Wailea Point 3004N°001
Maui, USA
Wailea
Oct 27 – Nov 10 · $491,509 for 14 nights
Smiling House brings together 9 hand-selected luxury condos in Maui — each one chosen for its setting, its design and the service around it. Maui pairs golden resort coastlines with volcanic peaks, waterfalls and some of Hawaii's best beaches. From intimate hideaways for two to expansive homes for family and friends, every condo is booked directly with our team — no middle-man, no surprises. Browse the homes below, then speak to a concierge who knows Maui first-hand about dates, rates and the details that make a stay effortless.
Updated October 2026
Grand Champions Golf Villas 150N°002
Maui, USA
Wailea
Nov 22 – 27 · $9,953 for 5 nights
Elua 2301N°003
Maui, USA
Wailea
Nov 3 – 8 · $24,919 for 5 nights
Elua 704N°004
Maui, USA
Wailea
Oct 25 – 30 · $12,860 for 5 nights
Maui Kamaole I217N°005
Maui, USA
Kihei
Oct 18 – 21 · $1,669 for 3 nights
Grand Champions Golf Villas 118N°006
Maui, USA
Wailea
Nov 24 – 29 · $9,502 for 5 nights
All 47 villas in Maui
Every home in Maui that can be booked with Smiling House, as a plain list.
- Discover Wailea Ekahi 39E - Breathtaking Ocean Views, Renovated, Wi-Fi, Split AC
- Ekahi 20G
- Ekolu 1403
- Elua 2301
- Elua 704
- Experience Wailea Ekahi 4E, Greenbelt Location, New Split-AC, Serene & Stylish!
- Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views!
- Grand Champions 55, Beautifully Renovated Single Level, Ocean Views, Split AC
- Grand Champions Golf Villas 118
- Grand Champions Golf Villas 150
- Grand Champions Golf Villas 54
- Ground Floor Beachfront Villa in Maui
- Hale Hui Kai 202 - Keawakapu Beach, Garden Views, Steps to the Beach, Split AC!
- Hale Hui Kai 208 - Ocean View Luxury Condo on the best beach on Maui, Split AC!
- Kamaole Nalu 305 - Breathtaking Ocean Views, Renovated, Ocean Front, Split AC!
- Kamaole Sands 10-403 - Stunning Renovation - Penthouse Level - Split AC - Look!
- Lush View Three Bedroom Villa in Maui
- Oceanfront One Bedroom Condo in Maui
- Oceanview Corner Villa in Maui
- Mana Kai 304 - Renovated Oceanfront 2BR/2BA Condo, Split AC, Beach Access, Views
- Mana Kai 314 - Experience Stunning Coastal Views on Keawakapu Beach, Split AC
- Mana Kai 410 - The Ultimate Maui Beach Condo Experience - Renovated - Split AC
- Mana Kai 811 - Oceanfront, Top Floor, Stunning Renovation, 2BR, Kings, Split AC
- Maui Hill 116 - Stunning Renovation - Split AC - 3bd/3ba - Expansive Ocean Views
- Maui Hill 70 - Spacious 3BR/3BA for 8, 2 King Suites, 3 Lanais, Pool, Near Beach
- Maui Kamaole A-206 - Prime Location, Stunning Renovation, Large Lanai, Split AC!
- Maui Kamaole I217
- Oceanfront Hale Hui Kai 313 Large Lanai, AC, Incredible Views on Keawakapu Beach
- Oceanfront Lauloa 106 - Luxe Ground Floor Condo, Steps to Beach, Sunsets & Surf!
- Oceanview Retreat | Walk to Beach & Restaurants
- Palms at Wailea 703 - Modern Renovation, Prime Location, Full AC, Close to Pool!
- Palms at Wailea 705 - Luxury Renovation, Prime Location, Close to Shops, Full AC
- Royal Mauian 309 - Direct Ocean Front, Renovated, Seconds to the Beach, Split AC
- Wailea Ekahi 12D - Budget Friendly Ocean View Studio w/ Lanai, Kitchen, WD, & AC
- Wailea Ekahi 20J - Secluded Garden Oasis Surrounded by Trees & Tropical Blooms
- Wailea Ekahi 24B, 1BR Ground-Floor Condo with 2 Baths, Split AC, Pool, Sleeps 4
- Wailea Ekahi 42C - Peekaboo Ocean Views, 2 Full Baths, King TempurPedic, Full AC
- Wailea Ekahi 45D - Ocean & Garden Views, Beautifully Renovated, Split AC, Wi-Fi!
- Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
- Wailea Ekolu 510 - Ocean Views, Private Lanais, Renovated 2-Story with Split AC!
- Wailea Elua 1104 - Ocean Views, Central A/C, Walk to Ulua Beach, Shops & Dining!
- Beautifully Renovated Ocean View Villa in Maui
- Contemporary Oceanfront Villa in Wailea
- Ocean View Luxury Condo in Wailea Maui
- Scenic Ocean View Villa in Wailea
- Wailea Luxury Retreat | Walk to Beach & Shops
- Wailea Point 3004
Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.
Condos in other destinations
Frequently asked
How do I book a condo in Maui?
Choose a home below and send an enquiry, or ask to book directly. A Smiling House concierge confirms availability and rates with the owner and handles the booking end to end — you deal with our team, not a faceless platform.
What's included when I rent a condo in Maui?
Every home is fully furnished and privately yours for the stay. Concierge support, and often housekeeping and local recommendations, come as standard; specific services vary by property and are listed on each home's page.
Is it cheaper to book direct with Smiling House?
Booking direct removes the platform mark-ups that sit on OTA listings, and puts you in touch with a team that knows Maui personally. You get the real home, the real price and a human who answers.
How many condos are available in Maui?
9 condos are featured here right now. Inventory changes as homes are booked and new ones join, so the collection is always current.