chuchoDiscover

Your trip

Kailua, Hawaii, United States Not sure where? Describe your trip to Chucho

When

Exact dates

Flexible dates

Prices are for example stays inside your window, each labeled with its actual dates. Hosts confirm availability.

Clear dates

Who

Add each child's age at check-out. Hosts confirm child rates and beds; prices shown are for everyone staying.

Guests is everyone staying, adults and children. Rentals check capacity against everyone; a hotel room's fit needs a quote.

Cancel

Kailua

Vacation homes in Kailua, Hawaii, United States · Room for at least 8

14 homes published by their hosts. Enquire or book directly with the host.

Of these 14 vacation homes in Kailua, 11 have a private pool, 11 sleep 10 or more, 11 have 4+ bedrooms and all have a workspace. Every home is listed by its host, who confirms dates and prices directly.

Filter these homes

14 homes · Kailua

Ali'i Point #12

Kailua, United States

3 bedrooms · 3 baths · sleeps 9 · shared pool

Oceanfront home on Ali'i Drive in Kailua-Kona, within a gated community of 16 residences, with three bedrooms and an additional loft.

Visit host websitegathervacations.com

Alohi Kai Estate

Kailua, United States

5 bedrooms · 5 baths · sleeps 12 · private pool

Alohi Kai Estate is a three-story oceanfront vacation home for up to 12 guests in a gated community in Kailua-Kona, Hawaii.

Visit host websitegathervacations.com

Blue Water

Kailua, United States

3 bedrooms · 3 baths · sleeps 10 · private pool

Blue Water is a two-story oceanfront home in gated Kona Bay Estates in Kailua-Kona, Hawaii, accommodating up to 10 guests.

Visit host websitegathervacations.com

Dolphin Manor

Kailua, United States

5 bedrooms · 6 baths · sleeps 18 · private pool

Dolphin Manor is a two-story oceanfront estate on the lava-rock shoreline of Kailua-Kona, within walking distance of downtown and Honl’s Beach.

Visit host websitegathervacations.com

Hahalua Bay Villa

Kailua, United States

4 bedrooms · 5 baths · sleeps 16 · private pool

Hahalua Bay Villa, also known as Manta Ray Bay Villa, is an oceanfront estate on Keauhou Bay in Kailua-Kona, on Hawaii’s Big Island.

Visit host websitegathervacations.com

Hale Joli

Kailua, United States

4 bedrooms · 3 baths · sleeps 8 · private pool

Hale Joli is a single-level hillside vacation home in Kailua-Kona, on Hawaii’s Big Island, with ocean views and a private heated infinity pool.

Visit host websitegathervacations.com

Hale Kai O'Kona #7

Kailua, United States

4 bedrooms · 4 beds · 3 baths · sleeps 8

A two-level oceanfront condo for eight on Ali‘i Drive in Kailua-Kona, with four bedrooms, three bathrooms and direct access to the lava-rock shoreline.

Visit host websitegathervacations.com

Ho'okipa Hale

Kailua, United States

3 bedrooms · 6 beds · 3 baths · sleeps 10 · private pool

Ho'okipa Hale is a three-bedroom, three-bathroom vacation home in Kailua-Kona with ocean views, a tropical garden and a private wade pool, accommodating up to ten guests.

Visit host websitegathervacations.com

Honu Hale

Kailua, United States

5 bedrooms · 3 baths · sleeps 16 · private pool

Honu Hale is a five-bedroom holiday home above the Kailua-Kona coastline, with views across Lyman's Bay and Holualoa Bay, multiple lanais and a private saltwater pool.

Visit host websitegathervacations.com

Kona Blue

Kailua, United States

4 bedrooms · 3 baths · sleeps 13 · private pool

Kona Blue is a 4,526-square-foot oceanfront home in Kailua-Kona on Hawaii’s Big Island, accommodating up to 13 guests with a private lap pool and direct shoreline access.

Visit host websitegathervacations.com

Kona One

Kailua, United States

4 bedrooms · 4 baths · sleeps 10 · private pool

Kona One is an oceanfront, four-bedroom home in guard-gated Kona Bay Estates in Kailua-Kona, with sandy shoreline frontage and a private heated courtyard pool.

Visit host websitegathervacations.com

Kona's Shangri La

Kailua, United States

5 bedrooms · 5 baths · sleeps 14 · private pool

A three-level oceanfront home above Lyman’s Bay on Ali‘i Drive in Kailua-Kona, with five bedrooms and five bathrooms, accommodating up to 14 guests.

Visit host websitegathervacations.com

Lymans Bay Hale

Kailua, United States

5 bedrooms · 5 beds · 3 baths · sleeps 10

A three-story, five-bedroom vacation home in Kailua-Kona, across the street from Lyman’s Bay, with ocean, beach and mountain views.

Visit host websitegathervacations.com

Mermaid Cove

Kailua, United States

4 bedrooms · 4 baths · sleeps 14 · private pool

Mermaid Cove is a 4,000-square-foot, three-level oceanfront estate in Kailua-Kona, with direct cove access and accommodation for up to 14 guests.

Visit host websitegathervacations.com

Filters

Your trip

Kailua, Hawaii, United StatesAdd datesAdd guests

Change destination, dates or guests

Prices need travel dates and a guest count. You can browse homes while you decide.

Type of stay

Rooms and beds

Pool

Amenities

Only what the host explicitly listed as available counts.

Collections

Clear all