Holiday rentals with a pool in Kailua

Find and book unique homes with a pool on Airbnb

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Popular amenities for Kailua rentals with a pool

House rentals with a pool

Superhost
Home in Waianae
4.82 out of 5 average rating, 51 reviews

@Marbella Lane - Blissful Studio in Makaha

KayleyRating, 5 stars1 month ago
Beautiful place. In a great location. Supplied with everything needed for our stay. Would definitely book again.
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 favourite
Home in Waianae
4.96 out of 5 average rating, 101 reviews

Family Oceanview Oasis, Hot Tub, 5min to beach

KristinaRating, 5 stars1 week ago
Our family had a wonderful vacation at Emma's place! The location, in the majestic Makaha Valley, was absolutely stunning! Emma's house was spacious, sparkling clean, and perfectly appointed in every way. The home is especially well suited for a family, with plenty of space for everyone. We immedately felt at home and able to unwind after a busy day of adventures around Oahu. By the end of our visit, my kids were ready to move in! Emma's house is the definition of indoor-outdoor living, with a brand new backyard complete with pretty landscaping, an outdoor cooking space with grill, a bar seating six, a comfortable seating area, and a hot tub! Just steps away is a private neighborhood pool great for families. Emma is a fabulous host who is responsive, flexible, and kind. She has thought of every detail to make this a great stay for a family of all ages, and she went out of her way multiple times to accomodate our family's needs. We look forward to returning again soon!
Superhost
Home in Waianae
4.92 out of 5 average rating, 37 reviews

Pakele Oahu by AvantStay | 5 Min to Makaha Beach

MaggieRating, 5 stars2 weeks ago
AvantStay Oahu was amazing throughout my booking process, leading up to my stay and throughout my stay in the rental home. The private community where the rental home is located is absolutely beautiful, and the security guards were very helpful at the gate leading into the gated community. The home was clean, beautiful and offered the accommodations and space that my family needed!
Guest favourite
Home in Makaha Valley
4.91 out of 5 average rating, 111 reviews

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10

AbhayRating, 5 stars1 month ago
Good place, modern, and had a nice view from the yard of the natural beauty. lots of toys to take to the beach and in a nice gated community
Guest favourite
Home in Makaha Valley
4.96 out of 5 average rating, 135 reviews

Kalo Homes - Makaha's Hidden Gem

JeremyRating, 5 stars5 days ago
In one word, AMAZING!!! Everything was exceptional, the only negative thing I can say is that now I have to buy a new bed at home because the bed at this place was incredible. The home was exactly as advertised, the views of the ocean were sensational. There were even extras for the beach such as coolers, snorkels, umbrellas, boogie boards and much more. Friendly and responsive hosts were there for us, even before we needed them. As long as you know where you are staying and are prepared for the drive, this place is a premium slice of heaven in heaven. Thank you for being part of our adventure.
Guest favourite
Home in Kahuku
4.94 out of 5 average rating, 16 reviews

Peek-a-Boo Ocean View

JuliusRating, 5 stars1 month 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 favourite
Home in Kahuku
4.95 out of 5 average rating, 38 reviews

Ocean Pearl

MikeRating, 5 stars1 week ago
This property was ideal for two couples with plenty of living space and yet private bedroom and bathroom facilities. Kitchen was very well equipped and whole property was clean and well maintained. Slight issue with air conditioning was quickly resolved, overall would thoroughly recommend.

Apartment rentals with a pool

Superhost
Apartment in Waikiki
4.93 out of 5 average rating, 99 reviews

Gorgeous Boutique Studio in Central Waikiki~

HannahRating, 5 stars3 weeks ago
Jayden’s place was perfect for a return trip home for my husband and me! The space was incredibly clean and comfortable with an oversized bed and TV, amazing shower, and lanai that overlooks the Ala Wai. It’s always a downer to have to pay for parking but parking on Oahu is a struggle everywhere, so we were grateful that the building at least had paid parking with in/out privileges available, and that everything in Waikiki was walkable from Jayden’s spot. We would definitely book this exact Airbnb again!
Guest favourite
Apartment in Waikiki
4.96 out of 5 average rating, 98 reviews

Waikiki Beachfront Home with Ocean and Beach View

AnnetteRating, 5 stars3 weeks ago
This condo in the Ilikai hotel was perfect for our trip to Oahu. Weili was always very responsive and answered all our questions. The unit was as presented and the view spectacular. I truly enjoyed the balcony. The beach chairs were a great addition and had pockets for our goodies. Trips to beach were easy. The filtered water pitcher was also appreciated and saved buying water. We will certainly return.
Guest favourite
Apartment in Waikiki
4.95 out of 5 average rating, 236 reviews

STUNNING PENTHOUSE - 100FT TO BEACH - LEGAL!!

XinRating, 5 stars6 days ago
Ryan is a great host. Awesome location. not even 3 mins from the beach. Perfect place to stay with a clean space. Everything you need for a comfortable stay.
Superhost
Apartment in Waikiki
4.93 out of 5 average rating, 109 reviews

41FL-Elegant High-FL Studio w/Ocean & City Views

NicolasRating, 5 stars3 weeks ago
I stayed at Jayden’s apartment in Waikiki and had a genuinely great experience. The apartment was clean, well-maintained, and exactly like the photos, maybe even better in person. It was spacious, comfortable, and had everything I needed for a relaxing stay. The highlight for me was the view, it was stunning. The location couldn’t have been better. It’s right in the heart of Waikiki, so getting to the beach, restaurants, shops, and local attractions was super convenient. Despite being close to everything, the apartment felt quiet and private, which was great for winding down after a day out. Jayden was a great host: clear communication, easy check-in, and quick to respond to any questions. Everything was smooth from start to finish. Overall, this was one of the best Airbnb experiences I’ve had!
Guest favourite
Apartment in Kahuku
4.83 out of 5 average rating, 374 reviews

Luxe Loft at Turtle Bay

UzielRating, 5 stars2 weeks ago
A clean, quiet, and private space during our time in Hawaii! Would recommend to anyone staying in North Shore.
Guest favourite
Apartment in Kahuku
4.93 out of 5 average rating, 229 reviews

SEArider TWO at Turtle Bay (1 bedroom / 1 bath)

NicholasRating, 5 stars2 weeks ago
We had a great stay! The home was clean, comfortable, and had all the essentials we needed — fridge, microwave, washer/dryer, and a small AC unit that kept things cool. The host was very responsive and accommodating throughout our stay, which we really appreciated. Overall, a great experience and we’d definitely stay again!
Superhost
Apartment in Waikiki
4.92 out of 5 average rating, 118 reviews

NEW*STUNNING Luxury 1BR Ocean View*Central Waikiki

KariRating, 5 stars3 weeks ago
Mari was very responsive and helped out if we had issues. Location is perfect! Beautiful beach views and large windows with great lighting all day! Many fans and an A/C unit. Balcony was great with the day bed and stools. Kid friendly, and a pack and play was provided. this property was a 5 minute walk to the beach and main drag of restaurants. Parking was a bit tight and you have to call the front desk to be let into the garage. Overall, an amazing stay and we would definitely book again!
Guest favourite
Apartment in Kahuku
4.97 out of 5 average rating, 157 reviews

Honu Hideout at Turtle Bay

LindsayRating, 5 stars3 weeks ago
Amazing place! We stayed with our 8 month old. Joel was so helpful with coordinating anything we needed for her. The place was well equipped for a family. It was a beautiful and peaceful location. Bed and linens were so comfortable. Gorgeous interior. Joel answered all of our questions quickly and made for a stress free vacation. We hope to come back again!

Quick stats about holiday rentals with a pool in Kailua

  • Total rentals

    90 properties

  • Nightly prices starting at

    ₹6,060 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    90 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Hawaii
  4. Honolulu County
  5. Kailua
  6. Rentals with pools