Holiday rentals near Kailua Pier
We found 2,478 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:14 Nov - 21 Nov
Image gallery for Three Palms
9.89.8 out of 10 rating
Exceptional
(48 reviews)
Three Palms
Kailua-Kona, HI
15% off
Price is AU$2,923
AU$2,923
AU$418 per night
includes taxes & fees
Image gallery for Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
1010 out of 10 rating
Exceptional
(154 reviews)
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Kailua-Kona, HI
8% off
Price is AU$3,957
AU$3,957
AU$565 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$41,317
AU$41,317
AU$5,902 per night
includes taxes & fees
Image gallery for Kona Lighthouse Hawaii - FAMILY BEACH HOUSE
1010 out of 10 rating
Exceptional
(32 reviews)
Kona Lighthouse Hawaii - FAMILY BEACH HOUSE
Kailua-Kona, HI
7% off
Price is AU$6,514
AU$6,514
AU$931 per night
includes taxes & fees
Image gallery for Panoramic Ocean Views! Luxury Estate - Pool, Hot Tub, Jacuzzi & Air Conditioning
9.69.6 out of 10 rating
Exceptional
(70 reviews)
Panoramic Ocean Views! Luxury Estate - Pool, Hot Tub, Jacuzzi & Air Conditioning
Kailua-Kona, HI
7% off
Price is AU$11,238
AU$11,238
AU$1,605 per night
includes taxes & fees
Image gallery for The Onion House "Architecture so full of life it seems to breathe"
1010 out of 10 rating
Exceptional
(163 reviews)
The Onion House "Architecture so full of life it seems to breathe"
Kailua-Kona, HI
7% off
Price is AU$10,039
AU$10,039
AU$1,434 per night
includes taxes & fees
Image gallery for Big 3BR / 4BA (3056sq ft) Kona Home with Pool/Jacuzzi, OceanView (Sleeps 16 max)
1010 out of 10 rating
Exceptional
(91 reviews)
Big 3BR / 4BA (3056sq ft) Kona Home with Pool/Jacuzzi, OceanView (Sleeps 16 max)
Kailua-Kona, HI
6% off
Price is AU$6,778
AU$6,778
AU$968 per night
includes taxes & fees
Image gallery for Upgraded Spacious 5-bedroom with AC, Private Pool/Spa next to Magic Sand beach
8.88.8 out of 10 rating
Excellent
(6 reviews)
Upgraded Spacious 5-bedroom with AC, Private Pool/Spa next to Magic Sand beach
Kailua-Kona, HI
6% off
Price is AU$11,528
AU$11,528
AU$1,647 per night
includes taxes & fees
Image gallery for Nalu Bliss- Amazing 2BR Waterfront Location on Alii Dr Close to Town and Beaches
1010 out of 10 rating
Exceptional
(97 reviews)
Nalu Bliss- Amazing 2BR Waterfront Location on Alii Dr Close to Town and Beaches
Kailua-Kona, HI
7% off
Price is AU$10,686
AU$10,686
AU$1,527 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 AU$4,074
AU$4,074
AU$582 per night
includes taxes & fees
Image gallery for Kona Condo with all the comforts of home
9.29.2 out of 10 rating
Wonderful
(79 reviews)
Kona Condo with all the comforts of home
Kailua-Kona, HI
14% off
Price is AU$1,941
AU$1,941
AU$277 per night
includes taxes & fees
Image gallery for Tropical Paradise Awaits: Stunning Hawaii Condo with Ocean Views!
1010 out of 10 rating
Exceptional
(99 reviews)
Tropical Paradise Awaits: Stunning Hawaii Condo with Ocean Views!
Kailua-Kona, HI
14% off
Price is AU$3,079
AU$3,079
AU$440 per night
includes taxes & fees
Image gallery for Charming Surfer's dream Hawaiian Home near Lyman Beach on Ali'i Drive
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Charming Surfer's dream Hawaiian Home near Lyman Beach on Ali'i Drive
Kailua-Kona, HI
14% off
Price is AU$3,520
AU$3,520
AU$503 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$3,359
AU$3,359
AU$480 per night
includes taxes & fees
Image gallery for Charming Holualoa Ranching-Era Estate near Kailua and Keauhou. Away from it all!
1010 out of 10 rating
Exceptional
(163 reviews)
Charming Holualoa Ranching-Era Estate near Kailua and Keauhou. Away from it all!
Holualoa, HI
7% off
Price is AU$8,432
AU$8,432
AU$1,205 per night
includes taxes & fees
Image gallery for Cozy studio with WiFi and AC that is within walking distance of Magic Sands Bch
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Cozy studio with WiFi and AC that is within walking distance of Magic Sands Bch
Kailua-Kona, HI
7% off
Price is AU$1,809
AU$1,809
AU$258 per night
includes taxes & fees
Image gallery for Beautiful Pool with Stunning Ocean and Sunset Views
9.49.4 out of 10 rating
Exceptional
(68 reviews)
Beautiful Pool with Stunning Ocean and Sunset Views
Kailua-Kona, HI
11% off
Price is AU$5,832
AU$5,832
AU$833 per night
includes taxes & fees
Image gallery for Kona coast studio, great rates free HS-WIFI, Parking, Walk to Magics & Kahalu'u
9.69.6 out of 10 rating
Exceptional
(154 reviews)
Kona coast studio, great rates free HS-WIFI, Parking, Walk to Magics & Kahalu'u
Kailua-Kona, HI
7% off
Price is AU$1,889
AU$1,889
AU$270 per night
includes taxes & fees
Image gallery for Ocean View - King Bed✨ Self Checkin and Out - Private Entry and Private Lanai
1010 out of 10 rating
Exceptional
(56 reviews)
Ocean View - King Bed✨ Self Checkin and Out - Private Entry and Private Lanai
Holualoa, HI
8% off
Price is AU$2,840
AU$2,840
AU$406 per night
includes taxes & fees
Image gallery for Ocean Front Condo at The Royal Sea-Cliff Resort
9.29.2 out of 10 rating
Wonderful
(72 reviews)
Ocean Front Condo at The Royal Sea-Cliff Resort
Kailua-Kona, HI
14% off
Price is AU$2,519
AU$2,519
AU$360 per night
includes taxes & fees
Image gallery for Da KONA WEST 305 - listen to the ocean waves crashing !! 30 + days stays
1010 out of 10 rating
Exceptional
(12 reviews)
Da KONA WEST 305 - listen to the ocean waves crashing !! 30 + days stays
Kailua-Kona, HI
7% off
Price is AU$1,997
AU$1,997
AU$285 per night
includes taxes & fees
Image gallery for Ocean Breeze Kona Home
9.69.6 out of 10 rating
Exceptional
(203 reviews)
Ocean Breeze Kona Home
Kailua-Kona, HI
14% off
Price is AU$8,798
AU$8,798
AU$1,257 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
(15 reviews)
A Beautiful View Beach House at Kahalu'u Bay! Snorkeling & Surfing ~ Steps Away!
Kailua-Kona, HI
8% off
Price is AU$7,306
AU$7,306
AU$1,044 per night
includes taxes & fees
Image gallery for Steps Away from Black Sand Beach
9.89.8 out of 10 rating
Exceptional
(102 reviews)
Steps Away from Black Sand Beach
Kailua-Kona, HI
7% off
Price is AU$4,365
AU$4,365
AU$624 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
Relaxing Kailua-Kona 2 bed/2 bath condo with central AC across street from beach
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Ocean Sunsets and Waking Up to the Sounds of Waves
Sleeps 5 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Oceanfront Sea Village #3212 retreat with stunning views and open living spaces
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
🏖️Beautiful Ocean Views | Close to Town | WIFI 🏖️
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Ocean Front 2 BR Condo-ocean views from every room. 2nd floor Kona Reef "A" bldg
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
61 reviews(61 reviews)
Beach/Ocean View Condo 🐬 Great Value, Walking Distance to Beach🏝️ and Town👣 Kona Reef B21
Sleeps 4 · 1 bedroom · 1 bathroom
8.88.8 out of 10
Excellentexcellent
41 reviews(41 reviews)
Top rated rentals - Kailua Pier
Great stay
1010 out of 10
Exceptionalexceptional
224 reviews(224 reviews)
Great location and property, we will be back! Thanks for having us :)
Marion M.
Stayed Oct 2024
Waaaaaay Above and Beyond!
1010 out of 10
Exceptionalexceptional
202 reviews(202 reviews)
Gale and her property a absolutely beautiful. Home made banana bread and anything else you could want in a rental are all provided with Gale’s special touch. Simply cannot rate this beautiful boutique property highly enough. 100% recommend to anyway wanting a fantastic hideaway home!
Tanya J.
Stayed Dec 2022
Thoroughly enjoyed our stay, very clean and tidy. Highlight was listening to the waves.
1010 out of 10
Exceptionalexceptional
134 reviews(134 reviews)
Waking up with ocean views while eating breakfast on the balcony was definitely our highlight. This place is well equipped with all of the cooking/utensils needed to enjoy a homely stay.
Jack R.
Stayed Oct 2022
Great views
1010 out of 10
Exceptionalexceptional
249 reviews(249 reviews)
Enjoyed my stay here - sound of surf is amazing! Pretty close to everything and easy walk to main shops etc. Pool area was great, parking area easy but still steps up or down, even with the lift. Found it hard on my own, being older, to lift suitcase up and down. Otherwise very nice unit.
Wendy B.
Stayed Sept 2019
Amazing
1010 out of 10
Exceptionalexceptional
110 reviews(110 reviews)
What can I say, what a beautiful house and beautiful location.
We thoroughly enjoyed our stay but unfortunately we only stayed for 5 days. We will defiantly be returning to Hawaii.
We shared this house with my wife's brother and his family which made 8 of us. Even though there is only 3 bedrooms there is plenty of room for 8. We were amazed to find the amount of extras left in the house which made our stay even more comfortable.
On another note, i would personally like to thank Cliff for helping my wife out after we had left the property. Once we had arrived in Honolulu we realized that my wife's medication was left behind in the fridge. I contact Cliff and he arrange for the postage of the meds to our hotel in Honolulu. THANK YOU!!!!
Once again thank you and we can't wait to return.
Happy Travelers
Coupe's & Allen's
Robert C.
Stayed June 2016
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