Kailua-Kona Vacation Rentals

Come explore the Big Island of Hawaii and stay in one of our many Kailua-Kona villas, condos, or houses. Stay oceanfront or just minutes from the beach. Bring the family to the Pacific coast and vacation in one of the many resorts located on the Hawaiian coast. Enjoy a large array of guest popular resort-style amenities and all the natural beauty of the Kailua-Kona.

Select from a range of 2 to 5 bedroom rentals that are ready to accommodate large families to intimate romantic getaways. Filter by properties with pool access, hot tubs, or by location on the island. There is always a place to stay in Kailua-Kona on the Big Island of Hawaii, book yours today.

Browse from our selection below or check out the rest of Big Island vacation rentals for more vacation options.

43 properties available

Very spacious with 1704 sq.ft of living, one bedroom downstairs with a queen bed, 36 inch flat screen TV/DVD player, full bath, full sized washer and dryer, gourmet fully stocked kitchen with custom Italian cabinetry and granite counter tops, plus dining and living space with a 42 inch flat screen TV, DVD player and entertainment center.Upstairs is

Luxury at Na Hale O Keauhou #N1

Townhouse | Kailua-Kona

As low as $165^.00 per night

We provide 2 beach chairs and 1 cooler for guest use. Beach towels are available for guests.In alignment with its coastal neighborhood, this home is designed to feel bright and energetic while also feeling laid-back. The living room combines cozy couches with colorful artwork and smart tv to create a space for unwinding between excursions and days

Kona Mansions | 5-minute Walk to Honl’s Beach

Kona Mansions | 5-minute Walk to Honl’s Beach 2

Kona Mansions | 5-minute Walk to Honl’s Beach 3

Kona Mansions | 5-minute Walk to Honl’s Beach 4

Kona Mansions | 5-minute Walk to Honl’s Beach 5

Kona Mansions | 5-minute Walk to Honl’s Beach 6

Kona Mansions | 5-minute Walk to Honl’s Beach

Condo | Kailua-Kona

As low as $75^.00 per night

This unit is a 1 bedroom, 1 bathroom ocean view condominium capable of accommodating up to 3 guests. Vacationers on this Big Island of Hawaii getaway will find themselves in an ideal location for several activities. Right across Alii Drive is Honl's Beach, a well-known option for surfers and a great spot to walk along the white sand. A short dri

Kona Mansions | Ocean Views & Amenities!

Kona Mansions | Ocean Views & Amenities! 2

Kona Mansions | Ocean Views & Amenities! 3

Kona Mansions | Ocean Views & Amenities! 4

Kona Mansions | Ocean Views & Amenities! 5

Kona Mansions | Ocean Views & Amenities! 6

Kona Mansions | Ocean Views & Amenities!

Condo | Kailua-Kona

As low as $75^.00 per night

Step into old Hawaiian charm inside this newly designer decorated cottage situated on one of Hawaii's prime oceanfront locations on Ali'i drive! This charming property offers a home-style feeling with a spacious comfortable interior and gorgeous oceanfront exterior setting perfect for lounging, dining, or simply taking in the ocean activities. Plea

Oceanfront Cottage in Kailua-Kona

House | Kailua-Kona

As low as $141^.00 per night

This elegant, one-of-a-kind Hawaiian estate within the exclusive gated community of Keauhou Estates features its own private natural-style saltwater pool and relax in a warm spa tub with gentle water flow. Our saltwater pool has a natural Hawaiian finish designed to blend with the landscape, giving it a lagoon-style appearance rather than the brigh

Hale Nene | Pool, Spa Tub & Ocean Views!

Hale Nene | Pool, Spa Tub & Ocean Views! 2

Hale Nene | Pool, Spa Tub & Ocean Views! 3

Hale Nene | Pool, Spa Tub & Ocean Views! 4

Hale Nene | Pool, Spa Tub & Ocean Views! 5

Hale Nene | Pool, Spa Tub & Ocean Views! 6

Hale Nene | Pool, Spa Tub & Ocean Views!

House | Kailua-Kona

As low as $375^.00 per night

This home is located in the desirable gated community of Keauhou-Kona Surf and Racquet Club and includes exciting onsite amenities such as tennis courts, a large swimming pool, and BBQ areas. You’ll also be close to many popular local destinations outside of the community. Kahalu’u Beach Park is just a short walk away as is the Keauhou Shopping Cen

Plan Your Hawaii Vacay at Grace's Oasis!

Plan Your Hawaii Vacay at Grace's Oasis! 2

Plan Your Hawaii Vacay at Grace's Oasis! 3

Plan Your Hawaii Vacay at Grace's Oasis! 4

Plan Your Hawaii Vacay at Grace's Oasis! 5

Plan Your Hawaii Vacay at Grace's Oasis! 6

Plan Your Hawaii Vacay at Grace's Oasis!

Condo | Kailua-Kona

As low as $125^.00 per night

There’s a community pool, surrounded by swaying trees and verdant foliage. Relax in the outdoor hot tub, and lounge on day beds. Make most of the well-stocked fitness center. The home is surrounded by sprawling manicured lawns, with a sizzling BBQ and a 6-seater al-fresco table on your private tiled lanai. The living room is bright and airy, with

Na Hale O Keauhou | Beach Views, Hot Tub & Pool

Na Hale O Keauhou | Beach Views, Hot Tub & Pool 2

Na Hale O Keauhou | Beach Views, Hot Tub & Pool 3

Na Hale O Keauhou | Beach Views, Hot Tub & Pool 4

Na Hale O Keauhou | Beach Views, Hot Tub & Pool 5

Na Hale O Keauhou | Beach Views, Hot Tub & Pool 6

Na Hale O Keauhou | Beach Views, Hot Tub & Pool

Townhouse | Kailua-Kona

As low as $200^.00 per night

Sit back and relax on your own private ocean front lanai and take in some of the best views on the Kona Coast. 2 bedrooms 2 full baths, one king bed, 1 queen are included in this spacious condo that boasts ocean views from every room. Central A/C, Sony TV, DVD, wireless internet available and a well appointed kitchen are just a few of the wonderful

Kona Reef #D31 | Lanai w/ Coastal Views 2

Kona Reef #D31 | Lanai w/ Coastal Views 3

Kona Reef #D31 | Lanai w/ Coastal Views 4

Kona Reef #D31 | Lanai w/ Coastal Views 5

Kona Reef #D31 | Lanai w/ Coastal Views 6

Kona Reef #D31 | Lanai w/ Coastal Views

Condo | Kailua-Kona

As low as $150^.00 per night

Guests staying in this romantic vacation rental will find themselves in an ideal location for all Hawaiian experiences. A leisurely stroll across Alii Drive takes you to the famous Magic Sands Beach and exquisite Magics Grill Restaurant, less than 100 feet away. Restaurants, shops, a golf course, and the pier are all within easy access on Alii Driv

Kona White Sands A4 | Romantic Ocean View!

Kona White Sands A4 | Romantic Ocean View! 2

Kona White Sands A4 | Romantic Ocean View! 3

Kona White Sands A4 | Romantic Ocean View! 4

Kona White Sands A4 | Romantic Ocean View! 5

Kona White Sands A4 | Romantic Ocean View! 6

Kona White Sands A4 | Romantic Ocean View!

Condo | Kailua-Kona

As low as $75^.00 per night

Located directly across the street from Magic Sands Beach and La'aloa Beach Park, enjoy this 2 bedroom, 2 bath condo with partial ocean views from the large lanai and both bedrooms. The unit features a King Size bed in the master, twin beds in the second bedroom (can be converted to King upon request at time of reservation, for a small fee), 49" Sa

White Sands Village #222 Across from Beach

White Sands Village #222 Across from Beach 2

White Sands Village #222 Across from Beach 3

White Sands Village #222 Across from Beach 4

White Sands Village #222 Across from Beach 5

White Sands Village #222 Across from Beach 6

White Sands Village #222 Across from Beach

Condo | Kailua-Kona

As low as $150^.00 per night

This vacation rental is perfect for a small family or group of friends as it can house up to 4 guests with 1 bedroom and 2 bathrooms. The home features ocean views and easy access to town. Great restaurants and shops are all within walking distance. Hale Halawai Park (this is maybe a 5-minute walk away, but not an actual park someone would hang out

Kona Alii | Oceanview Pool Shops & Restaurants

Kona Alii | Oceanview Pool Shops & Restaurants 2

Kona Alii | Oceanview Pool Shops & Restaurants 3

Kona Alii | Oceanview Pool Shops & Restaurants 4

Kona Alii | Oceanview Pool Shops & Restaurants 5

Kona Alii | Oceanview Pool Shops & Restaurants 6

Kona Alii | Oceanview Pool Shops & Restaurants

Condo | Kailua-Kona

As low as $75^.00 per night

Banyan Tree #305 features bamboo wood flooring and freshly painted interior, along with a spacious and well laid out floor plan, making this unit an ideal choice for families or couples. The living room has comfortable seating placed around a flat screen TV. Wifi is also provided for your convenience. Gather around for your favorite show at the end

Banyan Tree Condo W/ Pool & Ocean Front!

Banyan Tree Condo W/ Pool & Ocean Front! 2

Banyan Tree Condo W/ Pool & Ocean Front! 3

Banyan Tree Condo W/ Pool & Ocean Front! 4

Banyan Tree Condo W/ Pool & Ocean Front! 5

Banyan Tree Condo W/ Pool & Ocean Front! 6

Banyan Tree Condo W/ Pool & Ocean Front!

Condo | Kailua-Kona

As low as $150^.00 per night

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