Book Holiday Homes in Kihei

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Kihei

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A

Kihei
Stay at this vacation home in Kihei. Enjoy a beach locale, a fitness center, and a garden. Popular attractions Wailea Beach and Waipuilani Park are located ...
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖

Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖

Kihei
Stay at this vacation home in Kihei. Enjoy private pools, a garden, and patios. Popular attractions Wailea Beach and Waipuilani Park are located nearby.
Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖
Stunning Beachfront Private Home! Perfect for Families, Great Location!

Stunning Beachfront Private Home! Perfect for Families, Great Location!

Kihei
Book a stay at this beach vacation home in Kihei. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Wailea Beach and Maalaea Harbor are ...
Stunning Beachfront Private Home! Perfect for Families, Great Location!
Save an average of 15% on thousands of hotels when you're signed in
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

Kihei
Book a stay at this beach vacation home in Kihei. Enjoy free WiFi, private pools, and a beach locale. Our guests praise the pool and the helpful staff in our ...
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre
Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!

Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!

Kihei
Book a stay at this family-friendly vacation home in Kihei. Enjoy free WiFi, private pools, and a garden. Popular attractions Wailea Beach and Shops at Wailea ...
Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!
Blue Sky Escapes Vacation Home w/ big Oceanviews, Pool, Jacuzzi, 5min to beach

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

Kihei
Book a stay at this family-friendly vacation home in Kihei. Enjoy free WiFi, private pools, and a water park. Popular attractions Wailea Beach and Shops at Wailea ...
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

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

Kihei
Book a stay at this family-friendly vacation home in Kihei. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wailea Beach and Keawakapu ...
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach
Spacious Maui Beach House, Private Pool, AC, Sleeps 6

Spacious Maui Beach House, Private Pool, AC, Sleeps 6

Kihei
Stay at this vacation home in Kihei. Enjoy private pools, a garden, and tennis courts. Popular attractions Wailea Beach and Maalaea Harbor are located ...
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

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

Kihei
Stay at this vacation home in Kihei. Enjoy free WiFi, private pools, and a garden. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING
Don't see what you're looking for?
See all available properties in Kihei
View all properties
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.

Kihei Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Kihei vacation homes are the perfect way for you to wing it.

Holiday houses in Kihei let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Kihei in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Kihei adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Kihei with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Kihei vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Kihei Holiday Homes essential information

Accommodation
142 Holiday Homes
Lowest Price
NZ$612
Highest Price
NZ$2,017
Popular accommodation
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A, Spacious Family Beach House with Large Heated Pool; walk to Beach 🏖, Stunning Beachfront Private Home! Perfect for Families, Great Location!, Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre, Island Retreat Spacious 3B/3B Wailea Home Ocean View Private Pool & Hot Tub!, 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, Spacious Maui Beach House, Private Pool, AC, Sleeps 6, PRIVATE HOME OASIS-3 BEDROOM-OCEAN VIEWS-POOL-HOT TUB-METICULOUS CLEANING

Top trending hotels in Kihei

Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd, Kihei, HI
Fully refundableReserve now, pay when you stay
The price is NZ$612 per night from 17 Mar to 18 Mar
NZ$612
includes taxes & fees
17 Mar - 18 Mar
Stay at this 3.5-star hotel in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular ...
Maui Coast Hotel
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
The price is NZ$1,831 per night from 7 Mar to 8 Mar
NZ$1,831
includes taxes & fees
7 Mar - 8 Mar
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Four Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
The price is NZ$2,017 per night from 2 Mar to 3 Mar
NZ$2,017
includes taxes & fees
2 Mar - 3 Mar
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Grand Wailea Maui, A Waldorf Astoria Resort
Save an average of 15% on thousands of hotels when you're signed in
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
The price is NZ$1,964 per night from 15 Mar to 16 Mar
NZ$1,964
includes taxes & fees
15 Mar - 16 Mar
Stay at this 4.5-star luxury resort in Kihei. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Andaz Maui at Wailea Resort - a concept by Hyatt
Don't see what you're looking for?
See all available properties in Kihei
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.