Holiday rentals with a pool in Wailea-Makena

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Popular amenities for Wailea-Makena rentals with a pool

House rentals with a pool

Guest favourite
Home in Lahaina
5 out of 5 average rating, 6 reviews

Brand Newly Remodeled Luxury 2 BR - Kapalua Golf

StephanieRating, 5 stars3 months ago
We loved our stay at this place. The location in Kapalua and the beautiful grounds were unbeatable. There were just a few hiccups initially but they were resolved within 24 hours. Firstly the AC was not working which was hard with 2 young kids and the warm climate. The company was going to send a tech but he wouldn't be in until the next day so luckily my husband was able to fix it in the meantime. Secondly, we had ordered and paid for a pack and play which was supposed to be in the unit on arrival but did not arrive until 9 pm (already after my child needed to go to sleep). I was told this would be refunded by the lovely manager Scott who came to deliver the pack and play. He was also kind enough to lend us his binoculars for whale watching :) The unit itself is beautiful. Very new and clean and exactly as the photos. We would 100% rebook if staying back in Kapalua, Maui.
Guest favourite
Home in Kihei
4.96 out of 5 average rating, 24 reviews

Luana Kai C209

MireeRating, 5 stars3 weeks ago
Leslie’s place was a gem! If we are ever back to Maui, we would love to stay here again. The location was perfect for snorkeling, and Leslie’s local recommendations were awesome. The check in and out was very easy to follow. The place has beach chairs, boogie board, beach towels and so many more! We also appreciated the hot jacuzzi in the condo and the beach in the front.
Guest favourite
Home in Kihei
4.94 out of 5 average rating, 31 reviews

Oceanview Home with Private pool and hot tub

JennieRating, 5 stars1 month ago
Steve’s place is great and he is an excellent communicator and very invested in ensuring his guests have a great experience. We loved watching the sunset from the deck and the pool and game room were both so fun for our family. Lots of pantry staples on hand as well as some yummy snacks to greet us. The location is private and peaceful and we loved all the beautiful Hawaiian plants and geckos in the yard. Thanks for a great stay!
Guest favourite
Home in Wailuku
4.97 out of 5 average rating, 30 reviews

Maalaea Kai 307 - Maui Prime Oceanfront

HayleyRating, 5 stars1 week 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 favourite
Home in Kula
4.92 out of 5 average rating, 343 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

ReaganRating, 5 stars1 week ago
The new Kula Jewel is an amazing property with an incredible panoramic view of the island with an exceptionally cozy and spacious interior and a lovely porch. The main living area and kitchen were beautifully designed and highly functional which made us feel at home. The master bedrooom was so relaxing with a great mattress and was made even better when opening the windows at night and listening to the gentle rhythm of raindrops falling. The master bathroom design was brilliant. Pamela and the property manager Jim made sure our young daughter was well taken care of by setting up a comfortable pullout twin size bed in the Master so she could stay in the same room with us and not be scared. The other two bedrooms were spacious and well equipped, we just didnt need to use them. Pamela is the best host we have ever had the pleasure of working with on Airbnb. Her commnication was superb, recommendations for what to do and where to eat on the island spot on, and we cant wait to come back!
Guest favourite
Home in Kihei
4.82 out of 5 average rating, 11 reviews

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu

MichaelRating, 5 stars2 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
Home in Kaanapali
4.88 out of 5 average rating, 109 reviews

#1 Kaanapali Beach Modern Condo C101 Maui Eldorado

JesseRating, 5 stars8 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 favourite
Home in Lahaina
4.94 out of 5 average rating, 579 reviews

Maui direct ocean front . Super private

DaniellaRating, 5 stars3 weeks ago
The view was absolutely beautiful! This was a very peaceful and private oasis in Maui! I would love to come back and stay here again. The place was clean and the amenities were super nice! I stayed here with my boyfriend and it was the perfect space for us two.

Apartment rentals with a pool

Top guest favourite
Apartment in Wailea-Makena
5 out of 5 average rating, 84 reviews

Wailea Surf Shack: Golf, shopping & beaches!

DeborahRating, 5 stars5 days ago
We thoroughly enjoyed our stay! Great communication and instructions with the host! This unit includes everything you need to enjoy your vacation. My husband particularly liked how everything is well labeled :) This is a great location in Maui…close to beach, golf, shopping, restaurants and more! If we could give it more than 5 stars we would. 100% would stay here again!
Guest favourite
Apartment 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
Top guest favourite
Apartment in Kihei
5 out of 5 average rating, 56 reviews

Ohe'o || Wailea Ekahi Unit 28B || Lowered Rates

JeanRating, 5 stars1 month ago
This condo worked well for us. We were traveling with family who had rented other units in this complex. We liked ours best, due to its updated/well-stocked kitchen, paper/toiletry supplies, two bathrooms, wide lanai, convenient parking, comfortable bed, generous square footage, and beach/snorkeling gear. We enjoyed the absolute quiet (this unit is away from the road), but found lots to do, especially in the excellent main pool area and on the relatively-wide beach, with easy snorkeling and walking options (Wailea luxury resorts to the left; natural beauty to the right). If you're looking for family-friendly green space and don't mind a longish walk to the main pool/beach, consider this property. If you have mobility issues that make walking difficult or need onsite restaurants, high-end furnishings and spa-like baths, you might not be happy here. We found it very comfortable. It was evident to us that Jazlyn has put a lot of thought into meeting her guests' needs. Highly recommend.
Guest favourite
Apartment in Kihei
4.98 out of 5 average rating, 86 reviews

Maui Retreat Ekahi 50F -All YOU Need! 10% OFF WEEK

JenniferRating, 5 stars4 weeks ago
We’ve stayed in this complex a few times before and keep coming back because we always love it! Debra’s place is one of the best equipped ones we’ve stayed in! Kitchen made it easy to cook and beach equipment was appreciated. Being a second floor unit with high ceilings means it takes a while to cool down. Only one thing that could be improved: If you’re a person who likes to sleep with the ceiling fan on, the bedroom has one, but it really needs to be replaced — it’s very noisy (the one in the living room is silent in comparison). After a couple of nights with the noisy fan, we chose to keep it off and were reasonably comfortable with the AC unit. Otherwise we would stay again!
Top guest favourite
Apartment in Kihei
4.96 out of 5 average rating, 76 reviews

Modern Renovated Palms at Wailea Condo!

FranziskaRating, 5 stars2 weeks ago
The condo featured everything we could hope for to enjoy the beaches and our vacation with a baby including full kitchen equipment, various baby chairs, toys, a bathtub and beach equipment (umbrellas, beach chairs, boogie boards, beachwaggon...). We really liked the interior design, it made us feel more at home.
Top guest favourite
Apartment in Wailea
4.97 out of 5 average rating, 120 reviews

Romantic Beach Retreat, New King Bed & A+ Wi-fi

KaylaRating, 5 stars1 month ago
Sara is a fantastic host! She is very easy to communicate with, responds quickly and gives great recommendations. The condo is well situated across from Kamaole III (we watched the sunset there every night) and in close walking distance/short drive to other great beaches. Sara’s condo was a great home base and had everything we needed (beach chairs, umbrellas, beach towels etc.). We definitely would not hesitate to stay again!
Guest favourite
Apartment in Wailea
4.94 out of 5 average rating, 102 reviews

Spacious S. Kihei Suite New A/C across from Kam 3

AimeeRating, 5 stars3 months ago
Quick responses. Did not need to communicate much since the place was wonderful!
Superhost
Apartment in Wailea-Makena
5 out of 5 average rating, 22 reviews

Wailea Ekolu Village | 1205

DarylRating, 5 stars1 week ago
Enjoyed everything about this place. Love how close it was to walk to the mall and several restaurants. The beach was 4-5 min drive. The unit itself was spacious and felt very peaceful. Full kitchen and laundry in unit

Quick stats about holiday rentals with a pool in Wailea-Makena

  • Total rentals

    1.8K properties

  • Nightly prices starting at

    ₹5,138 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

Destinations to explore

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  4. Maui County
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  6. Rentals with pools