Kailua vacation rentals

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Popular amenities for Kailua vacation rentals

Kailua beach vacation rentals

Superhost
Apartment in Kailua
4.94 out of 5 average rating, 31 reviews

Private waterfront studio with pool and lake view

HelenRating, 5 stars11 months ago
Live Aloha in Kailua! I’ve been coming to Oahu for 15 years, this is by far my favorite space and place to stay in Hawaii. It is a quiet and safe neighborhood, everything you need for a day at the beach, and relaxing pool. Again, best place I’ve ever stayed at in Kailua. Close to beach and my favorite restaurants. The host is friendly and helpful with two wonderful doggies Zeus and Harvest, who I miss! This unit is affordable and gorgeous! Book it while you can! It is a gem! Pictures support experience and expectations. It is even more gorgeous than the photos. Have fun in the Sun. Aloha!
Superhost
Apartment in Waikiki
5 out of 5 average rating, 4 reviews

13th Fl Waikiki Shore - Ocean-front|King Bed|AC

LarissaRating, 5 stars2 weeks ago
My stay exceeded all of my expectations! The balcony view was beautiful and looked even better than the pictures. I was able to see the sunset and sunrise every day if I wanted to. On Friday nights, they have a free fireworks show so I watched this from the balcony. The place was very clean and the washer/dryer was a nice plus. I will definitely be coming back next time I’m in Hawaii!
Guest favorite
Condo in Waikiki
4.94 out of 5 average rating, 106 reviews

32nd Floor Penthouse. 3min walk to Waikiki Beach

TriciaRating, 5 stars2 weeks ago
Highly recommend this condo! The views were amazing and every time we walked in the door it was a treat! Endless blue ocean views. The hosts were always responsive. The only drawback was some construction noise from a nearby highrise but otherwise it was quiet. We will be back!
Guest favorite
Condo in Waikiki
4.88 out of 5 average rating, 113 reviews

()(Upgraded June.2021!)() 1 Bedroom oceanview

NicholeRating, 5 stars1 day ago
Beautiful modern clean condo just like the photos. Amazing unobstructed view of Waikiki Beach as the building sets right next to Ft DeRussy Park which houses the Army Museum. Loved opening the sliders to the whole condo and listening to the waves late at night. Beach chairs, noodles and snorkeling equipment was available so we didn't have to spend extra $ renting. The chairs were backpack style for easy carrying to the beach which was just steps off the building. Rick made check in and parking seamless. Very clean and modern bathroom with ceiling shower, hand held shower and warm water bidet. Great restaurants and shopping all within walking distance. Thank you!
Superhost
Tiny home in Hauula
5 out of 5 average rating, 3 reviews

Countryside Getaway

DanielaRating, 5 stars4 days ago
We enjoyed our stay here- we had a everything we needed for a comfortable stay. The space can heat up a bit during the day, but there are beautiful beaches to sit in the shade and cool off nearby. There are also some great food trucks close by as well. Don was very kind and lives nearby if anything is needed. It’s a good place to chill!!
Top guest favorite
Condo in Kahuku
4.99 out of 5 average rating, 157 reviews

Ranked in Top 5% Airbnb-Pua Moana at Turtle Bay

EnjoliRating, 5 stars1 week ago
We enjoyed our stay at Pua Moana. It is the perfect size for our small family. The unit is beautifully maintained, clean, and well stocked. We were able to walk to the beach and the Ritz. Scott takes pride in maintaining the unit and cares for his guests. He gave us a quick check-in orientation and tips/updates on things happening while we stayed. We will defiantly consider another stay at Pua Moana.
Guest favorite
Condo in Waianae
4.93 out of 5 average rating, 121 reviews

11D Hawaiian Princess - Mango Mele

JuanRating, 5 stars2 days ago
Very clean condo along with a great view. Surrounding area is a bit rough but property is private and secure. We were very happy with the communication, information, and overall experience. Thank you!
Superhost
Townhouse in North Shore
4.95 out of 5 average rating, 20 reviews

Sunset Hale

AngelaRating, 5 stars1 week ago
Our family of four ( including a 3 & 5 y/o) had a wonderful stay! The home had everything we needed and the location was amazing! A great reef to snorkel right out front of the unit while the kiddos rested. Our favorite beaches were less than a 5 minutes drive west of the unit and had no tourists, lots of trees for shade and opportunities to snorkel with turtles. Would highly recommend for those wanting a more quiet vacation spot.

Kailua home rentals

Guest favorite
Home in Waianae
4.93 out of 5 average rating, 121 reviews

Large family home 5 min from beach- newly built

SaraiRating, 5 stars1 month ago
Garret was a great host, very responsive and friendly. Had a great stay at his place, very close to the beach. The views are amazing around the home and had everything we needed at the house.
Guest favorite
Home in Waianae
4.97 out of 5 average rating, 70 reviews

Makaha Hale - New 3 BR Home

MinnieRating, 5 stars3 weeks ago
We had a wonderful stay at Melissa’s home in Makaha Valley! The house was clean, well-maintained, and had everything we needed—including thoughtful touches like toys for our baby, which made a big difference for our family. Melissa was incredibly responsive, friendly, and helpful throughout our stay. The location is peaceful and private, set within a secure gated community. It’s perfect for families with young children who are looking to relax and enjoy a slower pace. While most tourist attractions are about a 40-minute drive away, the setting more than makes up for it if you’re not planning to be out all day. Overall, we felt very comfortable and well taken care of. Would definitely recommend for families looking for a quiet, kid-friendly getaway (away from the hustle and bustle of touristy areas) on Oahu!
Superhost
Home in Waianae
4.82 out of 5 average rating, 28 reviews

@ Marbella Lane - Stunning Gem w/ MT & Ocean Views

LouisRating, 5 stars1 week ago
Stella’s home was absolutely lovely and had everything we needed. We had a small issue with the booking at first, but Stella handled it promptly and professionally. Check-in was smooth, and she continued to provide excellent care throughout our stay. I truly hope future guests feel confident booking this home—it’s a peaceful, well-managed place to stay.
Guest favorite
Home in Waianae
4.96 out of 5 average rating, 99 reviews

Family Oceanview Oasis, Hot Tub, 5min to beach

HalleyRating, 5 stars3 weeks ago
We had a fantastic stay at Emma’s beautiful home! It had everything our family needed, especially traveling with children. The house was spotless, comfortable, and incredibly well-stocked — from beach towels and boogie boards to coolers and chairs, Emma really thought of everything. The backyard and view were absolutely amazing, and being in a gated community made us feel very safe and at ease. Emma was extremely communicative and friendly throughout our stay, which made the whole experience even better. She truly goes above and beyond — we loved staying here and would absolutely come back!
Superhost
Home in Kahuku
4.86 out of 5 average rating, 284 reviews

Hawaiian Country Retreat - 30 day stays

WillRating, 5 stars2 weeks ago
Great place to stay, very near the beach. Excellent hosts. Overall great experience
Guest favorite
Home in Waianae
4.92 out of 5 average rating, 111 reviews

Beautiful 4-BR Home| Near Beach| Mountain View

JulietteRating, 5 stars1 week ago
Emma was great with accommodating us with our stay for the week. She was responsive and checked in on us throughout our stay to ensure our comfortability. The house was spacious and cozy made us feel right at home. Great safe place in gated community for my family with beautiful views and nearby beaches.
Guest favorite
Home in Hauula
5 out of 5 average rating, 19 reviews

Ocean View Vacation Home

Kyle And AjaRating, 5 stars2 months ago
This was our first time visiting Oahu as a family. The hosts were friendly and we enjoyed having the space to ourselves with a washer and dryer on site. We do appreciate how clean things were and the beach accessories that were available to use under the stairs. Plenty of beach towels, and bedding and we loved the location. You can also vaguely see the ocean from the kitchen window. Things to consider -windows need to be shut and locked while away. By the time we returned and opened windows by 6pm it was too hot to cook dinner and there was little breeze to cool the space. We made sure to pick up something to eat prior to returning. We were warmer than we liked sleeping at night but survived -don’t sleep with windows open if sensitive to noise. There’s a rooster that goes off throughout the night. -The Airbnb is the bottom floor of a house so you do hear footsteps occasionally, and the parking is up a tight, narrow driveway on a hill which accommodates one car at a time up and down
Superhost
Home in Waianae
4.75 out of 5 average rating, 12 reviews

Studio Nene by AvantStay | Chic, Cozy, King Bed

EstefaniRating, 5 stars1 week ago
This place was amazing. I would recommend to book this beautiful place to anyone ❤️ everything went nice and smooth. During our stay we needed an iron and they delivered it on time. This place was amazing!

Beach home rentals in Kailua

Guest favorite
Home in Waikiki
4.98 out of 5 average rating, 103 reviews

Waikiki Gem, Stunning Ocean View, Parking Included

NatalieRating, 5 stars1 month ago
Charlie’s place was just as pictured & more! The space is a corner unit located on the second highest floor & has beautiful views over looking the ocean, Waikiki beach, city & the mountains. The unit was very clean, perfectly designed & easily walkable to the beach & local restaurants. It was a perfect rental for our first trip to Hawaii & Charlie is an amazing helpful host!
Guest favorite
Home in North Shore
4.95 out of 5 average rating, 21 reviews

Waimea Bay Studio 1BD With Sauna - NS Oahu

SariahRating, 5 stars2 weeks ago
We had the best time here. So close to Waimea Bay which became our fav beach, it was less than a 10 min walk! Absolutely wonderful place to stay, also very kind and helpful host!
Guest favorite
Home in North Shore
4.98 out of 5 average rating, 94 reviews

One of a kind Beach front 2brm ocean and mnt views

TylerRating, 5 stars1 month ago
Great location with incredible scenery. It's a very quiet and private area. I would recommend staying here if you're looking to be away from the busyness of the city.
Superhost
Home in Kailua
4.78 out of 5 average rating, 76 reviews

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

KelseyRating, 5 stars1 month ago
We loved this place! It was definitely one of the more reasonable cost rentals in the Lanikai neighborhood but it didn’t disappoint. A few things of note: - the appliances are high end KitchenAide and Bosch. The cooktop is a two burner induction that you can put away when not in use. Toaster oven as well. Compact dishwasher and fridge is a one drawer fridge/ one drawer freezer that fits under counter - ample beach towels. Also beach chairs and umbrellas. - the pool was wonderful - less than 10 min walk to Lanikai Beach - do the pillbox hike up the ridge behind you if you want a good workout! We loved our week here. Always planned to cook out on the Weber grill but didn’t end up doing so. The patio was awesome at the end of each day and for morning coffee. Neighborhood was safe. Met the pest control guy and the pool guy while we were here- both really friendly. Would definitely choose this place again.
Guest favorite
Home in Kailua
4.96 out of 5 average rating, 25 reviews

Large Kailua Beach Home - Steps To The Beach!

SarahRating, 5 stars1 week ago
We had a great stay in Kailua! The house is very comfortable, and it’s only a couple minutes walk to the Kalamas beach access. When not at the beach (with the chairs, towels, boogie boards, and toys provided) or eating Island Snow, the kids loved playing in the yard and the play room, and watching movies in the living room. We ended up staying mostly in Kailua and Lanikai for beaches, shopping, and restaurants, with one morning at the botanical gardens in Kaneohe and one at Haunama Bay, and an afternoon at Bishop Museum after check-out. We’d love to stay here again, in this well-appointed and clean house with hosts who responded to our questions and provided clear guidance on the check-in and check-out process.
Guest favorite
Home in Kahuku
4.93 out of 5 average rating, 15 reviews

Peek-a-Boo Ocean View

JuliusRating, 5 stars4 weeks ago
Alex was very responsive when I needed help with some things. Taught me a trick with the shower. Reading their rule binder gave me a warm welcome vibe. I recommend if you’re staying around for a quick getaway.
Guest favorite
Home in Kahuku
4.94 out of 5 average rating, 36 reviews

Ocean Pearl

WendyRating, 5 stars4 days ago
We loved our stay here. The unit was perfect for a group of 5 women celebrating a reunion. Close to sharks cove and cute town of Haleiwa. Walking distance to several beaches. One very beautiful secluded beach that has turtles. The pool near the unit was lovely and the patio space was private and peaceful. The kitchen was perfectly equipped. It was also amazing to have snorkel equipment, beach chairs & boogie boards. Living space with large sectional couch was the best.
Superhost
Home in Haleiwa
4.67 out of 5 average rating, 195 reviews

Sunset Beach Vintage Cottage

KristopherRating, 5 stars2 months ago
We loved the place! Beach across the road and good food just a walk away. Morning coffee on the porch with the chickens/chicks running around was fun! Thanks again for creating such a great place for memories!

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.

  • Are there pet-friendly vacation rentals in Kailua?

    Four-legged friends are welcome in Kailua. Choose from more than 40 vacation rentals for guests traveling with pets.

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