HouseStay has supported families seeking flexible, temporary housing solutions. For job relocations, snowbirds, and military reassignments, Kailua has been a reliable destination for those needing a comfortable place to land.
In recent months, we’ve listed 3 fully furnished rentals, including 3 houses. These properties were equipped with amenities like No Smoking Allowed, Balcony, and Indoor Fireplace—perfect for creating a space that truly felt like home. Many rentals also included convenient utilities such as Trash Pick Up, WiFi, and Cable TV.
The average monthly rent for a 3 bedroom / 2 bath House in Kailua has hovered around $20,424 but have ranged between $1,659 and $32,760, giving future renters a helpful benchmark as they plan ahead. If you like Kailua, consider checking out nearby properties in Honolulu, Kahuku, Waialua, Waianae, and Lahaina, where similar family friendly monthly housing options may be available. Our listings are always being updated, so be sure to check back soon for new opportunities in Kailua!
HouseStay has featured a variety of homes that offered the perfect blend of comfort, style, and relaxation. From houses, these properties were thoughtfully curated to feel like a true vacation retreat.
Vacationers have enjoyed 3 unique properties located in the Kailua neighborhoods, close to popular attractions and entertainment options. Each home was equipped with amenities designed to elevate the leisure experience—like Balcony, Indoor Fireplace, and No Smoking Allowed for added comfort.
Utility packages often included essentials like Trash Pick Up, WiFi, and Cable TV, ensuring a smooth and enjoyable extended stay for travelers. With average monthly pricing for a 3 bedroom / 2 bath rental around $20,424, guests were able to plan memorable getaways that fit a variety of group sizes and budgets, with rentals from $1,659 to $32,760.
Nearby cities like Honolulu, Kahuku, Waialua, Waianae, and Lahaina may offer similar monthly vacation housing options. Our inventory updates regularly, so check back soon for a stylish and stress-free extended stay in Kailua.
HouseStay Guarantee
We perform in-depth background checks on Host and Tenants to create a community everyone can trust.
Roommate Free
HouseStay only offers entire accommodations. We don’t offer spare rooms or shared spaces.
Fully Furnished
All accommodations listed on HouseStay are fully furnished and include all utilities in the monthly rate.
Month-to-Month Flexibility
Not sure how long you’ll be staying? All listings are available for a minimum of 30 nights with no maximum.
Kailua, located on the windward side of Oahu in Hawaii, is a picturesque city that offers a perfect blend of beautiful beaches, lush parks, and a laid-back atmosphere. For families looking to book an extended stay furnished rental, Kailua provides a safe and family-friendly environment with excellent schools such as Kailua High School and Windward Community College nearby. Families relocating, military families, or snowbirds looking for monthly short-term rentals will appreciate the convenience and comfort of month-to-month fully furnished rentals in Kailua.
Digital nomads seeking a peaceful yet inspiring work environment will find Kailua to be a great city offering a serene setting with high-speed internet access. With popular co-working spaces available and plenty of outdoor activities like hiking, surfing, and paddleboarding, digital nomads can enjoy work-life balance in this vibrant city. Vacationers looking to escape the hustle and bustle of urban life can enjoy the tranquil beaches, popular attractions like the Lanikai Pillboxes hike, and a variety of shopping areas such as Kailua Town Center.
Business travelers and interns will find Kailua to be a convenient base with easy access to nearby cities like Honolulu and Kaneohe. Medical tourists seeking temporary housing for surgeries or medical procedures can benefit from the proximity to hospitals like Castle Medical Center. Students attending vocational schools or colleges in the area can also find affordable housing options in Kailua with access to popular parks like Kailua Beach Park and shopping areas such as Kailua Shopping Center. For travel nurses, sports professionals, entertainment professionals, and insurance housing for disaster recovery, Kailua offers a peaceful retreat with all the necessary amenities for a comfortable stay.