Book Holiday Homes in Kahoolawe

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Featured Holiday Homes in Kahoolawe

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
With a stay at this vacation home, you'll be centrally located in Kihei, within a 10-minute drive of Wailea Beach and Kalama Beach Park.
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
With a stay at this vacation home in Kihei (Central Kihei), you'll be steps from Kalama Beach Park and 2 minutes by foot from Kihei Town Center Shopping ...
Opens in a new windowKihei Maui Beach house - On the water
BEACHFRONT MAUI KIHEI HOUSE

BEACHFRONT MAUI KIHEI HOUSE

Kihei HI
With a stay at this vacation home in Kihei (Central Kihei), you'll be a 5-minute walk from Waipuilani Park and 6 minutes by foot from Waipuilani Beach.
Opens in a new windowBEACHFRONT MAUI KIHEI HOUSE
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Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view

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

Kihei HI
With a stay at this vacation home in Kihei (North Kihei), you'll be steps from Maalaea Bay Beaches and 8 minutes by foot from Sugar Beach.
Opens in a new windowSpecials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

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

Wailea HI
With a stay at this vacation home in Kihei (Wailea), you'll be within a 10-minute drive of Wailea Beach and Keawakapu Beach North.
Opens in a new windowAmazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Beachside townhome with AC & 2 pools - Short walk to ocean

Beachside townhome with AC & 2 pools - Short walk to ocean

Lahaina HI
When you stay at this vacation home in Lahaina, you'll be by the sea, within a 15-minute drive of Kaanapali Beach and Whalers Village.
Opens in a new windowBeachside townhome with AC & 2 pools - Short walk to ocean
272-6  Puamana 2 Bedroom Oceanfront  Remodeled!!

272-6 Puamana 2 Bedroom Oceanfront Remodeled!!

Lahaina HI
This beach vacation home is 5.3 mi (8.6 km) from Kaanapali Beach and 5.4 mi (8.8 km) from Whalers Village.
Opens in a new window272-6 Puamana 2 Bedroom Oceanfront Remodeled!!
Great for families, 3 bedroom tropical paradise steps to pool and ocean.

Great for families, 3 bedroom tropical paradise steps to pool and ocean.

Lahaina HI
With a stay at this vacation home in Lahaina, you'll be near the beach, within a 15-minute drive of Whalers Village and Lahaina Pali Trail.
Opens in a new windowGreat for families, 3 bedroom tropical paradise steps to pool and ocean.
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
With a stay at this vacation home in Kihei (Central Kihei), you'll be within a 15-minute drive of Wailea Beach and Makamakaole Trail.
Opens in a new windowGorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC
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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.

Kahoolawe 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 Kahoolawe vacation homes are the perfect way for you to wing it.

Holiday houses in Kahoolawe 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 Kahoolawe 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 Kahoolawe adventures, obvs.

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

Kahoolawe Holiday Homes essential information

Accommodation
150 Holiday Homes
Lowest Price
AU$462
Highest Price
AU$1,889
Popular accommodation
Island Surf with Ocean View - Across from popular Surf spot, Beach, and Shops, Kihei Maui Beach house - On the water, BEACHFRONT MAUI KIHEI HOUSE, Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view, Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area, Beachside townhome with AC & 2 pools - Short walk to ocean, 272-6 Puamana 2 Bedroom Oceanfront Remodeled!!, Great for families, 3 bedroom tropical paradise steps to pool and ocean., Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC

Top trending hotels in Kahoolawe

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$1,694 per night from 16 May to 17 May
AU$1,694
16 May - 17 May
includes taxes & fees
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.
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 AU$462 per night from 25 May to 26 May
AU$462
25 May - 26 May
includes taxes & fees
Located in Kihei (South Kihei), Maui Coast Hotel is a 5-minute walk from Kamaole Beach Park and 9 minutes by foot from Cove Park.
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 AU$1,889 per night from 31 May to 1 June
AU$1,889
31 May - 1 June
includes taxes & fees
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.
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 AU$1,389 per night from 25 May to 26 May
AU$1,389
25 May - 26 May
includes taxes & fees
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.
Opens in a new windowFour Seasons Resort Maui at Wailea
Don't see what you're looking for?
See all available properties in Kahoolawe
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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.

Top Picks

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^Subject to availability and chosen travel dates.