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Vacation rentals in Kailua

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Vacation rentals for every style

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Popular amenities for Kailua vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

Other great vacation rentals in Kailua

Guest suite in Kailua
5 out of 5 average rating, 15 reviews

Lanikai Garden Studio - Licensed Since 1985!

JohnRating, 5 stars40 months ago
Even better than we expected! (And we expected it to be great). The studio is larger than we thought and every detail is carefully thought out. The place is extremely clean and very close to the beach. Do not worry about privacy, the studio has its own gate and garden area. We hope to return soon.
Guesthouse in Kailua
4.79 out of 5 average rating, 179 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

GinaRating, 5 stars2 months ago
Thomas’ rental was an amazing private retreat for me. The ocean front location is spectacular. Waking up to the sunrise, going to sleep with the tradewinds and crashing waves. It’s on a lava beach so it’s rocky but I discovered a swimmable beach 13 houses down where green turtles sometimes swim beside you. Gorgeous scenery and a peaceful, private location. The interior was immaculate and well cared for. After going to Whole Foods prior to my arrival, I didn’t leave the premises except to head down to the beaches!!! Highly recommend. I hope to spend a longer time there next time I’m back in Oahu.
Superhost
Apartment in Waikiki
5 out of 5 average rating, 28 reviews

The Ocean Luxe in Waikiki, 1 Parking

MichaelRating, 5 stars2 weeks ago
We enjoy our stay this week at Charlie’s Place. New upgraded space. Easily assessable to everything in town. AC WORKS GREAT. FANS ARE IN THE UNIT AND HELP MOVE THE AIR but the best move was keeping the blinds closed. Night has you reaching for blankets. Big coffee lovers and we enjoyed the French press with some locally grown coffee from Green World Coffee farms. Other cool touch was the bidet, going home to purchase and install one. The pool being closed was the biggest let down but that will be done in a few weeks. We would stay again if in the area.
Superhost
Condo in Ewa
5 out of 5 average rating, 7 reviews

Aulani Disney Resort&Spa Studio!

AshleyRating, 5 stars3 weeks ago
This was our first stay at a Disney Resort. Aulani was amazing! Briana was a sweet host. We had a couple issues. We didn't get check in info until I asked for it (we were boarding plane to Hawaii and didn't have check-in confirmation yet). Briana was quick to respond to my message but we learned that you need the confirmation number to make reservations to do the daily activities so everything was already booked. (You need to reserve activities at least a couple weeks in advance). Also, the listing says King bed and queen sofa bed. It's actually reversed. The bed is a queen and the sofa bed is a king size. Bed was comfy but was definitely skinnier. When I lay across the bed my feet dangle... on the sofa bed my feet did not dangle. The sofa bed was definitely wider than the "king" bed. In addition, we were confused by what was included. Owner is a DVC member (Disney Vacation Club) so parking & 4 laundry tokens are included (claim daily at front desk). No discounts on food or at shops
Superhost
Condo in Hauula
4.93 out of 5 average rating, 30 reviews

Sandy Feet Retreat Beachfront!

JoshuaRating, 5 stars1 week ago
Our family of four stayed here and it was a bit tight but we thoroughly enjoyed our stay. The location is perfect. We snorkeled right in front of the airbnb with turtles and fish, was able to walk a mile down the beach and back when the tide was out, drove around the island and experienced true “Aloha”. We BBQ’d and ate out on the patio and relaxed in the lounge chairs. Was a very magical place for us. We would come back for sure!
Cottage in North Shore
4.88 out of 5 average rating, 119 reviews

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

SusannaRating, 5 stars1 month ago
We greatly enjoyed our time in his house. We had fantastic sunsets on the lanai. It was very relaxing to spent the afternoon on the lanai and to watch and hear the sea. You can easily reach a small beach from the house, which we only did for some late afternoon walks. We went snorkeling at Shark‘s Cove and at Waimea Beach, we could see a lot of fishes and turtles, inside and outside of the water. The location of the house was very good for us, you can easily reach different beaches, go on a sea shore hike or visit Pearl Harbour. The house was ideal for the two of us. We wanted to relax at the sea and do a lot of snorkeling and swimming which we could do every day. Peter was very friendly and helpful.
Superhost
Home in Makaha Valley
5 out of 5 average rating, 25 reviews

Kalo Homes - Breath of Life

Solei (So-LAY)Rating, 5 stars2 days ago
Aloha! 🌺 If I could give more than five stars, I would! We needed a big house for 6 adults on this family adventure. Driving up to the property - our jaws were dropped due to the beautiful mountains surrounding the area. We walked into the home and everyone was instantly happy with the layout. Had everything we needed. All the beach gear (we made great use chairs and boogie boards and beach towels). Providing bathroom items were an excellent touch - shampoo/conditioner/body wash/toilet paper. We walked outside and the hot tub with the covered lanai was AMAZING! The breeze while looking at the mountains to our right the ocean in front of us was simply heaven. The beaches on this side of the island are untouched by tourists. Sea lions came out of the water onto the shore! Highly recommend! Jerelle and Kerstan are excellent hosts! They went out of their way to ensure our trip was memorable. We will be back! Mahalo for the treats!! 🌺
Tent in Laie
4.71 out of 5 average rating, 77 reviews

North Shore Oahu Camping / Glamping Tent Laie #5

AshleyRating, 5 stars2 weeks ago
great place to stay, the tent was spacious and clean!
Show all

Quick stats about vacation rentals in Kailua

  • Total rentals

    360 properties

  • Total number of reviews

    11K reviews

  • Family-friendly rentals

    200 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    90 properties have a pool

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

Your guide to Kailua

Welcome to Kailua

With stretches of powdery white sand beaches, two reef-protected lagoons, and temperatures kept on the comfortable side of cool by ever-present trade winds, it’s no surprise Kailua is no longer the secret destination guarded by seasoned island vacationers that it once was. Located on the windward side of Oahu on a peninsula overlooking the crescent-shaped Kailua Bay and the Koolau Mountain range, Kailua is beloved for its small beach town vibe — a mellow yin to Honolulu’s metropolitan yang, with only a 25-minute drive separating the destinations.

There’s also an increasing possibility of rubbing well-tanned shoulders with vacationing celebrities drawn to the same soft sand beaches and tranquil aquamarine waters delivering on the promise of paradise. In Kailua you can revel in a variety of water sports. Hikers have a range of challenging trails to choose from, some leading to breathtaking mountaintop views, others to such secluded mountain-fed pools as Maunawili Falls, along with a network of leisurely footpaths awaiting within the 830 acres of Kawainui Marsh.

The best time to stay in a vacation rental in Kailua

With an average temperature of 81 degrees Fahrenheit, there’s really no bad time to stay in one of Kailua’s vacation rentals. Months spanning from spring through fall generally offer the best balance between agreeable (dry) days, with sparser crowds that spike after Thanksgiving. Kailua’s windward location on the island means sweltering heat will rarely be a concern here, and the weather is almost always pleasant. Mornings can be a little muggy, though, before the trade winds flush out the humidity, perpetually moving clouds overhead to reveal the shockingly blue skies. If you plan to travel from November through early spring, come prepared for rainfall, including footwear outfitted for muddy conditions.

Top things to do in Kailua

Lanikai Beach

Lanikai Beach is often described as one of the world’s greatest beaches, and it’s easy to see why, with its breathtaking stretches of sand and ocean overlooking two nearby islets, the Na Mokulua. The waters here are typically calm, with a protected coastline buffered from windpowered waves thanks to a sizable reef offshore, making it one of the more swimmable spots on Oahu. These placid coastal waters are hard to beat — especially for kayaking and paddleboarding — tempting the more adventurous to paddle around those two offshore islands colloquially referred to as the Mokes.

Kawainui Marsh

Binoculars and a camera are a must while visiting Kawainui Marsh, the state’s largest protected wetlands, a sanctuary where many of Oʻahu’s endemic, endangered, and migratory birds, fish, and other aquatic life can be observed in their natural habitat. Travel by foot or by bike along a paved three-mile round path in a watershed that fed ancient Hawaiians with its abundance.

BookEnds

If you identify as a bibliophile and/or a lover of Hawaiian history, you might lose yourself once entering the door of this small neighborhood bookstore. BookEnds is filled with an extensive collection of Hawaiiana reflecting the islands’ history through photography, arts and crafts, architecture, and music.

Frequently Asked Questions

  • How is the weather in Kailua?

    Kailua's weather remains warm throughout the year with an average temperature ranging from 70°F (21°C) to 85°F (29°C). It sees the most rain from November to March, while the driest months are June to September.

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

    Popular activities in Kailua include swimming, kayaking, or windsurfing at Kailua Beach, hiking the scenic trails such as the Olomana Trail, and exploring local markets like the Kailua Farmers Market. Visitors also enjoy sampling local cuisine at the many eateries in town.

  • What is the best time of year to visit Kailua?

    Kailua is mostly visited during the summer months, particularly from May to September. Around this time, visitors can enjoy events such as the Kailua Independence Day Parade in July. The period between December and April is also popular, especially for those looking to escape colder weather.

  • What are the best places to stay in Kailua?

    Visitors to Kailua often prefer staying in places close to its natural beauty. Lanikai, known for its beach, and Enchanted Lake, a residential area with a shopping center, are popular choices. Notably, Maunawili, with its proximity to hiking trails, also attracts nature lovers.

  • What are the best places to visit in Kailua?

    In Kailua, Lanikai Beach and Kailua Beach Park are frequented by sun-seekers and water sports enthusiasts. Nature lovers often explore the Maunawili Falls Trail and the Kawainui Marsh. The Kailua Farmers Market is a favorite among food enthusiasts for its local produce.

  • What are some hiking trails in Kailua?

    Kailua has several hiking trails for nature enthusiasts. The Olomana Trail, offering three peaks of varying difficulty, and the Maunawili Falls Trail, leading to a waterfall, are popular choices. The relatively easy Pillbox Hike offers great views of the town and ocean.

  • What are some family activities to do in Kailua?

    Families in Kailua can enjoy a day at the beach, try stand-up paddleboarding, or visit Kalapawai Market for a picnic lunch. They can also explore Pillbox Hike for a fun family adventure or visit the Thursday Night Farmers Market for a taste of local food and culture.

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

    From Kailua, day trips can include exploring the marine life at Hanauma Bay, hiking the Ko'olau Mountain Range, or visiting the Byodo-In Temple in the Valley of the Temples. Trips to the bustling city of Honolulu, just 19 km away, are also enjoyed by many.

  • Are there vacation rentals with a dedicated workspace in Kailua?

    Yes! Work meets play with ease at over 170 vacation rentals in Kailua featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in private suite rentals in Kailua?

    Experience the best of Kailua with our private suite rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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