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Holiday rentals in Kailua

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Top-rated holiday rentals in Kailua

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Guest favourite
A covered patio area is viewed, featuring a large umbrella providing shade over a small table. The entrance to the unit is visible in the background, framed by a railing and surrounded by greenery.
Home in Kailua
4.87 out of 5 average rating, 470 reviews

Kailua Beach Park - 1 BR Cottage

Kailua Beach was 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 a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/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 showers, sinks and plumbing fixtures April 2022!

Guest favourite
A serene beach scene captures the sun setting between two islands, casting a warm glow over the water. Gentle waves lap against the shore, while smooth rocks are visible in the foreground, providing a natural frame to the tranquil view.
Guest house in Kailua
4.92 out of 5 average rating, 123 reviews

Lanikai Oasis, Cozy Cottage 5 Min to Lanikai Beach

Lanikai Oasis, A Peaceful Island Retreat Tucked away in one of the most private and peaceful neighborhoods on Oʻahu, Lanikai Oasis is a serene cottage retreat just 5 minutes from Lanikai Beach, consistently ranked among the most beautiful beaches in the world. Perfect for a clean, calm, and relaxing vacation, this newly remodeled ohana unit offers modern comfort in a lush island setting. ideal for couples or quiet travelers seeking paradise. Hawaii Tax IDs GE-159-110-0416-01, TA-159-110-0416-01

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.
Guest house in Kailua
4.8 out of 5 average rating, 198 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

Top 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.
Apartment in Waianae
4.97 out of 5 average rating, 319 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
A tropical pathway leads from a sandy beach to the bright blue ocean, with gentle waves lapping against the shore. Lush greenery borders the scene, while distant hills are visible on the horizon under a partly cloudy sky.
Place to stay in Kailua
4.96 out of 5 average rating, 108 reviews

Nai’a Suite at La Bella’s-Walk to Beach-Licensed

La Bella’s B&B is a High End Luxury home filled with charm and a touch of farmhouse/beach elegance. Two Suites are available for booking. Owners live onsite. Starbucks, Safeway, Gas Stations and Eateries are right across the street. Nai’a (Dolphin) Suite Offers: -Kitchenette -Private Bathroom -Separate Entrance -AC and Powerful high end fan -King size bed w/luxury bedding If you want a beautiful garden, great host family and a short walk to the beach this is the place for you.

Top guest favourite
The open-concept living area is highlighted by a modern kitchen with sleek white cabinetry and a stainless-steel appliances, including a refrigerator and dishwasher. A spacious living room features a dark sectional couch and a dining table, with large windows offering ocean views.
Apartment in Waikiki
5 out of 5 average rating, 221 reviews

Ocean/Fireworks View Waikiki Walk to beach! 1BR

Renovated 1 bedroom/1 bathroom top floor apt in Waikiki. Beautiful 180 unobstructed panoramic ocean views from the Juliet balcony. See the Friday night fireworks and the sunset from the top! Queen size bed in bedroom. Bathroom has double sink, glass walk-in shower. Fully stocked kitchen. 24/7 security on site. Central A/C, Cable, WiFi included. Garage parking available for $33 a day. Five minute walk to Waikiki beach, Hilton hotel, Duke lagoon, and Ala Moana mall

Top guest favourite
Apartment in Downtown Honolulu
4.98 out of 5 average rating, 252 reviews

Modern 1 Bedroom Condo in Downtown Honolulu

Aloha and welcome! Newly remodeled, clean and cozy 1 bedroom, 1 bathroom condo is in the heart of downtown Honolulu. Enjoy the views of the harbor and the city. We are a quick 10 min drive to beautiful Waikiki. Come explore all Oahu has to offer - surfing, swimming, snorkeling, relaxing on the beach, hiking, shopping, fine dining and more! Then unwind and relax in the comfort of the condo. We welcome you and hope you enjoy paradise at an affordable price.

Guest favourite
Home in Kahuku
4.92 out of 5 average rating, 102 reviews

Turtle Bay Condo with Great Amenities

Experience Turtle Bay without resort pricing! - 1-bedroom + loft, 2-bath condo with king bed - Spacious living area with stylish furniture and flatscreen TV - Fully equipped kitchen and washer/dryer - Near beach - Access to 3 pools, tennis courts, and BBQ facilities - Beach gear provided - Close to attractions like Shark's Cove and Polynesian Cultural Center - Spotless unit with smooth communication throughout the stay.

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.
Guest house in Kailua
4.87 out of 5 average rating, 435 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.

Superhost
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.
Guest house in Kailua
4.79 out of 5 average rating, 169 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.

Top guest favourite
A balcony offers a view of the beach and ocean, framed by palm trees swaying in the breeze. The distant mountains create a serene backdrop. A round table and a chair are positioned on the balcony, providing a space to relax and enjoy the scenery.
Apartment in Waikiki
4.92 out of 5 average rating, 227 reviews

Ocean View Beach Condo with private lanai

The only on-the-beach oceanfront condominium building in Waikiki! This spacious studio features a private lanai with stunning ocean and mountains view. Ocean breeze and breathtaking sunsets are guaranteed! King size bed, split AC, fully equipped kitchen, beach gear, and unbeatable walking distance to top Waikiki attractions, shops, and restaurants. Your perfect beachfront getaway awaits! STR#294

Guest favourite
A dining table is placed in front of large windows, offering a view of the ocean and a palm tree swaying gently. The clear blue sky contrasts with the water's gentle waves, creating a serene atmosphere.
Apartment in Hauula
4.87 out of 5 average rating, 103 reviews

"Coconut Cottage by the Sea" Steps to the beach!

Enjoy a memorable visit when you stay in this unique sandy beachfront cottage! Incredible view of the ocean & you will love amazing sunrises right out your window! This special condo has a great little kitchen, brand new king bed. Perfect for swimming, snorkeling, paddleboarding & just relaxing! BBQ area, pool, gym, security & FREE parking!

Popular amenities for Kailua holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Kailua's top sights

Lanikai Beach

460 locals recommend

Kailua Beach Park

217 locals recommend

Lanikai Pillbox Hike

260 locals recommend

Other great holiday rentals in Kailua

Superhost
A cozy sleeping area is visible with a spacious bed topped with crisp white linens and a textured green pillow. A bedside table holds a blue and white lamp and a digital clock. Light enters through a nearby window, softly illuminating the space.
Tiny home in North Shore
4.9 out of 5 average rating, 42 reviews

North Shore Farm Cottage

Top guest favourite
A spacious living area features a comfortable king-size bed with a textured white coverlet. Modern furnishings include a light-colored sofa and a dining set, positioned near large glass doors that provide panoramic ocean views. Ceiling fans add a cooling touch to the bright, airy space.
Apartment in Waikiki
5 out of 5 average rating, 24 reviews

13th Fl Waikiki Shore Condo | King Bed |Ocean View

Camper van/Motorhome in Kailua
5 out of 5 average rating, 4 reviews

The Lebowski- Paradise Campervan

Guest favourite
The serene beach shoreline is depicted at sunset, with gentle waves lapping against the sandy edge. Clouds hover in the sky, tinged with soft golden light. Palm trees stand to the right, contributing to the tranquil coastal scene.
Flat in Hauula
5 out of 5 average rating, 8 reviews

Cozy Hauula Studio Getaway!

Top guest favourite
The spacious sleeping area features a king-size bed with ambient lighting, complemented by a plush area rug. Large glass doors lead to a balcony, offering unobstructed views of the ocean and sky, allowing natural light to fill the room.
Flat in Waikiki
4.97 out of 5 average rating, 65 reviews

Penthouse Upscale Oceanview King Studio Near Beach

Top guest favourite
An entrance is displayed, featuring a smooth wooden deck with two outdoor chairs positioned beside the door. Soft lighting illuminates the entryway, while lush greenery provides a tropical ambiance against the backdrop of a colorful sunset sky.
Guest house in Makaha Valley
5 out of 5 average rating, 16 reviews

Studio Nene - Ocean, King bed, Tropical Garden

Guest favourite
Guest suite in Kailua
4.85 out of 5 average rating, 40 reviews

Papaya Paradise "Mauka" Poolside Studio *Licensed*

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, 148 reviews

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

When is the best time to visit Kailua?

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Avg. price£186£186£168£168£177£177£177£172£160£151£164£161
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 holiday rentals in Kailua

  • Total holiday rentals

    Explore 340 holiday rentals in Kailua

  • Nightly prices starting at

    Kailua holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 11,150 verified reviews to help you choose

  • Family-friendly holiday rentals

    190 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    330 of Kailua holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.9 Average rating

    Kailua stays are highly rated by guests – averaging 4.9 out of 5!

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