Book Holiday Homes in Lanai

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Featured Holiday Homes in Lanai

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

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

2 out of 5
Lahaina
Book a stay at this beach vacation home in Kaanapali. Enjoy private pools, a beach locale, and a fitness center. Popular attractions Whalers Village and Kaanapali ...
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
The #1 Vacation Rental on Maui!!  Steps to Maui's Best Beach! Pickle Ball Ct!

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

Lahaina
Book a stay at this family-friendly vacation home in Napili. Enjoy private pools, a garden, and laundry facilities. Popular attractions Whalers Village and Kaanapali ...
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!
The #1 Luxury OCEAN FRONT Mansion!  Sleeps 32

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

lahina
Book a stay at this beach vacation home in Honokowai. Enjoy private pools, a beach locale, and a fitness center. Popular attractions Whalers Village and Kaanapali ...
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
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Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25

Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25

Lahaina
Book a stay at this beach vacation home in Kaanapali. Enjoy a beach locale, laundry facilities, and patios. Popular attractions Whalers Village and Kaanapali ...
Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25
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
Book a stay at this beach vacation home in Kapalua. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Whalers Village and Kaanapali Beach ...
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
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
Book a stay at this beach vacation home in Napili. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Whalers Village and Kaanapali Beach ...
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Kapalua Golf Villas by KBM Resorts

Kapalua Golf Villas by KBM Resorts

4 out of 5
Lahaina
Stay at this 4-star beach vacation home in Kapalua. Enjoy free parking, a beach locale, and free grocery shopping service. Popular attractions Whalers Village ...
Kapalua Golf Villas by KBM Resorts
Location, Location.... Just Steps Away from the Ocean!

Location, Location.... Just Steps Away from the Ocean!

Lahaina
Stay at this vacation home in Lahaina. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Kaanapali Beach and Whalers Village are located ...
Location, Location.... Just Steps Away from the Ocean!
Privacy In Paradise - Top Rated Vacation Home in West Maui

Privacy In Paradise - Top Rated Vacation Home in West Maui

Lahaina
Book a stay at this family-friendly vacation home in Launiupoko. Enjoy private pools, a fitness center, and a garden. Popular attractions Kaanapali Beach and ...
Privacy In Paradise - Top Rated Vacation Home in West Maui
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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
114 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool, The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!, The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25, Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!, Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!, Kapalua Golf Villas by KBM Resorts, Location, Location.... Just Steps Away from the Ocean!, Privacy In Paradise - Top Rated Vacation Home in West Maui

Top trending hotels in Lanai

Four Seasons Resort Lanai

Four Seasons Resort Lanai

5 out of 5
1 Manele Bay Road, Lanai City, HI
Stay at this 5-star luxury resort in Lanai City. Enjoy free parking, 2 outdoor pools, and a full-service spa. Our guests praise the property condition in our ...
Four Seasons Resort Lanai
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy, Lahaina, HI
Fully refundableReserve now, pay when you stay
Stay at this 4.5-star luxury hotel in Kaanapali. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property ...
The Westin Maui Resort & Spa, Ka'anapali
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr, Lahaina, HI
Fully refundableReserve now, pay when you stay
Stay at this 4-star beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the bar and the helpful staff in our ...
Royal Lahaina Resort & Bungalows
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OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
2525 Kaanapali Parkway, Lahaina, HI
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star beach resort in Kaanapali. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
OUTRIGGER Kaanapali Beach Resort
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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.