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Holiday Rentals in Kailua-Kona, HI

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All 744 Rentals in Kailua-Kona
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From
$103
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Pool, Dishwasher, Balcony & more
7 photos Details Reviews (4) Make Enquiry
From
$170
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Pool, Internet Access, Balcony & more
8 photos Details Reviews (9) Make Enquiry
From
$5,605
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 8
Air Conditioning, Washer, Internet Access & more
23 photos Details Reviews (1) Make Enquiry
Also consider
Beautiful Pool Home!~This Home Has It ALL!
4 Bedrooms, sleeps 8
$319 - $376 / night
Caryl's Ohana OPEN FALL Special $85/night Kona
1 Bedroom, sleeps 2
$86 - $143 / night
Kona Islander Inn 1 BDRM #208
1 Bedroom, sleeps 2
$148 - $159 / night
New 60" HDTV - BEAUTIFUL, LOVELY, LOCATION Last Minute Specials - Email Us Now FOR Your Special Rate
1 Bedroom, sleeps 4
$102 - $172 / night
From
$172
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Pool, Hot Tub, Grill & more
11 photos Details Reviews (3) Make Enquiry
From
$793
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 4
Pool, Washer, Dryer & more
13 photos Details Reviews (6) Make Enquiry
From
$109
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Pool, Satellite TV, Internet Access
11 photos Details Reviews (7) Make Enquiry
From
$113
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Pool, Hot Tub, Satellite TV & more
12 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 20 September 2014
My husband and I spent a couple of nights in Kailua-Kona and had some things planned right in town, so we wanted a place that was close by. We chose this place for the location...
5 of 5 stars Reviewed 7 August 2014
Just returned from a 3 night stay at #326 Kona Islander and had another great time. The bonus of the unit is the newly remodeled kitchenette with FULL-SIZED refrigerator. The...
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From
$149
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Pool, Satellite TV, Grill & more
11 photos Details Reviews (13) Make Enquiry
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From
$113
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Pool, Internet Access, Dishwasher & more
12 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 3 September 2014
My booking for this unit was done through FlipKey.com I never used this site before and was a little afraid...but how will you know unless you try. The reviews for this place did...
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From
$452
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Outdoor Pool, Wi-Fi, Balcony & more
24 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 22 July 2014
When I first contacted Sheila and Eddie, they provided all the necessary information to deal with the logistics of staying in the house. They settled any qualms I had in relation...
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From
$137
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Pool, Water Views, Balcony & more
21 photos Details Reviews (7) Make Enquiry
From
$217
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Satellite TV, Dishwasher
11 photos Details Reviews (11) Make Enquiry
From
$214
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Pool, Satellite TV, Internet Access
14 photos Details Reviews (14) Make Enquiry
From
$542
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Private Pool, Grill, Satellite TV & more
23 photos Details Reviews (1) Make Enquiry
From
$1,144
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Grill, Dishwasher, Satellite TV & more
11 photos Details Reviews (5) Make Enquiry
From
$1,487
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
Air Conditioning, Housekeeping Optional & more
15 photos Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 8 November 2010
My family of five from Toronto stayed at Ida's villa this year. Having never previously stayed at a villa, we had reservations. We should not have worried. The villa was beautiful...
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From
$114
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Grill, Satellite TV, Internet Access & more
14 photos Details Reviews (7) Make Enquiry
4 of 5 stars Reviewed 31 March 2014
The cottage is very quaint, and truly what we were looking for for this stay in Hawaii. Fresh air, flora galore,clear starry skies at night, and the sound of roosters when you...
5 of 5 stars Reviewed 2 March 2014
The cottage was clean and well stocked. It was a little chilly for me, but the owners said that January and February are the coolest months there. My husband loved the temperature.
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From
$149
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Shared Outdoor Pool (Heated), Grill, Dryer & more
15 photos Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 30 January 2013
The house is located 1000ft above the Kona coast in a green residential area, 10 minutes drive from both the airport and Kailua-Kona. The views are stunning, especially on sunset...
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From
$456
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Sauna, Air Conditioning, Garden & more
18 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 13 February 2014
This property is gorgeous! We stayed for ten days in January, 2014 and we just didn't want to leave. The ocean view in January was gorgeous and we were treated to the sight of...
5 of 5 stars Reviewed 3 September 2013
Loved sitting on the lanai watching all the activity on the ocean... dolphins, canoe races, boats... Kitchen is very well outfitted. We had all meals on the lanai; great view...
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From
$172
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
Satellite TV, Water Views, Balcony & more
20 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 7 March 2013
It was my husband and I's first time in Hawaii and this place makes me want to come back again and again. This place has everything you could possibly need and it is truly a home...
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From
$143
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Pool, Internet Access, Garden & more
11 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 25 February 2014
Our vacation rental was literally Kona Heaven. Very quiet neighbourhood 600 feet up the mountain from the airport with an unrestricted view of the ocean and great sunsets. Perfect...
5 of 5 stars Reviewed 30 October 2013
This property has the main house and two totally separate units. We stayed in the bigger unit that didn't have a kitchen, but we didn't need it. It's spacious, comfortable and...
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From
$229
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Satellite TV, Dishwasher & more
27 photos Details Reviews (23) Make Enquiry
5 of 5 stars Reviewed 20 September 2014
You just can't beat the location. RIGHT over the water on the 3rd floor. Its the view I've always always always wanted when staying near the beach. After all, what's the point of...
5 of 5 stars Reviewed 15 July 2014
Wow, what a vacation! This condo was excellent and close to everything. Easy trips to spectacular beaches and awesome snorkeling spots. Excellent restaurants are within a...
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From
$170
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Pool, Satellite TV, Garden & more
21 photos Details Reviews (12) Make Enquiry
3 of 5 stars Reviewed 29 March 2014
this unit does not have full kitchen you cook on hot plate and have toaster oven plenty of bugs and geckos has single bed if you sleep four they will sleep on floor and bugs...
4 of 5 stars Reviewed 5 February 2014
We stayed her for 3 nights as part of our honeymoon trip around Hawaii. We ate out every lunch and night so only used the kitchen for breakfast which it was able to accommodate...
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From
$1,030
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
Pool, Internet Access, Grill & more
13 photos Details Reviews (1) Make Enquiry
From
$519
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Internet Access, Waterfront
17 photos Details Reviews (19) Make Enquiry
From
$114
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Dryer, Balcony, Internet Access & more
9 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 15 May 2014
No words to describe our Holliday rental. A few...stunning, welcoming, clean, etc, etc. Would definitely stay through FlipKey again.
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From
$571
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Satellite TV, Grill & more
36 photos Details Reviews (4) Make Enquiry
From
$296
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
Private Outdoor Pool (Heated), Garden, Satellite TV & more
27 photos Details Reviews (5) Make Enquiry
5 of 5 stars Reviewed 29 June 2012
My husband and I have traveled to Europe and all over the United States and always prefer a home or condo rental to a hotel. By far, this home exceeded all of our expectations...
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From
$343
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Garden, Satellite TV, Balcony & more
14 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 13 November 2012
I took my parents, my son and daughter and my son-in-law to Hawaii in 2006 and stayed in the Hula Hut. It was excellent! Clean, spacious, great private pool and views, located...
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From
$205
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Pool, Grill, Balcony & more
43 photos Details Reviews (15) Make Enquiry
5 of 5 stars Reviewed 22 August 2014
Wonderful location, very clean and incredible spacious condo! The rooms a much larger than the photos suggested! It was very easy to book and Anita was professional and quick in...
5 of 5 stars Reviewed 1 August 2014
the property had everything we needed. we felt like we were at home. The facilities( pool,gym) were a great added bonus.
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From
$98
Per Night
Studio, 1 Bathroom, Sleeps 4
Bookings
Grill, Internet Access, Washer & more
52 photos Details Reviews (1) Make Enquiry
From
$514
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
Private Outdoor Pool (Unheated), Balcony & more
39 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 3 August 2014
Had a wonderful Hawaiian stay. This great tropical vacation home is spacious and clean. It was so nice to have a kitchen supplied with all you need to cook; pots, pans, utensils...
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From
$212
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Pool, Internet Access, Waterfront & more
15 photos Details Reviews (18) Make Enquiry
5 of 5 stars Reviewed 22 September 2014
We spent a week at this location and was not disappointed in the least with the location and the view. Everything was as advertised. Initially, I was attracted by the prospect...
5 of 5 stars Reviewed 8 July 2014
This Condo 4207 was clean and beautiful. Great location "Ocean Front" Everything we were hoping for to celebrate our Daughter's graduation from High School and Entry to the...
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From
$113
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
12 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 15 August 2014
Good size place (living room, kitchen) good value, appreciated the wifi, needs a few repairs, ac would be nice, has a nice lanai,
4 of 5 stars Reviewed 24 July 2014
First off, it was the perfect place for my family to stay, while we prepared for our son's big wedding day! We stayed for 5 days, making sure we got everything covered. From...
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From
$2,173
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 10
Private Outdoor Pool (Heated), Dishwasher, Garden & more
20 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 12 July 2013
This was a once in a lifetime holiday and far removed from our usual exploring trips. This magnificent home is not for those who are counting their pennies as it is by far and...
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From
$86
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
Internet Access, Housekeeping Optional, Satellite TV
17 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 14 July 2014
Great place with great hosts! Easy booking process. We were traveling on a budget and this rental exceeded our expectations. Even though the studio is adjacent to the main...
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From
$629
Per Night
6 Bedrooms, 6 Bathrooms, Sleeps 18
Bookings
15 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 10 January 2014
Stayed here with a team that was going to do the Queen Lil'l canoe race and had a fantastic time. Even before we arrived, the owners of the property was incredibly helpful to...
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From
$136
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Pool, Air Conditioning, Garden & more
23 photos Details Reviews (1) Make Enquiry
From
$182
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Shared Outdoor Pool (Heated), Dryer, Washer & more
69 photos Details Reviews (10) Make Enquiry
5 of 5 stars Reviewed 7 September 2014
The Good: Furnished, in ways, more richly than our own abode, this well-equipped house feels more like home than a rental. Nothing is rental-cheesy - there's even a pair of...
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From
$3,282
Per Night
15 Bedrooms, 11 Bathrooms, Sleeps 34
Pool, Private Beach, Private Fishing Lake/River & more
25 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 October 2013
We just returned from our second trip to the Big Island of Hawaii and had a wonderful stay at the Kona Beach Bungalows. We were travelling with several others, so rented three of...
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Suitability

  • Wheelchair access (70)
  • Elder access (176)
  • Suitable for children (236)
  • Pet friendly (3)
  • Smoking allowed (0)

Amenities

  • Internet (613)
  • All pools (572)
  • Public pool (476)
  • Other outdoor space (415)
  • Grill (404)
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Kailua Kona Vacation Rentals

Whether you are planning on surfing, diving, or just laying out in the sun, Kailua Kona is an amazing destination full of pristine beaches and local culture. A Kailua Kona vacation is sure to be unforgettable, but why not make it even more special by staying in your very own vacation rental instead of a hotel? There are a variety of Kailua Kona vacation rentals available, from a cozy one bedroom condo to a spacious rental house that can sleep the entire family. There is sure to be the perfect rental home to suit your needs and your style, so check out our great deals on Kailua Kona vacation rentals for your next trip.

A Kailua Kona Vacation

Kailua Kona is an ocean lover's paradise, full of beautiful sights and opportunities to explore. Enjoy the breathtaking view at Mauna Kea Summit and all that you can see from 13,796 feet high. To check out the sights underneath the water as well, take a dive with Big Island Divers and you will not believe your eyes. Surfer Bear Hawaii Surf Lessons can teach you and the entire family to catch some waves, or lay out in the sun at Manini'owali Beach and let your troubles melt away. Finish the day off with some delectable Hawaiian style drinks at Don's Mai Tai Bar and you may never want to leave. No matter how you spend your Kailua Kona vacation, you can rest assured knowing with vacation rentals you have chosen the most comfortable and convenient option for you and your family. A vacation rental offers you all the benefits of having a home away from home, and did you know it can even save you money?

Money Saving Vacation Rentals

Hotels can be expensive, especially when traveling with a large group. Luckily, with vacation rentals there is no need to worry about booking multiple hotel rooms when you can simply rent a vacation house that can fit your entire group. If you plan on staying a while, many Kailua Kona rental homes also offer a discounted rate on extended stays, so you can enjoy your vacation for longer while saving money. Rental homes offer so many benefits to you, your family, and your wallet, that it is a truly a win-win situation for your next trip to Kailua Kona.