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Holiday rentals in Kailua

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Quick stats about holiday rentals in Kailua

  • Total holiday rentals

    Explore 310 holiday rentals in Kailua

  • Nightly prices starting at

    Kailua holiday rentals start at €35 per night before taxes and fees

  • Verified guest reviews

    Over 10,170 verified reviews to help you choose

  • Family-friendly holiday rentals

    180 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    300 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!

Top-rated holiday rentals in Kailua

Guests agree: these stays are highly rated for location, cleanliness and more.

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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

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!

4.87 out of 5 average rating, 506 reviews
Top 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

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

Hawaii’s Best Kept Secret! The cottage is next to sandy coves, driftwood, shells, and Polo ponies in forested pastures. The ocean is excellent for snorkeling and fishing; there are 2 surf spots, & world-class windsurfing within 2 mile. Mountains behind us offer good hiking trails. The Colony has a nice pool, and a Pickle Ball court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021. Note: We have NO Air Conditioner, 3 ceiling fans, 2 desk fans & ocean

4.88 out of 5 average rating, 164 reviews
Superhost
A private lanai is seen through sliding glass doors, featuring two chairs and a small table overlooking the ocean. Lush palm trees are visible, with water glistening under the clear sky. The space has green turf flooring, providing a vibrant touch.
Apartment in Punaluu

"Endless Summer" Beachfront Condo w/ Full Kitchen!

Welcome to the beach! Your little piece of paradise! 1 bed w/ king bed & queen bed in the living room too! Directly on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped kitchen, washer/dryer in the condo & private lanai looking out at a spectacular beach with amazing ocean views! Enjoy incredible sunrises too! Pool, gym, BBQ area & WIFI. Close to may attractions like PCC, Kualoa Ranch & More!

4.76 out of 5 average rating, 169 reviews
Guest favourite
The image captures a wide sandy beach bordered by tranquil turquoise waters, with gentle waves lapping at the shore. Lush greenery and palm trees line the background, while distant islands are visible on the horizon under a bright, partly cloudy sky.
Home in Kailua

Large Kailua Beach Home - Steps To The Beach!

Spacious home for the entire family to enjoy! Just a few minutes walk to the soft sand & clear water of Kailua beach. Spend your days at the beach with your private, air conditioned oasis awaiting you for rest and relaxation. A short bike ride to Kailua Town with restaurants and shops. Lanikai Beach is less than a 5 minute drive away. Hike, bike ride, snorkel, swim, surf, boogie board, kayak, paddle board, kite surf, wind surf, and much more!! Some dates not shown - reach out to confirm avail!

4.87 out of 5 average rating, 85 reviews
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 Makaha

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.

4.97 out of 5 average rating, 344 reviews
Top guest favourite
The exterior of the cottage showcases a modern design with a welcoming front entrance and large windows. A two-car garage is visible on the right, while stunning mountain scenery frames the background. The sky is adorned with soft hues of pink and orange as the sun sets.
Cottage in Waianae

Cottage Nene - Luxury Home by Beaches & Mountains

Modern luxury meets valley tranquility. Built in 2022, this spacious 3-bed, 2.5-bath cottage hosts up to 8. Enjoy an airy living room with 14ft ceilings, premium furniture, and smart TVs. Step outside to a fully landscaped tropical yard with the best mountain views in the community, perfect for morning coffee or evening stargazing. Enjoy community pool, jacuzzi, and gym, all while being minutes away from world-class west-side beaches and hiking trails. Guaranteed cancellation in 48 hrs.

4.98 out of 5 average rating, 121 reviews
Top guest favourite
Apartment in Downtown Honolulu

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.

4.98 out of 5 average rating, 283 reviews
Top guest favourite
A sea turtle glides gracefully in the clear, turquoise water, just beneath the surface. In the background, two small islands rise against a bright blue sky dotted with fluffy white clouds, creating a serene coastal atmosphere.
Place to stay in Kailua

Tropical Kailua Retreat | Walk to Beach + Gym

Walk to one of Hawaii’s most beautiful beaches, explore Kailua by kayak or bike, and relax in your own tropical retreat. The Honu (Turtle) Suite at La Bella’s Bed & Breakfast offers privacy, comfort, and island charm just minutes from the beach. Enjoy a queen bed with luxury linens, air conditioning, a full kitchen, private bathroom, private entrance, and outdoor seating area surrounded by tropical gardens on Oʻahu’s beautiful Windward Coast.

4.96 out of 5 average rating, 133 reviews
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.
Guest house in Kailua

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.

4.88 out of 5 average rating, 465 reviews
Guest favourite
A vibrant pink hibiscus flower stands prominently in the foreground, with lush green foliage surrounding it. In the background, a corner of the apartment is visible, featuring a light green exterior and a covered area, enhancing the tropical atmosphere of the property.
Home in Kailua

Tropical Hideaway Near the Beach

We live in a quiet neighborhood which is close to the beach, bus stop or shopping. It’s a mile walking to Kailua beach. The apartment has a bedroom, living room/kitchenette and bathroom which are part of the house but has a separate entrance and private yard with a gate. We must rent on a monthly basis according to Hawaii vacation rentals. If you need a different amount of time please contact me. No pets allowed.

4.86 out of 5 average rating, 118 reviews
Guest favourite
Home in Kailua

60 second walk to Lanikai Beach. 2 Bedrooms w/ AC

Just a 60 second walk from world-famous Lanikai Beach, this unique 2-bedroom setup offers two private 1-bedroom studios. Each studio features its own kitchenette, dining area, sofa, private balcony, and full bathroom. Enjoy cool A/C, fast Wi-Fi, and thoughtful touches throughout. Relax, explore, and soak in the best of Lanikai.

4.93 out of 5 average rating, 30 reviews
Guest favourite
A serene beach area features gentle waves lapping at the shore. A sailboat rests on the soft, sandy beach, surrounded by a calm aqua-blue ocean. Lush greenery and houses frame the sandy expanse under a clear blue sky with scattered clouds.
Home in North Shore

Haleiwa Dream Location

Newly renovated home, excellent location, just 650 feet walking distance to beach and 5-minute bike ride to Haleiwa Town. This is a great getaway for singles, couples, or families wishing to explore without needing to drive. 30-day minimum rental required. Note the beach in the top photo is directly across the street.

4.81 out of 5 average rating, 335 reviews

Popular amenities for Kailua holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Kailua's top sights

Lanikai Beach

471 locals recommend

Kailua Beach

176 locals recommend

Lanikai Pillbox Hike

265 locals recommend

Kailua Beach Park

217 locals recommend

Kalama Beach Park

44 locals recommend

Kailua Beach Adventures

55 locals recommend

Other great holiday rentals in Kailua

Top guest favourite
A spacious studio is highlighted by a king-size bed adorned with a green floral quilt. Comfortable seating is provided by two armchairs and wooden chairs positioned around a table. Large windows offer views of tropical greenery, while a bathroom is visible in the background.
Guest suite in Kailua

Lanikai Garden Studio - Licensed - Since 1985!

5.0 out of 5 average rating, 28 reviews
Superhost
Home in Kailua

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

4.71 out of 5 average rating, 94 reviews
Guest favourite
Tiny home in Kailua

Disconnect Off Grid

5.0 out of 5 average rating, 6 reviews
Top guest favourite
A serene pathway leads toward the cottage, bordered by lush greenery and a manicured lawn. The ocean glistens in the distance under a bright blue sky, with a palm tree gently swaying nearby. Large windows of the cottage offer views of the tranquil waters.
Cottage in North Shore

Island Jewel, North Shore Bliss

5.0 out of 5 average rating, 92 reviews
Guest favourite
Flat in Kawela Bay

North Shore Hideaway

5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Waianae

Lani Kai Ocean View Villa Sleeps 12 Pool + Hot Tub

5.0 out of 5 average rating, 24 reviews
Guest favourite
A private hot tub sits elegantly on a patio, illuminated with soft ambient lighting as the sunset casts a soothing palette across the sky. Lush greenery surrounds the area, and a well-maintained lawn is complemented by a pathway of decorative stones.
Home in Makaha Valley

Single Level Home|Beach 6 Min|Spacious Backyard

4.95 out of 5 average rating, 40 reviews
Superhost
Home in Manoa

Hale Hoomalie- Peaceful Manoa Valley Retreat near

5.0 out of 5 average rating, 8 reviews

When is the best time to visit Kailua?

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Avg. price€193€196€197€195€194€197€206€200€186€177€192€188
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.

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