Family-friendly vacation rentals in Kailua-Kona

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Popular amenities for Kailua-Kona family-friendly rentals

Family-friendly home rentals with a pool

Guest favorite
Townhouse in Waimea
4.92 out of 5 average rating, 162 reviews

Amazing, spacious 2BD townhome. Pool/Beach Club!

MichaelRating, 5 stars1 month ago
A great condo for your vacation. Walk to the beach and nearby resorts. comfortable furniture and beds. Well equipped kitchen. Great birding from the patio. Close to the community pool and hot tub. The beach club access is a nice benefit.
Superhost
Condo in Kailua-Kona
4.71 out of 5 average rating, 66 reviews

Wonderful Sunsets and Pool

WayneRating, 5 stars2 months ago
It was just what we needed for our stay Thanks
Guest favorite
Home in Kailua-Kona
4.95 out of 5 average rating, 153 reviews

Private Pool - 180° Ocean View - Minutes to Beach

MitkoRating, 5 stars3 months ago
Sandra's home was very nice and has a beautiful backyard. We rented the downstairs portion (with the private pool). We really appreciated the extra amenities provided (beach chairs, body boards, wagon, cooler). We used all of these items when we went to the beach. The yar d, fruit trees, and view are immaculate. We were able to pick fresh fruit each morning (star fruit, guava, oranges). This is definitely an experience that you can not replicate at any hotel, our family really enjoyed this. Thank you Sandra for sharing your beautiful home with us!
Guest favorite
Townhouse in Keauhou
4.88 out of 5 average rating, 185 reviews

Tropical Living in Oceanfront Resort 31

KariRating, 5 stars1 week ago
We really enjoyed our stay! We loved how it was just a short walk to the beach or pool. Brad was a wonderful host, incredibly welcoming and responsive. The space was perfect for our family. We loved the trunk full of beach toys, the lanai, being able to cook & do laundry.
Guest favorite
Townhouse in Waikoloa
4.98 out of 5 average rating, 151 reviews

Your 3BD Island Paradise Awaits

SkyRating, 5 stars4 weeks ago
The location of the townhome was perfect for us. Seth is a great host and does a great job of communicating. We will definitely return.
Superhost
Home in Keauhou
4.83 out of 5 average rating, 23 reviews

Kona Blue Vacations Holua Kai: Pool/Spa/AC/Views

MarkRating, 5 stars10 months ago
Beautiful place and great to work with! Would do it all over again
Superhost
Home in Captain Cook
4.93 out of 5 average rating, 106 reviews

Beautiful Home With Private Pool on Kealakekua Bay

NeilRating, 5 stars2 weeks ago
The Pagoda House is a destination in itself! We explored the island from there, but also spent time just hanging out in the garden and pool. GORGEOUS! It was well appointed for our extended family gathering.
Guest favorite
Home in Kailua-Kona
4.87 out of 5 average rating, 78 reviews

Kona Palm House 3 Bed/2.5 Bath with Pool

TaylorRating, 5 stars3 weeks ago
Monica's place was EXCELLENT. Views were absolutely stunning--we loved watching the sunset on the upper lanai every night. The home had ample amenities--enough towels to go around, beds were comfortable, bathrooms were stocked, kitchen had everything necessary to cook delicious family meals. It is up in the mountains so a bit cooler than at sea level but we did not mind at all! A glorious escape from the bitter Midwestern winter!

Family-friendly home rentals with air conditioning

Guest favorite
Guesthouse in Waimea
4.95 out of 5 average rating, 128 reviews

Mango Hale Cottage

FayeRating, 5 stars2 weeks ago
We loved staying at The Mango Cottage ! It’s a sweet and comfortable place in a wonderful location near the ocean in Puako. Scott is a friendly and helpful host. We have stayed in the cottage several times and plan to visit again. Many thanks Scott- Faye & Fred
Guest favorite
Condo in Kailua-Kona
4.96 out of 5 average rating, 162 reviews

Ali'i Banyan Breeze*

DennisRating, 5 stars1 week ago
Great condo, super well-equipped and maintained. Great bed, perfectly clean, and well-equipped kitchen. Hosts communicated at a perfect level: just enough information but no deluge, and always kind and in the interest of service. The description is accurate but realize that it is 2 buildings and one road away from the water (in many of the photos). It is set back from Ali'i Road, so the traffic noise is minimal - very quiet even on the lanai. Location is nice: the farther you get from the center of town, the less busy things are.
Guest favorite
Townhouse in Keauhou
4.96 out of 5 average rating, 125 reviews

Direct Ocean Front Corner Townhouse AC Pickleball

MikeRating, 5 stars1 month ago
Jim’s place was the perfect location close to a lot of amenities with a spectacular view. We didn’t spend much time there except to sleep and have coffee in the morning. The a/c was so nice to sleep in and views were magical. Will definitely be back, perfect space for 2 couples to make a beautiful Hawaiian base camp for our activities, and great place to relax with spectacular view and comfortable space.
Guest favorite
Guest suite in Kailua-Kona
4.89 out of 5 average rating, 423 reviews

Kona-Amazing sunset, Ocean/POOL/AC/Great loc

ChrisRating, 5 stars2 weeks ago
Loved the pool and the puzzles. Very accommodating for a last minute booking. Clean and comfortable.
Guest favorite
Condo in Kailua-Kona
4.85 out of 5 average rating, 191 reviews

DirectlyOnTheOcean AC Beachgear Pool Park Elevator

JeffreyRating, 5 stars1 week ago
Our stay at Konamazing was wonderful. The accommodations were great and the ocean views amazing. The provided beach chairs, umbrella and snorkel gear came in handy and were included in the rental. The condo was just a short walk to some of our favorite Kona restaurants and shops. We loved drinking our morning coffee on the lanai, and in the evening, we enjoyed watching the sunset and waves crashing below. The pool was clean and refreshing after a day of exploring the island.
Superhost
Home in Kailua-Kona
4.95 out of 5 average rating, 41 reviews

5 Bdrm  Trade winds, Airport and the Sea

CaitlinRating, 5 stars14 months ago
We had a wonderful stay. Jun’s place is exactly as described - very tidy, has all amenities needed and very organised. We were two large families coming from overseas, the split-level living options suited us perfectly. The living spaces were easy with the kids and balconies all maximised the amazing view from TradeWinds. The outside areas weren’t child-friendly - the back / sides contained sharp items of furniture and structures that made it hard for us to allow the kids outside. There was one proper grassy space but it was on the main road. Our kids were able to enjoy the indoor spaces and balconies when we were home, but they couldn’t really play outside. The location is wonderful from a view perspective - it’s ten mins drive (min) to anywhere but we didn’t mind. Jun is a very helpful and responsive host, as was his Property Manager Azusa. Overall we had a wonderful stay and Christmas. If you’re looking for an easy, large space with amazing views - you can’t go past TradeWinds.
Superhost
Condo in Kailua-Kona
4.8 out of 5 average rating, 322 reviews

Charming Condo in the Heart of Kona, Pool & A/C

KarenRating, 5 stars4 weeks ago
We would definitely recommend Jenna’s place. It is suitable for a couple with a nice bedroom and bathroom. The kitchen and living room area are percent for relaxing and making meals. Lots of dishes and utensils available. The towels are soft! Bed & bedding are all nice and fresh! The additional beach chairs, beach mats, umbrella & cooler were all great to have available to use. Thank you for sharing your place with us during our visit to Kona. Easy to find this great location thanks to accurate instructions provided. The pool area is great for lounging and watching the sunset. Thanks again!!
Guest favorite
Apartment in Kailua-Kona
4.86 out of 5 average rating, 409 reviews

Spacious Retreat in Kona - Paradise near Kona

MarkRating, 5 stars1 week ago
Our place was clean,plenty of room and lots of patio area to enjoy the evenings. Location worked well for us during our stay. Also all the suggestions she had for restaurants, things to do and beaches to visit were extremely helpful. Would go back again.

Family-friendly home rentals with a kitchen

Superhost
Home in Holualoa
4.91 out of 5 average rating, 476 reviews

Holualoa Elua (clean, comfortable, Taxes included)

AzaleaRating, 5 stars1 week ago
Cute little house close to town but still private with a great view. It’s 15 from town. They provide some beach items and the house is more spacious than we thought! Great for 4 people
Guest favorite
Guest suite in Kailua Kona
4.98 out of 5 average rating, 109 reviews

Our Sun Spot

KaoriRating, 5 stars1 week ago
It was a very clean, lovely place to stay. The host was very friendly and lived upstairs, so we felt safe and secure during our stay. It was a quiet place on high ground. We were also soothed by the view of the ocean and sunsets from the window. I would love to stay here again when I come back to the Big Island!
Guest favorite
Cottage in Kailua-Kona
4.94 out of 5 average rating, 145 reviews

Foster's Ohia Hale

VictoriaRating, 5 stars1 week ago
This place is so much more beautiful in person! We stayed with a baby and toddler and had everything we needed, including a pack-and-play! My daughter loved spending time with the cat Ollie outside. It helped her feel at home since we have a cat named Oliver. She loved playing in the bath. The house was clean and comfy, with plenty of blankets to keep us warm. Kathryn and Bill were helpful and friendly. I would recommend staying here. It’s by far the most beautiful part of the island, away from the hustle and bustle but close to stores when you need something. We explored the whole island in a week and returned to a relaxing place to sleep.
Superhost
Condo in Waimea
4.87 out of 5 average rating, 69 reviews

Kulalani at Mauna Lani Treasure w/ Beach Club Pass

StarleneRating, 5 stars1 week ago
It was perfect for our family of 6. The highlight was the private beach club. It was so safe and had great snorkeling
Superhost
Home in Holualoa
4.89 out of 5 average rating, 120 reviews

Private Home with Ocean View

AlexRating, 5 stars2 weeks ago
This space was very cool with amazing views of the ocean. The space was very clean. We ran out of propane for the hot water and the host replied immediately and replaced the empty tanks without hesitation, very attentive and reachable. It was a pleasure staying here. I recommend this space to anyone visiting the big island!
Guest favorite
Apartment in Kailua-Kona
4.93 out of 5 average rating, 46 reviews

Hawaii Vacation! Kailua-Kona Getaway

AlyssaRating, 5 stars1 month ago
Warren's condo was a great place to stay for our vacation. The property feels like home and all the other guests were friendly and everyone gathers each night at sunset to watch the sun go down. The unit is well stocked for any day trip needs. Warren's instructions were clear and tips around the unit were listed for care of items. Would 10/10 recommend and would stay there again.
Guest favorite
Apartment in Kailua-Kona
4.91 out of 5 average rating, 141 reviews

Entire Kailua-Kona apartment with OCEAN VIEW

MaryRating, 5 stars2 weeks ago
5-Stars! Absolutely amazing stay! The location is perfect, with breathtaking 180-degree sunset views that made every evening unforgettable.The hosts, Jon and Marilu were incredibly friendly, responsive, and went above and beyond to make sure everything was perfect. Highly recommend to anyone looking for a fantastic getaway!"
Guest favorite
Condo in Waikoloa Village
4.9 out of 5 average rating, 84 reviews

Cooks Landing at Hali'i Kai family vacation condo

JustynaRating, 5 stars1 week ago
It was our dream Destination. Best vacation ever. So nice well organized and kind hosts! Beautiful surrounding. Ideal weather. We did not want to drive a car anywhere as there was so much to do. Very relaxing. Stunning views.

Quick stats about vacation rentals that are family-friendly in Kailua-Kona

  • Total rentals

    900 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    20K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    750 properties have a pool

  • Rentals with dedicated workspaces

    530 properties have a dedicated workspace

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