Holiday Homes in Wailea-Makena

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Wailea-Makena

Central 1 bedroom gorgeous beaches

The price is NZ$1,417
includes taxes & fees
17 Aug - 18 Aug
Central 1 bedroom gorgeous beaches

Luxury Oceanview Wailea Retreat [Hōkū Hale]

The price is NZ$2,196
includes taxes & fees
18 Aug - 19 Aug
Luxury Oceanview Wailea Retreat [Hōkū Hale]

Wailea Ekahi Village | 47D

Wailea Ekahi Village | 47D

Wailea Ekahi Village | 47B

The price is NZ$1,679
includes taxes & fees
27 Aug - 28 Aug
Wailea Ekahi Village | 47B

🏝️SUMMER-Booking Now-2🛌 2🛁 Beautiful Oceanview, Great Location Across the Beach🏝️

"This unit is comfortable and stocked with everything you need. It takes a day or so to figure out all the remotes but after that it's easy to operate everything. I would have given this unit 5 stars with the exception of we had to clean the fridge upon arrival before we could use it. The rental and property staff were quick to respond and wonderful to work with. We would stay in this unit again. "
The price is NZ$1,625
includes taxes & fees
27 Aug - 28 Aug
🏝️SUMMER-Booking Now-2🛌 2🛁 Beautiful Oceanview, Great Location Across the Beach🏝️

Experience luxury in a spacious 900 sq ft condo in South Kihei, featuring 2 bedrooms with king beds

The price is NZ$1,464
includes taxes & fees
27 Aug - 28 Aug
Experience luxury in a spacious 900 sq ft condo in South Kihei, featuring 2 bedrooms with king beds

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (4)
"It was a last minute stay and it had what we needed. "
The price is NZ$433
includes taxes & fees
17 Aug - 18 Aug
Yonegan Maui Getaways - Haiku

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

The price is NZ$528
includes taxes & fees
15 Aug - 16 Aug
Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

10.0 out of 10, Exceptional, (67)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
The price is NZ$4,540
includes taxes & fees
25 Aug - 26 Aug
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Oceanview Retreat in Puamana – Steps from the Beach & Surf

10.0 out of 10, Exceptional, (1)
"This property had everything you would want in a vacation home. Great location. We enjoyed the beach, community pool and grounds. The photos were exactly as pictured. We had a great time in your home. Thank you for hosting us."
The price is NZ$1,806
includes taxes & fees
21 Aug - 22 Aug
Oceanview Retreat in Puamana – Steps from the Beach & Surf

Charming Direct Oceanfront North Shore Beach House

9.0 out of 10, Wonderful, (33)
"We had a great time at this VRBO! It was so clean and was the perfect lay out for our family. The beds were comfortable and the views were gorgeous! We will definitely be staying again. "
The price is NZ$1,341
includes taxes & fees
18 Aug - 19 Aug
Charming Direct Oceanfront North Shore Beach House

Sugar Beach 106 - Ground Floor next to the 5 Miles of Sandy Beach

The price is NZ$876
includes taxes & fees
28 Aug - 29 Aug
Sugar Beach 106 - Ground Floor next to the 5 Miles of Sandy Beach

Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121

10.0 out of 10, Exceptional, (186)
"The property was amazing and was well stocked in both the kitchen as well as for all supplies. We loved our stay here and the immediate access from the patio to the beach area was amazing. We would stay here again!"
The price is NZ$1,153
includes taxes & fees
20 Aug - 21 Aug
Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121

Haiku Hale - 3 Bedroom Maui Getaway!

10.0 out of 10, Exceptional, (4)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
The price is NZ$1,777
includes taxes & fees
30 Aug - 31 Aug
Haiku Hale - 3 Bedroom Maui Getaway!

Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

The price is NZ$959
includes taxes & fees
16 Aug - 17 Aug
Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

Sugar Beach PH17 - Direct Oceanfront 1 bedroom

The price is NZ$969
includes taxes & fees
18 Aug - 19 Aug
Sugar Beach PH17 - Direct Oceanfront 1 bedroom

New! The Aloha Cottage in Puamana, Maui Hawaii

9.6 out of 10, Exceptional, (85)
"Great place to stay. We all enjoyed the area and Lahaina was incredible."
The price is NZ$1,608
includes taxes & fees
17 Aug - 18 Aug
New! The Aloha Cottage in Puamana, Maui Hawaii

Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach

10.0 out of 10, Exceptional, (6)
"Clean, cozy and nicely designed. This condo has an amazing view and access to the beach and pool. Kitchen is well equipped, even has a milk warmer/frother which I appreciate so much as a lover of lattes. We'll happily stay here again on our next trip to Maui. "
The price is NZ$1,216
includes taxes & fees
18 Aug - 19 Aug
Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach

Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC

10.0 out of 10, Exceptional, (3)
"This place was exactly what our family (3 adults and 2 toddlers) needed. It was immaculately clean, walkable to a very private beach, and had everything needed for our stay to be perfect (toys, beach gear, towels, kitchen necessities, etc). We would 100% rebook "
The price is NZ$2,335
includes taxes & fees
15 Aug - 16 Aug
Pualei Beach House 3-bedroom townhome in phenomenal Lahaina with WiFi, AC

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

9.8 out of 10, Exceptional, (109)
"The property was clean, well maintained, and in a sweet, quiet neighborhood-a perfect home base for lots of day trips around Maui with tons of toys for beach-going. We hope to visit again! And a beautiful backyard and amenities!"
The price is NZ$1,010
includes taxes & fees
24 Aug - 25 Aug
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Wailea-Makena Hotel Reviews