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Latest Vacation Rentals in Kailua Kona HI (25)

2 Br Condo Vacation Rental In Kailua Kona, Hawaii

Welcome to Keauhou Kona Surf & Racquet Club, Unit #3-202! This beautiful, DIRECT oceanfront condo is Hawaiian Living at it's finest! Hear the ocean directly from the living room, lanai, and master...

Created Jul 20, 2026

1 Br Hotel Vacation Rental In Kailua-kona, Hawaii

Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell...

Created Jul 20, 2026

5 Br Private Vacation Home Vacation Rental In Kailua-kona, Hawaii

Summary:Discover the ultimate family retreat in Kailua-Kona! This exquisite 5-bedroom house boasts a private pool, sauna, and stunning ocean views. Enjoy luxurious amenities, from the chef's...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua-kona, Hawaii

Welcome to your perfect island getaway in Kailua-Kona! This beautifully updated condo is just 2 blocks from the beach and 1 block from the vibrant restaurants and shops along Ali'i Drive, putting...

Created Jul 20, 2026

2 Br Apartment Vacation Rental In Kailua-kona, Hawaii

Welcome to Living on Island Time your private retreat on the Kona Country Club Golf Course with sweeping ocean and fairway views. Watch sunsets over the Pacific right from your lanai, just minutes...

Created Jul 20, 2026

3 Br Hotel Resort Vacation Rental In Kailua-kona, Hawaii

Get ready for the ultimate family escape to paradise at Wyndham Kona Hawaiian Resort on the breathtaking Big Island of Hawaii! Nestled along the stunning Kona coastline, this family-friendly resort...

Created Jul 20, 2026

2 Br Condo Vacation Rental In Kailua-kona, Hawaii

Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.With the ocean just a short walk away, this condo is the perfect home base for all your vacationing needs. Inside...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua-kona, Hawaii

Summary:Amazing oceanfront condo with hot tub, pool, W/D, & grill - gorgeous ocean viewThe Space:Sail away to this ideally located, oceanfront Hawaiian condo! Here, you'll be just a few steps away...

Created Jul 20, 2026

1 Br Hotel Resort Vacation Rental In Kailua-kona, Hawaii

Featuring a private balcony, this one-bedroom villa features a fully equipped kitchen, dining room, living room with a TV and DVD player, and in-room laundry facilities. The private bathroom...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua-kona, Hawaii

Island Serenity at WorldMark Kona Spacious 1BR Suite with Lanai Product Description 1 Bedroom 1 Bath Multiple Beds Sleeps 4 Located in an area once regarded by King Kamehameha as one of the most...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua Kona, Hawaii

Welcome to Hale Kona Kai 211. This charming one-bedroom Kona vacation rental offers stunning lagoon and partial ocean views. With a layout of 576 square feet, Hale Kona Kai 211 comfortably...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua Kona, Hawaii

E-24 at the Kona Isle is a high in demand Direct Oceanfront Corner End Unit on the 2nd Floor of Building E. This gorgeous condominium has jaw dropping ocean & sunset views from your Lanai. Enjoy...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua-kona, Hawaii

Lovely condo! Tile in Kitchen, dining and bath areas. The unit is approximately 850 SF. It is best suited for 4 but can accommodate up to 6. It is completely turnkey and furnished, ready for your...

Created Jul 20, 2026

2 Br Condo Vacation Rental In Kailua-kona, Hawaii

This beautiful condo is located in the heart of downtown Kailua-Kona. Two bedrooms with private baths, and king size beds and flat screen TV. The loft bedroom opens to the private sun deck with...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua-kona, Hawaii

Summary:Updated 2nd-floor condo in heart of Kona with lanai, pool, grillsThe Space:This nicely updated, second-floor condo (no elevator) is in the heart of Kailua-Kona and is perfect for a romantic...

Created Jul 20, 2026

4 Br Private Vacation Home Vacation Rental In Kailua Kona, Hawaii

Important Resort Notices* Please note that the annual Chairman's Club Event will take place at the Four Seasons Resort at Hualalai from Monday, November 30 through Saturday, December 5, 2026....

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Kailua-kona, Hawaii

Welcome to our charming 2-bedroom vacation home in Kalaoa! Nestled just a short 11-minute drive from the vibrant Kailua Pier, this property offers the perfect blend of comfort and convenience for...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua Kona, Hawaii

vrKCV - Sea Village 4104, Professionally Managed by Kona Coast VacationsTrue Oceanfront Kona Condo | Ground Floor, No Stairs | Sunset Views Front-row sunsets. Unobstructed ocean views. Easy ground-...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua Kona, Hawaii

Kona Makai#1-103 is one of the best located ground floor units in the entire complex! Being 2 units away from the very west ocean end of building 1, the location is undeniably too perfect. This...

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Kailua-kona, Hawaii

Aloha Spirit is a 2 bedroom, one bathroom town-home, with living area and kitchenette (refrigerator, toaster oven, and microwave- no oven or stove). It is located on the bottom floor and accessed...

Created Jul 20, 2026

3 Br Condo Vacation Rental In Kailua-kona, Hawaii

Aloha!Welcome to Pineapple Place Reimagined! Our 2 bed 1 bath condo in lovely Kona sleeps 6, with access to an amazing oceanfront pool! In fact we just learned its the only residential ocean front...

Created Jul 20, 2026

2 Br Private Vacation Home Vacation Rental In Kailua Kona, Hawaii

This ideally-located, 2-bedroom, 2-bath ocean view villa is the perfect size and features beautiful ocean, golf course, and sunset views and sleeps up to 4. Beach access and all of the resorts...

Created Jul 20, 2026

3 Br Condo Vacation Rental In Kailua-kona, Hawaii

Welcome to your home in paradise! Feel the peaceful trade winds and soak in the island atmosphere from this beautifully remodeled 2-bedroom townhome with bonus loft bedroom at the renowned Kona...

Created Jul 20, 2026

1 Br Condo Vacation Rental In Kailua-kona, Hawaii

Escape to this delightful condo in picturesque Kailua-Kona. This cozy retreat features a bedroom with a comfortable bed and a charming living room with a sofa bed for additional guests. Enjoy...

Created Jul 20, 2026

2 Br Condo Vacation Rental In Kailua Kona, Hawaii

Keauhou Kona Surf & Racquet Club#5-104 DIRECT OCEANFRONT, BEST GROUND FLOOR CORNER! REMODELED!AMAZING PROPERTYAIR CONDITIONING AVAILABLE IN CONDO NOW! Welcome to unit #5-104 at the Keauhou Kona...

Created Jul 20, 2026

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