Holiday rentals near Kailua Pier
We found 2,588 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:15 Aug - 22 Aug
Image gallery for Ultra private oceanfront gated compound with pool & spa just minutes from town.
1010 out of 10 rating
Exceptional
(47 reviews)
Ultra private oceanfront gated compound with pool & spa just minutes from town.
Kailua-Kona, HI
8% off
Price is NZ$49,213
NZ$49,213
NZ$7,030 per night
includes taxes & fees
Image gallery for 5★Resort like paradise, heated pool, ocean views, AC, peaceful gated community.
1010 out of 10 rating
Exceptional
(40 reviews)
5★Resort like paradise, heated pool, ocean views, AC, peaceful gated community.
Kailua-Kona, HI
7% off
Price is NZ$10,515
NZ$10,515
NZ$1,502 per night
includes taxes & fees
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
11% off
Price is NZ$8,574
NZ$8,574
NZ$1,225 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$7,112
NZ$7,112
NZ$1,016 per night
includes taxes & fees
Image gallery for Luxury Private Vacation | 180° Ocean View | AC | Pool | WiFi
9.89.8 out of 10 rating
Exceptional
(59 reviews)
Luxury Private Vacation | 180° Ocean View | AC | Pool | WiFi
Kailua-Kona, HI
8% off
Price is NZ$17,131
NZ$17,131
NZ$2,447 per night
includes taxes & fees
Image gallery for Luxury Home With Amazing Ocean View Above Kealakekua Bay -BIG lanai with HOT TUB
9.89.8 out of 10 rating
Exceptional
(102 reviews)
Luxury Home With Amazing Ocean View Above Kealakekua Bay -BIG lanai with HOT TUB
Captain Cook, HI
7% off
Price is NZ$6,826
NZ$6,826
NZ$975 per night
includes taxes & fees
Image gallery for Beautiful Kona Hawaiian 2BR/2BA Villa
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Beautiful Kona Hawaiian 2BR/2BA Villa
Kailua-Kona, HI
8% off
Price is NZ$6,439
NZ$6,439
NZ$920 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$3,770
NZ$3,770
NZ$539 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$3,978
NZ$3,978
NZ$568 per night
includes taxes & fees
Image gallery for Ocean Front !!...Watch The Surfers And Smell the Ocean...Minutes to the beach.
9.69.6 out of 10 rating
Exceptional
(199 reviews)
Ocean Front !!...Watch The Surfers And Smell the Ocean...Minutes to the beach.
Kailua-Kona, HI
8% off
Price is NZ$11,517
NZ$11,517
NZ$1,645 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$2,879
NZ$2,879
NZ$411 per night
includes taxes & fees
Image gallery for Exquisite Sunset & Renovated Oceanview Condo - 10% Discount on 7 day booking
1010 out of 10 rating
Exceptional
(58 reviews)
Exquisite Sunset & Renovated Oceanview Condo - 10% Discount on 7 day booking
Kailua-Kona, HI
7% off
Price is NZ$3,656
NZ$3,656
NZ$522 per night
includes taxes & fees
Image gallery for Luxury Beachfront Gated retreat in-town pool/spa/AC BBQ private & secure
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Luxury Beachfront Gated retreat in-town pool/spa/AC BBQ private & secure
Kailua-Kona, HI
7% off
Price is NZ$17,000
NZ$17,000
NZ$2,429 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$4,175
NZ$4,175
NZ$596 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$8,782
NZ$8,782
NZ$1,255 per night
includes taxes & fees
Image gallery for Enjoy Panoramic Ocean Sunset Views From Your Private, Gated Residence
9.69.6 out of 10 rating
Exceptional
(90 reviews)
Enjoy Panoramic Ocean Sunset Views From Your Private, Gated Residence
Kailua-Kona, HI
10% off
Price is NZ$18,064
NZ$18,064
NZ$2,581 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$8,280
NZ$8,280
NZ$1,183 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$3,031
NZ$3,031
NZ$433 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$3,362
NZ$3,362
NZ$480 per night
includes taxes & fees
Image gallery for Gated Keauhou Residences w/Ocean Views & Pool!
9.69.6 out of 10 rating
Exceptional
(79 reviews)
Gated Keauhou Residences w/Ocean Views & Pool!
Kailua-Kona, HI
10% off
Price is NZ$19,842
NZ$19,842
NZ$2,835 per night
includes taxes & fees
Image gallery for Spectacular Oceanfront Condo With Beautiful Sunsets
9.69.6 out of 10 rating
Exceptional
(116 reviews)
Spectacular Oceanfront Condo With Beautiful Sunsets
Kailua-Kona, HI
7% off
Price is NZ$4,550
NZ$4,550
NZ$650 per night
includes taxes & fees
Image gallery for Kona Islander Hawaiian Style Poolside
1010 out of 10 rating
Exceptional
(12 reviews)
Kona Islander Hawaiian Style Poolside
Kailua-Kona, HI
7% off
Price is NZ$2,333
NZ$2,333
NZ$333 per night
includes taxes & fees
Image gallery for 🍍Oceanfront Condo & Walking Distance to Beach and Town! 🏖 - Hale Kona Kai 207
8.88.8 out of 10 rating
Excellent
(38 reviews)
🍍Oceanfront Condo & Walking Distance to Beach and Town! 🏖 - Hale Kona Kai 207
Kailua-Kona, HI
5% off
Price is NZ$3,557
NZ$3,557
NZ$508 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$2,411
NZ$2,411
NZ$344 per night
includes taxes & fees
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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)
Dolphin House Oceanfront Estate
Sleeps 11 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
98 reviews(98 reviews)
Ohana Retreat - The Real Hawaiian Experience
Sleeps 18 · 8 bedrooms · 8 bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Newly Renovated 2BR 2BA Condo in the Heart of Kona | Kona Plaza
Sleeps 4 · 2 bedrooms · 2 bathrooms
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
164 reviews(164 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)
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