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Vacation rentals in Kailua

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Top-rated vacation rentals in Kailua

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Guest favourite
The beach features soft, golden sand stretching alongside clear turquoise waters. Lush greenery lines the shore, providing a natural backdrop. Gentle waves lap against the rocks near the water's edge, while distant mountains are visible under a partly cloudy sky.
Home in Kailua
4.9 out of 5 average rating, 344 reviews

Kailua Beach Park - 2 BR Cottage

Kailua Beach is once again been rated as the best beach in the USA for 2019, by Dr. Beach. "The cottage is directly across the street from Kailua Beach Park and less than two minutes walk to step into the ocean at the beach. This a legal vacation rental, license1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new shower, sink and plumbing fixtures April 2022!

Top guest favourite
Place to stay in Kailua
4.97 out of 5 average rating, 123 reviews

Honu Suite at La Bella’s-Walk to Beach-Licensed

No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family that lives onsite and close to amenities. Our luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation. The Honu (Turtle) Suite: -AC -Queen bed -Full kitchen -Private bathroom This suite is extra private -located away from the rest of the living quarters.

Guest favourite
A tranquil outdoor area features a 60-foot lap pool surrounded by lush greenery and natural rock elements. A wooden dining table with an umbrella is positioned nearby, offering a view of the ocean in the background and a waterfall cascading into the pool.
Guesthouse in Kailua
4.8 out of 5 average rating, 196 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

Guest favourite
A scenic sunset view highlights the horizon over calm waters, with soft waves lapping against the sandy beach. In the foreground, a decorative dolphin sculpture adds a touch of charm to the balcony railing, while lush greenery frames the view.
Condo in Waianae
4.97 out of 5 average rating, 311 reviews

Beachfront Getaway - Hawaiian Princess Condo

Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

Guest favourite
The image displays a waterfront view featuring a low-rise condominium surrounded by lush palm trees and mountains in the background. The water appears calm and reflective under a bright blue sky with scattered clouds, creating a serene coastal atmosphere.
Apartment in Hauula
4.74 out of 5 average rating, 188 reviews

30 Steps to the beach! Sleeps 4 TA154-814-0544-01

My place is close to Kaya's Country General Store across the Street Polynesian Cultural Center Laie Temple Laie Point Shark's Cove Marine Sanctuary (snorkeling) Sunset Beach Pipeline Waimea Falls Park Waimea Bay Kahana Bay The Crouching Lion The Old Sugar Mill Kualoa Ranch-horseback riding, 3 wheeling, mountain biking. Where Jurassic Park and Lost were filmed., public transport. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Top guest favourite
An aerial view captures the surrounding landscape near Turtle Bay, showcasing the proximity to the ocean. The layout includes green lawns, tennis courts, and the marked unit within a cluster of residences, all set against a backdrop of blue waters and a clear sky.
Condo in Kahuku
4.9 out of 5 average rating, 167 reviews

North Shore Getaway - Newly renovated!

Enjoy the amazing experience of staying at Turtle Bay without resort pricing! Our condo has all the amenities you need (fully stocked kitchen, comfortable king bed with air conditioning, washer and dryer). Enjoy our two heated swimming pools, tennis courts, pickle ball courts, and charcoal BBQ. We are just a 5 minute walk from the beach. We are located on the ground floor with a beautiful lanai to enjoy a relaxing cup of coffee while the kiddos are free to run around!

Guest favourite
A serene beach scene is presented, with soft golden sand stretching along the shoreline. Gentle waves lap at the coast, reflecting a clear blue sky dotted with fluffy clouds. Lush palm trees line the beach, providing a tropical ambiance to the picturesque landscape.
Condo in Hauula
4.8 out of 5 average rating, 134 reviews

"The Honu Hale" Beachfront Condo w/ View & Kitchen

SPECIAL PRICE! Welcome to your little piece of paradise! On a beautiful white sandy beach. Great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Punaluu is on the Windward side of Oahu away from all the crowds of town yet close to lots of amazing things to do! PCC, North Shore beaches & big wave surfing! There is a fully equipped kitchen, 2 beds for you & your guests. Washer/dryer in the unit & a private lanai!

Top guest favourite
An aerial view captures the sandy beach stretching along the coastline, bordered by lush green hills. Crystal-clear turquoise waters gently lap the shore, with a few beachgoers enjoying the day. Colorful umbrellas are dotted along the beach, creating a vibrant contrast against the natural surroundings.
Guest suite in Makaha Valley
4.95 out of 5 average rating, 164 reviews

Slice of Paradise-Studio-Sleeps 4-same$ for 2 as 4

Enjoy this beautiful, private, brand new studio nestled in the mountains of Makaha Valley. This is located in a gated community with 24 hour security. Minutes from year round surfing and golfing. This is a LEGAL vacation rental. Private yard on a perimeter lot with unobstructed ocean and mountain views and just a few minutes drive to many clean, sand bottom beaches. Any combination of 4 guests is okay as long as there is a max of 2 adults.

Guest favourite
Guest suite in Kailua
4.87 out of 5 average rating, 151 reviews

Kailua Rental for Med/Long Term ($1,500/month)

Escape to beautiful Kailua and enjoy our cozy guest suite! Located in a quiet cul-de-sac, this unit provides modern amenities, a new full-sized bed and direct access to your own private lanai. Mountain views, nearby attractions, shopping, dining, and world-class beaches ensure an ideal destination for your next retreat! We welcome minimum stays of 30 days or more. Please contact for inquiry details. * 30 night minimum

Top guest favourite
A spacious sleeping area is highlighted by a king-size bed dressed in a white coverlet. A futon is positioned alongside, complemented by decorative pillows. Soft natural light enters through multiple windows, while indoor plants add a touch of greenery to the peaceful ambiance.
Guesthouse in Kailua
4.87 out of 5 average rating, 425 reviews

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal (NUC short term rental #1990/NUC-1819, Tax map key: 43073024) *not impacted by Honolulu ordinances banning short term **RECENTLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Kupono Services.

Guest favourite
Home in North Shore
4.79 out of 5 average rating, 103 reviews

North shore Studio with sauna! - Walk to beach!

Legal Nightly Vacation Rental (No 30-day contracts) A cozy, island-style unit with a loft bed, perfect for an authentic Hawaiian getaway. The unit includes High speed WiFi, 65 inch Smart TV, Split unit AC, sauna, an outdoor shower, an outdoor gym, a sun deck, and private access. Located within walking distance to famous Waimea Bay and other beautiful spots, this space offers convenience, comfort, and island charm.

Guest favourite
A serene beach scene features soft white sand leading to clear turquoise waters. Gentle waves lap against the shoreline under a bright blue sky with scattered clouds. Lush greenery borders the beach, providing a natural frame to the picturesque landscape.
Guesthouse in Kailua
4.79 out of 5 average rating, 166 reviews

Kailua Beach Cottage - 1990/NUC-1797

WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.

Popular amenities for Kailua vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Kailua's top sights

Lanikai Beach

459 locals recommend

Kailua Beach Park

217 locals recommend

Lanikai Pillbox Hike

259 locals recommend

Other great vacation rentals in Kailua

Camper/RV in Kailua

The Lebowski- Paradise Campervan

Top guest favourite
A view of the shoreline featuring a mountainous landscape, partially covered by green vegetation. The calm water reflects the bright blue sky, with a few white clouds gently drifting overhead. The natural scenery suggests a peaceful coastal environment.
Condo in Waikiki
4.95 out of 5 average rating, 73 reviews

Peaceful cozy comfortable apartment

Guest favourite
A spacious living area features a king bed with light linens, complemented by a backdrop of ocean views through large glass doors. A contemporary sofa and bar seating with stools create a relaxed atmosphere, with a smart TV providing entertainment options.
Apartment in Waikiki
5 out of 5 average rating, 26 reviews

20F-High Floor Ocean View-Ilikai-1BR-Waikiki Beach

Guest favourite
The image captures a sunset view over the ocean, framed by palm trees and a neighboring cottage's overhang. A grassy area leads to the water’s edge, where calm waves meet the shore. Light reflects off the water, creating a serene ambiance.
Cottage in North Shore
4.87 out of 5 average rating, 141 reviews

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

Guest favourite
A modern cottage is illuminated by warm light, showcasing its elegant exterior against a colorful sunset sky. The lush landscaping features tropical plants and soft outdoor lighting. The backdrop reveals a mountain range, further enhancing the serene atmosphere of the Makaha Valley.
Cottage in Makaha Valley
4.97 out of 5 average rating, 89 reviews

Cottage Nene - Luxury Home by Beaches & Mountains

Guest favourite
Apartment in Waikiki
5 out of 5 average rating, 8 reviews

19FL-Newly Renovated Banyan- Stunning 1BR/Parking

Guest favourite
The living room features a large 75-inch HDTV mounted on a textured accent wall, complemented by a cozy modular sofa and armchair. A central round coffee table sits atop a soft area rug, and the space flows into a modern kitchen with stylish pendant lighting.
Apartment in Waikiki
4.9 out of 5 average rating, 42 reviews

23F-Newly Renovated-Diamond Head View-1BR/Parking~

Home in Kaneohe
4.91 out of 5 average rating, 64 reviews

Luxury, Private Kaneohe Bay Home

When is the best time to visit Kailua?

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Avg. price$341 CAD$342 CAD$308 CAD$308 CAD$324 CAD$324 CAD$324 CAD$315 CAD$293 CAD$313 CAD$306 CAD$316 CAD
Avg. temp22 °C22 °C23 °C24 °C24 °C26 °C26 °C27 °C26 °C26 °C24 °C23 °C

Frequently Asked Questions

  • What are the best places to stay in Kailua?

    Stays in central Kailua let you explore vibrant shops and restaurants, while accommodations near Lanikai offer relaxed beach access. Both areas are frequently suggested for those looking for a local experience.

  • What are the best things to do in Kailua with kids?

    Kailua Beach Park has gentle waves for swimming, and the Kalapawai Market is known for casual snacks and treats. Kayaking on the bay and exploring nearby nature trails are also frequently suggested for families.

  • What are some of the best things to do in Kailua?

    Explore kayaking or paddleboarding in the calm bay, hike up to the Lanikai Pillboxes, and unwind at Kailua Beach Park. Kailua’s farmers' markets, local eateries, and bike paths are also frequently suggested.

  • How is the weather in Kailua?

    Kailua has warm temperatures throughout the year, ranging from about 65–85°F (18–30°C). Rain is more frequent in winter and early spring, while summers are sunnier with less rainfall.

  • When is the best time to visit Kailua?

    May through September has warmer temperatures around 70–85°F (21–30°C) and less rainfall, making it a popular time for beach outings. Late spring and early fall are often enjoyed for smaller crowds and local festivals.

  • What are the best places to visit in Kailua?

    Frequently suggested spots in Kailua include the white sands of Kailua Beach Park, the scenic Lanikai Beach, and the Pillbox Hike for panoramic coastal views. The neighborhood also has inviting local markets and art galleries.

  • What are some hiking trails in Kailua?

    The Lanikai Pillbox Hike is frequently suggested for its scenic coastal views and moderate climb. Locals also explore forested paths in nearby natural reserves, where you can experience native plants and ocean breezes.

  • What are some family activities we can do in Kailua?

    Families can explore calm swimming beaches, rent bikes for easy paths, or visit local playgrounds in Kailua. Kayaking, visiting markets, or observing wildlife at Kawainui Marsh are also popular choices among visitors with children.

  • What are some of the best day trip ideas from Kailua?

    Day trips around Kailua can include exploring lush botanical gardens, visiting the North Shore’s surf spots, or hiking in forested preserves. The area also has popular historic sites and cultural centers within easy reach.

  • Are there any pet friendly accommodations available in Kailua?

    Many accommodations in Kailua are pet friendly, especially around central neighborhoods and residential areas. Parks and outdoor cafes make it convenient for guests traveling with pets.

  • What are some local tips for visiting Kailua?

    Weekdays generally feel quieter at popular beaches, and early mornings are good for catching sunrise views from Lanikai. Remember to respect local customs, pack out what you bring, and use reef-safe sunscreen to protect marine life.

  • What is Kailua known for?

    Kailua is known for its wide, sandy beaches, calm turquoise waters, and relaxed community vibe. The area has scenic hiking, local food spots, and opportunities to experience traditional Hawaiian culture.

  • What are the best hidden gems to explore in Kailua?

    Kailua has quiet local beaches, shaded marsh trails for birdwatching, and small independent shops where you can explore local crafts. Consider wandering untouristed sections of Kailua Beach or the nearby Kawainui Marsh trail for a more laid-back experience.

  • What are the best foods to try in Kailua?

    Kailua has fresh poke bowls, local plate lunches, and tropical fruit smoothies that are often recommended. Shave ice and pastries from neighborhood bakeries add to the area’s favorite flavors.

  • What should I bring for a trip to Kailua?

    Pack light, breathable clothing, swimwear, reef-safe sunscreen, and a sun hat for comfort in Kailua's warm weather. If you plan to hike or explore nature, closed-toe shoes and a reusable water bottle are often recommended.

  • What is the nightlife in Kailua like?

    Kailua has a relaxed nightlife scene with welcoming bars, laid-back dining spots, and venues that occasionally feature live music. Most nightlife is concentrated in town, and evenings often center around enjoying local flavors in a casual atmosphere.

  • What are the most popular events or festivals in Kailua?

    Kailua frequently hosts street fairs, annual parade celebrations around holidays, and open-air art markets. Late spring and holiday weekends are often filled with local music, food, and craft events.

  • Are there family friendly vacation rentals in Kailua?

    Kailua has many family-friendly rentals, often located near beaches or local parks. These options typically include amenities like kitchens, outdoor space, and easy access to nearby attractions.

Quick stats about vacation rentals in Kailua

  • Total vacation rentals

    Explore 340 vacation rentals in Kailua

  • Nightly prices starting at

    Kailua vacation rentals start at $55 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    200 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    340 of Kailua vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront, and Gym across Kailua rentals

  • 4.8 Average rating

    Kailua stays are highly rated by guests—averaging 4.8 out of 5!

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