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Kailua-Kona Vacation Rentals

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949 rentals in Kailua-Kona.

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Alii Magic Sands Vacation Rental 3 min walk to Beach, vacation rental in Kailua-Kona

Alii Magic Sands Vacation Rental 3 min walk to Beach

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Perfect 10 *** Ocean View Pool Waterfall Hot Tub, vacation rental in Kailua-Kona

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

5 bedrooms
5 bathrooms
Sleeps 13
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**AWESOME OCEAN FRONT 7th FL PENTHOUSE** Kona Ali'i Complex, vacation rental in Kailua-Kona

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean View Estate, vacation rental in Kailua-Kona

Ocean View Estate

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai., vacation 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
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2 bdrm 2 ba condo across from White Sands Beach, vacation rental in Kailua-Kona

2 bdrm 2 ba condo across from White Sands Beach

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfall House, vacation rental in Kailua-Kona

Waterfall House

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Casa De Emdeko 219 2 Bdrm DIRECT Ocean Front CORNER unit, Wrap around Lanai!, vacation 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
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Comfortable Oceanfront Getaway in a Tranquil Setting, vacation rental in Kailua-Kona

Comfortable Oceanfront Getaway in a Tranquil Setting

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Extra Large studio room 2x size of pictured room, vacation rental in Kailua-Kona

Extra Large studio room 2x size of pictured room

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Koana Breeze-Breathtaking Sunset & Ocean Views, Hot Tub Living at its finest!, vacation rental in Kailua-Kona

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Magic Sands olukai Cabana Kailua Kona, Hawaii - 1500 sq ft, vacation rental in Kailua-Kona

The Magic Sands olukai Cabana Kailua Kona, Hawaii - 1500 sq ft

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kahaluu Bay Across from Snorkel Beach - Ocean View, vacation rental in Kailua-Kona

Kahaluu Bay Across from Snorkel Beach - Ocean View

2 bedrooms
2 bathrooms
Sleeps 6
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Kona Surf & Racquet Unit 7-103, vacation rental in Kailua-Kona

Kona Surf & Racquet Unit 7-103

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kona Bali Kai 317 Direct Oceanfront, vacation rental in Kailua-Kona

Kona Bali Kai 317 Direct Oceanfront

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Kona Makai 1-301 DIRECT OCEANFRONT, TOP FLOOR, BEST CORNER IN KONA MAKAI!, vacation 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
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Kailua Kona Oceanview - Keauhou Akahi, vacation rental in Kailua-Kona

Kailua Kona Oceanview - Keauhou Akahi

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Ohana Retreat on the Big Island 8 bedrooms, vacation rental in Kailua-Kona

Amazing Ohana Retreat on the Big Island 8 bedrooms

8 bedrooms
9 bathrooms
Sleeps 18
Match: Sleeps
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Kailua-Kona Apartment w/ Pool, Deck & Ocean Views!, vacation rental in Kailua-Kona

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

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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One bedroom Kona Makai condo in Kailua-Kona Hawaii, vacation rental in Kailua-Kona

One bedroom Kona Makai condo in Kailua-Kona Hawaii

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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‘Living Aloha’ Condo w/ 2 Master Suites & A/C!, vacation rental in Kailua-Kona

‘Living Aloha’ Condo w/ 2 Master Suites & A/C!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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KKSR#5104 DIRECT OCEANFRONT, BEST GROUND FLOOR CORNER! REMODELED!, AC!!!, vacation rental in Kailua-Kona

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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KKSR3202 DIRECT OCEANFRONT, Spacious, 2nd Flr, vacation rental in Kailua-Kona

KKSR3202 DIRECT OCEANFRONT, Spacious, 2nd Flr

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dual-Suite Escape | AC, Ocean & Sunset Views | Oceanfront Pools, Spa & Tennis, vacation rental in Kailua-Kona

Dual-Suite Escape | AC, Ocean & Sunset Views | Oceanfront Pools, Spa & Tennis

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stylish Ocean-View Apartment with Pool & Spa | Walk to Kahalu’u Beach Park, vacation rental in Kailua-Kona

Stylish Ocean-View Apartment with Pool & Spa | Walk to Kahalu’u Beach Park

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Holualoa Bay Villas: 106 Beautiful Oceanview, AC, Elevators, Wifi!, vacation rental in Kailua-Kona

Holualoa Bay Villas: 106 Beautiful Oceanview, AC, Elevators, Wifi!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kona Isle C28. Corner Unit, 2nd Floor, Ocean Views, & Air Conditioning!, vacation rental in Kailua-Kona

Kona Isle C28. Corner Unit, 2nd Floor, Ocean Views, & Air Conditioning!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Surf and Racquet 5102 2/2 oceanfront, vacation rental in Kailua-Kona

Surf and Racquet 5102 2/2 oceanfront

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

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sea Village 2nd floor Direct Oceanfront unit with extensive upgrades, vacation rental in Kailua-Kona

Sea Village 2nd floor Direct Oceanfront unit with extensive upgrades

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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OceanView Plumeria Suite, kitchenette,Sprechen Deutsch. Bears' Place Guest House, vacation rental in Kailua-Kona

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Great Ocean Views! 2007 Built Penthouse at Kahaluu, vacation rental in Kailua-Kona

Great Ocean Views! 2007 Built Penthouse at Kahaluu

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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KONA ISLE - Truly Unique Oceanfront/Garden Condo, vacation rental in Kailua-Kona

KONA ISLE - Truly Unique Oceanfront/Garden Condo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Kona Oceanfront Private Home, 2 Bedroom + bonus room, 3 bath, sleeps 8, vacation 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
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Fabulous Ocean Views! 2005 Built 3-Bed at Kahaluu, vacation rental in Kailua-Kona

Fabulous Ocean Views! 2005 Built 3-Bed at Kahaluu

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Carson's Mountain Cabin with hot tub and fireplace! Special winter deal...., vacation rental in Kailua-Kona

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Seaside Zen Cottage on the Beach in Kailua Kona, vacation rental in Kailua-Kona

Seaside Zen Cottage on the Beach in Kailua Kona

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Foster's Ohia Hale, vacation rental in Kailua-Kona

Foster's Ohia Hale

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Updated Tranquil Getaway | Plunge Pool, Ping-Pong & Sunset Ocean Views, vacation rental in Kailua-Kona

Updated Tranquil Getaway | Plunge Pool, Ping-Pong & Sunset Ocean Views

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Plantation Manager's Beach House - Kailua Kona, vacation rental in Kailua-Kona

Plantation Manager's Beach House - Kailua Kona

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sunsets & Surfers - Kona Reef Ocean Front Unit, vacation rental in Kailua-Kona

Sunsets & Surfers - Kona Reef Ocean Front Unit

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Retreat in Kona, vacation rental in Kailua-Kona

Spacious Retreat in Kona

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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12/20-12/26 Available!!! Ahhh.... PARADISE ~Fab OCEAN VIEW, Snorkel, Surf,Bike, vacation 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
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Beachfront Oceanview, 2 bedroom 2 bath, Sleeps 6, vacation rental in Kailua-Kona

Beachfront Oceanview, 2 bedroom 2 bath, Sleeps 6

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wow!  Awesome Kailua Ocean View and Convenient Too!, vacation rental in Kailua-Kona

Wow! Awesome Kailua Ocean View and Convenient Too!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Private Kona Oceanfront Hawaiian Beach House directly on Kahaluu Bay, vacation rental in Kailua-Kona

Elegant Private Kona Oceanfront Hawaiian Beach House directly on Kahaluu Bay

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Aloha Condos, Kanaloa at Kona, Condo 3602 2BR 2BA, Sleeps 4, vacation rental in Kailua-Kona

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Best of Kona: pool, hot tub, walk to ocean, free wifi, newly remodeled, vacation 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
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BEAUTIFUL Beachfront / Top Floor / Air Con / Walk to Town, vacation rental in Kailua-Kona

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hawaii County Certified! Hale Hina - Perfection in Paradise!, vacation rental in Kailua-Kona

Hawaii County Certified! Hale Hina - Perfection in Paradise!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Frequently Asked Questions about Kailua-Kona

Kailua Kona Vacation Rentals
Whether you are planning on surfing, diving, or just laying out in the sun, Kailua Kona is an amazing destination full of pristine beaches and local culture. A Kailua Kona vacation is sure to be unforgettable, but why not make it even more special by staying in your very own vacation rental instead of a hotel? There are a variety of Kailua Kona vacation rentals available, from a cozy one bedroom condo to a spacious rental house that can sleep the entire family. There is sure to be the perfect rental home to suit your needs and your style, so check out our great deals on Kailua Kona vacation rentals for your next trip.
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Kailua Kona Vacation Rentals
Whether you are planning on surfing, diving, or just laying out in the sun, Kailua Kona is an amazing destination full of pristine beaches and local culture. A Kailua Kona vacation is sure to be unforgettable, but why not make it even more special by staying in your very own vacation rental instead of a hotel? There are a variety of Kailua Kona vacation rentals available, from a cozy one bedroom condo to a spacious rental house that can sleep the entire family. There is sure to be the perfect rental home to suit your needs and your style, so check out our great deals on Kailua Kona vacation rentals for your next trip.
A Kailua Kona Vacation
Kailua Kona is an ocean lover's paradise, full of beautiful sights and opportunities to explore. Enjoy the breathtaking view at Mauna Kea Summit and all that you can see from 13,796 feet high. To check out the sights underneath the water as well, take a dive with Big Island Divers and you will not believe your eyes. Surfer Bear Hawaii Surf Lessons can teach you and the entire family to catch some waves, or lay out in the sun at Manini'owali Beach and let your troubles melt away. Finish the day off with some delectable Hawaiian style drinks at Don's Mai Tai Bar and you may never want to leave. No matter how you spend your Kailua Kona vacation, you can rest assured knowing with vacation rentals you have chosen the most comfortable and convenient option for you and your family. A vacation rental offers you all the benefits of having a home away from home, and did you know it can even save you money?
Money Saving Vacation Rentals
Hotels can be expensive, especially when traveling with a large group. Luckily, with vacation rentals there is no need to worry about booking multiple hotel rooms when you can simply rent a vacation house that can fit your entire group. If you plan on staying a while, many Kailua Kona rental homes also offer a discounted rate on extended stays, so you can enjoy your vacation for longer while saving money. Rental homes offer so many benefits to you, your family, and your wallet, that it is a truly a win-win situation for your next trip to Kailua Kona.