Luxury Vacation Rentals with a Private Pool in Kailua-Kona

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 39 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Kailua-Kona

Piko Nani property photo 1

Piko Nani

3 bedrooms•3.5 baths
New
Kona Bay Shores property photo 1
Iconic

Kona Bay Shores

5 bedrooms•6 baths
11,118 US dollars for 3 nights•

~$985 less than other sites

Pakui Street Estate (149) at Hualalai Resort property photo 1
Luxury

Pakui Street Estate (149) at Hualalai Resort

3 bedrooms•3.5 baths
12,281 US dollars for 5 nights•
New

~$930 less than other sites

Blue Hawaii property photo 1

Blue Hawaii

3 bedrooms•3.5 baths
New
Ke Alaula Estate (124) at Hualalai Resort property photo 1
Luxury

Ke Alaula Estate (124) at Hualalai Resort

4 bedrooms•4.5 baths
16,716 US dollars for 5 nights•
New

~$1,260 less than other sites

Aloha Kona Condos 1604 property photo 1

Aloha Kona Condos 1604

1 bedroom•2 baths
1,369 US dollars for 3 nights•

~$120 less than other sites

Hale Pua property photo 1
Luxury

Hale Pua

5 bedrooms•6 baths
6,051 US dollars for 3 nights•
New

~$455 less than other sites

Holua Kai #26 property photo 1

Holua Kai #26

3 bedrooms•3 baths
3,244 US dollars for 3 nights•
New

~$240 less than other sites

Welcome to private poolside luxury in Kailua-Kona

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.

Available soon in Kailua-Kona

Kona Bay Shores property photo 1
Iconic

Kona Bay Shores

5 bedrooms•6 baths
11,118 US dollars for 3 nights•

~$985 less than other sites

Blue Hawaii property photo 1

Blue Hawaii

3 bedrooms•3.5 baths
2,046 US dollars for 3 nights•
New

~$175 less than other sites

Aloha Kona Condos 1604 property photo 1

Aloha Kona Condos 1604

1 bedroom•2 baths
1,369 US dollars for 3 nights•

~$120 less than other sites

Hale Pua property photo 1
Luxury

Hale Pua

5 bedrooms•6 baths
6,051 US dollars for 3 nights•
New

~$455 less than other sites

Holua Kai #26 property photo 1

Holua Kai #26

3 bedrooms•3 baths
3,244 US dollars for 3 nights•
New

~$240 less than other sites

Fairways Villa (104A) at Hualalai Resort property photo 1

Fairways Villa (104A) at Hualalai Resort

3 bedrooms•3.5 baths
5,105 US dollars for 3 nights•
New

~$385 less than other sites

Holua Kai #8 property photo 1

Holua Kai #8

3 bedrooms•2.5 baths
2,049 US dollars for 3 nights•
New

~$155 less than other sites

Hainoa Estate (122) at Hualalai Resort property photo 1
Luxury

Hainoa Estate (122) at Hualalai Resort

4 bedrooms•4.5 baths
10,053 US dollars for 3 nights•

~$760 less than other sites

Featured private pool vacation rentals in Kailua-Kona

Kona Bay Shores property photo 1
Iconic

Kona Bay Shores

5 bedrooms•6 baths
11,118 US dollars for 3 nights•

~$985 less than other sites

Pakui Street Estate (149) at Hualalai Resort property photo 1
Luxury

Pakui Street Estate (149) at Hualalai Resort

3 bedrooms•3.5 baths
12,281 US dollars for 5 nights•
New

~$930 less than other sites

Ke Alaula Estate (124) at Hualalai Resort property photo 1
Luxury

Ke Alaula Estate (124) at Hualalai Resort

4 bedrooms•4.5 baths
16,716 US dollars for 5 nights•
New

~$1,260 less than other sites

Hale Pua property photo 1
Luxury

Hale Pua

5 bedrooms•6 baths
6,051 US dollars for 3 nights•
New

~$455 less than other sites

Fairways Villa (104A) at Hualalai Resort property photo 1

Fairways Villa (104A) at Hualalai Resort

3 bedrooms•3.5 baths
5,105 US dollars for 3 nights•
New

~$385 less than other sites

Kona Blue property photo 1
Luxury

Kona Blue

4 bedrooms•3.5 baths
6,612 US dollars for 5 nights•
New

~$585 less than other sites

Ke Alaula Estate (144) at Hualalai Resort property photo 1
Luxury

Ke Alaula Estate (144) at Hualalai Resort

5 bedrooms•5.5 baths
19,302 US dollars for 5 nights•
New

~$1,460 less than other sites

Kona Bay property photo 1
Luxury

Kona Bay

4 bedrooms•3.5 baths
8,597 US dollars for 4 nights•

~$760 less than other sites

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

Piko Nani property photo 1

Piko Nani

3 bedrooms•3.5 baths
New
Kona Bay Shores property photo 1
Iconic

Kona Bay Shores

5 bedrooms•6 baths
11,118 US dollars for 3 nights•

~$985 less than other sites

Pakui Street Estate (149) at Hualalai Resort property photo 1
Luxury

Pakui Street Estate (149) at Hualalai Resort

3 bedrooms•3.5 baths
12,281 US dollars for 5 nights•
New

~$930 less than other sites

Blue Hawaii property photo 1

Blue Hawaii

3 bedrooms•3.5 baths
New
Ke Alaula Estate (124) at Hualalai Resort property photo 1
Luxury

Ke Alaula Estate (124) at Hualalai Resort

4 bedrooms•4.5 baths
16,716 US dollars for 5 nights•
New

~$1,260 less than other sites

Aloha Kona Condos 1604 property photo 1

Aloha Kona Condos 1604

1 bedroom•2 baths
1,369 US dollars for 3 nights•

~$120 less than other sites

Hale Pua property photo 1
Luxury

Hale Pua

5 bedrooms•6 baths
6,051 US dollars for 3 nights•
New

~$455 less than other sites

Holua Kai #26 property photo 1

Holua Kai #26

3 bedrooms•3 baths
3,244 US dollars for 3 nights•
New

~$240 less than other sites

View all homes

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

Outdoor pool (39)
Ocean view (33)
Jacuzzi (29)
Hot tub (29)
Heated pool (15)
Beachfront (5)
Waterfront (13)
Gym (18)
Sauna (1)
Outdoor shower (2)
Sound system (16)
Beach access (3)
Beach essentials (3)
Bbq area (35)
Balcony (34)
Beach umbrellas (1)

More popular private pool destinations near Kailua-Kona

Private pool vacation rentals in Waimea
Private pool vacation rentals in Kihei
Private pool vacation rentals in Koloa
Private pool vacation rentals in Princeville

Other popular amenities & vacation types in Kailua-Kona

Family vacation rentals in Kailua-Kona
Large group vacation rentals in Kailua-Kona
Beachfront vacation rentals in Kailua-Kona
Hot tub vacation rentals in Kailua-Kona
Discover more beyond the pool in Kailua-Kona

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 Piko Nani, Wander Kona Bay Shores, and 3BD Pakui Street Estate (149) at Hualalai Resort. 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 39 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.