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Kailua Vacation Rentals with pool(170)

170 Results
$1,500 - $1,800
per night
5 - 14 night min stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
5 - 14 night min stay
(29)
$3,675 - $8,050
per week
7 - 14 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 - 14 night min stay
(17)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(25)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
5 night min stay
(70)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
(26)
  • Studio,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 3
(40)
  • Studio,
  • 1 BA,
  • Sleeps 3
3 night min stay
(30)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(31)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
(5)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
(29)
$5,565 - $8,400
per week
7 - 14 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
7 - 14 night min stay
(25)
$5,250 - $6,825
per week
7 - 14 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 - 14 night min stay
(11)
$4,550 - $5,565
per week
7 - 14 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 - 14 night min stay
(18)
  • 7 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 14
1 - 7 night min stay
2 Reviews
$5,600 - $8,365
per week
7 night min stay
  • 8 BR,
  • 4 BA,
  • Sleeps 18
7 night min stay
(7)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 7 night min stay
(15)
  • 6 BR,
  • 3 BA,
  • Sleeps 13
5 - 10 night min stay
(3)
$4,865 - $8,750
per week
7 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
7 night min stay
(7)
$795 - $895
per night
6 - 10 night min stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 18
6 - 10 night min stay
(27)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
(9)
$650 - $850
per night
5 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
5 - 14 night min stay
(3)
$3,465 - $4,900
per week
7 - 14 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 - 14 night min stay
(13)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 17
5 night min stay
(16)
  • 5 BR,
  • 5 BA,
  • Sleeps 14
5 - 10 night min stay
(26)
$7,350 - $13,300
per week
7 - 14 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 - 14 night min stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(13)
$9,100 - $14,000
per week
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 - 14 night min stay
1 Review
  • 5 BR,
  • 4 BA,
  • Sleeps 15
7 night min stay
(24)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night min stay
2 Reviews
$18,340 - $37,100
per week
7 - 14 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
7 - 14 night min stay
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Recent Kailua Reviews

Beautiful Condo Inside and Out! Highly recommended

5 of 5
We stayed at this condo in March. The unit was clearly remodeled recently and was beautiful inside. There was a combination lock on the front door, so there was no need to fumble with keys. The ocean in the back yard was beautiful, and the pool was great (and very large). We had a great time!
  • Submitted: Mar 30, 2015
  • Stayed: Mar 2015

Class Act!

5 of 5
From the beginning of my efforts to plan a Kailua vacation, Tricia was always very accommodating, helpful and truthful. As a result, it should not have been a surprise to see the little oasis that she and Eric have created, but it was. Frankly, the pictures do not do this one bedroom house justice. The residence and grounds were spotless, and my wife and I felt very much at home. It was hard to believe that the place was connected to the main house - and we both enjoyed the quiet and peaceful setting (augmented by a gorgeous koi pond right outside the window)! We cooked most of our meals in the house (kitchen is very well-supplied) and enjoyed most of them on the side patio. The location is only a few blocks from Kailua Beach (which, I may add, is probably the nicest beach I've ever visited!). I would not hesitate to rent this property again.
  • Submitted: Feb 16, 2015
  • Stayed: Feb 2015

Perfect home for multigenerational family reunion

5 of 5
We were impressed with Trinity from start to finish! Don't hesitate to book this property, as it's a great value! Our party of 12 (4 couples with 4 kids under 6), found this home to meet our needs quite well! The space was comfortable, clean, and roomy enough for us to spread out when we desired privacy or to congregate. There was ample dining space both indoors and out! We loved the comfy outdoor furniture and the covered lanai! Walk to the beach was an easy 5 minutes and the beach was pristine: white sand, silky waves and not busy! The kitchen was large and well stocked (even some spices for cooking which is not typical at rentals). The induction stove impressed with it's speed of boiling water, but we were frustrated with lack of non-stick pans and had some challenges in that regard. The beds were adequate but not the most comfortable and we might have slept a little better if we had more pillowcases to use on the decorative pillows. Trinity connected us with a baby gear rental company. With a home that caters to families, it would be helpful if some more of basics were available i.e more beach umbrellas, buckets/toys, perhaps a pack n play or stools for the bathrooms or booster seats. We were impressed however with the amount of cozy beach towels that were provided! The property was also very generous with full size shampoos, conditioners and body wash in each bathroom as well as lots of dish & laundry soaps. Unfortunately, a few days into our stay, we noticed some of the toilets grew a grimy ring around the waterline which worsened throughout our stay. Love the double shower in the Master! This home was close to perfect given multiple needs and desires of our large family. What would have completed our wish list: a hot tub, a bar fridge and more pillows for sleeping. None of these things are deal-breakers. We thoroughly enjoyed our stay and our family reunion. The kids are all asking to go back to the "Hawaii house!"
  • Submitted: Feb 4, 2015
  • Stayed: Jan 2015