Explore Kailua Vacation Rentals

About Kailua Vacation Rentals

Explore more than 451 vacation rentals available in Kailua. These accommodations, including vacation homes and HawaiiVillas properties, boast excellent amenities and exceptional value, blending comfort and luxury. Enjoy spaciousness and convenience at a HawaiiVillas property in Kailua.

Looking for last-minute deals or the best available offers on cottages, condos, private villas, and large vacation homes? With HawaiiVillas in Kailua, you can effortlessly compare various options with a simple click. Whether you seek properties with swimming pools, hot tubs, pet-friendly policies, or expansive master suites with large screen TVs, you'll find vacation rentals by owner (RBOs) and other popular Airbnb-style accommodations near Kailua. The average room size in accommodations near Kailua is 1347.77 ftยฒ. Prices average $802 per night.

HawaiiVillas streamlines and secures your search for vacation rentals in Kailua, often offering savings of 30-40% compared to hotel prices. Start your search today and book with confidence.

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Top Rental Accommodation Types in Kailua

Type Count
Vacation Homes 289
Holiday Apartments 98
Cottages 37
Villas 17

Use these Quick Filters to Find a Vacation Rental in Kailua

โ˜… Pro Tip: HawaiiVillas simplifies comparison of top listings across various online vacation rental platforms like Booking.com and others. Use the Advanced Filter feature to switch effortlessly between HawaiiVillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, property types, cancellation policies, prices, and more. These tools streamline the search for your ideal accommodation for your next vacation in Kailua.

Weather in Kailua, HI

View the weather forecast for Kailua before booking your Kailua Vacation Rentals to confirm your best time to go.

December - February
High 79ยฐF       Low 64ยฐF
March - May
High 83ยฐF       Low 66ยฐF
June - August
High 84ยฐF       Low 69ยฐF
September - November
High 84ยฐF       Low 66ยฐF

Your Guide to Vacation Rentals in Kailua

Are you dreaming of a tropical getaway to escape the hustle and bustle of everyday life? Look no further than Kailua, a picturesque beach town on the island of Oahu in Hawaii. With its crystal-clear waters, secluded beaches and easy access to popular tourist attractions, Kailua is indeed a paradise waiting to be explored. When it comes to choosing your accommodation, vacation rentals are the perfect option to make your stay as comfortable and memorable as possible. In this guide, we'll help you navigate the world of Kailua vacation rentals, from the different types available to finding the perfect one that meets your needs and budget.

Why Choose Kailua for Your Oahu Vacation

The Beauty of Kailua Beach

At the heart of Kailua's charm is undoubtedly its breathtaking beach, which is consistently ranked as one of the most beautiful in the world. With its turquoise waters and powdery white sands, it's no surprise that this beach is a popular spot for both tourists and locals alike. Whether you're into swimming, sunbathing, or just relaxing by the shoreline, Kailua beach offers something for everyone.

One of the unique features of Kailua Beach is its calm waters, which make it a perfect spot for kayaking, paddleboarding, and windsurfing. The beach is also home to several small islands that are easily accessible by kayak, offering a fun and adventurous day trip for those looking to explore the area.

For those interested in marine life, Kailua Beach is also a great spot for snorkeling. The waters are teeming with colorful fish and other sea creatures, making it a truly unforgettable experience.

The Laid-Back Atmosphere

Unlike the more touristy areas of Oahu, Kailua offers a laid-back and relaxed atmosphere that's perfect for anyone looking to escape the hustle and bustle of city life. With its small-town feel, you'll have the chance to truly unwind and enjoy the natural surroundings.

One of the best ways to experience Kailua's laid-back vibe is to take a stroll through the town's charming boutiques and cafes. The area is known for its unique shops and locally-owned restaurants, offering a taste of the island's authentic culture and cuisine.

For those looking for a more active way to unwind, Kailua also offers several hiking trails that provide stunning views of the island's lush vegetation and mountain ranges. The Lanikai Pillbox Hike is a popular choice, offering panoramic views of the ocean and surrounding islands.

Proximity to Popular Attractions

Despite its secluded location, Kailua offers easy access to some of the island's most famous tourist attractions. From Pearl Harbor to the legendary North Shore surf beaches, Kailua is ideally situated for exploring all the island has to offer.

One of the most popular day trips from Kailua is a visit to the Polynesian Cultural Center, which offers a glimpse into the diverse cultures of the Pacific Islands. The center features interactive exhibits, live performances, and authentic cuisine from the region.

For those interested in history, a visit to the USS Arizona Memorial at Pearl Harbor is a must-see. The memorial honors the lives lost during the attack on Pearl Harbor and provides a sobering reminder of the sacrifices made during World War II.

And of course, no trip to Oahu is complete without a visit to the famous North Shore surf beaches. From Waimea Bay to Pipeline, the North Shore is known for its massive waves and world-class surfing competitions.

No matter what your interests may be, Kailua offers a perfect balance of relaxation and adventure, making it an ideal destination for your next Oahu vacation.

Types of Vacation Rentals in Kailua

Located on the east coast of Oahu, Kailua is a picturesque town known for its stunning beaches, crystal-clear waters, and laid-back Hawaiian vibe. Whether you're planning a romantic getaway, a family vacation, or a solo adventure, Kailua has a vacation rental that's sure to meet your needs and budget. Here are some of the most popular rental types:

Beachfront Properties

There's nothing quite like waking up to the sound of the ocean and stepping outside to feel the sand between your toes. Beachfront properties in Kailua offer the ultimate in luxury and convenience, with unobstructed ocean views and easy beach access. From cozy cottages to sprawling mansions, these properties vary in size and amenities, but all offer the chance to be right on the sand. Imagine spending your days lounging on the beach, swimming in the ocean, and watching the sunset from your private lanai.

Private Homes and Villas

If you're traveling with family or a large group, a private home or villa may be the perfect option. These rentals often come equipped with multiple bedrooms, full kitchens, and plenty of outdoor space, giving you a home-away-from-home feel. Many of these properties also feature private pools, hot tubs, and other luxurious amenities. Imagine hosting a family barbecue in your backyard, or relaxing in the pool after a day of exploring the island.

Condos and Apartments

For those on a budget or seeking a more low-key experience, condos and apartments are an excellent choice. These rentals offer all the amenities you need while providing you with a cozy and comfortable home base. Many of these properties are located just a short walk from the beach, and offer stunning views of the ocean or the mountains. Imagine cooking your own meals in a fully-equipped kitchen, or relaxing on your private lanai with a cup of coffee in the morning.

Bed and Breakfasts

For a more personalized experience, consider staying at a local bed and breakfast. These charming properties offer a more intimate look at Kailua culture while ensuring you feel right at home from the moment you arrive. Many bed and breakfasts are located in historic homes or buildings, and offer unique amenities like homemade breakfasts, guided tours, and cultural activities. Imagine waking up to the smell of freshly-baked banana bread, or learning to hula dance from a local expert.

No matter what type of vacation rental you choose in Kailua, you're sure to have an unforgettable experience. With its stunning natural beauty, rich cultural heritage, and endless opportunities for adventure, Kailua is the perfect destination for your next Hawaiian vacation.

How to Find the Perfect Kailua Vacation Rental

Are you planning a trip to Kailua and want to make sure you find the perfect vacation rental? Look no further! With so many options available, finding the right rental can seem overwhelming. However, with a little bit of research and planning, you can find the perfect place to call home during your stay.

Kailua is a beautiful town located on the east coast of Oahu, Hawaii. It's known for its stunning beaches, crystal-clear waters, and laid-back atmosphere. Whether you're traveling solo, with a partner, or with your family, Kailua has something to offer everyone.

Determine Your Budget

One of the first things to consider when searching for a vacation rental in Kailua is your budget. It's important to establish how much you're willing to spend on your accommodation to ensure you don't overspend and end up with a hefty bill at the end of your trip. Keep in mind that Kailua is a popular destination, and prices can vary depending on the time of year you're traveling.

However, don't let a tight budget discourage you from finding the perfect rental. With a little bit of research, you can find affordable options that still offer all the amenities you need.

Identify Your Must-Have Amenities

Another crucial factor to consider when searching for a vacation rental in Kailua is the amenities you require. Do you need a full kitchen to cook your own meals? Do you want a beachfront location with stunning views? Are you looking for a rental with Wi-Fi or air conditioning?

Identifying your must-have amenities before beginning your search will help you narrow down your options and ensure you find a rental that meets all your needs.

Research Rental Platforms and Agencies

There are many platforms and agencies that offer vacation rentals in Kailua. It's worth considering all the options before selecting one. Some popular platforms to check out include Google search, Airbnb, VRBO, and Trip Advisor. Each platform has its own benefits and drawbacks, so it's essential to do your research and find the one that best suits your needs.

You can also consider working with a rental agency that specializes in Kailua vacation rentals. These agencies can provide you with personalized recommendations and help you find the perfect rental for your trip.

Read Reviews and Testimonials

Finally, before booking your rental, make sure to read reviews and testimonials from previous guests. These can give you a good sense of what to expect from the property and whether it meets guests' expectations. Look for reviews that mention cleanliness, amenities, and location, as these are often the most important factors for travelers.

By following these tips, you'll be well on your way to finding the perfect vacation rental in Kailua. With its stunning beaches, warm weather, and laid-back atmosphere, Kailua is the perfect destination for your next vacation.

Tips for a Smooth Vacation Rental Experience

Booking a vacation rental in Kailua can be an exciting and stress-free experience. However, to ensure that your stay goes off without a hitch, it's important to keep a few things in mind. Here are some tips to help you have a smooth vacation rental experience:

Understand the Rental Agreement

Before finalizing your booking, it's important to read and understand the rental agreement. This document will outline important details such as security deposits, check-in and check-out times, and cancellation policies. By understanding these details in advance, you can avoid any surprises and ensure that your stay is enjoyable.

It's also a good idea to ask the property owner or manager any questions you may have about the rental agreement. This can help you clarify any confusing details and ensure that you're fully informed before your stay.

Communicate with the Property Owner or Manager

Another important tip is to communicate with the property owner or manager before your stay. This can help you establish a positive relationship and ensure that they know what to expect from you as a guest.

You can use this opportunity to ask any questions you may have about the rental property or the surrounding area. For example, you may want to ask about nearby restaurants, local attractions, or the best beaches to visit in Kailua.

Plan for Check-In and Check-Out

It's also important to plan your check-in and check-out times in advance. This includes any travel arrangements required to get to and from the rental property.

By planning ahead, you can ensure that you arrive at the rental property on time and avoid any unnecessary stress. You may also want to consider packing a small bag with essentials such as snacks, water, and a change of clothes, in case you arrive before the rental property is ready for check-in.

Be a Respectful Guest

Finally, it's important to be a respectful guest during your stay. This includes treating the rental property with care and following any rules listed in the rental agreement.

For example, you may be asked to avoid smoking in certain areas of the property or to keep noise levels down after a certain time of day. By following these rules, you can help ensure that your stay is enjoyable for both you and the property owner or manager.

By keeping these tips in mind, you can have a stress-free and enjoyable vacation rental experience in Kailua. With its stunning beaches and laid-back atmosphere, Kailua is the perfect destination for a romantic getaway or a family vacation.

Frequently Asked Questions About Kailua?

What are the top vacation rentals in Kailua?

Currently, HawaiiVillas lists over 451 properties in the Kailua area for 2025, with more being added continuously. By consolidating listings from various websites, HawaiiVillas provides a wide selection of top properties in Kailua.

How many vacation rentals have private pools in Kailua?

Discover 76 vacation rentals featuring private pools near Kailua. Highly-rated HawaiiVillas properties with swimming pool access include:

Which vacation homes in Kailua are best for families?

If you're searching for a family-friendly vacation residence in Kailua, explore one of these highly-rated properties, all praised for their excellent reviews among families or groups visiting Kailua:

How many Hawaii.Villas vacation rentals are available in Kailua?

At present, HawaiiVillas showcases more than 451 properties available in the Kailua area for 2025, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Kailua.

Nearby Neighborhood (7)โ€ฏ
Neighborhood Property Count
Kalama Tract Vacation Rentals in Kailua, Hawaii 147
Lanikai Vacation Rentals in Kailua, Hawaii 71
Coconut Grove Vacation Rentals in Kailua, Hawaii 314
Enchanted Lake Vacation Rentals in Kailua, Hawaii 411
Keolu Hills Vacation Rentals in Kailua, Hawaii 396
Palolo Vacation Rentals in Kailua, Hawaii 140
Kuulei Tract Vacation Rentals in Kailua, Hawaii 432

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