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
With a stay at this vacation home in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Polo Beach.
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
With a stay at this vacation home in Kihei, you'll be by the sea, within a 10-minute drive of Wailea Beach and Keawakapu Beach North.
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
When you a stay at this vacation home in Kihei, you'll be on the beach, within a 5-minute walk of Waipuilani Park and Lava Fields.
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
With a stay at this vacation home in Kihei (Halama Street), you'll be within a 15-minute drive of Wailea Beach and Coast Guard Beach.
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
With a stay at this vacation home in Kihei, you'll be on the beach, just a 1-minute walk from Maalaea Bay Beaches and 8 minutes by foot from Sugar Beach.
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
With a stay at this vacation home in Kihei, you'll be by the ocean, within a 15-minute drive of Wailea Beach and Kamaole Beach Park 2.
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Wonderful Wailea Condo Lanai Water Views

Wonderful Wailea Condo Lanai Water Views

3 out of 5
10 Wailea Ekolu Pl, Kihei, HI
With a stay at this vacation home in Kihei (Wailea), you'll be within a 10-minute drive of Wailea Beach and Shops at Wailea.
Wonderful Wailea Condo Lanai Water Views
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
With a stay at this vacation home in Kihei (Wailea), you'll be within a 10-minute walk of Wailea Beach and Shops at Wailea.
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

OCEANFRONT HOME*UNINTERRUPTED*HOT TUB*PRIVATE GEM

Kihei
With a stay at this vacation home, you'll be centrally located in Kihei, within a 15-minute drive of Wailea Beach and Makamakaole Trail.
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
185 Holiday Homes
Lowest Price
AU$526
Highest Price
AU$1,811
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, Wonderful Wailea Condo Lanai Water Views, Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center, 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 AU$526 per night from 31 Mar to 1 Apr
AU$526
includes taxes & fees
31 Mar - 1 Apr
Located in Kihei, Maui Coast Hotel is in a shopping district, a 3-minute walk from Kamaole Beach Park and 6 minutes by foot from Cove Park.
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 AU$1,771 per night from 1 Apr to 2 Apr
AU$1,771
includes taxes & fees
1 Apr - 2 Apr
With a stay at Grand Wailea Maui, A Waldorf Astoria Resort in Kihei (Wailea), you'll be within a 10-minute walk of Wailea Beach and Shops at Wailea.
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 AU$1,395 per night from 1 Apr to 2 Apr
AU$1,395
includes taxes & fees
1 Apr - 2 Apr
With a stay at Four Seasons Resort Maui at Wailea in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Polo Beach.
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 AU$1,811 per night from 26 Apr to 27 Apr
AU$1,811
includes taxes & fees
26 Apr - 27 Apr
With a stay at Fairmont Kea Lani Maui in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Wailea Blue Golf Course.
Fairmont Kea Lani 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.