Holiday rentals near Kailua Pier
We found 2,448 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:3 Oct - 10 Oct
Image gallery for Three Palms
9.89.8 out of 10 rating
Exceptional
(47 reviews)
Three Palms
Kailua-Kona, HI
8% off
Price is AU$3,277
AU$3,277
AU$468 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 AU$8,124
AU$8,124
AU$1,161 per night
includes taxes & fees
Image gallery for The “Promise Tree” is a great family gathering place in Kailua Kona!
1010 out of 10 rating
Exceptional
(144 reviews)
The “Promise Tree” is a great family gathering place in Kailua Kona!
Kailua-Kona, HI
8% off
Price is AU$17,503
AU$17,503
AU$2,500 per night
includes taxes & fees
Image gallery for Charming Kaloko Mountain Cottage with hot tub - private,secluded and cozy!!
9.89.8 out of 10 rating
Exceptional
(79 reviews)
Charming Kaloko Mountain Cottage with hot tub - private,secluded and cozy!!
Kailua-Kona, HI
7% off
Price is AU$2,387
AU$2,387
AU$341 per night
includes taxes & fees
Image gallery for Immaculate; Air Cond; Ocean/Garden views;GIG WiFi6 S
1010 out of 10 rating
Exceptional
(80 reviews)
Immaculate; Air Cond; Ocean/Garden views;GIG WiFi6 S
Kailua-Kona, HI
7% off
Price is AU$4,043
AU$4,043
AU$578 per night
includes taxes & fees
Image gallery for Ultra private oceanfront gated compound with pool & spa just minutes from town.
1010 out of 10 rating
Exceptional
(50 reviews)
Ultra private oceanfront gated compound with pool & spa just minutes from town.
Kailua-Kona, HI
8% off
Price is AU$40,261
AU$40,261
AU$5,752 per night
includes taxes & fees
Image gallery for Kope Cottage -1 BR -1B-Endless Views
1010 out of 10 rating
Exceptional
(62 reviews)
Kope Cottage -1 BR -1B-Endless Views
Holualoa, HI
7% off
Price is AU$3,510
AU$3,510
AU$501 per night
includes taxes & fees
Image gallery for Fall discounts Ali'i Dr location, Clean, salt water pool by Poke shack
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Fall discounts Ali'i Dr location, Clean, salt water pool by Poke shack
Kailua-Kona, HI
8% off
Price is AU$3,741
AU$3,741
AU$534 per night
includes taxes & fees
Image gallery for Charming Mountain Hideaway — Cozy Escape Near the Coast
1010 out of 10 rating
Exceptional
(29 reviews)
Charming Mountain Hideaway — Cozy Escape Near the Coast
Kailua-Kona, HI
7% off
Price is AU$4,022
AU$4,022
AU$575 per night
includes taxes & fees
Image gallery for Beach House: Oversized Lanai with Indoor/Outdoor Flow. EZ Stroll to Magic Sands!
1010 out of 10 rating
Exceptional
(25 reviews)
Beach House: Oversized Lanai with Indoor/Outdoor Flow. EZ Stroll to Magic Sands!
Kailua-Kona, HI
7% off
Price is AU$4,441
AU$4,441
AU$634 per night
includes taxes & fees
Image gallery for Kona's only Oceanfront pool! Pineapple Pl Reimagined! Cozy 2/1 Condo, sleeps 6,
8.88.8 out of 10 rating
Excellent
(13 reviews)
Kona's only Oceanfront pool! Pineapple Pl Reimagined! Cozy 2/1 Condo, sleeps 6,
Kailua-Kona, HI
8% off
Price is AU$6,400
AU$6,400
AU$914 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
(84 reviews)
2.7 Acres of Exceptional, Secluded Retreat - Close to Beach & Shopping!
Kailua-Kona, HI
7% off
Price is AU$7,582
AU$7,582
AU$1,083 per night
includes taxes & fees
Image gallery for Beautiful Kona Hawaiian Resort - 2BR/2BA Deluxe Unit
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Beautiful Kona Hawaiian Resort - 2BR/2BA Deluxe Unit
Kailua-Kona, HI
8% off
Price is AU$6,376
AU$6,376
AU$911 per night
includes taxes & fees
Image gallery for Guest house on gated acre estate, Sleeps up to 7; Great for Events, too
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Guest house on gated acre estate, Sleeps up to 7; Great for Events, too
Kailua-Kona, HI
7% off
Price is AU$3,342
AU$3,342
AU$477 per night
includes taxes & fees
Image gallery for New Listing, Oceanfront condo, breathtaking views!
8.48.4 out of 10 rating
Very good
(12 reviews)
New Listing, Oceanfront condo, breathtaking views!
Kailua-Kona, HI
7% off
Price is AU$5,718
AU$5,718
AU$817 per night
includes taxes & fees
Image gallery for Direct Ocean View in the Heart of Kailua-Kona/ At startline for Ironman!
9.89.8 out of 10 rating
Exceptional
(115 reviews)
Direct Ocean View in the Heart of Kailua-Kona/ At startline for Ironman!
Kailua-Kona, HI
7% off
Price is AU$3,982
AU$3,982
AU$569 per night
includes taxes & fees
Image gallery for the cozy large studio 30+days stays
9.89.8 out of 10 rating
Exceptional
(6 reviews)
the cozy large studio 30+days stays
Kailua-Kona, HI
8% off
Price is AU$3,782
AU$3,782
AU$540 per night
includes taxes & fees
Image gallery for Stunning Ocean Front Estate Home right on Keauhou Bay!!
9.69.6 out of 10 rating
Exceptional
(62 reviews)
Stunning Ocean Front Estate Home right on Keauhou Bay!!
Kailua-Kona, HI
7% off
Price is AU$34,640
AU$34,640
AU$4,949 per night
includes taxes & fees
Image gallery for My Ohana 30+ days
9.89.8 out of 10 rating
Exceptional
(18 reviews)
My Ohana 30+ days
Kailua-Kona, HI
8% off
Price is AU$4,646
AU$4,646
AU$664 per night
includes taxes & fees
Image gallery for Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course with Pool.
1010 out of 10 rating
Exceptional
(23 reviews)
Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course with Pool.
Kailua-Kona, HI
9% off
Price is AU$7,976
AU$7,976
AU$1,139 per night
includes taxes & fees
Image gallery for Newly renovated, ocean view, steps from downtown
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Newly renovated, ocean view, steps from downtown
Kailua-Kona, HI
8% off
Price is AU$8,133
AU$8,133
AU$1,162 per night
includes taxes & fees
Image gallery for 4 bedroom/ 3 bath luxury home with A/C, steps to community pool, oceanview
9.69.6 out of 10 rating
Exceptional
(5 reviews)
4 bedroom/ 3 bath luxury home with A/C, steps to community pool, oceanview
Kailua-Kona, HI
8% off
Price is AU$19,056
AU$19,056
AU$2,722 per night
includes taxes & fees
Image gallery for Amazing 🏄♀️ Oceanfront Penthouse 🐬 Newly Renovated! - Banyan Tree 403C 🌅
9.49.4 out of 10 rating
Exceptional
(84 reviews)
Amazing 🏄♀️ Oceanfront Penthouse 🐬 Newly Renovated! - Banyan Tree 403C 🌅
Kailua-Kona, HI
5% off
Price is AU$7,807
AU$7,807
AU$1,115 per night
includes taxes & fees
Image gallery for Stunning Luxury Estate 🌺 Superb Private Lanai & Breathtaking Sunsets! 🌅 Keauhou Luxury Estate
1010 out of 10 rating
Exceptional
(68 reviews)
Stunning Luxury Estate 🌺 Superb Private Lanai & Breathtaking Sunsets! 🌅 Keauhou Luxury Estate
Kailua-Kona, HI
5% off
Price is AU$12,664
AU$12,664
AU$1,809 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Kailua Pier
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Find the best place to stay - Kailua Pier
Tropical downtown suite w/private hot tub & gazebo, washer & dryer, patio
Sleeps 10 · 5 bedrooms · 5 bathrooms
9.09.0 out of 10
Wonderfulwonderful
22 reviews(22 reviews)
Nicely Renovated. In The Heart of Kailua-Kona, Just Steps From the Ocean.
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
166 reviews(166 reviews)
Kona Plaza#215 Remodeled unit IN HEART OF KONA TOWN! AC & Elevators!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
96 reviews(96 reviews)
Kona Plaza#212: Kona Hawaii Beach Vacation Rental: AC, Pool, Modern, WiFi!
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Centrally Located Downtown Gem
Sleeps 12 · 5 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
70 reviews(70 reviews)
Beach Condo, Lovely, Clean, Comfy Heart of Kona! Poolside, Hot Tub, Beach Stuff
Sleeps 2
9.09.0 out of 10
Wonderfulwonderful
76 reviews(76 reviews)
Top rated rentals - Kailua Pier
Good stay. some issues
1010 out of 10
Exceptionalexceptional
116 reviews(116 reviews)
Waaaaaay Above and Beyond!
1010 out of 10
Exceptionalexceptional
200 reviews(200 reviews)
Great views
1010 out of 10
Exceptionalexceptional
244 reviews(244 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
More for lessMore space, more privacy, more amenities — more value