Kailua Vacation Rentals
Soak up scenic escapism on Oahu - with our beautiful Kailua vacation rentals with pools, located near the best beaches & beauty spots.
About our Kailua vacation rentals
Escape to paradise with our Kailua vacation rentals, featuring a stunning selection of 2 to 8-bedroom villas that offer the perfect blend of luxury and comfort.
Each property boasts a private pool and a prime beachfront location, allowing you to enjoy the gentle ocean breezes and breathtaking views right at your doorstep. With a unique appeal tailored to suit every guest, our villas provide a tropical oasis where you can unwind and rejuvenate.
To enhance your stay, we offer optional Concierge Services, ensuring you have everything you need for an unforgettable Hawaiian getaway.
Things to do
- Kailua Beach ParkFamed for its powdery white sands and turquoise waters, this beach park is perfect for swimming, kayaking and carefree relaxation. It’s also a popular spot for windsurfing and paddleboarding due to its gentle trade winds.
- Kayaking to the Mokulua IslandsRent a kayak and paddle out to the nearby Mokulua Islands for an adventurous day on the water. The islands offer secluded beaches and a chance to spot native wildlife, including seabirds and sea turtles.
- Surf in Oahuailua is a great base for a day trip to Oahu's famous North Shore, known for its legendary surf breaks. Explore charming towns, try famous local shrimp trucks, and watch world-class surfers in action.
- Soak up Lanikai BeachJust minutes from Kailua, Lanikai Beach offers postcard-perfect scenery with calm, crystal-clear waters. Ideal for snorkeling, sunbathing, and enjoying the breathtaking view of the nearby Mokulua Islands.
- Maunawili Falls TrailThis lush rainforest trail leads to the beautiful Maunawili Falls, where you can take a refreshing dip in the natural pool. The hike offers a serene escape into nature, with vibrant tropical landscapes along the way.
- Hike the Lanikai Pillbox TrailThis moderately challenging hike offers incredible panoramic views of Lanikai Beach, Kailua Bay, and the Mokulua Islands. It's a short but rewarding trail, perfect for those looking to combine a workout with stunning scenery.
- Go to the Kailua Farmers’ MarketSample local Hawaiian produce, artisanal goods, and fresh-cooked dishes. It's the perfect place to experience the island’s farm-to-table culture and grab a delicious meal.
- Go shopping in KailuaSpend a day browsing the unique shops and boutiques in Kailua Town, offering everything from local crafts and art to beachwear and Hawaiian gifts. It's a great way to pick up a souvenir to remember your trip!
Award winning portfolio of the best vacation homes and villas in the world’s top destinations
Experienced vacation rental and villa experts to help you find the perfect home
Enjoy 5-star hotel concierge services and dedicated local support with every stay
Kailua Vacation Home Concierge
Our optional Kailua Concierge Services are designed to make your Hawaiian getaway truly exceptional. From private car hire, charter boat rentals, and private chefs to family equipment rental, babysitting, and luxurious in-villa spa treatments, we offer everything you need for a seamless and personalized vacation rental experience. Enjoy tailor-made private tours and excursions that allow you to explore the island like never before. All this and more awaits, on a Top Villas stay.
Kailua Vacation Homes with Pool
Our collection of 2 to 8-bedroom Kailua Vacation Homes with pool offer the perfect setting for honeymoons, groups, and families seeking a sun-drenched tropical retreat. Many of our luxury Kailua vacation homes also feature hot tubs, adding an extra touch of luxury to your stay. Set in lush and private tropical gardens, our Kailua vacation homes offer an oasis of calm and serenity for alfresco dining and relaxation. Whether you're lounging by the pool or enjoying the peaceful surroundings, our Kailua vacation homes with pool access promise an unforgettable Hawaiian escape.
With over 100,000 happy guests every year, you can book your next stay with us with total confidence.