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Holiday Rentals in Kailua-Kona, HI

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From
$139
Per Night
1 / 8
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1 Bedroom, 1 Bathroom, Sleeps 4
Pool, Water Views, Internet Access & more
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$1,609
Per Week
1 / 22
4 Bedrooms, 3 Bathrooms, Sleeps 8
Washer, Internet Access, Satellite TV & more
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$6,428
Per Week
1 / 27
4 Bedrooms, 4 Bathrooms, Sleeps 8
Pool, Satellite TV, Internet Access & more
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Also consider
Oceanfront Kona Reef-You'll be only 60' from waves
1 Bedroom, sleeps 4
$114 - $225 / night
WHALE  STUDIO  w VIEW @ KONA HAWAII GUEST HOUSE
Sleeps 6
$99 - $146 / night
Newly Remodeled Oceanfront Luxury Villa
4 Bedrooms, sleeps 10
$1,675 - $3,465 / night
T!he Hukilau - Keauhou Kona Surf and Racquet Club
3 Bedrooms, sleeps 6
$133 / night
From
$118
Per Night
1 / 7
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1 Bedroom, 2 Bathrooms, Sleeps 2
Pool, Water Views, Hot Tub & more
Details Reviews (1) Make Enquiry Similar Properties
4 of 5 stars Reviewed 10 March 2014
Really nice spot. Well equipped, clean, quiet and a beautiful view. Close to lots of activities and amenities. I'd stay here again.
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From
$422
Per Night
1 / 15
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3 Bedrooms, 2 Bathrooms, Sleeps 8
Pool, Satellite TV, Internet Access & more
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$837
Per Night
1 / 23
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7 Bedrooms, 7 Bathrooms, Sleeps 17
Private Pool, Hot Tub, Balcony & more
Details Reviews (15) Make Enquiry Similar Properties
4 of 5 stars Reviewed 26 March 2013
Our extended family (8 adults and 3 children) stayed at O'oma plantation Feb 16-24, 2013. It is a beautiful house with many bedrooms and bathrooms which allowed us all to have...
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$321
Per Night
1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 5
Pool, Grill, Balcony & more
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5 of 5 stars Reviewed 13 November 2014
After going to Kona for almost 20 years and staying in many different condo complexes, the search for the perfect vacation condo is over. Beautiful views from a wide, spacious...
5 of 5 stars Reviewed 16 July 2014
Our 7 day stay at this apartment recently exceeded our expectations. This particular apartment (#314) is as close as one could get to the sea, with 180 degree uninterrupted...
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From
$321
Per Night
1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 2
Pool, Internet Access, Hot Tub & more
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5 of 5 stars Reviewed 12 July 2014
I am not much for reviews, but this was a fantastic place. Very comfortable. Reasonably priced for what you get. There is a lot to do in the area, however, you probably won't do...
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From
$251
Per Night
1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Internet Access, Air Conditioning & more
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$173
Per Night
1 / 23
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4 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
Satellite TV, Water Views, Balcony & more
Details Reviews (8) Make Enquiry Similar Properties
5 of 5 stars Reviewed 5 November 2014
This was the perfect vacation home for our family. The house has every amenity you could imagine from a BBQ grill and fully stocked pantry of food to enough snorkel gear and...
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
$526
Per Night
1 / 23
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3 Bedrooms, 3 Bathrooms, Sleeps 6
Private Pool, Grill, Satellite TV & more
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From
$1,733
Per Night
1 / 15
3 Bedrooms, 4 Bathrooms, Sleeps 6
Washer, Internet Access, Dishwasher & more
Details Reviews (3) Make Enquiry Similar Properties
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
$456
Per Night
1 / 24
4 Bedrooms, 3 Bathrooms, Sleeps 10
Wi-Fi, Balcony, Dryer & more
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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
$144
Per Night
1 / 25
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Internet Access, Satellite TV & more
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3 of 5 stars Reviewed 25 March 2014
We really enjoyed our stay. The unit is spacious but a little cramped for 6 people. Awesome sunsets. Neighbours friendly. A great place for a family.
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From
$144
Per Night
1 / 17
2 Bedrooms, 2 Bathrooms, Sleeps 4
Pool, Hot Tub, Washer & more
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5 of 5 stars Reviewed 15 July 2014
We (My husband , my adult daughter and myself) stayed here for 5 nights. The villa looks just like the photos. The villa is clean, beautifully decorated and very comfortable. We...
5 of 5 stars Reviewed 19 May 2014
This was our first vacation on the big island and after much research on where to stay we picked the perfect spot. The condo is equipped with everything that you will need and...
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From
$116
Per Night
1 / 9
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1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Dryer, Balcony, Internet Access & more
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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
$1,155
Per Night
1 / 13
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3 Bedrooms, 3 Bathrooms, Sleeps 8
Internet Access, Grill, Dishwasher & more
Details Reviews (5) Make Enquiry Similar Properties
From
$127
Per Night
1 / 12
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2 Bedrooms, 1 Bathroom, Sleeps 3
Pool, Satellite TV
Details Reviews (29) Make Enquiry Similar Properties
2 of 5 stars Reviewed 15 June 2014
Looking at the reviews on this site and others, Kona Magic Sands #109 sounds pretty hit or miss. We stayed at Kona Magic Sands unit #109 in March 2014, and unfortunately our stay...
2 of 5 stars Reviewed 1 October 2012
Location of Magic Sands 109 is perfect for... ** being 30' from the waves of the Pacific pounding on the seawall ** being next to the White Sands beach...
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From
$139
Per Night
1 / 13
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2 Bedrooms, 1 Bathroom, Sleeps 4
Shared Outdoor Pool (Heated), Safe, Satellite TV & more
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5 of 5 stars Reviewed 5 August 2014
Physical setting- House location is convenient, easily driven to and located at an altitude of 1,000 feet up from the coast which allows for cooler temps and a lovely breeze...
5 of 5 stars Reviewed 3 November 2013
Having spent a week in the two-bedroom unit in January, this time we stayed in the studio. Although it is just one room it is spacious, comfortable and full of light. The outside...
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From
$347
Per Night
1 / 14
3 Bedrooms, 2 Bathrooms, Sleeps 8
Dryer, Water Views, Washer & more
Details Reviews (2) Make Enquiry Similar Properties
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
$116
Per Night
1 / 13
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1 Bedroom, 1 Bathroom, Sleeps 2
Grill, Satellite TV, Internet Access & more
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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
$144
Per Night
1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Pool, Garden, Internet Access & more
Details Reviews (2) Make Enquiry Similar Properties
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
$496
Per Night
1 / 17
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4 Bedrooms, 3 Bathrooms, Sleeps 8
Internet Access, Waterfront
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From
$2,195
Per Night
1 / 19
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4 Bedrooms, 5 Bathrooms, Sleeps 10
Private Outdoor Pool (Heated), Dishwasher, Garden & more
Details Reviews (1) Make Enquiry Similar Properties
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
$635
Per Night
1 / 15
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6 Bedrooms, 6 Bathrooms, Sleeps 18
Bookings
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5 of 5 stars Reviewed 20 October 2014
We came to Hawaii with 16 people, including 6 kids, and this house was perfect for us. It is laid out sort of like a little hotel with a common lanai & kitchen (each room had...
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
$99
Per Night
1 / 52
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Studio, 1 Bathroom, Sleeps 4
Bookings
Grill, Internet Access, Washer & more
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From
$172
Per Night
1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Pool, Satellite TV, Garden & more
Details Reviews (12) Make Enquiry Similar Properties
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
$780
Per Night
1 / 39
5 Bedrooms, 4 Bathrooms, Sleeps 9
Private Outdoor Pool (Unheated), Washer, Water Views & more
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5 of 5 stars Reviewed 11 November 2014
We stayed here for ironman week, and rented this property from Kona fun travel. The property was great and the view was incredible. There was virtually everything we could want in...
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From
$404
Per Night
1 / 15
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3 Bedrooms, 3 Bathrooms, Sleeps 6
Private Pool, Satellite TV, Air Conditioning & more
Details Reviews (3) Make Enquiry Similar Properties
5 of 5 stars Reviewed 20 October 2014
Ironman competitor and supporters rented this well appointed,immaculate vacation house.The pool and gardens were spacious and private.Those amazing sunsets ...memorable.We so much...
5 of 5 stars Reviewed 15 June 2014
We couldn't have asked for a nicer place to stay. Super clean, beautifuly decorated, beatiful yard and pool. It was everything that the pictures represented. We stayed here for...
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From
$576
Per Night
1 / 36
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Satellite TV, Grill & more
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From
$114
Per Night
1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Pool, Hot Tub, Satellite TV & more
Details Reviews (7) Make Enquiry Similar Properties
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
$519
Per Night
1 / 39
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6 Bedrooms, 5 Bathrooms, Sleeps 12
Booking
Private Outdoor Pool (Unheated), Balcony & more
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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
$127
Per Night
1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Pool, Washer, Grill & more
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3 of 5 stars Reviewed 10 April 2014
This condo is totally adequate as a a low cost vacation rental. The location is really good, you can walk all over Kailua town. It is rather loud as a night has moved in next door...
2 of 5 stars Reviewed 30 June 2011
While this condo is centrally located and contains the basic necessities for a couple visiting Kailua-Kona, be careful what you're getting yourself into and don't expect a refund...
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From
$3,314
Per Night
1 / 25
15 Bedrooms, 11 Bathrooms, Sleeps 34
Pool, Private Beach, Private Fishing Lake/River & more
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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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From
$375
Per Night
1 / 10
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4 Bedrooms, 4 Bathrooms, Sleeps 10
Internet Access
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2 of 5 stars Reviewed 24 September 2014
We rented this house for our family trip to big island hawaii. The house is in a great location, just a couple of blocks from two nice beaches and app 10-15 by car to town...
5 of 5 stars Reviewed 25 February 2014
This is a lovely house, with large bedrooms, an amazingly well equipped kitchen and excellent outdoor space. Everything you could possibly need for a great vacation is close by...
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From
$433
Per Night
1 / 29
5 Bedrooms, 3 Bathrooms, Sleeps 10
Private Outdoor Pool (Unheated), Housekeeping Optional & more
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5 of 5 stars Reviewed 18 August 2014
We stayed in this fantastic home for three week this time. The house is located in a quiet neighborhood up the slopes of the Hualalai Volcano with the most commanding view of the...
5 of 5 stars Reviewed 16 July 2014
We just finished an amazing week at Huck's Tropical Hideaway. We would love to go back tomorrow! This rental was exactly what we hoped for. It has 5 bedrooms and accommodated...
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From
$924
Per Night
1 / 13
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3 Bedrooms, 4 Bathrooms, Sleeps 8
Pool, Grill, Internet Access & more
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From
$110
Per Night
1 / 10
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Pool, Satellite TV, Air Conditioning & more
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4 of 5 stars Reviewed 24 October 2014
Chris was quick with responses and helpful advice as well as supplying a clean, well located condo. He has given the use of all conveniences necessary for a satisfying stay...
5 of 5 stars Reviewed 1 September 2014
I can't say enough positive about this condo. The condo itself is fully equipped and spotless. Meals on the lanai were wonderful, the grounds are so beautiful. So nice having...
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$173
Per Night
1 / 27
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2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Shared Outdoor Pool (Heated), Internet Access & more
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4 of 5 stars Reviewed 23 March 2014
My husband and I really enjoyed our island vacation from this eloquent location. The neighbourhood is pleasant, and the estate is amazing! We ate citrus fruit from the mature...
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$110
Per Night
1 / 8
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Satellite TV, Internet Access, Grill & more
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2 of 5 stars Reviewed 21 September 2014
We were so looking forward to our stay here,judging by the pictures and reviews a wonderful place to stay! Let's go with the pros first: close to airport,away from traffic and...
5 of 5 stars Reviewed 24 August 2013
I stayed with Caryl for almost a month, originally I had plans to split my vacation by staying in two different ohanas in different parts of Kona, but I found that I really liked...
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Suitability

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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.