Kai VistaN°001
Big Island, USA
Kailua Kona
Apr 1 – 8 · $11,797 for 7 nights
Smiling House brings together 12 hand-selected luxury condos in Big Island — each one chosen for its setting, its design and the service around it. Hawaii's Big Island is the archipelago's largest and most varied, pairing the resort coastline of Kohala with volcanoes, rainforest and snorkelling bays. 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 Big Island first-hand about dates, rates and the details that make a stay effortless.
Updated October 2026
NHH3 Kai Nani HaleN°002
Big Island, USA
Kailua Kona
Feb 28 – Mar 7 · $5,658 for 7 nights
HK3B Hale LuanaN°003
Big Island, USA
Waikoloa
Oct 23 – 26 · $1,025 for 3 nights
KK3201 Hale Moana KaiN°004
Big Island, USA
Kailua Kona
Nov 27 – Dec 1 · $1,886 for 4 nights
Kahaluu Bay VillasN°005
Big Island, USA
Kailua Kona
Dec 14 – 17 · $4,387 for 3 nights
Kona Pacific B-308N°006
Big Island, USA
Kailua Kona
Nov 22 – 25 · $3,108 for 3 nights
All 35 villas in Big Island
Every home in Big Island that can be booked with Smiling House, as a plain list.
- Panoramic Ocean-View Retreat in Mauna Lani
- Ocean View Two Bedroom Villa in Big Island
- Luxury Oceanfront Two Bedroom Retreat in Big Island
- Sunset Ocean-View Retreat in Mauna Lani
- Private Pool Six Bedroom Villas in Big Island
- 77-6386 Hale Alii Honu Kai
- 78-6650 Hale Lula o' Nai'a
- 78-Pili Kona Hale Pili
- Enjoy Ocean Views from Mauna Lani Point A105
- Ocean View Gated Villa in Big Island
- HK3B Hale Luana
- Hale Moana
- True Oceanfront Two Bedroom Villa in Big Island
- KE264 Keauhou Lani
- KK3201 Hale Moana Kai
- Heated Pool Villa in Big Island
- Kahaluu Bay Villas
- Kai Vista
- Keauhou Akahi 208
- Keauhou Palena 901
- Direct Beach Access Two Bedroom Villa in Big Island
- Kona Coast Resort 5-203
- Kona Pacific B-308
- Kona Riviera Villas 103
- Makolea 23
- Golf Course View Villa in Big Island
- Beach Club Three Bedroom Villa in Big Island
- Oceanview Infinity Pool Villa in Big Island
- Mauna Lani Point, stunning sunset and ocean views
- NHH3 Kai Nani Hale
- Contemporary Oceanview Retreat in Big Island
- Relax & Unwind in Paradise, Kulalani 203
- Relax & Unwind in Paradise, The Islands K3
- Private Pool Villa in Big Island
- White Sands Village 232
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 Big Island?
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 Big Island?
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 Big Island personally. You get the real home, the real price and a human who answers.
How many condos are available in Big Island?
12 condos are featured here right now. Inventory changes as homes are booked and new ones join, so the collection is always current.