Maui Vista

AnnRating, 5 starstoday
Last minute booking for us and man did we get lucky finding this unit available! Nothing negative to say about it and sad to leave. We’ll be back!!
Guest favorite
A dining area features a circular bar with four woven stools and multi-colored pendant lights overhead. The textured orange walls and bamboo ceiling create a warm ambiance. A small desk with a chair is visible against the wall, along with decorative artwork and shelving.
Condo in Wailea
4.94 out of 5 average rating, 52 reviews

Gorgeous Condo in Wailea Ekahi Village!

JamieRating, 5 stars1 month ago
We had the most lovely stay at this resort! Jordan’s place is exactly like the photos and is beautifully private. While you cannot exactly see the ocean from the condo—the trees and foliage has now grown too high—we loved opening the late sliding doors and listing to the ocean whenever we were at the home. The kitchen was wonderfully stocked and we loved having access to all of the coffee and appliances supplied. The walk to the beach is easy and the pool has all the amenities you can imagine. There a many places to eat, grab coffee, and activities in a close drive to the location. We did see a singular cockroach inside near where a screened window was ajar. Jordan was very responsive when we message him about this. We had absolutely no concerns about the cleanliness of the condo throughout the rest of our stay. Overall, this was a tropical luxury stay perfect for a honeymoon filled with privacy and easy access to all things one could want in Maui.
Guest favorite
A clear view of a heated swimming pool is presented, surrounded by a landscaped area featuring lush tropical plants. Sun loungers with green umbrellas are positioned around the pool, offering shaded seating. The pool area is enclosed by a decorative fence and is visible through nearby foliage.
Condo in Wailea-Makena
4.96 out of 5 average rating, 605 reviews

Wailea Resort studio suite

ShelleeRating, 5 stars1 week ago
The place is excellent. I recommend it. The location is magnificent. We will definitely come back.
Top guest favorite
The studio features a spacious bed adorned with neutral-toned bedding. Light wood furniture complements the decor. Floor-to-ceiling glass doors open to a lanai with outdoor seating, framed by palm trees, offering a stunning view of the ocean.
Condo in Kihei
5 out of 5 average rating, 5 reviews

Wailea Ekahi Village | 12B

EddieRating, 5 stars7 months ago
Great location with a view of the water though not necessarily the beach. The place has recently been updated and would be great for a couple. We liked the shaded patio and the cold AC. Ice machine worked well too in the fridge though as this is a studio I recommend you turn it off before going to bed. We didn’t cook at all but everything was there (except salt and pepper). Beach chairs were also provided and towels of course. Washer and dryer were newer and clean. We didn’ use them much. Lighting in the unit was nice, with dimmers throughout. This was useful when waking up or going to bed. A nice comfort addition that we appreciated. It’s a 4 minute walk to the beach and the pavilion. We went in October and the pool and beach were not too busy and the people were respectful. It was quiet and peaceful. The pool house is a great location to have a coffee or a beer at and watch sunset or listen to the waves. We would recommend this place. Great value and location.

Quick stats about vacation rentals with a pool in Wailea, Wailea-Makena

  • Total rentals

    1.8K properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    45K reviews

  • Family-friendly rentals

    1K properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    1K properties have a dedicated workspace

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