Book Holiday Homes in Kihei

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Featured Holiday Homes in Kihei

OCEAN BLISS  Oceanfront Private Home

OCEAN BLISS Oceanfront Private Home

Kihei
Book a stay at this beach vacation home in Kihei. Enjoy free WiFi, private pools, and a beach locale. Our guests praise the helpful staff in our reviews. Popular ...
OCEAN BLISS Oceanfront Private Home
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal

CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal

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 Keawakapu Beach ...
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal
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
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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
Stay at this vacation home in Kihei. Enjoy tennis courts, patios, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. Popular ...
Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC
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
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui

Kihei
Stay at this vacation home in Kihei. Enjoy free WiFi, a garden, and patios. Popular attractions Wailea Beach and Kihei Boat Ramp are located nearby.
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

Wailea
Stay at this vacation home in Kihei. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Wailea Beach and Shops at Wailea are located ...
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
Wonderful Wailea Condo Lanai Water Views

Wonderful Wailea Condo Lanai Water Views

3 out of 5
10 Wailea Ekolu Pl, Kihei, HI
Stay at this 3-star vacation home in Kihei. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Wailea Beach and Shops at Wailea are ...
Wonderful Wailea Condo Lanai Water Views
OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

Kihei
Book a stay at this beach vacation home in Kihei. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Wailea Beach and Makamakaole Trail are located ...
OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM
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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
186 Holiday Homes
Lowest Price
NZ$580
Highest Price
NZ$1,996
Popular accommodation
OCEAN BLISS Oceanfront Private Home , CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal, Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A, Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC, Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre, Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui, Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center, Wonderful Wailea Condo Lanai Water Views, OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

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$580 per night from 28 Apr to 29 Apr
NZ$580
includes taxes & fees
28 Apr - 29 Apr
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
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$1,945 per night from 3 Apr to 4 Apr
NZ$1,945
includes taxes & fees
3 Apr - 4 Apr
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
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$1,532 per night from 15 Apr to 16 Apr
NZ$1,532
includes taxes & fees
15 Apr - 16 Apr
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
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Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is NZ$1,996 per night from 26 Apr to 27 Apr
NZ$1,996
includes taxes & fees
26 Apr - 27 Apr
Stay at this 4.5-star luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Fairmont Kea Lani Maui
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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.