Search Vacation Homes in Kaupakulua

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Homes in Kaupakulua

Yonegan Maui Getaways - Haiku
Garden

Yonegan Maui Getaways - Haiku

3.0 star property
9.4 out of 10, Exceptional, (6)
"Loved having the hot tub to come home to!!"
$212 nightly
The price is $232
Oct 5 - Oct 6
Total with taxes and fees
Yonegan Maui Getaways - Haiku
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC
Outdoor dining

Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

10.0 out of 10, Exceptional, (129)
"Plenty of room. Great kitchen for lots of cooks."
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Outdoor pool, a heated pool

Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

10.0 out of 10, Exceptional, (86)
"It was fantastic. "
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
A heated pool

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

9.8 out of 10, Exceptional, (103)
"Beautiful property"
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
Menuhene Shores 604, Oceanfront Bliss with Incredible Whale Watching Views
Outdoor dining

Menuhene Shores 604, Oceanfront Bliss with Incredible Whale Watching Views

Menuhene Shores 604, Oceanfront Bliss with Incredible Whale Watching Views
Entire home in Kihei within walking distance to beaches, shopping and dining!
Outdoor dining

Entire home in Kihei within walking distance to beaches, shopping and dining!

9.4 out of 10, Exceptional, (56)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: this place is amazing!!! The back yard is a shady plumeria paradise. the back porch has a view of the ocean. The house was clean and well cared for. I would love to stay here again!"
Entire home in Kihei within walking distance to beaches, shopping and dining!
4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi
Pool

4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi

10.0 out of 10, Exceptional, (56)
"Well appointed and fantastic location. Wonderful sunsets and loved watching all the goings on in the park next door. The private pool was like our own little oasis. Would definitely recommend to any group going to Maui. "
4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi
Kihei Maui Beach house - On the water
Property grounds

Kihei Maui Beach house - On the water

9.8 out of 10, Exceptional, (58)
"Mark was wonderful to work with. Some things could use some updates but overall it was a great location and we had a great stay."
Kihei Maui Beach house - On the water
Kaiholo Hale
Beach nearby

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (201)
"Area was quiet but close to amenities. We could drive anywhere on Maui easily. There was a lovely beach less than a block from the suite with good snorkeling and friendly locals. Bed in the suite was very comfortable, and it had everything we needed for a relaxing vacation."
Kaiholo Hale
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
On the beach, sun loungers, beach towels

Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

9.8 out of 10, Exceptional, (205)
"Perfect home for a large group. Beach is across the street the back to the pool when the waves got to be to much for our little ones. Great property manager! Great location! "
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
Exceptional Upcountry Villa with breathtaking views
Outdoor pool

Exceptional Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (44)
"Beautiful views and beautiful accommodations! We loved being in the up country and this house was perfect for my family of five. "
Exceptional Upcountry Villa with breathtaking views
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Exterior

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (228)
"I absolutely love staying here! It’s a new yearly tradition and great location! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Oceanfront Hideaway on the Beach
On the beach

Oceanfront Hideaway on the Beach

10.0 out of 10, Exceptional, (1)
"We really enjoyed this house! It had everything we needed and more! They provided beach chairs and umbrellas, all the kitchen necessities, and even a high chair and port-a-crib for the baby! It was clean and spacious. Host was been very efficient and friendly. "
$1,724 nightly
The price is $2,015
Oct 27 - Oct 28
Total with taxes and fees
Oceanfront Hideaway on the Beach
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Property grounds

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

9.8 out of 10, Exceptional, (76)
"Phenomenal property for your stay in Hana - especially for a large group "
$988 nightly
The price is $1,156
Oct 2 - Oct 3
Total with taxes and fees
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches Await
On the beach

Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches Await

9.4 out of 10, Exceptional, (49)
"We had a great time "
Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches Await
Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais!
Property grounds

Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais!

9.8 out of 10, Exceptional, (78)
"Perfect location, well equipped unit, outstanding water front property"
Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais!
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In
Beach nearby, sun loungers, beach towels

Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In

10.0 out of 10, Exceptional, (174)
"We had a great time. The house was very well organized and equipped "
Ocean View Retreat – Walk to Town and Beaches– A/C – Fast WiFi - Self Check-In
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Interior

Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!

10.0 out of 10, Exceptional, (35)
"Lovely place. The pool is awesome as is the home itself. So nice it was hard to leave to explore other parts of the island. "
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Outdoor dining

Mountain to Ocean Views Pole House @ Maui Adventure Villa

9.8 out of 10, Exceptional, (230)
"Will certainly be returning"
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
Beach nearby, sun loungers, beach towels

Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View

10.0 out of 10, Exceptional, (68)
"stayed for one week with family and enjoyed the place very much. The host is very attentive and quick to respond to all questions/requests. We will come back."
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
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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Top Kaupakulua Hotel Reviews

Hilton Grand Vacations Club Maui Bay Villas

Hilton Grand Vacations Club Maui Bay Villas

10/10 Excellent
"Nice property, close to the ocean, great pools and loved our hotel room. Stayed in a two bedroom / 2 bath. Close drive to Wailea. "
christiane 4-night trip
Posted 2 days ago
Hilton Grand Vacations Club Maui Bay Villas

Find out more about Kaupakulua

Find out more about Kaupakulua

Kaupakulua Vacation Homes information

Number of reviews
1,677
Accommodation
219 Vacation Homes
Lowest Price
$232
Highest Price
$2,015

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