Book Holiday Homes in Kahoolawe

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Featured Holiday Homes in Kahoolawe

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

Kihei
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
Kihei Maui Beach house - On the water

Kihei Maui Beach house - On the water

Kihei
With a stay at this vacation home in Kihei (Halama Street), you'll be steps from Kalama Beach Park and 2 minutes by foot from Kihei Town Center Shopping ...
Kihei Maui Beach house - On the water
Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis.

Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis.

Lahaina
With a stay at this vacation home in Lahaina, you'll be on the beach, within a 15-minute drive of Whalers Village and Lahaina Pali Trail.
Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis.
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Entire home in Kihei within walking distance to beaches, shopping and dining!

Entire home in Kihei within walking distance to beaches, shopping and dining!

Kihei
With a stay at this vacation home in Kihei, you'll be within a 15-minute drive of Wailea Beach and Charley Young Beach.
Entire home in Kihei within walking distance to beaches, shopping and dining!
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
With a stay at this vacation home in Kihei (Halama Street), you'll be steps from Kalama Beach Park and 3 minutes by foot from Kihei Town Center Shopping ...
4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi
Privacy In Paradise - Top Rated Vacation Home in West Maui

Privacy In Paradise - Top Rated Vacation Home in West Maui

Lahaina
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.
Privacy In Paradise - Top Rated Vacation Home in West Maui
BEACHFRONT MAUI KIHEI HOUSE

BEACHFRONT MAUI KIHEI HOUSE

Kihei
With a stay at this vacation home in Kihei, you'll be on the beach, just a 5-minute walk from Waipuilani Park and 6 minutes by foot from Waipuilani Beach.
BEACHFRONT MAUI KIHEI HOUSE
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
Oceanview Retreat in Puamana – Steps from the Beach & Surf

Oceanview Retreat in Puamana – Steps from the Beach & Surf

Lahaina
The price is AU$1,821 per night from 7 Oct to 8 Oct
AU$1,821
7 Oct - 8 Oct
includes taxes & fees
With a stay at this vacation home in Lahaina, you'll be by the sea, within a 15-minute drive of Whalers Village and Lahaina Pali Trail.
Oceanview Retreat in Puamana – Steps from the Beach & Surf
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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
158 Holiday Homes
Lowest Price
AU$451
Highest Price
AU$1,821
Popular accommodation
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center, Kihei Maui Beach house - On the water, Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis., Entire home in Kihei within walking distance to beaches, shopping and dining!, 4 bedroom beach home with added sofa bed, ocean view, swimming pool, Jacuzzi , Privacy In Paradise - Top Rated Vacation Home in West Maui, BEACHFRONT MAUI KIHEI HOUSE, Gorgeous Home Across from Beach - 5 BR + Opt. Cottage / 4 Bath / AC, Oceanview Retreat in Puamana – Steps from the Beach & Surf

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$451 per night from 28 Sept to 29 Sept
AU$451
28 Sept - 29 Sept
includes taxes & fees
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
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is AU$1,694 per night from 19 Sept to 20 Sept
AU$1,694
19 Sept - 20 Sept
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.
Fairmont Kea Lani Maui
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$1,322 per night from 16 Sept to 17 Sept
AU$1,322
16 Sept - 17 Sept
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.
Grand Wailea Maui, A Waldorf Astoria Resort
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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$1,096 per night from 26 Sept to 27 Sept
AU$1,096
26 Sept - 27 Sept
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.
Wailea Beach Resort - Marriott, Maui
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.

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^Subject to availability and chosen travel dates.