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Holiday Rentals in Hawaii/Kailua-Kona

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 705 Rentals in Kailua-Kona
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From
$117
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Grill, Other outdoor space, Public pool & more
17 photos Details
Reviews (20) Make Enquiry
From
$134
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
Fitness Room, Public pool, Pool & more
17 photos Details
Reviews (1) Make Enquiry
From
$95
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Internet, Water Views, Suitable for children & more
14 photos Details
Reviews (2) Make Enquiry
Also consider
Kona-2 Bedroom-big Ocean View (Wow)
2 Bedrooms, sleeps 4
$124 - $170 / night
A Taste of Hawaiian Luxury  with an Ocean View
2 Bedrooms, sleeps 6
$159 - $254 / night
Summer in Kona What a Dream, with a View - $85/nt
1 Bedroom, sleeps 4
$90 - $143 / night
Luxury with Panoramic Ocean Views on Golf Course
2 Bedrooms, sleeps 4
$133 - $159 / night
From
$105
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Internet, Other outdoor space, Water Views & more
33 photos Details
Reviews (15) Make Enquiry
From
$127
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Housekeeping Optional, Water Views, Grill & more
20 photos Details
Reviews (1) Make Enquiry
From
$423
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Wheelchair access, Water Views, Elder access & more
18 photos Details
Reviews (4) Make Enquiry
From
$154
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Shared Outdoor Pool (Heated), Wheelchair access & more
23 photos Details
Reviews (1) Make Enquiry
From
$199
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Air Conditioning, Internet, Staffed Property & more
24 photos Details
Reviews (3) Make Enquiry
Get the List
From
$345
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
Internet
10 photos Details
Reviews (6) Make Enquiry
From
$158
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Other outdoor space, Public pool, Hot Tub & more
25 photos Details
Reviews (11) Make Enquiry
From
$105
Per Night
Studio, 1 Bathroom, Sleeps 3
Garden, Pool, Other outdoor space & more
36 photos Details
Reviews (2) Make Enquiry
From
$186
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Elder access, Water Views & more
19 photos Details
Reviews (1) Make Enquiry
From
$126
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Hot Tub, Internet, Housekeeping Optional & more
24 photos Details
Reviews (11) Make Enquiry
From
$159
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
Parking, Housekeeping Optional, Fitness Room & more
27 photos Details
Reviews (1) Make Enquiry
From
$101
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Garden, Grill, Suitable for children & more
8 photos Details
Reviews (6) Make Enquiry
From
$148
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Grill, Canoe, Other outdoor space & more
19 photos Details
Reviews (2) Make Enquiry
From
$151
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Washer/Dryer, Water Views, Other outdoor space & more
20 photos Details
Reviews (1) Make Enquiry
From
$207
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Public pool, Pool, Private Pool & more
15 photos Details
Reviews (3) Make Enquiry
From
$145
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Suitable for children, Public pool, Water Views & more
19 photos Details
Reviews (4) Make Enquiry
From
$106
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Parking, Washer/Dryer, Internet & more
9 photos Details
Reviews (1) Make Enquiry
From
$635
Per Night
6 Bedrooms, 4 Bathrooms, Sleeps 16
Parking, Children's Pool & more
17 photos Details
Reviews (6) Make Enquiry
From
$105
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Water Views, Private pool, Air Conditioning & more
16 photos Details
Reviews (2) Make Enquiry
From
$147
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Internet, Suitable for children & more
29 photos Details
Reviews (7) Make Enquiry
From
$133
Per Night
Studio, 1 Bathroom, Sleeps 4
Internet, Parking, Other outdoor space & more
16 photos Details
Reviews (9) Make Enquiry
From
$122
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Housekeeping Optional, Public pool & more
24 photos Details
Reviews (5) Make Enquiry
From
$104
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Internet, Suitable for children, Grill & more
12 photos Details
Reviews (2) Make Enquiry
From
$101
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Other outdoor space, Washer/Dryer, Public pool & more
16 photos Details
Reviews (1) Make Enquiry
From
$286
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Hot Tub, Parking, Air Conditioning & more
3 photos Details
Reviews (1) Make Enquiry
From
$148
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Pool, Public pool, Water Views & more
10 photos Details
Reviews (15) Make Enquiry
From
$116
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Hot Tub, Public pool, Pool & more
23 photos Details
Reviews (1) Make Enquiry
From
$143
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Parking, Washer/Dryer, Grill & more
24 photos Details
Reviews (6) Make Enquiry
From
$223
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Grill, Parking & more
21 photos Details
Reviews (3) Make Enquiry
From
$138
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
Other outdoor space, Parking, Pool & more
8 photos Details
Reviews (1) Make Enquiry
From
$518
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
Internet, Parking, Other outdoor space & more
10 photos Details
Reviews (18) Make Enquiry
From
$138
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Wheelchair access, Public pool, Hot Tub & more
15 photos Details
Reviews (1) Make Enquiry
From
$148
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Waterfront, Air Conditioning, Boat Available & more
9 photos Details
Reviews (15) Make Enquiry
From
$95
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Garden, Parking, Other outdoor space & more
35 photos Details
Reviews (1) Make Enquiry
From
$175
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Grill, Water Views, Hot Tub & more
13 photos Details
Reviews (10) Make Enquiry
From
$186
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Fitness Room, Grill, Internet
18 photos Details
Reviews (15) Make Enquiry
From
$186
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Other outdoor space, Grill, Hot Tub & more
5 photos Details
Reviews (27) Make Enquiry
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Book Online(470)
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Suitability

  • Wheelchair access (64)
  • Elder access (179)
  • Suitable for children (237)
  • Pet friendly (6)
  • Smoking allowed (0)

Amenities

  • Internet (563)
  • All pools (534)
  • Public pool (458)
  • Other outdoor space (408)
  • Grill (370)
  • View all amenities
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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.