
Cottage holiday rentals in Wailea, Wailea-Makena
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Top-rated cottage rentals in Wailea, Wailea-Makena
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Popular amenities for cottage rentals in Wailea, Wailea-Makena
Cottage rentals with a hot tub

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

Hawaiian DreamTemple- Tropical Oasis BBPH20120004
The house itself is beautiful and unique. The location is great. It is somewhat remote and generally with easy access to small towns and beaches within 10 to 15 minutes. The host was helpful and responsive. Hot tub was great and access to the pool was easy.

Luxury Upcountry retreat with breathtaking views!
My wife and started our honeymoon at this AirBnB. We spent three amazing days at the "Jungalow" house. We woke up every morning to a breathtaking view of the ocean from the cool and breezy mountainside of Haleakala, where the AirBnB is located. We just spent our time soaking in the surroundings each morning, and enjoying the French press coffee that was provided. We fell asleep each night to the sounds of wind and birds in the trees, and I even refilled the bird feeder near the downstairs window with host-provided bird seed. If you want a place to reset and be at peace with life, then this is the place that you need to go. My wife and I also found plenty of shopping just down the mountain in the nearby town of Makawao, and we explored many other parts of the island, too. Nothing is very far away from anything else in Maui. If you want an adventure, then you should go to the top of Haleakala like we did, or just stay at pool/sauna at the AirBnB :) This place is the real deal.

★Haleakala Cottage - PRIVATE HOT TUB, POOL ACCESS
What a lovely place! Soooo little bugs in a forest environment. Very clean! Sharyn is very responsive, always so welcoming and friendly! She made the place extra special for me and my wife. Will totally recommend her👍👍👍
Private cottage rentals

Ho'okipa Rose - Peace and Serenity
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!

Beautiful Beach Cottage: lush garden paradise
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! :)

Maui Meadows Ocean View Cottage
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!

3B/2B FamilyVacationComfort HawaiianaCharm Central
Perfect for our small group of friends to be able to catch up and explore the island together! Just wish our stay could have been longer. Beautiful and quaint. My wife ended up using one of the rooms as a bridal suite to get ready and had a great time!

Luxury Cottage,Saltwater Spa-Close to Beach,Dining
This place was 5 stars all-around! Jenni provided everything we could think of - and more! This was the perfect stay for my partner and I, having that romantic Maui vacation feel. We hope to be back!! Mahalo!!

HALEKALANI - Paradise in Upcountry
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!

Lani Paradise Oceanfront Cottage
What can I say - this Airbnb is a 10/10! The hosts were super friendly and gave fantastic recommendations (as well as an amazing welcome basket!) They were also each to reach in case we had questions. The place is fully stocked with everything you could need for the beach and/or pool. The view alone was worth every penny. I hope one day to be back in this amazing place! What a beautiful and relaxing retreat.

Romantic and Private Cottage and Gazebo for two!
We LOVED everything about this location. Iao Valley is so special and the location of the AirBNB itself was perfect for getting all around the island. We visited at the end of March and never ran the AC once. It was hot during the afternoon but the morning/late afternoon/evening cool off, with the winds blowing into the valley were so perfect. AND the birdsong in the morning was so beautiful that I recorded it and sent it to my family (minus the rooster song- but that's just Maui living for ya). If you want a good cocktail check out Ester's Fair Prospect, they have a nice selection of liquor and a fun vibe, located in the city of Wailuku right next door to this place. Also we loved the goodies that were left in the fridge. The pineapple on the island is SOOO good. Sooooooo good. Forget the banana bread hype... just eat the pineapples and bananas fresh! Mahalo!
Luxury cottage rentals

Kaanapali Spacious Cottage Walk to the Beach ICC30
The area was great and quiet.

Honeymoon Haven: Ocean Vista & Bamboo Temple Bliss
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

Pono Plantation Maui-3 Bedroom Cottage
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!

Thai Hale: Eco Retreat with OCEAN VIEW & Waterfall
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!

Private 2 bedroom cottage with pool
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!

Haiku Nani, County Licensed
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!!

Private Hawaiian Cottage Gem 3/2 🌺 Stellar Lanai
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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- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Kaipukaihina
- Laie
- Honolua Bay
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Pahoa Beach
- Wailea Beach
- Manele Golf Course
- Hāmoa Beach
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- Maui Ocean Center
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- Old Lahaina Luau
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- Wailea Golf Club
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