Best Vacation Homes in Kailua
10.0
Oceanfront
Ocean View
Balcony/Terrace
View
10.0
Parking
Internet
Child Friendly
Accessibility
10.0- Oceanfront
- Ocean View
- Balcony/Terrace
- View
10.0- Oceanfront
- Ocean View
- Balcony/Terrace
- View
9.2- Oceanfront
- Ocean View
- View
Breakfast
10.0- Ocean View
- Balcony/Terrace
- View
Kitchen
9.6- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
Kailua Luxury Rentals
10.0
Private Pool- Oceanfront
Pool- Ocean View
10.0- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
9.8- Private Pool
- Oceanfront
Hot Tub- Pool
- Private Pool
- Oceanfront
- Hot Tub
Fireplace/Heating
- Private Pool
- Oceanfront
- Hot Tub
Spa
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
10.0- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
Kailua Pet Friendly Vacation Rentals
10.0- Oceanfront
- Ocean View
- Balcony/Terrace
- View
9.0
Private Beach- Oceanfront
- Ocean View
- Balcony/Terrace
10.0- Oceanfront
- Hot Tub
- Pool
- Ocean View
Pet Friendly- Parking
Air Conditioner- Internet
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
- Pet Friendly
- Parking
- Internet
- Child Friendly
Kailua Large Vacation Homes
10.0- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- Pool
- Balcony/Terrace
- View
- Parking
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
10.0- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
Why Choose Rent By Owner for your Kailua Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Kailua Vacation Rentals
Where are the best neighborhoods to stay in Kailua?
Exploring the neighborhoods to stay in Kailua, Hawaii allows you to experience the authentic charm and relaxed vibe of this beautiful coastal town. Whether you prefer a quiet retreat close to pristine beaches or a lively area with local boutiques and eateries, Kailua offers a variety of options to match your vacation style. By choosing the right neighborhood, you'll enjoy convenient access to the natural beauty and welcoming community that make this location a sought-after destination. With trustworthy vacation rentals available, planning your perfect Hawaiian getaway has never been easier.
Lanikai
Known for its pristine beaches and tranquil surroundings, this neighborhood offers a peaceful retreat close to the scenic shoreline, making it ideal for those seeking relaxation and natural beauty.
View 66+ Rentals in LanikaiCoconut Grove
This charming area provides a cozy community atmosphere with easy access to local shops and outdoor activities, perfect for enjoying the laid-back island lifestyle.
View 498+ Rentals in Coconut GroveKalama Tract
Offering a mix of residential comfort and convenient amenities, here you can experience easy access to Kailua’s vibrant town while enjoying a welcoming neighborhood vibe.
View 114+ Rentals in Kalama TractKuulei Tract
Situated close to key beaches and parks, this neighborhood is suited for travelers who wish to explore Kailua’s outdoor attractions from a comfortable base.
View 483+ Rentals in Kuulei TractEnchanted Lake
Surrounded by lush greenery and serene water features, this area offers a peaceful environment perfect for unwinding after a day of exploring the region.
View 455+ Rentals in Enchanted LakeKeolu Hills
Perched on elevated terrain, Keolu Hills presents stunning views and a quiet setting, making it an appealing choice for visitors interested in scenic vistas and exclusivity.
View 437+ Rentals in Keolu HillsPalolo
Located nearby in Honolulu, this neighborhood grants convenient access to urban attractions while still offering a comfortable place to stay when visiting Kailua and the surrounding regions.
View 167+ Rentals in PaloloBest Times to Visit Kailua
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as timing your trip to this destination allows you to enjoy pleasant weather and avoid peak crowds in the area.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm weather ideal for beach activities and outdoor exploration in this destination. It's a lively time with increased visitors, making it perfect for those seeking vibrant local events.
Winter Holidays (December to February)
The holiday season draws visitors looking to enjoy mild winter weather while escaping colder climates elsewhere. You'll find this period offers pleasant days for sightseeing and holiday festivities in the area.
Off-Season Highlights
Spring (March to May)
This springtime period provides a quieter atmosphere, making it an excellent opportunity for relaxing and exploring this region's natural beauty without large crowds.
Fall (September to November)
Autumn offers mild weather and fewer visitors, giving you a more peaceful experience while enjoying the scenic vistas of this area. It’s a great time for affordable stays and serene surroundings.
Weekly Weather Forecast for Kailua
How to Book Your Kailua Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Kailua
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for al fresco meals in a tropical setting.
- Relax by private swimming pools that offer a refreshing escape from the sun.
- Take advantage of lush, landscaped gardens that enhance your outdoor experience.
- Benefit from shaded lanai spaces ideal for lounging or entertaining al fresco.
- Make use of outdoor showers to rinse off after beach days in this coastal region.
- Explore nearby pathways and trails for walking, jogging, or biking through scenic surroundings.
- Secure parking facilities suited for exploring the area's popular outdoor attractions.
Top Attractions Around Kailua
What attractions are nearby?
Here, you can explore a variety of outdoor activities and water-based adventures just minutes from your vacation rental, making the most of the stunning natural surroundings of this tropical destination.
Family Activities
- Hiking at the Koolau Mountains: Explore scenic trails through lush landscapes that offer stunning views and memorable family adventures in this region’s natural beauty.
- Relaxing on Kailua Beach: Spend a day lounging or swimming in the calm, turquoise waters of the area’s renowned beach, perfect for family fun and picnics.
- Visiting the Nuuanu Pali Lookout: Enjoy breathtaking vistas from this iconic lookout, providing an educational experience about the area's history and geology for all ages.
- Exploring local markets and cultural events: Discover vibrant markets and festivals where your family can indulge in regional flavors and learn about the area's rich heritage.
Adult Activities
- Snorkeling at Kailua Beach Park: Discover the vibrant marine life just offshore by exploring the clear, inviting waters in this popular destination for water enthusiasts.
- Hiking the Lanikai Pillboxes: Enjoy panoramic ocean views and lush scenery as you trek to historic military bunkers that offer one of the most scenic overlooks here.
- Kayaking to the Mokulua Islands: Paddle across calm waters to these picturesque islands, where you can enjoy secluded beaches and spectacular coastal scenery.
- Shopping and dining in Kailua Town: Immerse yourself in local culture by browsing boutique shops and savoring delicious island cuisine in this charming area.
Other Places to Stay in Kailua, HI
Coconut Grove
Kuulei Tract
Ulu Po Heiau State Monument
Pohakupu
Kalama Beach Park
Kailua Bay Beach
Enchanted Lake
Keolu Hills
Maunawili
Marine Corps Base Hawaii
Kalama Tract
Lanikai
Kailua Travel Tips
How Can You Make the Most of Your Stay?
- Explore local beaches: Take advantage of the area's renowned beaches by planning your days around swimming, sunbathing, or surfing in the warm Hawaiian waters.
- Visit outdoor markets and eateries: Savor authentic regional flavors and support local vendors at vibrant markets and casual dining spots nearby.
- Engage in outdoor activities: Make the most of the region’s natural beauty with activities like kayaking, hiking, or paddleboarding suited for all skill levels.
- Discover hidden gems: Go beyond the typical tourist spots to uncover lesser-known scenic spots and tranquil areas that showcase the true essence of this destination.
Transportation Options
- Car Rentals: Renting a car provides the most flexibility to explore this scenic region at your own pace, with numerous rental agencies conveniently located nearby.
- Public Bus Services: The local bus system offers an affordable and eco-friendly way to travel around the area, connecting you to key beaches and attractions.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft offer quick, reliable transportation directly from your vacation rental here.
- Bicycle Rentals: Biking is an enjoyable and eco-conscious option for discovering the laid-back atmosphere and beautiful scenery of this destination.
Local Customs Options
- Ho‘okupu: Respectful gift-giving is an important part of local customs, especially when visiting homes or participating in cultural events here.
- Hoʻoponopono: This traditional Hawaiian practice of reconciliation and forgiveness emphasizes the importance of harmony and respectful communication during your stay.
- Kākou Spirit: Embracing the communal spirit fosters a sense of unity and shared responsibility among visitors and locals alike in the area.
- Respect for the ‘Aina: Showing reverence for the land by practicing environmentally conscious behaviors helps preserve the natural beauty of this destination.
Kailua Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Kailua?
There are a lot of options in Kailua. If you plan on staying in the Kailua area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kailua:
- Place in Paradise-Kailua Beachfront Short term Lic#1990/NUC-1802
- PRIVATE BEACHFRONT RENTAL
- Walker Beach House - Lanikai Ocean Front Lic.#1990/NUC-1757
- Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
- 'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
- Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
- Available and legal for stays less than 30 days.
- Kailua Oceanfront Villa with Heated Pool & Spa
- Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
- Come relax on the lake! Beautiful lake and mountain views. Kayaks included.
2. How many vacation rentals have private pools in Kailua?
There are 77 vacation rentals with private pools near Kailua. Top-rated RBO homes that have access to a swimming pool include:
- Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access! 30+ Nights
- Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
- Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
- LANIKAI Plantation Cottage located only 3 houses from famous Lanikai Beach
3. Which vacation homes in Kailua are best for families?
If you are looking for a family-friendly vacation home in Kailua, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Kailua:
4. How many Rentbyowner vacation rentals are available in Kailua?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 437 in the Kailua area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Kailua.
5. What is the cancellation policy for vacation rentals in Kailua, Hawaii?
6. Are there any house rules I should be aware of before booking a vacation rental here?
7. How do I ensure my booking for a Kailua vacation rental is secure?
8. What amenities are typically included in vacation rentals here?
9. How far in advance should I book a vacation rental in this area?
Kailua Top Rated Vacation Rentals
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Hot Tub
- Pool
10.0- Private Pool
- Hot Tub
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Hot Tub
- Pool
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Pool
- Ocean View
- Balcony/Terrace
- View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
