Photo by Tim & Nat ✈

Search Vacation Homes in Kaupo

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 49 Vacation Homes in Kaupo with updated reviews, rates, and availability.

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (377)
"Loved everythibg about our stay! The kitchen was incredibly well stocked and spacious. Great location!"
The price is AED 716
AED 1,465 total
includes taxes & fees
23 May - 24 May
Fisher's Hana Bay Hale, Across from Hana Bay

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (176)
"One week enjoying the Hana area"
The price is AED 1,286
AED 2,196 total
includes taxes & fees
8 Jun - 9 Jun
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

9.6 out of 10, Exceptional, (376)
"My favorite part of the property was the outdoor bed on the screen-in porch, had the best night of sleep of my whole vacation sleeping outside"
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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

10.0 out of 10, Exceptional, (220)
"Stunning and immaculate country home perfect for your Maui adventure. Comfortable and beautiful accommodation centrally located to all attractions. We would stay here again 💯! "
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

9.8 out of 10, Exceptional, (224)
"What an amazing place to stay and enjoy beautiful Hana. The home is clean, comfortable and updated. We loved the property and how well kept the landscaping - it gives you a feeling of a high-end resort! Will stay her again!"
The price is AED 1,286
AED 2,563 total
includes taxes & fees
26 May - 27 May
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (167)
"Very spacious! 10 min short trip from Hana and 5 min to waianapanapa state park"
The price is AED 1,230
AED 2,336 total
includes taxes & fees
18 May - 19 May
Beautiful Home in paradise!

Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub

9.8 out of 10, Exceptional, (167)
"Fantastic location. We stayed here with family when we were in town for a wedding. Such a special place to wake up each morning and watch the ocean. The home was very spacious and comfortable for a large group. "
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub

Waterfall House - Private House Overlooking the Ocean!

9.8 out of 10, Exceptional, (24)
"Pros: Incredible setting and the grounds are beautiful. Whale watching from the hot tub was probably the highlight of our trip. The pool gets the perfect amount of sun on the nice days. The whole property is very calm and relaxing. The people onsite are incredibly friendly and do not disturb the guests.Cons:The circle bed in the listing photos in incredibly uncomfortable. Getting in and out you or rolling or kneeling on marble to get on a mattress that has seen better decades. We would've slept...
Waterfall House - Private House Overlooking the Ocean!

Luxury Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (39)
"This place is great. The views are incredible. We had a great time here and would have loved to stay longer. Watching the sunset from the hot tub, cooling down in the pool afterwards, lying in bed watching the moon set in the mornings. The quiet and peacefulness of the upcountry. Memories we will never forget."
Luxury Upcountry Villa with breathtaking views

Fabulous views! Exclusive pool, spa and private 1 acre yard.

10.0 out of 10, Exceptional, (133)
"We had a great stay! The property is beautiful and close to beaches, restaurants, and groceries. It was exactly what our family of four was looking for."
Fabulous views! Exclusive pool, spa and private 1 acre yard.

Hana Ocean Palms Bungalows

9.6 out of 10, Exceptional, (112)
"A really lovely property in Hana. Thank you for having us! "
Hana Ocean Palms Bungalows

Kula Luxury Retreat With Stunning Ocean & Mountain Views!

10.0 out of 10, Exceptional, (72)
"We spent an amazing week here. If you are looking for peace and quiet with a stunning view and gracious hosts, this is the place! We will definitely stay here again!"
Kula Luxury Retreat With Stunning Ocean & Mountain Views!

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

10.0 out of 10, Exceptional, (62)
"After months of searching for a spot and planning a family Christmas/New Year vacation for me and my extended family, including 4 toddlers, we settled on the this property on Maui. Simply put, it was perfect for all of us. Beautiful compound on a stunning piece of property with hosts who jumped through hoops to be sure we were happy and comfortable. The 10 days we spent on Maui will forever be a special memory for me and my family and we hope to stay at the at this beautiful B&B again someday....
The price is AED 5,124
AED 10,136 total
includes taxes & fees
19 May - 20 May
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!

10.0 out of 10, Exceptional, (47)
"Eve's place was in a great location for us and was such a pretty and relaxing place in the jungle! Great beds and such a neat place to stay!"
PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!

PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

9.8 out of 10, Exceptional, (72)
"Home exceeded our expectations. Private beautiful backyard and clean home. Quick access to everywhere we needed to go and had chairs and towels for the beach. Highly recommend this property! "
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

Hana Homestead by the Beach

9.8 out of 10, Exceptional, (133)
"The view from this house is absolutely amazing!! It overlooks Hana bay and the lighthouse. You can literally sit in the hot tub on the front porch and watch the sunset over the bay!"
The price is AED 1,756
AED 4,549 total
includes taxes & fees
31 May - 1 Jun
Hana Homestead by the Beach

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

9.8 out of 10, Exceptional, (73)
"My family and my oldest daughter’s family stayed together for a long weekend. Close to everything and a wonderful home. "
The price is AED 2,274
AED 3,999 total
includes taxes & fees
28 May - 29 May
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Beautiful house in the Upscale Maui Meadows neighborhood

10.0 out of 10, Exceptional, (6)
"Fantastic property and great hosts! The pool house is perfect for a family that might need separation throughout the stay, and the property is very nice and clean. "
Beautiful house in the Upscale Maui Meadows neighborhood

One-of-a-Kind Maui Getaway!

10.0 out of 10, Exceptional, (108)
"Wonderful Property for our family. Perfect location and house is fully as advertised. Lee made the stay even better - Freddy was also an awesome host "
One-of-a-Kind Maui Getaway!

Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

9.8 out of 10, Exceptional, (86)
"Wonderful home with nice amenities."
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach
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

Other property types in Kaupo

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

9.6 out of 10, Exceptional, (376)
"My favorite part of the property was the outdoor bed on the screen-in porch, had the best night of sleep of my whole vacation sleeping outside"
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Oceanview Condo in Hana-Let the ocean lull you to sleep

9.2 out of 10, Wonderful, (93)
"Heavenly Hana is a unique destination, far away from the busy and commercial Hawaii, and more like the idyllic image of the lush garden, soothing ocean waves and gentle breezes. Ocean View Condo provides all of what is perfect about Hana."
The price is AED 815
AED 1,572 total
includes taxes & fees
22 May - 23 May
Oceanview Condo in Hana-Let the ocean lull you to sleep

Wailea Ekolu - CoralTree Residence Collection

3.5 star property
8.8 out of 10, Excellent, (253)
"Amazing place to stay! Great area, stunning views. Very walkable "
Wailea Ekolu - CoralTree Residence Collection
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.