Book Holiday Homes in Kihei

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Featured Holiday Homes in Kihei

Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops

Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops

Kihei HI
Stay at this holiday home in Kihei. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Wailea Beach and Maui Fish Pipe are located ...
Opens in a new windowIsland Surf with Ocean View - Across from popular Surf spot, Beach, and Shops
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

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

Kihei HI
Stay at this beach holiday home in Kihei. Enjoy free Wi-Fi, private pools and a beach locale. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowSpecials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
Oceanfront Private Home

Oceanfront Private Home

Kihei HI
Stay at this beach holiday home in Kihei. Enjoy free Wi-Fi, private pools and a beach locale. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowOceanfront Private Home
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Modern 3 Bedroom Family Friendly Kihei Home Near Beach

Modern 3 Bedroom Family Friendly Kihei Home Near Beach

Kihei HI
Stay at this holiday home in Kihei. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Wailea Beach and Cove Park are located nearby.
Opens in a new windowModern 3 Bedroom Family Friendly Kihei Home Near Beach
Exclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!

Exclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!

Kihei HI
Stay at this holiday home in Kihei. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Wailea Beach and Wailea Blue Golf Course are ...
Opens in a new windowExclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!
Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View

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

Kihei HI
Stay at this golf holiday home in Kihei. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Wailea Beach and Shops at Wailea are located ...
Opens in a new windowGorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View
Sleeps 10, Family Favorite, Fully Upgraded Modern Renovation and Decorated

Sleeps 10, Family Favorite, Fully Upgraded Modern Renovation and Decorated

Kihei HI
Stay at this holiday home in Kihei. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Wailea Beach and Shops at Wailea are located ...
Opens in a new windowSleeps 10, Family Favorite, Fully Upgraded Modern Renovation and Decorated
Entire home in Kihei within walking distance to beaches, shopping and dining!

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

Kihei HI
Stay at this holiday home in Kihei. Enjoy a garden, laundry facilities and tennis courts. Popular attractions Wailea Beach and Charley Young Beach are located ...
Opens in a new windowEntire home in Kihei within walking distance to beaches, shopping and dining!
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

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

Wailea HI
Stay at this family-friendly holiday home in Kihei. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Wailea Beach and Keawakapu Beach South ...
Opens in a new windowAmazing House with Pool, Spa, Cabana & More Kihei Wailea Area
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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
156 Holiday Homes
Lowest Price
NZ$546
Highest Price
NZ$2,308
Popular accommodation
Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops, Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view, Oceanfront Private Home, Modern 3 Bedroom Family Friendly Kihei Home Near Beach, Exclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!, Gorgeous 2 Story Townhouse on The Blue Golf Course in Wailea with Ocean View, Sleeps 10, Family Favorite, Fully Upgraded Modern Renovation and Decorated, Entire home in Kihei within walking distance to beaches, shopping and dining!, Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

Top trending hotels in Kihei

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$1,745 per night from 9 May to 10 May
NZ$1,745
9 May - 10 May
includes taxes & fees
Stay at this luxury resort in Kihei. Enjoy free Wi-Fi, 9 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
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$546 per night from 5 May to 6 May
NZ$546
5 May - 6 May
includes taxes & fees
Stay at this hotel in Kihei. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the breakfast and the pool in their reviews. Popular attractions ...
Opens in a new windowMaui Coast Hotel
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is NZ$2,308 per night from 2 May to 3 May
NZ$2,308
2 May - 3 May
includes taxes & fees
Stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa and 6 restaurants. Our guests praise the helpful staff and the property condition ...
Opens in a new windowFairmont Kea Lani Maui
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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$1,697 per night from 30 Apr to 1 May
NZ$1,697
30 Apr - 1 May
includes taxes & fees
Stay at this luxury resort in Kihei. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowFour Seasons Resort Maui at Wailea
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.

Top Picks

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^Subject to availability and chosen travel dates.