Book Holiday Homes in Lanai

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Featured Holiday Homes in Lanai

272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

Lahaina
With a stay at this vacation home, you'll be centrally located in Lahaina, within a 15-minute drive of Whalers Village and Lahaina Pali Trail.
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water
The #1 Luxury OCEAN FRONT Mansion!  Sleeps 32

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

lahina
When you stay at this vacation home in Honokowai, you'll be on the beach, within a 10-minute drive of Kaanapali Beach and Whalers Village.
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2 out of 5
Lahaina
When you stay at this vacation home in Kaanapali, you'll be on the beach, a 4-minute drive from Whalers Village and 7 minutes from Kaanapali Beach.
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
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Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Lahaina
When you stay at this vacation home in Napili, you'll be by the sea, within a 15-minute drive of Napili Bay and Whalers Village.
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

Lahaina
When you stay at this vacation home in Kahana, you'll be on the beach, a 5-minute drive from Napili Bay and 9 minutes from Kaanapali Beach.
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
The #1 Vacation Rental on Maui!!  Steps to Maui's Best Beach!

The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!

Lahaina
When you stay at this vacation home in Napili, you'll be by the sea, within a 15-minute drive of Napili Bay and Whalers Village.
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

Lahaina
When you stay at this vacation home in Kapalua, you'll be by the sea, within a 15-minute drive of Napili Bay and Whalers Village.
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

Lahaina
When you stay at this vacation home in Kaanapali, you'll be next to a golf course, a 4-minute drive from Whalers Village and 6 minutes from Kaanapali Beach.
Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH
Lana’i Oasis and Gem, The Artist's House

Lana’i Oasis and Gem, The Artist's House

Lanai
The price is AU$1,241 per night from 10 Mar to 11 Mar
AU$1,241
includes taxes & fees
10 Mar - 11 Mar
With a stay at this vacation home in Lanai City, you'll be near the beach, just a 2-minute walk from Munro Trail and 10 minutes by foot from Lanaʻi Culture & ...
Lana’i Oasis and Gem, The Artist's House
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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.

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

Holiday houses in Lanai 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 Lanai 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 Lanai adventures, obvs.

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

Lanai Holiday Homes essential information

Accommodation
71 Holiday Homes
Lowest Price
AU$995
Highest Price
AU$2,227
Popular accommodation
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water, The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, #1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool, Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!, Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana, The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!, Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!, Private home with POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH, Lana’i Oasis and Gem, The Artist's House

Top trending hotels in Lanai

Four Seasons Resort Lanai

Four Seasons Resort Lanai

5 out of 5
1 Manele Bay Road, Lanai City, HI
The price is AU$2,227 per night from 13 Mar to 14 Mar
AU$2,227
includes taxes & fees
13 Mar - 14 Mar
When you a stay at Four Seasons Resort Lanai in Lanai City, you'll be on the beach, just steps from Hulopoe Beach and Kaluakoi Point.
Four Seasons Resort Lanai
Sensei Lanai, A Four Seasons Resort

Sensei Lanai, A Four Seasons Resort

5 out of 5
1 Keomoku Hwy, Lanai City, HI
With a stay at Sensei Lanai, A Four Seasons Resort in Lanai City, you'll be near the beach, just a 1-minute walk from Lanai Pine Sporting Clays and 13 minutes ...
Sensei Lanai, A Four Seasons Resort
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4 out of 5
2365 Kaanapali Pkwy, Lahaina, HI
Fully refundableReserve now, pay when you stay
The price is AU$1,119 per night from 8 Mar to 9 Mar
AU$1,119
includes taxes & fees
8 Mar - 9 Mar
When you stay at The Westin Maui Resort & Spa, Ka'anapali in Kaanapali, you'll be on the beach, just steps from Kaanapali Beach and 5 minutes by foot from Whalers ...
The Westin Maui Resort & Spa, Ka'anapali
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Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
200 Nohea Kai Dr, Lahaina, HI
Fully refundableReserve now, pay when you stay
The price is AU$995 per night from 13 Mar to 14 Mar
AU$995
includes taxes & fees
13 Mar - 14 Mar
With a stay at Hyatt Regency Maui Resort & Spa in Kaanapali, you'll be on the beach, a 3-minute walk from Kaanapali Beach and a 3-minute drive from Whalers ...
Hyatt Regency Maui Resort & Spa
Don't see what you're looking for?
See all available properties in Lanai
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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.