Kailua 5, Kailua vacation rentals in Hawaii, pool and terrace view, Top Villas

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.

Kailua 3 ocean view hammock, Top Villas Kailua vacation rentals

Things to do

  • Kailua things to do, white sand beach
    Kailua Beach Park
    Famed 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.

  • Mokulua Islands, kayaking, view, Kailua in Hawaii
    Kayaking to the Mokulua Islands
    Rent 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.

  • Things to do in Kailua, trip to Oahu, surfer north shore
    Surf in Oahu
    ailua 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.

  • Lanikai beach, aerial view, Kailua, Hawaii beach, Top Villas
    Soak up Lanikai Beach
    Just 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.

  • Things to do in Kailua, Hawaii waterfall
    Maunawili Falls Trail
    This 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.

  • Things to do in Kailua, Lanikai Pillbox Trail, view
    Hike the Lanikai Pillbox Trail
    This 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.

  • Kailua farmers market, pineapples, Hawaii
    Go to the Kailua Farmers’ Market
    Sample 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.

  • Things to do in Kailua, sunglasses, tourist shops
    Go shopping in Kailua
    Spend 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!

Luxury Vacation Rentals

Award winning portfolio of the best vacation homes and villas in the world’s top destinations

Travel Planners

Experienced vacation rental and villa experts to help you find the perfect home

Concierge & Support

Enjoy 5-star hotel concierge services and dedicated local support with every stay

Concierge services, Top Villas, in-villa spa treatments, tropical massage

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, Kailua 9, Top Villas

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.

Book with Confidence

With over 100,000 happy guests every year, you can book your next stay with us with total confidence.

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