Cottage holiday rentals in Wailea, Wailea-Makena

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Popular amenities for Wailea, Wailea-Makena cottage rentals

Cottage rentals with a hot tub

Cottage in Haiku-Pauwela
5 out of 5 average rating, 10 reviews

Privacy, Luxury, Ocean View Cottage, HotTub, K-Bed

MaileRating, 5 stars4 months ago
we enjoyed our week long stay at Hank's place. the area is beautiful and there is a lot to do. Hank had a number of useful kitchen amenities and was very friendly and accommodating! thank you!
Top Guest favourite
Cottage in Haiku-Pauwela
4.98 out of 5 average rating, 88 reviews

Leilani's "Leimomi" Cottage - County Licensed

KatherineRating, 5 stars6 days ago
Margit's listening showed an availability for the time we would be traveling. Airbnb noted this fact as "a rare find", which turned out to be totally true! The home was spotless, well appointed, and welcoming. It was easy to get settled in with our luggage and groceries. The yard was beautifully landscaped and peaceful. The rental fee is very competitive. Margit replied to messages in a quick and friendly manner. We couldn't have been happier with our choice in lodging.
Superhost
Cottage in Haiku-Pauwela
4.82 out of 5 average rating, 205 reviews

Hawaiian DreamTemple- Tropical Oasis BBPH20120004

KelseyRating, 5 stars5 days ago
My aunt and I loved this place. Its located in a private neighborhood and the property itself is beautiful. The cottage is well laid out and absolutely gorgeous inside. The hot tub was clean and was a great way to wind down after a long day. 10/10 recommend this place.
Top Guest favourite
Cottage in Makawao
4.99 out of 5 average rating, 196 reviews

Luxury Upcountry retreat with breathtaking views!

JamesRating, 5 stars4 weeks ago
We wish we could have stayed longer. David a Dawn put a lot of hard work into the space. The pool/hottub and sauna were very clean and enjoyable. The Jungalow itself felt very private and great sunset. Everything you could need is there for you kitchen, bathroom, fireplace, plenty of seating everywhere . The open air and big windows make you feel like you’re living outside. The porch and balcony were great for relaxing on. Plenty of parking and easy to get in and out. The property itself is gorgeous. Great flowers plants and trees, smelled great everywhere you went. Plenty of places to go from the property and they were very helpful in telling us the best spots to check out. Thanks for sharing your house with us Dave and Dawn!
Top Guest favourite
Cottage in Maui
4.97 out of 5 average rating, 204 reviews

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS

CherylRating, 5 stars1 week ago
We really had a nice relaxing stay. The stars at night while in the hot tub made it so relaxing. The shower situation was a surprise but, I got over it quickly. The personal touches made it very romantic. The special treats were more than what I expected. Sharyn, your place was above and beyond my expectations and I wish I could have stayed one more day!

Private cottage rentals

Superhost
Cottage in Paia
4.74 out of 5 average rating, 23 reviews

Walk to small beach, charming cottage

MarlaRating, 5 stars5 months ago
Lovely well appointed place, perfect for 3 adults. Thoughtful amenities to make cooking and beach going easy. No AC needed as the breeze through all of the windows was great. So nice to have laundry facilities, and a great little grocery and small beach a block away. Very clear folder with directions and recommendations, as well as lots of Maui guidebooks on the shelf. A very comfortable stay!
Top Guest favourite
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 83 reviews

Ho'okipa Rose - Peace and Serenity

MartinRating, 5 stars2 months ago
Rosa and Carl are wonderful hosts. They were very kind and helpful providing lots of tips for trips. Accomodation was perfect, refreshments waiting for us after long fly from Europe. Fully recommended. Mahalo!
Top Guest favourite
Cottage in Kihei
5 out of 5 average rating, 54 reviews

Beautiful Beach Cottage: lush garden paradise

JenniferRating, 5 stars3 months ago
We love Maui and are so thrilled to have found such a lovely place to stay. Katherine and Dean couldn’t have been more welcoming, helpful and kind. Kihei is a terrific base for exploring and enjoying the island. As we drove out to head to the airport, we all said it was the best Airbnb experience we have had (among many wonderful Airbnb experiences and basically no bad ones). We will be back! :)
Top Guest favourite
Cottage in Kihei
4.98 out of 5 average rating, 51 reviews

Maui Meadows Ocean View Cottage

GrittRating, 5 stars4 months ago
We absolutely loved the cottage! Tom and Denise were very kind and gave us a lot of helpful information on activities and restaurants in the area. The cottage had great extras like snorkeling gear, beach towels etc. In the morning, we were woken up by the beautiful sound of birds which we will miss dearly back home! We were super happy a late check-out was possible as our flight was in the evening. Highly recommend booking with Tom and Denise (and their adorable dog), would 100 percent book again!
Guest favourite
Cottage in Paia
4.84 out of 5 average rating, 83 reviews

Charming Cottage in Kuau near Mama’s Beach

E.P.Rating, 5 stars10 months ago
Had the best time! Thank you for a wonderful stay!! Such a bonus to meet the owners and feel so welcomed into their cozy space. We will come back if we can!!!
Guest favourite
Cottage in Wailuku
4.92 out of 5 average rating, 12 reviews

3B/2B FamilyVacationComfort HawaiianaCharm Central

TravisRating, 5 stars3 weeks ago
Really enjoyed this beautiful home on the Island of Maui. It was my first time on Maui with my family. The outdoor patio area was very nice. The location was convenient and close to nearby areas on the Island. Emma was an excellent host and friendly. She gave great recommendations of activities to do on the island and was a great communicator.
Top Guest favourite
Cottage in Kihei
4.98 out of 5 average rating, 265 reviews

Luxury Cottage,Saltwater Spa-Close to Beach,Dining

LauraRating, 5 stars4 days ago
This was such a lovely stay! Jenni’s place was so clean & beautiful. I have never stayed in an Airbnb that was as well stocked as this one. The location was perfect — a short walk from restaurants & the water & close to everywhere we wanted to go.
Guest favourite
Cottage in Kula
4.96 out of 5 average rating, 361 reviews

HALEKALANI - Paradise in Upcountry

H. S. Rating, 5 stars3 weeks ago
We had a wonderful stay! The house was beautiful, with a lovely garden and a stunning view. Everything was clean, comfortable, and exactly as described. The host was very responsive and helpful throughout our stay. We enjoyed our time here and would definitely stay again. Highly recommend!

Luxury cottage rentals

Guest favourite
Cottage in Maui County
4.8 out of 5 average rating, 160 reviews

Honeymoon Haven: Ocean Vista & Bamboo Temple Bliss

NissimRating, 5 stars1 month ago
Maui Eco Retreat was nothing short of magical. The energy on the grounds was something I never expected—calming, vibrant, and deeply rejuvenating. From the moment we booked, the pre-arrival communication made us feel completely at ease, setting the tone for an unforgettable stay.We arrived at 10 PM and were greeted by William, who welcomed us with such warmth and enthusiasm. His passion for the retreat was evident, making us feel instantly at home. We stayed for four nights in the Bamboo Temple, a serene sanctuary with the most breathtaking ocean and sunrise views. Waking up at 6 AM was effortless when rewarded with the golden light streaming through the massive bay window—an experience in itself. Our mornings started with a quick 10-minute drive to grab coffee before returning to our beautifully equipped room to prepare breakfast. The retreat had everything we needed, including a fully equipt kitchen. After breakfast, I would head to the yoga studio for a 60-minute flow, followed by
Cottage in Lahaina
4.71 out of 5 average rating, 56 reviews

Pono Plantation Maui-3 Bedroom Cottage

AndresRating, 5 stars16 months ago
Katherine was very helpful with recommendations of activities! She followed up to see if we made it safely to her home. Katherine’s home had all the amenities and more, including beach chairs, boogie boards and more things to take to the beach. She also checked up on us to see if we needed anything. Thank you!
Top Guest favourite
Cottage in Haiku-Pauwela
5 out of 5 average rating, 84 reviews

Haiku Hideaway - Stand-alone 2 bedroom farm house

BryanRating, 5 stars4 weeks ago
Absolutely wonderful stay, the place was clean, well appointed, private, and beautiful. My kids were the first ones in when we arrived, and they ran back downstairs to tell me how nice and clean the place was. Cary and his family were wonderful and welcoming, but gave plenty of privacy and space. The outdoor dining area was wonderful, and the kitchen was shockingly well-stocked. Bathroom is large, clean, and also fully stocked. Highly recommended, will definitely be returning when we get the chance, this is a great little Haiku hidden gem.
Cottage in Kihei
4.96 out of 5 average rating, 25 reviews

Private 2 bedroom cottage with pool

AlmaRating, 5 stars14 months ago
My family enjoyed staying in the cottage while on vacation. It has everything you need. The pool was perfect. My 12 year old son used the pool every day. The cottage is close to the beach, too. Best vacation so far!
Guest favourite
Cottage in Maui County
4.78 out of 5 average rating, 73 reviews

Thai Hale: Eco Retreat with OCEAN VIEW & Waterfall

EllenRating, 5 stars1 month ago
Such a lovely and magical place to stay! So peaceful and quiet. William was the best. Extremely helpful and responsive! Will be back next year!
Superhost
Cottage in Haiku-Pauwela
4.97 out of 5 average rating, 63 reviews

Haiku Nani, County Licensed

SarahRating, 5 stars3 months ago
This home is stunning! The gardens around the home are more beautiful and peaceful than the photos and the house was absolutely perfect for two couples. The small towns of Haiku-Pauwela, Pa'ia, and Makawao are wonderful and have so much character. The management team, Margit and AJ, were incredibly helpful and kind. There was a big storm on the islands the day we were to depart - flight cancelled, power outages, flooding, etc. They welcomed us back to the house for 3 more nights (we couldn't get a flight out until then). Margit and her husband offered to come pick us up at the airport and bring us back to the house, brought lanterns and flashlights to the house since there was no power... all during a crazy storm! We felt so taken care of and they were so kind. AJ in the office helped out with the rebooking for the 3 nights... SO MUCH ALOHA, all around!! We would DEFINITELY come stay here again. Mahalo!!
Superhost
Cottage in Lahaina
4.62 out of 5 average rating, 87 reviews

Private Hawaiian Cottage Gem 3/2 🌺 Stellar Lanai

MaximeRating, 5 stars4 months ago
We LOVED our stay at Nic’s place in Kaanapali. The cottage was spacious and we really liked the lanai (roofed patio). Nic was super accomodating and helped us with any question we had. We were about a 10 minutes walk from a top beach, with turtles and white sand. We took advantage of the amenities in the small complex (prestine pool, shuffle board and parking). We were also very happy that they provided us with a park and play for the baby. Mahalo !

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