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

Compare 34 Vacation Homes in Kaupo with updated reviews, rates, and availability.

STHA-2017/0002 Across from Hana Bay

9.6 out of 10, Exceptional, (337)
"This is an older place that has been kept in excellent condition. Very nice, clean, and comfortable. Everything in the place is neat and clean. The instructions from the owner, impeccable. Anything and everything you could possibly need to know is described. Good location to food and beach. "
STHA-2017/0002 Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay

9.6 out of 10, Exceptional, (341)
"Great place. Wish we had coffee too"
The price is AED 716
AED 1,461 total
includes taxes & fees
2 Jan - 3 January 2025
Fisher's Hana Bay Hale, Across from Hana Bay

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

9.8 out of 10, Exceptional, (208)
"We had a wonderful stay. The house was as advertised regarding all amenities. Very clean, well maintained and well stocked. The only surprise was no microwave. Check in and out quite seamless. One of the better properties I've rented "
The price is AED 1,286
AED 2,559 total
includes taxes & fees
16 Jan - 17 January 2025
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

10.0 out of 10, Exceptional, (169)
"Nice week stay- location was great. Very quiet and walking to a beach. Loved the house and grounds. Enjoyed the geekos."
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'

Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!

10.0 out of 10, Exceptional, (13)
"The property is fantastic and had everything we needed. Great response from the property manager and very clean. The evening breeze was the best and just hearing the ocean all night was so calming."
Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!

Private & Fabulous views! Exclusive pool, spa and 1 acre yard

10.0 out of 10, Exceptional, (126)
"From the minute we entered this residence, we were in love. From the cleanliness to the view, the property and the pool, it was all nothing short of amazing! It was the perfect home base for our families first trip to Maui and it will definitely be the place we stay in the future! "
Private & Fabulous views! Exclusive pool, spa and 1 acre yard

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (158)
"Great spot for enjoying in and around Hana. Beautiful and spacious with great scenery. We even shot some family pictures there. Quiet and peaceful - great spot to relax."
Beautiful Home in paradise!

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

9.8 out of 10, Exceptional, (67)
"We would stay in this home again, 10/10- the only downside is we enjoyed being in the house so much we were not motivated to explore the island! The pool is lovely- a nice sized pool to enjoy as a family of four. I spent most of my time on the back deck, enjoying the view of the pool with the ocean in the distance. The landscaping is top-notCh and there are a variety of curious birds and little lizards to watch. The bedrooms are spacious and comfortable, the kitchen is well-appointed. We had a...
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

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

9.8 out of 10, Exceptional, (68)
"We had a very relaxing time at this property! Such a beautiful place. We will definitely stay again. "
The price is AED 2,975
AED 4,899 total
includes taxes & fees
31 Dec - 1 January 2025
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Dolphin Room at Maui Eco Retreat: Ocean Views & Private Waterfall!

10.0 out of 10, Exceptional, (4)
"This place is a true slice of heaven. We stayed in a house with its own kitchen and dining area and a garden terrace with a stunning view over the ocean surrounded by incredible nature.. it has access to a private waterfall which is one of the most beautiful and enchanting places I've ever been. I can't recommend this place highly enough. Everyone was wonderful and our stay was amazing. I hope we will be back"
Dolphin Room at Maui Eco Retreat: Ocean Views & Private Waterfall!

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

9.8 out of 10, Exceptional, (77)
"What a great place! Clean and accessible to all the beaches in Wailea and Kihei. The views from the deck were incredible. The neighborhood is very safe. The people we spoke with outside were very friendly. Will stay there on our next trip for sure! Mahalo! "
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

10.0 out of 10, Exceptional, (53)
"There were 9 of us for this stay and the house was perfect for all of us! We had plenty of room to spread out after being tired from the beach all day, or the huge family room was optimal for watching a movie or hanging out. The pool was a lot of fun and everything was easy to figure out around the house. The host was very kind and gave recommendations as well as checked on us to make sure we had what we needed! Would love to come back! "
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach

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

10.0 out of 10, Exceptional, (210)
"Only problem was getting into the house - code would not work, apparently an internet problem. Cypher Lock on upstairs door was in process of being replaced so had to use a single physical key. Otherwise, loved the house, the amenities (provided beach gear, grill, washer/driers, kitchen, etc. Master bed high for short-legged oriental. Relationship with owner exceptional."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!

10.0 out of 10, Exceptional, (11)
"We were beyond pleased with our stay. The home had everything we needed, and the views were magnificent. The short stroll down to the black sand beach was absolutely gorgeous. Loved it!"
Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!

Up Country spacious Newly remodeled kitchen close to beach, airport, UpCountry

9.6 out of 10, Exceptional, (30)
"Few of my sons teammates grouped together for a recent baseball tournament! House was perfect! Close to the field. Saved us by being able to make breakfast everyday!"
Up Country spacious Newly remodeled kitchen close to beach, airport, UpCountry

Hana Homestead by the Beach

9.8 out of 10, Exceptional, (132)
"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 2,825
AED 5,936 total
includes taxes & fees
14 Jan - 15 January 2025
Hana Homestead by the Beach

Upcountry Kula - Private House On The Slopes Of Haleakala - Multi-Island View

10.0 out of 10, Exceptional, (159)
"This was the perfect retreat at the end of a day spent exploring the island."
Upcountry Kula - Private House On The Slopes Of Haleakala - Multi-Island View

Beautiful house in the Upscale Maui Meadows neighborhood

10.0 out of 10, Exceptional, (4)
"What an exceptional way to celebrate our 50th wedding anniversary! My husband & I took our family with us to Maui to stay in this outstanding home. Thank you for sharing your home with us! The property manager Diane was awesome! She was such a beautiful person and our family experienced a lifetime of memories in which she was a vital part! Thank you for all of the great memories, the wine was a lovely touch, the grandchildren and adults alike enjoyed the coconut water, the mango’s and the...
Beautiful house in the Upscale Maui Meadows neighborhood

Luxury Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (37)
"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

Mahina Cottage, Mahina Cottage

9.8 out of 10, Exceptional, (9)
"This is a beautiful property centrally located for all of the many activities we had scheduled for our visit to Maui. The home was clean, very private, and just as advertised. The owners have tried to make everything you could possibly need available, including beach chairs, snorkel gear, boogie boards, ice coolers, beach towels, etc. It is a great property and one I will use again if traveling to Maui."
Mahina Cottage, Mahina Cottage
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.
Don't see what you're looking for?
See all available properties in Kaupo
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Kaupo

Wailea Ekolu - CoralTree Residence Collection

3.5 star property
8.8 out of 10, Excellent, (246)
"We loved this property! It was more then what we were expected, so comfortable and quiet and super clean and very spacious, we will stay here again."
Wailea Ekolu - CoralTree Residence Collection

STHA-2017/0002 Across from Hana Bay

9.6 out of 10, Exceptional, (337)
"This is an older place that has been kept in excellent condition. Very nice, clean, and comfortable. Everything in the place is neat and clean. The instructions from the owner, impeccable. Anything and everything you could possibly need to know is described. Good location to food and beach. "
STHA-2017/0002 Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay

9.6 out of 10, Exceptional, (341)
"Great place. Wish we had coffee too"
The price is AED 716
AED 1,461 total
includes taxes & fees
2 Jan - 3 January 2025
Fisher's Hana Bay Hale, Across from Hana Bay
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.