
Kaanapali Holiday Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Kaanapali holiday rentals





5. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
6. Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access
Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access
7. Top Floor, Corner Unit, Pool View, Kaanapali Beach
Top Floor, Corner Unit, Pool View, Kaanapali Beach
8. Summertime Special Prices!! Book Now!
Summertime Special Prices!! Book Now!Find holiday rentals that suit your style
Top Kaanapali Hotel Reviews

OUTRIGGER Kaanapali Beach Resort
Find out more about Kaanapali
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kaanapali holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Kaanapali. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Kaanapali. Seeing all the best attractions is bound to make you fall in love with Kaanapali. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Kaanapali short-term rentals, that won’t be hard to do.
Explore a world of travel with Expedia
- Napili Hotels
- Hotels near Kapalua Beach
- Honokowai Hotels
- Hotels near Black Rock
- Hotels near Whalers Village
- Downtown Lahaina Hotels
- Kahana Hotels
- Kaanapali Hotels
- Hotels near Kaanapali Beach
- Hotels near West Maui
- Cheap Hotels in Napili-Honokowai
- Beach Hotels in Napili-Honokowai
- Historic Hotels in Kaanapali
- Boutique Hotels in Kaanapali
- Luxury Hotels in Kaanapali
- Cheap Hotels in Kaanapali
- Hotels with Parking in Kaanapali
- Family Hotels in Kaanapali
- Beach Hotels in Kaanapali
- Luxury Hotels in Lahaina
- Family Hotels in Lahaina
- Spa Hotels in Lahaina
- Hotels with Pool in Lahaina
- Golf Hotels in Lahaina
- Cheap Hotels in Lahaina
- All Inclusive Hotels in Lahaina
- Hotels with Parking in Lahaina
- Apartments in West Maui
- Apartments in Lahaina
- Condo Rentals in Lahaina
- Inns in Lahaina
- Resort in Lahaina
- Holiday Homes in Lahaina
- Holiday Parks in Lahaina
- B&B in Lahaina
- Condo Rentals in Kahana
- Resort in Kahana
- Condominium Resort in Kaanapali
- Serviced Apartments in Kaanapali
- Holiday Homes in Kaanapali
- Cottages in Kaanapali
- Villas in Kaanapali
- Resort in Kaanapali
- B&B in Kaanapali
- Apartments in Kaanapali
- Condo Rentals in Kaanapali
- Condo Rentals in Honokowai
- Holiday Homes in Napili-Honokowai
- Holiday Homes in Kapalua
- Aston Resorts in Kaanapali
- Hilton Hotels in Kaanapali
- Classic Resorts in Lahaina
- Aqua Hotels in Lahaina
- Flights from Bozeman (BZN) to Kapalua (JHM)
- Flights from Steamboat Springs (HDN) to Kapalua (JHM)
- Flights from Joinville (JOI) to Kapalua (JHM)
- Flights from Boa Vista (BVB) to Kapalua (JHM)
- Flights from Dundee (DND) to Kapalua (JHM)
- Flights from Christchurch (CHC) to Kapalua (JHM)
- Flights from Orlando (MCO) to Kapalua (JHM)
- Flights from Eagle (EAA) to Kapalua (JHM)
- Flights from Honolulu (HNL) to Kapalua (JHM)
- Flights from Kwigillingok (KWK) to Kapalua (JHM)
- Flights from Toksook Bay (OOK) to Kapalua (JHM)
- Flights from Altus (AXS) to Kapalua (JHM)
- Flights from Salerno (QSR) to Kapalua (JHM)
- Flights to Lahaina
- Flights to Kaanapali
- Flights from West Maui
















































































