Book Holiday Homes in Kahoolawe

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Featured Holiday Homes in Kahoolawe

DISCOUNTED OCTOBER Special - Oceanfront Private Home

DISCOUNTED OCTOBER Special - Oceanfront Private Home

Kihei HI
With a stay at this vacation home in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Polo Beach.
Opens in a new windowDISCOUNTED OCTOBER Special - Oceanfront Private Home
Puamana Ocean Front Tropical Paradise 226-1

Puamana Ocean Front Tropical Paradise 226-1

Lahaina HI
With a stay at this vacation home in Lahaina, you'll be on the beach, within a 15-minute drive of Whalers Village and Launiupoko Beach Park.
Opens in a new windowPuamana Ocean Front Tropical Paradise 226-1
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
With a stay at this vacation home in Kihei (Central Kihei), you'll be steps from Kalama Beach Park and 3 minutes by foot from Kihei Town Center Shopping ...
Opens in a new window4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi
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Beachside townhome with AC, 3 pools, & pickleball - Walk to ocean

Beachside townhome with AC, 3 pools, & pickleball - 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, 3 pools, & pickleball - Walk to ocean
Privacy In Paradise - Top Rated Vacation Home in West Maui

Privacy In Paradise - Top Rated Vacation Home in West Maui

Lahaina HI
With a stay at this vacation home in Launiupoko, you'll be near the beach, within a 15-minute drive of Kaanapali Beach and Launiupoko Beach Park.
Opens in a new windowPrivacy In Paradise - Top Rated Vacation Home in West Maui
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
With a stay at this vacation home, you'll be centrally located in Kihei, within a 10-minute drive of Wailea Beach and Ulua Beach Park.
Opens in a new windowBreath taking ocean and volcano views! Pool,Close to beaches and everything else
Oceanfront Hideaway on the Beach

Oceanfront Hideaway on the Beach

Kihei HI
The price is AU$4,451 per night from 20 Dec to 21 Dec
AU$4,451
20 Dec - 21 Dec
includes taxes & fees
With a stay at this vacation home in Kihei (Central Kihei), you'll be steps from Makamakaole Trail and 6 minutes by foot from Saint Theresa Church.
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
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
272-6  Puamana 2 Bedroom Oceanfront  Remodeled!!

272-6 Puamana 2 Bedroom Oceanfront Remodeled!!

Lahaina Hawaii
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!!
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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
155 Holiday Homes
Lowest Price
AU$444
Highest Price
AU$4,451
Popular accommodation
DISCOUNTED OCTOBER Special - Oceanfront Private Home, Puamana Ocean Front Tropical Paradise 226-1, 4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi , Beachside townhome with AC, 3 pools, & pickleball - Walk to ocean, Privacy In Paradise - Top Rated Vacation Home in West Maui, 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, 272-6 Puamana 2 Bedroom Oceanfront Remodeled!!

Top trending hotels in Kahoolawe

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$444 per night from 15 Dec to 16 Dec
AU$444
15 Dec - 16 Dec
includes taxes & fees
Located in Kihei (South Kihei), Maui Coast Hotel is a 3-minute walk from Kamaole Beach Park and 6 minutes by foot from Cove Park.
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 AU$1,339 per night from 19 Dec to 20 Dec
AU$1,339
19 Dec - 20 Dec
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
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$1,242 per night from 15 Dec to 16 Dec
AU$1,242
15 Dec - 16 Dec
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
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 AU$1,177 per night from 9 Jan to 10 Jan
AU$1,177
9 Jan - 10 Jan 2026
includes taxes & fees
With a stay at Wailea Beach Resort - Marriott, Maui in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Shops at Wailea.
Opens in a new windowWailea Beach Resort - Marriott, Maui
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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.

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^Subject to availability and chosen travel dates.