Luxury Vacation Rentals with a Private Pool in Kailua
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 2 private pool vacation rentals – enter your dates for availability.
Welcome to private poolside luxury in Kailua
Slip into island ease with Wander's collection of luxury private pool vacation rentals in Kailua, Hawaii. These modern estates and refined island homes bring hotel polish to a private setting, pairing airy interiors with seamless indoor outdoor living.
Each home centers around a sparkling private pool framed by tropical landscaping and generous lounge space. Expect chef ready kitchens, plush bedrooms, spa style baths, dedicated workstations, and ultra fast WiFi. Our properties are impeccably maintained, professionally cleaned, and supported by 24/7 concierge service. When you book a Wander, the photos match the experience and every detail feels effortless.
Highlights in Kailua
Discover a paradise of pristine white-sand beaches, turquoise waters, and scenic coastal hikes on Oahu's beautiful windward side.
Kailua Beach Park
Lanikai Beach
Lanikai Pillbox Hike (Ka'iwa Ridge Trail)
Mokulua Islands
Kailua Town Farmers' Market
Kawai Nui Marsh State Wildlife Sanctuary
Kalama Beach 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.
Most popular amenities for private pool vacation rentals in Kailua
More popular private pool destinations near Kailua
Other popular amenities & vacation types in Kailua
Discover more beyond the pool in Kailua
Set on Oahu’s windward side, Kailua pairs crystalline water and powder soft sand with the emerald folds of the Ko'olau Range. Pastel sunrises rise over the Mokulua islets, trade winds keep the air fresh, and the bay’s gentle break invites lingering days by the shore.
Find your rhythm with morning paddles to the Mokes, reef snorkeling in clear lagoons, kite friendly breezes along Kailua Beach, and scenic hikes to panoramic pillbox lookouts. The setting feels both relaxed and refined, with nature always close at hand. This is why Wander's luxury private pool vacation rentals in Kailua, Hawaii are the perfect choice, whether you are traveling for work or leisure.
FAQs: Vacation Rentals in Kailua
Why should I book a Wander in Kailua 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 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?
Some of our most popular private pool vacation rentals in Kailua include Wander Kailua Beachside, Wander Kailua Villa, and Wander Kailua Villa. 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?
Wander offers 2 private pool vacation rentals in Kailua, 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?
You can check-in to Wander private pool vacation rentals in Kailua after 4.00pm and check-out before 10.00am.
Do Wander’s private pool vacation rentals in Kailua have WiFi access?
Yes. Every Wander home in Kailua 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.