
Wailea-Makena 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 Wailea-Makena holiday rentals

3. Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
4. Romantic 1 BR Condo with King Tempurpedic
Romantic 1 BR Condo with King Tempurpedic
5. Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
6. Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
7. Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
Gorgeous Luxury Ocean View Top Floor Corner Unit, AC, Pool, Free Parking, Wi-fi
8. Grand Champions | Ocean View 3 BR | Car Incl. w/ 6+ Nights | GCH-134 by KBM
Grand Champions | Ocean View 3 BR | Car Incl. w/ 6+ Nights | GCH-134 by KBMFind holiday rentals that suit your style
Top Wailea-Makena Hotel Reviews

Days Inn by Wyndham Maui Oceanfront
Find out more about Wailea-Makena
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 Wailea-Makena 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 Wailea-Makena. 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 Wailea-Makena. Seeing all the best attractions is bound to make you fall in love with Wailea-Makena. 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 Wailea-Makena short-term rentals, that won’t be hard to do.
Explore a world of travel with Expedia
- Condominium Resort in Wailea-Makena
- Resort in Wailea-Makena
- Condo Rentals in Wailea-Makena
- Holiday Homes in Wailea-Makena
- Guest Houses in Kihei
- Hostels in Kihei
- Resort in Kihei
- Cottages in Kihei
- B&B in Kihei
- Villas in Kihei
- Condo Rentals in Kihei
- Condominium Resort in South Maui
- Safari Tentalow in Maui
- Hilton Hotels in Kihei
- Independent Hotels in Kihei
- Best Western Hotels in Kihei
- Maui Condo and Home Hotels in Kihei
- Banyan Tree Hotels in Kihei
- Okura Hotels & Resorts in Kihei
- Destination Hotels in Kihei
- Aston Resorts in Kihei
- Hilton Hotels in Wailea
- Diamond Resorts in Maui
- Hawaiian Hotels in Maui
- Outrigger Hotels in Maui
- Maalaea Hotels
- Hotels near Kalama Beach Park
- Keokea Hotels
- Halama Street Hotels
- Wailea Hotels
- Hotels near Keawakapu Beach North
- Hotels near Ahihi Bay
- Hotels near Shops at Wailea
- Hotels near Ulua Beach
- Hotels near Little Beach
- Kihei Hotels
- Hotels near Wailea Beach
- Hotels near Kamaole Beach Park 3
- Hotels near Kamaole Beach Park
- Beach Hotels in Wailea-Makena
- Luxury Hotels in Wailea-Makena
- Hotels with Pool in Wailea-Makena
- Cheap Hotels in Wailea-Makena
- Lgbt Welcoming Hotels in Maui
- Historic Hotels in Kihei
- Cheap Hotels in Kihei
- Luxury Hotels in Kihei
- Boutique Hotels in Kihei
- All Inclusive Hotels in Kihei
- Golf Hotels in Kihei
- Family Hotels in Kihei
- Beach Hotels in Kihei
- All Inclusive Hotels in Wailea
- Boutique Hotels in Wailea
- Romantic Hotels in Wailea
- Beach Hotels in Wailea
- Family Hotels in Wailea
- Cheap Hotels in Wailea
- Luxury Hotels in Wailea
- Hotels with Pool in South Maui
- Beach Hotels in South Maui
- Cheap Hotels in South Maui
- Ace Rental Cars in Wailea
- Priceless Car Rental Rental Cars in Wailea
- Thrifty Car Rental Rental Cars in Kihei
- Priceless Car Rental Rental Cars in Kihei
- Ace Rental Cars in Kihei
- Budget Rental Cars in South Maui
- Thrifty Car Rental Rental Cars in South Maui
- Ace New Zealand Rental Cars in South Maui
- First Car Rental Rental Cars in South Maui
- Drive on Holidays Rental Cars in Maui
- Car hire Kihei
- Car hire near Wailea


















































































