Book Holiday Homes in Kihei

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Featured Holiday Homes in Kihei

DISCOUNTED OCTOBER Special - Oceanfront Private Home

DISCOUNTED OCTOBER Special - 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 windowDISCOUNTED OCTOBER Special - Oceanfront Private Home
4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi

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

Kihei HI
Stay at this family-friendly holiday home in Kihei. Enjoy free Wi-Fi, private pools and a water park. Popular attractions Wailea Beach and Kihei Town Center ...
Opens in a new window4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi
Breath taking ocean and volcano views! Pool,Close to beaches and everything else

Breath taking ocean and volcano views! Pool,Close to beaches and everything else

Kihei HI
Stay at this golf holiday home in Kihei. Enjoy private pools, a garden and laundry facilities. Popular attractions Wailea Beach and Keawakapu Beach South are ...
Opens in a new windowBreath taking ocean and volcano views! Pool,Close to beaches and everything else
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Oceanfront Hideaway on the Beach

Oceanfront Hideaway on the Beach

Kihei HI
Stay at this beach holiday home in Kihei. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Wailea Beach and Coast Guard Beach are ...
Opens in a new windowOceanfront Hideaway on the Beach
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, laundry facilities and concierge services. 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
Kihei Maui Beach house - On the water

Kihei Maui Beach house - On the water

Kihei HI
Stay at this beach holiday home in Kihei. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Wailea Beach and Kihei Town Center Shopping ...
Opens in a new windowKihei Maui Beach house - On the water
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
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

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

Kihei HI
Stay at this holiday home in Kihei. Enjoy laundry facilities, tennis courts and patios. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowGorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC
Very Best Deluxe Ocean View...Panoramic View....First Class!!

Very Best Deluxe Ocean View...Panoramic View....First Class!!

Wailea-Makena HI
Stay at this family-friendly holiday home in Kihei. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Wailea Beach and Wailea Blue Golf Course ...
Opens in a new windowVery Best Deluxe Ocean View...Panoramic View....First Class!!
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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
165 Holiday Homes
Lowest Price
NZ$509
Highest Price
NZ$1,534
Popular accommodation
DISCOUNTED OCTOBER Special - Oceanfront Private Home, 4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi , Breath taking ocean and volcano views! Pool,Close to beaches and everything else, Oceanfront Hideaway on the Beach, Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops, Kihei Maui Beach house - On the water, Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view, Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC, Very Best Deluxe Ocean View...Panoramic View....First Class!!

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$509 per night from 14 Dec to 15 Dec
NZ$509
14 Dec - 15 Dec
includes taxes & fees
Stay at this hotel in Kihei. Enjoy free Wi-Fi, 2 outdoor pools and 3 hot tubs. Our guests praise the breakfast and the pool in their reviews. Popular attractions ...
Opens in a new windowMaui 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$1,534 per night from 19 Dec to 20 Dec
NZ$1,534
19 Dec - 20 Dec
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
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$1,422 per night from 14 Dec to 15 Dec
NZ$1,422
14 Dec - 15 Dec
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
Save an average of 15% on thousands of hotels when you're signed in
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr Kihei HI
The price is NZ$1,349 per night from 9 Jan to 10 Jan
NZ$1,349
9 Jan - 10 Jan 2026
includes taxes & fees
Stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa and 4 restaurants. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowWailea Beach Resort - Marriott, Maui
Don't see what you're looking for?
See all available properties in Kihei
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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.

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^Subject to availability and chosen travel dates.