Holiday rentals near Kailua Pier
We found 2,600 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals within easy reach of Kailua Pier that provide the perfect home base for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you expect for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Kailua Pier
Showing deals for:25 Jul - 1 Aug
Image gallery for Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.
1010 out of 10 rating
Exceptional
(45 reviews)
Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.
Kailua-Kona, HI
8% off
Price is NZ$10,010
NZ$10,010
NZ$1,430 per night
includes taxes & fees
Image gallery for Wyndham Kona Hawaiian - 2BR/2BA Deluxe Unit
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Wyndham Kona Hawaiian - 2BR/2BA Deluxe Unit
Kailua-Kona, HI
8% off
Price is NZ$6,986
NZ$6,986
NZ$998 per night
includes taxes & fees
Image gallery for Take advantage of our SUMMER SPECIAL DISOUNTS on this beautiful property
1010 out of 10 rating
Exceptional
(169 reviews)
Take advantage of our SUMMER SPECIAL DISOUNTS on this beautiful property
Kailua-Kona, HI
7% off
Price is NZ$3,704
NZ$3,704
NZ$529 per night
includes taxes & fees
Image gallery for Newly renovated, ocean view, steps from downtown
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Newly renovated, ocean view, steps from downtown
Kailua-Kona, HI
7% off
Price is NZ$4,217
NZ$4,217
NZ$602 per night
includes taxes & fees
Image gallery for Private Kona Villa, Pano Ocean Views! Walk to Magic Sands, Private Pool & Spa
9.89.8 out of 10 rating
Exceptional
(81 reviews)
Private Kona Villa, Pano Ocean Views! Walk to Magic Sands, Private Pool & Spa
Kailua-Kona, HI
7% off
Price is NZ$10,889
NZ$10,889
NZ$1,556 per night
includes taxes & fees
Image gallery for Kona Oceanfront complex I Updated I AC I Heated Pool I Best Location
9.69.6 out of 10 rating
Exceptional
(40 reviews)
Kona Oceanfront complex I Updated I AC I Heated Pool I Best Location
Kailua-Kona, HI
7% off
Price is NZ$2,828
NZ$2,828
NZ$404 per night
includes taxes & fees
Image gallery for One Bedroom, First Floor, Fully Furnished Condo
9.69.6 out of 10 rating
Exceptional
(145 reviews)
One Bedroom, First Floor, Fully Furnished Condo
Kailua-Kona, HI
7% off
Price is NZ$2,426
NZ$2,426
NZ$347 per night
includes taxes & fees
Image gallery for Hawaiian paradise at Kona Isle
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Hawaiian paradise at Kona Isle
Kailua-Kona, HI
7% off
Price is NZ$3,186
NZ$3,186
NZ$455 per night
includes taxes & fees
Image gallery for Private Home with Pool in Secure Gated Community on Kona Country Club Fairway
9.09.0 out of 10 rating
Wonderful
(69 reviews)
Private Home with Pool in Secure Gated Community on Kona Country Club Fairway
Kailua-Kona, HI
6% off
Price is NZ$9,530
NZ$9,530
NZ$1,361 per night
includes taxes & fees
Image gallery for ENJOY RESORT LIVING 2 Beds/2 Baths Ocean Views
9.89.8 out of 10 rating
Exceptional
(20 reviews)
ENJOY RESORT LIVING 2 Beds/2 Baths Ocean Views
Kailua-Kona, HI
7% off
Price is NZ$4,373
NZ$4,373
NZ$625 per night
includes taxes & fees
Image gallery for A Beautiful View Beach House at Kahalu'u Bay! Snorkeling & Surfing ~ Steps Away!
1010 out of 10 rating
Exceptional
(13 reviews)
A Beautiful View Beach House at Kahalu'u Bay! Snorkeling & Surfing ~ Steps Away!
Kailua-Kona, HI
8% off
Price is NZ$7,923
NZ$7,923
NZ$1,132 per night
includes taxes & fees
Image gallery for Gorgeous Ocean View, Comfortable Cool Elevation, Close to Everything!
9.89.8 out of 10 rating
Exceptional
(47 reviews)
Gorgeous Ocean View, Comfortable Cool Elevation, Close to Everything!
Kailua-Kona, HI
7% off
Price is NZ$8,627
NZ$8,627
NZ$1,232 per night
includes taxes & fees
Image gallery for Kona coffee farm retreat, with full ocean views near Kailua Kona!
1010 out of 10 rating
Exceptional
(28 reviews)
Kona coffee farm retreat, with full ocean views near Kailua Kona!
Honalo, HI
11% off
Price is NZ$7,104
NZ$7,104
NZ$1,015 per night
includes taxes & fees
Image gallery for Awesome Ocean Views From Ground Floor, A/C, Recent Remodel, WI-FI
9.89.8 out of 10 rating
Exceptional
(64 reviews)
Awesome Ocean Views From Ground Floor, A/C, Recent Remodel, WI-FI
Kailua-Kona, HI
7% off
Price is NZ$2,978
NZ$2,978
NZ$425 per night
includes taxes & fees
Image gallery for "Hale Maluhia" - Cottage with expansive ocean views in central Kailua Kona.
1010 out of 10 rating
Exceptional
(100 reviews)
"Hale Maluhia" - Cottage with expansive ocean views in central Kailua Kona.
Kailua-Kona, HI
7% off
Price is NZ$3,084
NZ$3,084
NZ$441 per night
includes taxes & fees
Image gallery for Spectacular Oceanfront Condo With Beautiful Sunsets
9.69.6 out of 10 rating
Exceptional
(115 reviews)
Spectacular Oceanfront Condo With Beautiful Sunsets
Kailua-Kona, HI
7% off
Price is NZ$4,469
NZ$4,469
NZ$638 per night
includes taxes & fees
Image gallery for Incredible Absolute Oceanfront Penthouse 🏝️ The Living Room Faces The Ocean! 🐠 KSR 1-305
9.29.2 out of 10 rating
Wonderful
(52 reviews)
Incredible Absolute Oceanfront Penthouse 🏝️ The Living Room Faces The Ocean! 🐠 KSR 1-305
Kailua-Kona, HI
5% off
Price is NZ$8,039
NZ$8,039
NZ$1,148 per night
includes taxes & fees
Image gallery for 1 bdrm peakaboo ocean view walk to Turtle Beach, Alii Garden Mkt,Kona Village-1D
9.49.4 out of 10 rating
Exceptional
(6 reviews)
1 bdrm peakaboo ocean view walk to Turtle Beach, Alii Garden Mkt,Kona Village-1D
Kailua-Kona, HI
7% off
Price is NZ$2,368
NZ$2,368
NZ$338 per night
includes taxes & fees
Image gallery for Newly Renovated Ocean View Condo 🐳 Stunning Views From The Lanai! 🌅 Kona Reef E-22
9.89.8 out of 10 rating
Exceptional
(106 reviews)
Newly Renovated Ocean View Condo 🐳 Stunning Views From The Lanai! 🌅 Kona Reef E-22
Kailua-Kona, HI
5% off
Price is NZ$3,705
NZ$3,705
NZ$529 per night
includes taxes & fees
Image gallery for Gated Community Located Within Walking Distance To The Beach
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Gated Community Located Within Walking Distance To The Beach
Kailua-Kona, HI
7% off
Price is NZ$5,270
NZ$5,270
NZ$753 per night
includes taxes & fees
Image gallery for 2.7 Acres of Exceptional, Secluded Retreat - Close to Beach & Shopping!
1010 out of 10 rating
Exceptional
(82 reviews)
2.7 Acres of Exceptional, Secluded Retreat - Close to Beach & Shopping!
Kailua-Kona, HI
7% off
Price is NZ$6,928
NZ$6,928
NZ$990 per night
includes taxes & fees
Image gallery for Wow! Awesome Kailua Ocean View, Pool, and Convenient Too!
1010 out of 10 rating
Exceptional
(106 reviews)
Wow! Awesome Kailua Ocean View, Pool, and Convenient Too!
Holualoa, HI
7% off
Price is NZ$4,462
NZ$4,462
NZ$637 per night
includes taxes & fees
Image gallery for FLASH SALE 🏝 Amazing Ocean Views Over Lush Golf Course! 🌅 - Country Club Villas 226 🩴
9.49.4 out of 10 rating
Exceptional
(42 reviews)
FLASH SALE 🏝 Amazing Ocean Views Over Lush Golf Course! 🌅 - Country Club Villas 226 🩴
Kailua-Kona, HI
5% off
Price is NZ$4,162
NZ$4,162
NZ$595 per night
includes taxes & fees
Image gallery for KONA ALII 306 OCEANFRONT CONDO, 1 BDRM 2 BTH, AMAZING VIEW IN THE HEART OF KONA
9.89.8 out of 10 rating
Exceptional
(128 reviews)
KONA ALII 306 OCEANFRONT CONDO, 1 BDRM 2 BTH, AMAZING VIEW IN THE HEART OF KONA
Kailua-Kona, HI
7% off
Price is NZ$3,366
NZ$3,366
NZ$481 per night
includes taxes & fees
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Find the best place to stay - Kailua Pier
Dolphin House Oceanfront Estate
Sleeps 11 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
Ohana Retreat - The Real Hawaiian Experience
Sleeps 18 · 8 bedrooms · 8 bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Exclusive area. SW Infinity Pool, Putting Green, Private yard, Ocean Views
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Private Pool | Central AC | Concierge Included | vrKCV
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
A/C and Ocean front pool, 1bedroom Condo on Ali’i drive in the heart of Kona ❤️
Sleeps 4 · 1 bedroom · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
57 reviews(57 reviews)
Kona Shores - It's a Honu World. Small complex on Alli'i Drive
Sleeps 4 · 1 bathroom
8.08.0 out of 10
Very goodvery good
13 reviews(13 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
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