We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes in Kailua-Kona

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 km
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
1046 rentals in Kailua-Kona.
Sort by:
Tripadvisor Sort
306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai., holiday rental in Kailua-Kona

306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Alii Magic Sands Vacation Rental 3 min walk to Beach, holiday rental in Kailua-Kona

Alii Magic Sands Vacation Rental 3 min walk to Beach

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A Perfect 10 *** Ocean View Pool Waterfall Hot Tub, holiday rental in Kailua-Kona

A Perfect 10 *** Ocean View Pool Waterfall Hot Tub

5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
**AWESOME OCEAN FRONT 7th FL PENTHOUSE** Kona Ali'i Complex, holiday rental in Kailua-Kona

**AWESOME OCEAN FRONT 7th FL PENTHOUSE** Kona Ali'i Complex

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Great Ocean Views! 2007 Built Penthouse at Kahaluu, holiday rental in Kailua-Kona

Great Ocean Views! 2007 Built Penthouse at Kahaluu

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
KKSR#5104 DIRECT OCEANFRONT, BEST GROUND FLOOR CORNER! REMODELED!, AC!!!, holiday rental in Kailua-Kona

KKSR#5104 DIRECT OCEANFRONT, BEST GROUND FLOOR CORNER! REMODELED!, AC!!!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
KONA ISLE - Truly Unique Oceanfront/Garden Condo, holiday rental in Kailua-Kona

KONA ISLE - Truly Unique Oceanfront/Garden Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa De Emdeko 219 2 Bdrm DIRECT Ocean Front CORNER unit, Wrap around Lanai!, holiday rental in Kailua-Kona

Casa De Emdeko 219 2 Bdrm DIRECT Ocean Front CORNER unit, Wrap around Lanai!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Comfortable Oceanfront Getaway in a Tranquil Setting, holiday rental in Kailua-Kona

Comfortable Oceanfront Getaway in a Tranquil Setting

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
2 bdrm 2 ba condo across from White Sands Beach, holiday rental in Kailua-Kona

2 bdrm 2 ba condo across from White Sands Beach

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Save time - get the best Kailua-Kona rentals sent straight to your email!
Koana Breeze-Breathtaking Sunset & Ocean Views, Hot Tub Living at its finest!, holiday rental in Kailua-Kona

Koana Breeze-Breathtaking Sunset & Ocean Views, Hot Tub Living at its finest!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Kailua Kona Oceanview - Keauhou Akahi, holiday rental in Kailua-Kona

Kailua Kona Oceanview - Keauhou Akahi

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Kona Bay Seaclusion-Oceanfront with Pool, holiday rental in Kailua-Kona

Kona Bay Seaclusion-Oceanfront with Pool

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Oceanfront-Incredible Views, Surf Break & Romantic Sunsets at Bali Kai 223, holiday rental in Kailua-Kona

Oceanfront-Incredible Views, Surf Break & Romantic Sunsets at Bali Kai 223

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Amazing Ohana Retreat on the Big Island 8 bedrooms, holiday rental in Kailua-Kona

Amazing Ohana Retreat on the Big Island 8 bedrooms

8 bedrooms
9 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
One bedroom Kona Makai condo in Kailua-Kona Hawaii, holiday rental in Kailua-Kona

One bedroom Kona Makai condo in Kailua-Kona Hawaii

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Kona Makai 1-301 DIRECT OCEANFRONT, TOP FLOOR, BEST CORNER IN KONA MAKAI!, holiday rental in Kailua-Kona

Kona Makai 1-301 DIRECT OCEANFRONT, TOP FLOOR, BEST CORNER IN KONA MAKAI!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Outstanding 4 BR / 3 BA Oceanfront Home with saltwater 'Queen's Bath', holiday rental in Kailua-Kona

Outstanding 4 BR / 3 BA Oceanfront Home with saltwater 'Queen's Bath'

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Kailua-Kona Apartment w/ Pool, Deck & Ocean Views!, holiday rental in Kailua-Kona

Kailua-Kona Apartment w/ Pool, Deck & Ocean Views!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Waterfall House, holiday rental in Kailua-Kona

Waterfall House

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
OceanView Plumeria Suite, kitchenette,Sprechen Deutsch. Bears' Place Guest House, holiday rental in Kailua-Kona

OceanView Plumeria Suite, kitchenette,Sprechen Deutsch. Bears' Place Guest House

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Fabulous Ocean Views! 2005 Built 3-Bed at Kahaluu, holiday rental in Kailua-Kona

Fabulous Ocean Views! 2005 Built 3-Bed at Kahaluu

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Amazing Kona Oceanfront Private Home, 2 Bedroom + bonus room, 3 bath, sleeps 8, holiday rental in Kailua-Kona

Amazing Kona Oceanfront Private Home, 2 Bedroom + bonus room, 3 bath, sleeps 8

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Carson's Mountain Cabin with hot tub and fireplace! Special winter deal...., holiday rental in Kailua-Kona

Carson's Mountain Cabin with hot tub and fireplace! Special winter deal....

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Seaside Zen Cottage on the Beach in Kailua Kona, holiday rental in Kailua-Kona

Seaside Zen Cottage on the Beach in Kailua Kona

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Foster's Ohia Hale, holiday rental in Kailua-Kona

Foster's Ohia Hale

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Plantation Manager's Beach House - Kailua Kona, holiday rental in Kailua-Kona

Plantation Manager's Beach House - Kailua Kona

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious Retreat in Kona, holiday rental in Kailua-Kona

Spacious Retreat in Kona

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunsets & Surfers - Kona Reef Ocean Front Unit, holiday rental in Kailua-Kona

Sunsets & Surfers - Kona Reef Ocean Front Unit

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
12/20-12/26 Available!!! Ahhh.... PARADISE ~Fab OCEAN VIEW, Snorkel, Surf,Bike, holiday rental in Kailua-Kona

12/20-12/26 Available!!! Ahhh.... PARADISE ~Fab OCEAN VIEW, Snorkel, Surf,Bike

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Beachfront Oceanview, 2 bedroom 2 bath, Sleeps 6, holiday rental in Kailua-Kona

Beachfront Oceanview, 2 bedroom 2 bath, Sleeps 6

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Wow!  Awesome Kailua Ocean View and Convenient Too!, holiday rental in Kailua-Kona

Wow! Awesome Kailua Ocean View and Convenient Too!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Aloha Condos, Kanaloa at Kona, Condo 3602 2BR 2BA, Sleeps 4, holiday rental in Kailua-Kona

Aloha Condos, Kanaloa at Kona, Condo 3602 2BR 2BA, Sleeps 4

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Elegant Private Kona Oceanfront Hawaiian Beach House directly on Kahaluu Bay, holiday rental in Kailua-Kona

Elegant Private Kona Oceanfront Hawaiian Beach House directly on Kahaluu Bay

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Best of Kona: pool, hot tub, walk to ocean, free wifi, newly remodeled, holiday rental in Kailua-Kona

Best of Kona: pool, hot tub, walk to ocean, free wifi, newly remodeled

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
BEAUTIFUL Beachfront / Top Floor / Air Con / Walk to Town, holiday rental in Kailua-Kona

BEAUTIFUL Beachfront / Top Floor / Air Con / Walk to Town

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Hawaii County Certified! Hale Hina - Perfection in Paradise!, holiday rental in Kailua-Kona

Hawaii County Certified! Hale Hina - Perfection in Paradise!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
SPECIAL FOR 2021! BREATHTAKING OCEAN VIEWS DELUXE 1/1 CASA DE EMDEKO B#135, holiday rental in Kailua-Kona

SPECIAL FOR 2021! BREATHTAKING OCEAN VIEWS DELUXE 1/1 CASA DE EMDEKO B#135

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Kona Oceanfront Top Floor Condo 30ft from Shore - Amazing View, Wifi, A/C, holiday rental in Kailua-Kona

Kona Oceanfront Top Floor Condo 30ft from Shore - Amazing View, Wifi, A/C

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Paradise isn't lost, it is here in KAILUA-KONA, holiday rental in Kailua-Kona

Paradise isn't lost, it is here in KAILUA-KONA

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Oceanfront - Kanaloa at Kona - Newly Remodeled, holiday rental in Kailua-Kona

Oceanfront - Kanaloa at Kona - Newly Remodeled

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Aloha Condos, Kanaloa at Kona, Condo 2602, Oceanfront, AC, Renovated, holiday rental in Kailua-Kona

Aloha Condos, Kanaloa at Kona, Condo 2602, Oceanfront, AC, Renovated

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
WINTER SALE! PEGGYS PENTHOUSE, OCEAN/SUNSET/SURFER  VIEW ,BEACH GEAR bucket list, holiday rental in Kailua-Kona

WINTER SALE! PEGGYS PENTHOUSE, OCEAN/SUNSET/SURFER VIEW ,BEACH GEAR bucket list

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Breathtaking Kona Home - Heated Pool / Air conditioning and Beautiful Sunsets, holiday rental in Kailua-Kona

Breathtaking Kona Home - Heated Pool / Air conditioning and Beautiful Sunsets

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Lovely Spacious Oceanfront 2 Bedroom Airconditioned Condo w/ Amazing Ocean Views, holiday rental in Kailua-Kona

Lovely Spacious Oceanfront 2 Bedroom Airconditioned Condo w/ Amazing Ocean Views

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Direct Oceanfront, Big Wave Penthouse-1,200 sq ft, Stunning View. Free,fast WiFi, holiday rental in Kailua-Kona

Direct Oceanfront, Big Wave Penthouse-1,200 sq ft, Stunning View. Free,fast WiFi

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Direct Ocean View : Top Floor : End Unit : Wrap-Around Lanai : 5* Reviews, holiday rental in Kailua-Kona

Direct Ocean View : Top Floor : End Unit : Wrap-Around Lanai : 5* Reviews

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Gorgeous remodeled condo Oceanfront! SUNSET!, holiday rental in Kailua-Kona

Gorgeous remodeled condo Oceanfront! SUNSET!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
The Seaview at Kona Pacific, 5th floor, Ocean view, 1 Bed/2 Bath, holiday rental in Kailua-Kona

The Seaview at Kona Pacific, 5th floor, Ocean view, 1 Bed/2 Bath

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Oceanfront Vacation Rental Kailua Kona, holiday rental in Kailua-Kona

Oceanfront Vacation Rental Kailua Kona

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Previous