Book Holiday Homes in Kahoolawe

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Featured Holiday Homes in Kahoolawe

WOW! Stunning Ocean Views, Large Deck &Luxury Beds

WOW! Stunning Ocean Views, Large Deck &Luxury Beds

Kihei
With a stay at this vacation home in Kihei, you'll be within a 10-minute drive of Wailea Beach and Keawakapu Beach North.
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
Private & Fabulous views!  Exclusive pool, spa and 1 acre yard

Private & Fabulous views! Exclusive pool, spa and 1 acre yard

Kihei
With a stay at this vacation home in Kihei (Wailea), you'll be within a 10-minute drive of Wailea Beach and Ulua Beach Park.
Private & Fabulous views! Exclusive pool, spa and 1 acre yard
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
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Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!

Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!

Kihei
With a stay at this vacation home in Kihei, you'll be on the beach, within a 15-minute drive of Wailea Beach and Maalaea Bay Beaches.
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!

Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!

Kihei
A stay at this vacation home places you in the heart of Kihei, within a 15-minute walk of Pilates Maui and Sanctuary Education Center Whale Watch Center.
Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!
Modern 3 Bedroom Family Friendly Kihei Home Near Beach

Modern 3 Bedroom Family Friendly Kihei Home Near Beach

Kihei
With a stay at this vacation home in Kihei, you'll be by the sea, within a 15-minute drive of Wailea Beach and Cove Park.
Modern 3 Bedroom Family Friendly Kihei Home Near Beach
Spacious Maui Beach House, Private Pool, AC, Sleeps 6

Spacious Maui Beach House, Private Pool, AC, Sleeps 6

Kihei
With a stay at this vacation home in Kihei, you'll be by the sea, just a 5-minute walk from Waipuilani Park and 6 minutes by foot from Waipuilani Beach.
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2

Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2

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.
Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
Spacious Hawaiian home 50 steps from Sugar Beach!

Spacious Hawaiian home 50 steps from Sugar Beach!

Kihei
With a stay at this vacation home in Kihei, you'll be a 1-minute walk from Maalaea Bay Beaches and 8 minutes by foot from Sugar Beach.
Spacious Hawaiian home 50 steps from Sugar Beach!
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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
83 Holiday Homes
Lowest Price
AU$1,105
Highest Price
AU$1,514
Popular accommodation
WOW! Stunning Ocean Views, Large Deck &Luxury Beds, Private & Fabulous views! Exclusive pool, spa and 1 acre yard , Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui, Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !!!, Private Luxury Villa in Kihei. Just moments walk to the beach. 10/10 reviews!, Modern 3 Bedroom Family Friendly Kihei Home Near Beach, Spacious Maui Beach House, Private Pool, AC, Sleeps 6, Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2, Spacious Hawaiian home 50 steps from Sugar Beach!

Top trending hotels in Kahoolawe

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is AU$1,105 per night from 1 Dec to 2 Dec
AU$1,105
includes taxes & fees
1 Dec - 2 Dec
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$1,514 per night from 1 Dec to 2 Dec
AU$1,514
includes taxes & fees
1 Dec - 2 Dec
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$1,440 per night from 30 Nov to 1 Dec
AU$1,440
includes taxes & fees
30 Nov - 1 Dec
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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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$1,202 per night from 14 Dec to 15 Dec
AU$1,202
includes taxes & fees
14 Dec - 15 Dec
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.