Kailua-Kona Vacation Rentals

Kailua-Kona is the Big Island's top vacation destination. Its sunny climate and pristine beaches make Kailua-Kona the perfect tropical destination for families and couples alike. You will find over 500 vacation rentals here, ranging from affordable studios and one-bedroom condos to spacious upscale apartments, houses and villas. There is so much to see and do in Kailua-Kona. The town is the perfect place for ocean and outdoor recreational activities. If you like watersport adventures, you can go surfing, diving, boating, snorkeling and swimming. If you enjoy shopping, you will find many shops, boutiques, art galleries and restaurants in Kailua-Kona, as well as numerous historical sites. Browse through this fine selection of Kailua-Kona vacation rentals below and find your perfect home away from home.

Browse Kailua-Kona Vacation Rentals by condo/hotel name:

» Alii Cove	» Alii Lani	» Alii Park Place
» Alii Villas	» Banyan Tree	» Casa De Emdeko
» Hale Kona Kai	» Holualoa Bay Villas	» Kailua Bay Resort
» Kalanikai	» Kona Bali Kai	» Kona Bay Estates
» Kona by the Sea	» Kona Hawaiian Resort	» Kona Islander Inn
» Kona Isle	» Kona Magic Sands	» Kona Makai
» Kona Mansions	» Kona Nalu	» Kona Onenalo
» Kona Reef	» Kona Shores	» Sea Village
» Royal Kahili	» Royal Sea Cliff	» White Sands Village

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AWESOME 7TH FLOOR PENTHOUSE CONDO - OCEAN, SUNRISE & SUNSET VIEWS

Punahele Penthouse Condo will fast become your favorite place to stay in Kailua-Kona! Punahele Penthouse is on the 7th (top) floor of the Kona Ali'i Condo Complex which is located in the heart of Kailua-Kona. You're within walking distance to ...

2 bedroom
2 bathroom
Sleeps 6

91 reviews

from $425

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VERY PRIVATE, expansive ocean VIEWS, close to BEST BEACH

Guests walk in and we see wow on their faces...gourmet kitchen, ocean views, huge bedrooms.

"perfect for a family reunion"
"cool at night was just right"
"close to the best beach in Hawaii"
"your own private estate"
"amazing...

5 bedroom
6 bathroom
Sleeps 18

75 reviews

from $735

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Penthouse Unit built 2007, Across from Kahaluu Beach, Fantastic Ocean Views!

Love to snorkel and want to see over 100 species of tropical fish & turtles? Then why not stay right across the street from Hawaii's best snorkeling beach?! Our modern beachfront unit offers gorgeous ocean/sunset views and the easiest access ...

2 bedroom
2 bathroom
Sleeps 4

216 reviews

from $283

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Sunset in Paradise Oceanfront 1BR/1BA Condo at Kona Reef Fast WiFi & Central AC

Enjoy sunset views every night from this beautifully updated 1br 1ba condo steps from Downtown Kailua-Kona village with AC in both the living room and bedroom (rare!).

Sunset in Paradise is your private paradise with gorgeous ocean views ...

1 bedroom
1 bathroom
Sleeps 4

86 reviews

from $275

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Kona Reef A22 - Direct Ocean Front Condo - Private Lanai - Next to Honl's Beach!

Welcome to our beautifully decorated ocean front condo in paradise - Kona Reef A-22.

Our condo is our home away from home, so we respectfully request a maximum of 2 adult guests and no children under 18.

Whether this is your ...

1 bedroom
1 bathroom
Sleeps 2

106 reviews

from $299

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

This breathtaking 3 Bedroom plus bunkroom, 2 bath single level home is located just minutes from Kailua, Kona and some of the most beautiful beaches in Hawaii. Everything in this house is new! Fresh full remodel just completed. This includes a ...

4 bedroom
2 bathroom
Sleeps 8

138 reviews

from $708

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Stunning 5 Star Ocean View Condo with all the Amenities!

Our unit is spacious with high ceilings, ceiling fans, fabulous sunlight, and gorgeous ocean views. This elevated third story unit affords a wonderful lanai with a view overlooking manicured golf courses, tropical flowers, natural lava ...

3 bedroom
3 bathroom
Sleeps 6

82 reviews

from $384

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Magic Sands Home Steps From The Beach. Air Conditioned. No Cleaning Fee!

Welcome to this wonderful 3 bedroom / 2 bathroom duplex home only a 3 min walk from Magic Sands Beach. Just remodeled and professionally decorated, this charming vacation getaway has all of the comforts you desire in your home away from home, ...

3 bedroom
2 bathroom
Sleeps 7

90 reviews

from $406

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

*** For more details and more pictures, go to our website at BIGWAVEHAWAII•COM***

The Big Wave Penthouse is arguably in the best location on the Big Island. Consider this:

• Facing west, you're guaranteed a front-row seat every...

2 bedroom
2 bathroom
Sleeps 6

162 reviews

from $395

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Kona Condo at Magic Sands Beach-Ocean Views-Top Floor-Quiet

Aloha and welcome to our condo at White Sands Village. Brand new to the rental market, this wonderfully appointed 2-bedroom, 2-bathroom top floor condo offers everything you’ll need to enjoy your stay in Kailua-Kona and the Big Island Of ...

2 bedroom
2 bathroom
Sleeps 6

74 reviews

from $291

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Oceanfront Condo, Free 5G Wi-Fi, King Bed, Hot Tub/Pool

Was recently completely remodeled.
Our oceanfront condo is 23ft. from the ocean and is located on the 2nd floor and offers spectacular sunsets.
Watch the surfers and the dolphins from your lanai.
A Short walk to town and over 20 ...

1 bedroom
1 bathroom
Sleeps 2

203 reviews

from $269

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Beautiful ocean view, close to town and beaches!

Guests are sure to treasure a memorable vacation experience in our active and friendly neighborhood. We have a 2 story home and offer our comfortably furnished lower level 2 bedrooms/1 bath, with ceiling fans throughout, and free WI-FI. The ...

2 bedroom
1 bathroom
Sleeps 4

9 reviews

from $215

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Stunning, Romantic Cottage on Slope of Hualalai

On the Kona side, safe and away from the volcanic activity, the Cottage awaits you.

The perfect, peaceful getaway for those on a honeymoon or looking for a relaxing, romantic experience. This warm, welcoming, newly-built and finely ...

1 bedroom
1 bathroom
Sleeps 2

178 reviews

from $261

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Private Cottage In The Rain Forest TA065882726401

Cozy, private rain forest retreat cottage situated above Kona in the Kaloko Mauka Honua'ula Forest Reserve. Located on a 3-acre property, this cottage is set away in a lush forest of Ohia trees and Hapu'u tree ferns. Enjoy the sweet aroma of ...

1 bedroom
1 bathroom
Sleeps 2

99 reviews

from $160

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Red Ginger Garden Studio

Peaceful, well appointed room with private entrance ,down a flight of stairs, overlooking our back yard garden of fruit trees and red ginger blooms. Private bath with shower, queen bed, walk in closet, kitchenette, outdoor seating; Wake up and ...

1 bedroom
1 bathroom
Sleeps 2

104 reviews

from $138

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Wonderful Ocean View –Totally Renovated-On Golf Course

STVR-19-358846 - Relax and pamper yourself in luxury in this well-appointed condo. On the golf course with Spectacular Ocean views. This is NOT your average condo rental! This condo has had an extensive high-end renovation and interior ...

2 bedroom
2 bathroom
Sleeps 4

80 reviews

from $190

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OCEANFRONT BEACH HOUSE WITH SUNSET VIEWS AND PRIVATE POOL

Kona Bay Estates is a gated and patrolled oceanfront community. The Sunset Beach House offers 2700 square feet of luxurious space. It is just 500 meters from the sea. Opening walls of glass offer indoor-outdoor living with spectacular views of ...

3 bedroom
4 bathroom
Sleeps 8

100 reviews

from $1,100

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Your Hawaiian vacation starts here!

Kona Shores is a great location right on Alii Drive, a Hawaii Scenic Byway (Ala Loa Foot Trail). A lovely complex with an oceanfront pool & BBQ area for easy island living! Ground floor, end unit with easy access to Alii Drive and just one mile ...

0 bedroom
1 bathroom
Sleeps 4

134 reviews

from $118

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Your Hawaiian Vacation Starts Here! II

Kona Shores is a great location right on Alii Drive (Hawaii Scenic Byway). A lovely complex with oceanfront pool & BBQ area for easy island living! Ground floor with easy access to Alii Drive and just one mile to downtown Kona, shopping, ...

0 bedroom
1 bathroom
Sleeps 4

145 reviews

from $116

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Hualalai Haliipua Villa 104 - Spectacular Sunset Views + Newly Renovated 2023

Haliipua Villas are the newest generation of multi-family villas at Hualalai offering an array of designer finishes throughout the home. Special features include luxurious mahogany finishes, island-inspired ceiling treatments, enhanced ...

3 bedroom
4 bathroom
Sleeps 6

5 reviews

from $1,943

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Hualalai Waiulu Villa 137D ~ inmaculate & spacious with great views

This spacious 3 bedroom, 3.5 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 2642 square feet ...

3 bedroom
4 bathroom
Sleeps 6

15 reviews

from $1,700

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Hualalai Palm Villa130A ~ stunning sunset views~signature garden shower

One of the largest floor plans of any villa at Hualalai, this spacious and centrally located 3 bedroom, 3 bath villa is ideal for your Hawaii getaway. Extra bedding available with a "bonus" living room on the first level. The down-stairs suite ...

3 bedroom
3 bathroom
Sleeps 6

26 reviews

from $1,795

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Hualalai Palm Villa 140C~popular townhome on the 15th Fairway~2 golf carts

The spacious floor plan includes a downstairs master bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and ...

3 bedroom
3 bathroom
Sleeps 6

21 reviews

from $1,593

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OCEAN VIEWS* LUXURY AND LOCATION AT HUALALAI RESORT TWO GOLF CARTS

Located in the Award Winning Resort Community of Hualalai Four Seasons.

Enjoy the sounds of the ocean serenade, the magic of sunsets, and whale watching during the winter months, from this recently updated garden level Hillside Villa. ...

3 bedroom
3 bathroom
Sleeps 6

8 reviews

from $1,850

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Keauhou Convenience, Ocean Views, Newly Renovated, AC in Bedrooms, Wrap-Around Lanai

Welcome to Keauhou Lani, an exquisite private residence located in the desirable gated community of Keauhou Estates.

Step into the grand entry of Keauhou Lani's 4 bedroom, 3.5 bathrooms, 4,750 sq. ft. home plus, 1,700 sq. ft. covered ...

4 bedroom
4 bathroom
Sleeps 8

75 reviews

from $899

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Beautiful Estate Home at Hualalai Resort Luxury Views Location 3 Golf Carts**

Gorgeous, Contemporary, Newer Home Exemplifies Luxury and ease of Living in our Island Paradise. This 5-bedroom, 5 1/2 bath pod-style estate home is exceptionally appointed and designed to take full advantage of the temperate climate and island ...

5 bedroom
6 bathroom
Sleeps 10

4 reviews

from $4,952

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Hualalai Fairway Villa 116C - NEWLY Renovated, 2 golf carts, BEST LOCATION.

Newly renovated villa from top to bottom. A 3 bedroom, 3.5 bath luxury villa conveniently located in the heart of Hualalai Resort overlooking the 15th hole of the Jack Nicklaus designed Hualalai Golf Course. Ground floor single level floor plan ...

3 bedroom
4 bathroom
Sleeps 6

13 reviews

from $1,900

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🏖️Ocean View | Private | AC | Child Friendly | Salt Water Pool | vrKCV

vrKCV - Hawaiian Honu House, Professionally Managed by Kona Coast Vacations

Hawaiian Honu House is a winner in so many ways. This updated home is fully air conditioned, with individual temperature controls for each bedroom. This is the ...

3 bedroom
2 bathroom
Sleeps 6

72 reviews

from $521

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Live Aloha! Pacific View, Lanai and Laundry-Kanaloa

Kanaloa at Kona #2203: Inside, you’ll find a bright living area with generous seating and a large flat screen television, perfect for entertaining your friends and family! The suite’s full size galley kitchen has Koa wood cabinetry, ...

2 bedroom
2 bathroom
Sleeps 4

12 reviews

from $300

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Central A/C Double Master Suite Home in the Exclusive Ali'i Point community!

Exquisite 2-bedroom, 2.5 bath house located in a private gated community on Ali'i Drive! With only 16 homes in this community, you can expect peace and serenity staying here on your Hawaiian vacation.

Featuring an air-conditioned home ...

2 bedroom
3 bathroom
Sleeps 6

18 reviews

from $350

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