Luxury Vacation Rentals with a Private Pool in Kailua-Kona

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 8 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Kailua-Kona

Kailua-Kona, Hawaii

Wander Big Island Breeze

Next avail.

Dec 3 - Dec 4

Kailua-Kona, Hawaii

Wander Big Island Cove

Wander Big Island Garden

Next avail.

Dec 20 - Dec 21

Kailua-Kona, Hawaii

Wander Big Island Escape

Next avail.

Dec 24 - Dec 25

Kailua-Kona, Hawaii

Wander Kona Bay Shores

Wander Big Island Bay

Next avail.

Feb 25 - Mar 2

Kailua-Kona, Hawaii

Wander Big Island Lush

Welcome to private poolside luxury in Kailua-Kona

Claim your own slice of the Kona Coast with Wander. Our luxury private-pool vacation rentals in Kailua-Kona blend five-star consistency with the privacy of a standalone home.

Think saltwater or heated pools that spill toward the horizon, sunset lanais, and effortless indoor-outdoor living. Inside, find chef-ready kitchens, plush bedrooms, central air, ultra fast WiFi, and dedicated workspaces. Every stay includes pristine cleaning, 24/7 concierge, and homes that look exactly like the photos.

Choose from ocean-view villas and quiet hillside retreats framed by lava rock and palms, each designed for privacy and total relaxation.

Popular private pool vacation rentals in Kailua-Kona

Wander Kona Bay Shores

Wander Big Island Breeze

Next avail.

Dec 3 - Dec 4

Kailua-Kona, Hawaii

Wander Big Island Garden

Next avail.

Dec 20 - Dec 21

Kailua-Kona, Hawaii

Wander Big Island Escape

Next avail.

Dec 24 - Dec 25

Kailua-Kona, Hawaii

Wander Big Island Bay

Next avail.

Feb 25 - Mar 2

Kailua-Kona, Hawaii

Wander Big Island Cove

Wander Big Island Lush

Next avail.

Dec 9 - Dec 12

Featured private pool vacation rentals in Kailua-Kona

Kailua-Kona, Hawaii

Wander Big Island Escape

Next avail.

Dec 24 - Dec 25

Kailua-Kona, Hawaii

Wander Big Island Garden

Next avail.

Dec 20 - Dec 21

Kailua-Kona, Hawaii

Wander Big Island Cove

Wander Big Island Bay

Wander Big Island Breeze

Next avail.

Dec 3 - Dec 4

Kailua-Kona, Hawaii

Wander Kona Bay Shores

Next avail.

Dec 3 - Dec 4

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Highlights in Kailua-Kona

Discover a sun-drenched paradise where historic Hawaiian culture meets world-famous coffee farms and vibrant Pacific Ocean adventures.

Ali'i Drive

Hulihe'e Palace

Pu'uhonua o Hōnaunau National Historical Park

Kealakekua Bay State Historical Park

Kona Coffee Living History Farm

Kamakahonu National Historic Landmark

Magic Sands Beach Park

Kaloko-Honokōhau National Historical Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Kailua-Kona

Kailua-Kona, Hawaii

Wander Big Island Breeze

Next avail.

Dec 3 - Dec 4

Kailua-Kona, Hawaii

Wander Big Island Cove

Wander Big Island Garden

Next avail.

Dec 20 - Dec 21

Kailua-Kona, Hawaii

Wander Big Island Escape

Next avail.

Dec 24 - Dec 25

Kailua-Kona, Hawaii

Wander Kona Bay Shores

Wander Big Island Bay

Next avail.

Feb 25 - Mar 2

Kailua-Kona, Hawaii

Wander Big Island Lush

Most popular amenities for private pool vacation rentals in Kailua-Kona

Outdoor Dining Area (8)

Patio (7)

Beach Umbrellas (1)

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Discover more beyond the pool in Kailua-Kona

Kailua-Kona rests on the sunny leeward side of Hawai‘i Island, where black lava meets cobalt water and trade winds stay gentle. The microclimate delivers warm days and clear evenings with sky-to-ocean sunsets.

From Holualoa’s coffee orchards to the calm bays around Keauhou, the Kona coast pairs adventure with a relaxed rhythm. Views to Hualalai and Mauna Loa set a dramatic backdrop for snorkeling, paddling, sportfishing, and waterfront strolls. This is why Wander's luxury private-pool vacation rentals in Kailua-Kona are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Kailua-Kona

Why should I book a Wander in Kailua-Kona over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.

Every home in Kailua-Kona delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Kailua-Kona?

Some of our most popular private pool vacation rentals in Kailua-Kona include Wander Kona Bay, Wander Kona Bay Shores, and Wander Big Island Breeze. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Kailua-Kona?

Wander offers 8 private pool vacation rentals in Kailua-Kona, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Kailua-Kona?

You can check-in to Wander private pool vacation rentals in Kailua-Kona after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Kailua-Kona have WiFi access?

Yes. Every Wander home in Kailua-Kona has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.