
Villa holiday rentals in Wailea-Makena
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Top-rated villa rentals in Wailea-Makena
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Popular amenities for villa rentals in Wailea-Makena
Private villa rentals

Luxurious Two Bedroom near I’ao Valley w/ Haleakal
We loved this place. A perfect 3 nights stay to start our week in Maui before heading to a resort in Kapalua. We also hung out a lot in the neighborhood for coffee and breakfast. Eric is very friendly and helpful throughout our stay and accommodated our luggage storage request for our checkout day.

Chic Villa 6 – Beach Vibes & Walkable Paradise!
This place was a gem! Our favorite stay in the islands so far. The grounds of the property are beautifully maintained and the pool is amazing, specially after a long day of exploring. The location is terrific as it is within walking distances to some great restaurants and coffee shops and less than a 10 minute drive away from the shops at Wailea. You also have a direct view to the sunset right across the street so I suggest grabbing a drink and sitting on the bench there to enjoy. The airbnb itself is super clean, well stocked, and beautifully decorated. You cannot go wrong with this place specially if you want a more boutique feel to your vacation.

Chic Villa 2 | Modern Vibes by the Ocean
Incredible stay. Couldn’t ask for a better location. The Villa felt super private, yet we were close to many local hotspots. Would love to stay here again. One downside, the bed is a little firm. Gal was super accommodating too. We had several hours until our flight after checkout, and he allowed us to use some of the beach equipment for one last beach trip.

Ocean Front Cottage, 30 steps to the beach!
This place was absolutely amazing and will be the only place I stay in Maui! Walkable to lots of restaurants and grocery store and just a few steps to the beach. We had a fabulous time.

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6
Everything went so smoothly and our week at the villa with our kids was so wonderful. We loved the space, the resort amenities, the access to the beach and everything things else Maui has to offer. What a dream! We will definitely be returning!

Luxury at it's Finest, Truly a Home away from Home
Great spot in Maui for a family vacation! Well appointed spot in a super location. Easy access to the suite and all the amenities within. Clear instructions around the place for operating everything. Would absolutely recommend to anyone looking for a family friendly place in the Kihei/ Wailea area.

Luxurious 1BR Near I'ao Valley, Bright and Modern!
We had a wonderful stay at the Blue Door Villa in Wailuku! The home is beautifully renovated with a stunning kitchen and bathroom. It’s perfect for families, fully equipped with various appliances, laundry, and even a sauna. The location is super convenient, close to local shops, restaurants, grocery stores, and the airport. Our host Eric was incredibly responsive and helpful throughout our stay. Highly recommend!

Newly Remodeled 2 Bed/2 Bath - Close to Beach
Overall good experience. Appreciated the newly renovated building
Luxury villa rentals

Kapalua Ridge 2422. Luxurious remodeled townhouse!
We just can't say enough good things. Pictures looked excellent but you never know what you'll find in reality. Our unit was even better than the pictures. Host was amazing. Neighborhood is peaceful. Close to two awesome beaches. Beaches not over crowded. We almost had one to ourselves. If we're back in Maui this will be the first place I call. The price is simply amazing for what you get.

Kapalua Ridge 1711- Platinum Oceanview Villa
This is an excellent villa and we had a wonderful time. It is very well appointed, super clean, and the host is extremely easy to work with. The view is incredible and the surf noise is amazing. Highly recommended!!!

Panoramic Ocean-View Villa steps from the beach!
This was such a beautiful place for us to stay when we visited Maui for a family wedding! The condo is huge and well-furnished with everything you need. The views are just breathtaking and the location is wonderful. We had such a great time staying here and would come back again for sure!

Come Play on Maui & Save $ ~Ocean Front Kapalua
Gorgeous Condo -Spectacular Location This condo was perfect for our family of four. Everything we needed we provided, and we were grateful for the well stocked dishes and cookware. The Master suite has an incredible view and we enjoyed watching whales while drinking our coffee. The bedding and linens were high quality. The entire property is beautifully maintained and this condo was sparkling clean. We’ve recommended this property to all our friends who are planning a trip to Maui. There’s no better place to stay!

Kapalua Ridge 1915- Platinum Ocean View Villa
This was the perfect spot for our stay on Maui. It’s close enough to the resort hotels to enjoy their amenities and activities, but just far enough away to truly relax in peace and quiet. The beach is only a 10-minute walk and feels wonderfully private. The condo itself was a getaway all on its own, with beautiful views and cool breezes—we never even needed the AC. The kitchen was a standout: it had everything we could possibly need. Beyond the basics like cold filtered water, a coffee maker, toaster, and plenty of ice, there was even a Ninja blender, a full variety of pots and pans, baking dishes, and glassware. Honestly, you could cook an entire Thanksgiving dinner here. We ended up making a lot of meals at home, enjoying the views from the patio. We also used the grill by the pool, and while we spent most of our time at the beach, both pools looked great. This was definitely the spot to be on Maui. Highly recommend.

Kapalua Ridge 2821-22- Luxury FULL Ocean Views
Absolutely gorgeous and stunning views. We spent most of our time in the lanai, staring out into the horizon, trying to spot whales and watching the waves break on Oneloa Beach (north side) and Makaluapuna Point. The entire time you can hear the waves break. Everything about the view, the sound of the Ocean, birds chirping, morning sun, view of Molokai calms is like food for your soul. Both bedrooms have their own lanai and ocean views. Even the primary bathroom has ocean views you can take in while showering. Everything is clean, artful decor, nice solid furniture and plenty of cookware and other utensils for cooking. Host is very helpful, proactive and super nice. It was hard to leave the ocean views and go back to normal life.

Kapalua Ridge 613-15- Lowest Summer Rates!
Great experience! Beautiful home and every practical, was near many beautiful beaches and had great amenities around. The area was very easy to get to and was private yet still central and close to a lot of things. Would recommend to anyone and would stay here again!

Platinum Kapalua Ridge 1412- Discounted Rates
My stay at The Ridge was so restful, which was exactly what I needed. The complex is so well-maintained, you just get to relax from your first minutes. If you don’t want to do a lot of driving, I recommend placing a Safeway or Target order before you land and doing pick up. Or take The Ridge up on their service to stock for you. I rented a snorkel set from a local company recommended by The Ridge and it was excellent. I watched whales from my balcony—it was magical! Overall, I would definitely stay at The Ridge in the future.
Villa rentals with a pool

Westin Nanea Kaanapali Ocean Villa 2BR Sleeps 6
Great host, used the Westin amenities. Would rent here again and David was very responsive as well as helpful. Would do a full week vs a few days in the future.

Ocean View Villa at Villas by the Cove!
This airbnb was a gem of a find. It's a villa with other Airbnbs on the property. Very lush and has a super jungle feel, yet very modern. We stayed in Villa #5 with an ocean view from the deck which was great! The other units are all lower with no view. Villa 5 has its own private gate entrance. Lots of privacy and easy access to come and go. The pool was beautiful. Super helpful to have laundry facility. We went from california to honolulu then maui and this airbnb was perfect for my boyfriend & I after a week of traveling. We cooked! The livingroom sofa is a pull out bed and we utilized it to watch a lil TV, the ocean, the surfers, and the pool & beautiful palm trees. There's a small beach parking lot across the back street and it does draw people of all types but there were no issues. Everything needed was provided - beach chairs, umbrella, boogie boards, small ice chest. Perfect for 2! I would totally stay again - Villa #5 was the best topper to our Maui trip! Thanks Gal!

Westin Kaanapali Ocean Resort Villas North Studio
Absolutely perfect, exactly as David stated. Thank you so much for the stay. I would 1000000% go through you again any time.

Chic Villa 6 – Beach Vibes & Walkable Paradise!
This place was a gem! Our favorite stay in the islands so far. The grounds of the property are beautifully maintained and the pool is amazing, specially after a long day of exploring. The location is terrific as it is within walking distances to some great restaurants and coffee shops and less than a 10 minute drive away from the shops at Wailea. You also have a direct view to the sunset right across the street so I suggest grabbing a drink and sitting on the bench there to enjoy. The airbnb itself is super clean, well stocked, and beautifully decorated. You cannot go wrong with this place specially if you want a more boutique feel to your vacation.

Westin Nanea Kaanapali Ocean Villa 1BR Premium
David was terrific to work with. I was late to booking one of his options and he came through with a better one very quickly. He was very communicative, provided great insight and made the booking completely smooth. Our family loved the Westin Nanea Villas and will definitely be looking to go back. It was a great getaway and highly recommend this property. You can use the sister property pool next door as well as walk to the beach in about 20 steps. I will be working with David again as he is top notch.

Westin Kaanapali Resort North 1BR IslandView Villa

Westin Kaanapali Beach Resort IslandView 1BR Villa
Quick stats about villa rentals in Wailea-Makena
Total rentals
50 properties
Nightly prices starting at
$409 SGD before taxes and fees
Total number of reviews
570 reviews
Family-friendly rentals
50 properties are a good fit for families
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Maui
- Kaanapali Beach
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- Laie
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