Kaupakulua Vacation Rentals

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Check prices for these dates

Tonight
Apr 16 - Apr 17
Tomorrow
Apr 17 - Apr 18
This weekend
Apr 18 - Apr 20
Next weekend
Apr 25 - Apr 27

Vacation Rentals in Kaupakulua

Wailea Ekahi - CoralTree Residence Collection
Exterior

Wailea Ekahi - CoralTree Residence Collection

3.0 star property
9.2 out of 10, Wonderful, (530)
"Was nice to come back to your own place after a long day of exploring. No resort traffic/business. Great especially for families. "
Wailea Ekahi - CoralTree Residence Collection
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1050)
"Had a gift bag waiting for us! Easy pool and beach access"
Sugar Beach Resort
Castle Kama'ole Sands
Deluxe Condo, 3 Bedrooms | Balcony

Castle Kama'ole Sands

3.0 star property
8.0 out of 10, Very Good, (2222)
"Clean and sufficient but could have used updated furniture"
Castle Kama'ole Sands
Wailea Grand Champions - CoralTree Residence Collection
2 outdoor pools

Wailea Grand Champions - CoralTree Residence Collection

3.0 star property
9.0 out of 10, Wonderful, (703)
"We forgot some work equipment after checking out and it was brought to the Coral Collection management. Nakai contacted us and ensured we got it back. Overall a great stay in a lovely unit."
Wailea Grand Champions - CoralTree Residence Collection
Maui Sunset
View from property

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (422)
"Pros: Beautiful view, well maintained property, great location with access to activities and restaurants while right on a fairly quiet beach, kitchen was well equipped for a rental, Wi-fi worked well Cons: The construction noise while we were there was intermittently insanely load, the beds are small, the pool is full sunrise to sunset "
Maui Sunset
Wailea Beach Villas
2 outdoor pools, free cabanas, pool umbrellas

Wailea Beach Villas

4.5 star property
9.8 out of 10, Exceptional, (170)
"We had nice scenic view of the ocean and great house to vacation in!😁"
Wailea Beach Villas
Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV

Maui Beach Vacation Club

2.5 star property
8.4 out of 10, Very Good, (735)
"Nothing special, but a good place to lay your head with the added benefit of being right by the beach. Lots of good restaurants nearby and close enough to a lot of the activities. No AC wasn’t that bothersome. "
Maui Beach Vacation Club
Maui Schooner Resort
Condo, 2 Bedrooms | Terrace/patio

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (451)
"We liked everything there. Beautiful place!"
Maui Schooner Resort
Kihei Akahi
Beach nearby

Kihei Akahi

3.0 star property
8.2 out of 10, Very Good, (588)
"Second time there…. Easy access; walkable. "
Kihei Akahi
Aston Maui Hill
Outdoor pool, open 8:00 AM to 9:30 PM, sun loungers

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (795)
"Nice landscape and large suite"
Aston Maui Hill
Kihei Ali'i Kai Condos with Ocean View and Parking
Beach nearby, white sand, beach towels

Kihei Ali'i Kai Condos with Ocean View and Parking

4.0 star property
9.6 out of 10, Exceptional, (4)
"Ali'i Kai is just a short walk to my favorite cafe on Maui: That's a Wrap...and then from there just a short walk to one of the most beautiful, walkable beaches in Kihei. I used to live in an Ali'i Kai condo, so this was like coming home. Incredible, all-around!"
Kihei Ali'i Kai Condos with Ocean View and Parking
Palms at Wailea Maui
Outdoor pool

Palms at Wailea Maui

3.5 star property
8.4 out of 10, Very Good, (493)
"Location, the views, the swimming pool, friendly staff and the general layout and upkeep of the property."
Palms at Wailea Maui
Maui Kamaole
Exterior

Maui Kamaole

3.5 star property
8.8 out of 10, Excellent, (831)
"Great place for families - close to everything!"
Maui Kamaole
Maui Banyan Vacation Club
Aerial view

Maui Banyan Vacation Club

3.0 star property
8.0 out of 10, Very Good, (340)
"Great spot located next to the beach"
Maui Banyan Vacation Club
Wailea Ekolu - CoralTree Residence Collection
2 outdoor pools

Wailea Ekolu - CoralTree Residence Collection

3.5 star property
8.8 out of 10, Excellent, (251)
"loved it"
Wailea Ekolu - CoralTree Residence Collection
Wailea Elua- CoralTree Residence Collection
2 outdoor pools

Wailea Elua- CoralTree Residence Collection

3.5 star property
9.4 out of 10, Exceptional, (243)
"Perfect condo for a week in Maui. Excellent location, quick walk to the pool/beach but up a bit so it was super quiet. Close to shops, bars, restaurants and grocery stores. Easy check-in/check-out process also! Will definitely stay here again! "
Wailea Elua- CoralTree Residence Collection
Sugar Beach Resort - Maui Condo & Home
Outdoor pool

Sugar Beach Resort - Maui Condo & Home

3.0 star property
8.4 out of 10, Very Good, (512)
"Very nice. They need more help in the bar and sandwich shop"
Sugar Beach Resort - Maui Condo & Home
Hale Kamaole
2 outdoor pools, sun loungers

Hale Kamaole

3.0 star property
8.4 out of 10, Very Good, (336)
"Liked the grab bars in the bathroom, unit was comfy and quiet was equipped with everything needed. Loved the view from the balcony of the ocean and sunset."
Hale Kamaole
Kihei Ali'i Kai D202 1 Bedroom Condo
Condo, 1 Bedroom | Beach

Kihei Ali'i Kai D202 1 Bedroom Condo

3.0 star property
Kihei Ali'i Kai D202 1 Bedroom Condo
Wonderful South Maui Beach Condos
Exterior

Wonderful South Maui Beach Condos

3.5 star property
9.4 out of 10, Exceptional, (22)
"We had a fantastic stay at Wonderful South Maui Beach Condos. The condo had everything we needed — a fully equipped kitchen, bed linens, towels, snorkeling gear, and even a beach chair. The area was peaceful and felt very safe. There’s a great shared Weber grill available, and the beach is just a short walk away. Grocery stores and delicious cafes are nearby. Highly recommend!"
Wonderful South Maui Beach Condos
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.
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Other types of properties in Kaupakulua you may be interested in

Maui Coast Hotel
2 outdoor pools, open 7:00 AM to 10:00 PM, cabanas (surcharge)

Maui Coast Hotel

3.5 star property
9.4 out of 10, Exceptional, (1771)
"Really nice resort style hotel. We stayed in Kai building looked new and clean. Walking distance to beach, eating and shopping. "
The price is NT$7,867
NT$10,775 total
includes taxes & fees
May 1 - May 2
Maui Coast Hotel
Four Seasons Resort Maui at Wailea
Club Ocean Front One Bedroom Suite | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1000)
"Luxury and opulence at its best!"
The price is NT$22,909
NT$27,024 total
includes taxes & fees
May 2 - May 3
Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

4.5 star property
9.4 out of 10, Exceptional, (1003)
"Na"
The price is NT$32,787
NT$40,593 total
includes taxes & fees
May 7 - May 8
Fairmont Kea Lani Maui
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.

Frequently asked questions

Are there vacation rentals in Kaupakulua?

Yes, there are vacation rentals near top sights in Kaupakulua, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Kaupakulua has to offer?

Kaiholo Hale: You might want to consider this vacation home rental near Kaupakulua, which is by the ocean and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

How many vacation rentals are there in Kaupakulua?

Choose from 3 Expedia vacation rentals in Kaupakulua for a memorable vacation.

What’s there to see and do in Kaupakulua?

While exploring the area, visit family-friendly sights like Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters, or get outside and enjoy nature at Twin Falls. Hookipa Beach Park and Kuau Bay Beach are a couple of places you'll find in the larger area.

What’s a vacation rental in Kaupakulua like?

Vacation rentals are privately owned properties you can book for a long or short time in Kaupakulua. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family gatherings.