Kailua-Kona Vacation Rentals

Kailua-Kona is a lively town on the Big Island's west coast, offering a mix of oceanfront relaxation, cultural landmarks, and vibrant dining and shopping. Popular beaches like Magic Sands, Kahalu'u Beach Park, and Honl's Beach provide excellent snorkeling and sunsets. Our curated vacation rental selection includes oceanfront condos, resort-style communities, and private homes - perfect for couples, families, or group travelers. Enjoy amenities like pools, lanais, and proximity to Ali'i Drive attractions. Start your Big Island adventure in Kailua-Kona today.

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Hualalai Fairway Villa 104D - overlooking the 15th tee

Upper level 2-bedroom, 2-bath villa overlooking the 15th tee of the Hualalai Golf Course with stunning Mauna Kea, Island of Maui and horizon views of the ocean. Designed by Honolulu-based Architect Warren Sunnland, the Fairway Villas at Hualalai are located within a...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Hualalai Waiulu Villa 137D

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 of living space and a 414...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kailua-Kona, Hawaii

Oceanfront Kailua-Kona Home, Walk to Kahaluu, Wifi & AC

Welcome to Hale Lula o' Nai'a – "House of the Dolphins" – your oceanfront retreat on scenic Alii Drive!Ideally situated just north of Kahalu'u Beach Park in Kailua-Kona, this prime location offers easy access to surfing, paddle boarding, and snorkeling.Designed for...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Surfers & Sunsets-Kona Reef Ocean Front Unit

Watch the Surfers from Your Lanai - Kona Reef Ocean Front UnitLight and Airy with direct Ocean Views from the Lanai, Living and Kitchen areas. Large Ocean Front 611 square foot condo with a full 128 square foot Lanai. This fully equipped Ocean Front 3rd floor condo is...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua-Kona, Hawaii

Kona Hillside Estate - Gated Property with Lap Pool

Welcome to our family's private gated estate located on the beautiful hillside of Hualalai mountain in Kailua-Kona. We recently renovated our 4,000 SF home and enjoy hosting guests when we have availability since 2022.Guests will appreciate soaring ceilings, open living...

🛏 7 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 19
📍 Kailua-Kona, Hawaii

AMAZING OCEAN VIEW Popular White Sands Village Steps To The Beach!!!

Hale Lihi LaniOcean View Vacation Rental at White Sands Village. We are located 4 miles south of charming Kailua-Kona Village and directly across from Kona's spectacular Magic Sands Beach. You will enjoy beautiful ocean views and dreamy sunsets from our large covered...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua-Kona, Hawaii

Partial Ocean View 2 Double Beds at Outrigger Kona Resort and Spa

Your adventure to the Kona Coast starts at this oceanfront Big Island property, just steps away from the sun, sand, and surf. Guests will enjoy spectacular dining options, including a waterfront restaurant and poolside bar. The on-site spa and fitness center offer a...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Kona Acres Vacation Home

This vacation home is your destination if you desire privacy, have a family or want a laid-back vacation. This luxury home is ideal for large family gatherings. The house is located on a secluded one-acre, tropically landscaped lot in a quiet, quality Hawaii...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Fabulous Kona Reef Resort Ocean Front - Penthouse Floor - 2 BR/2 BA Condo

This fully air-conditioned beautiful oceanfront corner unit is less than 30 feet from the water's edge. Enjoy spectacular sunsets from your large lanai, watch the surfers, para-sailers, boogie boarders, playful dolphins, turtles, whales and passing cruise ships.Fall...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua-Kona, Hawaii

Alii Villas #332 On Ocean Fantastic View. Watch Dolphins, boats and canoes go by

Come enjoy a fabulous time in an ocean front property in Kailua-Kona Hawaii. This unit is a 2 bedroom, 2 bath home at a premier location at Ali'i Villas. The décor of this unit has been done in cool coastal and has just been remodeled top to bottom. Shoji screens can...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Konas#1Rated Oceanfront Pool4 Bdrm Home Walk2Town Ironman Thanksgiving Christmas

Location Location Location!! VRBO 496440 Happy Wahoo Wednesday, we have some great dates available! The Ironman buoy is right in front of the house and is also a Spinner Dolphin magnet as the buoy attracts little bait fish! Fish eat fish and we also have a resident...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

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 decoration including art from...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Updated 2-bed, 2-bath White Sands unit with ocean views, AC & modern amenities

Turn moments into memories at the iconic White Sand Village unit #301. This beautifully, fully-remodeled, and refurnished property is everything the luxury traveler is looking for. You have a front-row view of Magic Sands in this two-bedroom, two-bathroom corner unit...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

Gorgeous and high end 4 bedroom plus bonus (sleeping) loft, located in prime gated community, sleeps 12. Very large landscaped yard, fantastic ocean view, central A/C, plunge pool, top appliances (sub zero) granite kitchen beautiful bedrooms, fabulous artwork and only a...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 12
📍 Kailua-Kona, Hawaii

Prime Oceanfront Kona Reef Vacation Condo - D Building

Location, Location, Location - Oceanfront - D Building.Direct View through Towering Palms into Kailua Bay.Watch the Dolphins, Whales, Parasailers, Surfers and Beautiful Hawaiian Sunsets from your Oceanfront Lanai.Listen to the soothing sounds of the ocean and feel the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua-Kona, Hawaii

Your Tropical Kona Retreat - Breezy Condo Steps from Beach

The perfect blend of comfort and convenience. Shaded by palm trees and on the second floor, the light breeze keeps the temperature perfect. The one bedroom/one bathroom unit features a fully stocked kitchen, private lanai with garden view, and a dedicated parking spot....

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Spacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona

Introducing Akela Ka Hale Kai, affectionately known as Lucky 42 at Kona Bay Estates.Experience unmatched relaxation with our special spring rate beginning at $1649 per night (N++). Delve into a serene seaside retreat, where every aspect is designed with your utmost...

🛏 5 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

Ocean Views ! Excellent Proximity to Hualalai Resort Amenities ! Includes Golf Cart

Located in the Award Winning Resort Community of Hualalai Four Seasons.Beautiful ocean views from this delightful two bedroom Garden Level Villa. Spacious Lanai with lounge seating extends seamlessly to a large lawn area. Enjoy the sounds of the ocean and glances of the...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Exceptional Oceanfront Luxury Condo - Fully updated, AC, Top Floor, Quiet

Absolute direct oceanfront top floor, two-bedroom condo located in the heart of Kailua-Kona, Hawaii.Step inside and take in stunning ocean views from your private balcony—welcome to paradise!AC in all spaces, fully updated with high-quality furnishings throughout.From...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Kahalu’u Surf and Snorkel Beachfront Paradise, with Hot Tub

Incredible views of the bay and surfers! Modern house(built 2014) with A/C, across the street from Kahalu’u Beach. This is the BEST snorkeling and surfing in Kona. Surfboards,The Kona Trolley stop, and food trucks are steps away. The house has a hot tub, 4 bedrooms,...

🛏 4 Bedrooms
🛁 1 Bathroom
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

Jungle Retreat in Kona Cloud Forest Sanctuary, An unforgettable Cloud Forest Sanctuary retreat exper

Wake up in your cozy private jungle retreat immersed in the lush serenity of the Kona Cloud Forest Sanctuary. During your stay in our Sanctuary, experience our guided forest tours, yoga, sound baths, and more. Enjoy a morning walk for fresh brew and coffee tours at...

🛏 5 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

Kailua-Kona Condo w/ Pool & Ocean Views

A tropical Hawaiian getaway awaits your arrival at this updated Kona Coast condo perched above Keauhou Bay! Upon entering the unit, guests of this 2-bed, 2-bath property are treated to a quintessential island experience with a contemporary flair. Whether guests spend...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

🌊 EPIC Oceanfront Condo at Hale Kona Kai #403, TOP FLOOR, ELEVATOR, CENTRAL AC 🐬

Aloha and welcome to HONU HIDEAWAY at Hale Kona Kai #403. This is the absolute destination should you want a relaxing vacation getaway on the Kona coast. The location of this condo complex adds convenience as fun activities and amenities are within walking distance. The...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua-Kona, Hawaii

Sept-Oct Special! 1,800! Hualalai Four Seasons 5-Bedroom House Close to Resort

"Ka Hale Ulu Le'a" means "House of Happiness" in Hawaiian, and this is the feeling you experience when entering this Hualalai property.This 5-bedroom, 5 Bathroom Family Oasis sleeps 10 for the ultimate family getaway, in a prime, close-in location at the exclusive Four...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

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 the ocean and a private...

🛏 3 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Wyndham Kona Hawaiian Resort

Please note, that some holiday weeks require a seven-night stay, please confirm with an agent. Prime weeks and holiday weeks have higher rates, your agent will send you an initial quote based on the dates you have chosen.Thank you for choosing Dash Realty Group of...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua-Kona, Hawaii

Tranquil Keauhou Resort Condo with Ocean View & Resort Amenities

Escape to paradise at Keauhou Resort Condo 139, a charming 1-bedroom retreat in Kailua-Kona, Hawaii. This beautifully updated condo offers a peaceful getaway with no neighbors above or below, ensuring privacy and tranquility. The inviting living room features high open...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Cozy 1-bedroom with AC and WiFi in enjoyable Kailua-Kona

Welcome to Hale Kai Hideaways, Bungalow A. Vacation at this cute apartment centrally located in the heart of Kona. Alii Garden's open-air marketplace is a five-minute walk, where you will find Shaka's tacos, local coffee & tons of souvenirs. Turtles Beach, a local...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua-Kona, Hawaii

Kona Penthouse 2 Bedroom: Relax and Unwind Aloha Style

Top-floor Kona retreat with stunning ocean views!This 2,000 sq. ft. unit features one king-size and one queen-size bed, hosting up to 4 guests. Perfectly located near downtown Kona's restaurants, shops, and farmers market, tucked in a family-friendly neighborhood. Fully...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Oceanfront - Kanaloa at Kona - Newly Remodeled

OCEANFRONT CONDO - As Kona residents for 25 years, our desire is to share ALOHA. This is your opportunity to Experience Tropical Paradise, spectacular sunsets year-round, spouting whales in winter, and frolicking dolphins. This secluded and prestigious 18 acre Resort is...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Oceanfront Luxury Home with Beach Access and Private Pool - 5 bed/5 bath

Perfect for Families and Large Groups!Overlooking the dramatic Kona Coast, an oceanfront Oasis; sits Mele Kai — a luxurious island sanctuary welcoming guests in search of unforgettable memories and warm Hawaiian hospitality on Hawaii’s Big Island. Oceanfront suites...

🛏 4 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

Oceanfront Living at Luxurious Mermaid Manor in Kailua-Kona, Hawaii

Welcome to your oceanfront home in the heart of Kailua-Kona! At Mermaid Manor, the ocean is literally your backyard—no road, no fences, just lava rocks and tidepools steps from your door. While some homes across the street may say "oceanfront," we invite you to truly...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Hale Hina ~ Private, Peaceful, Perfection!

Welcome to Hale Hina - The Home of the Hawaiian Goddess of Sunrises, Sunsets, Coral Reefs, and the Moon! Our home is very special, and has many fabulous features and amenities, including the most important and maybe the most intangible one: Hale Hina is our vacation...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Stunning Ocean View Beach Front Villa at Kahaluu

Enjoy this resort quality 2 bed 2 bath Penthouse condo with exceptional ocean views across the street from Kona's famous Kahalu'u Beach. Relax in the sand, learn to surf, snorkel with the turtles and tropical fish. All this is just steps away from your door.- Beautiful...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Gorgeous remodeled condo Oceanfront! SUNSET! <br>

Elegance on a budget! This quiet third floor end unit has spectacular ocean views from throughout the condo. Our air-conditioned condo overlooks the beautifully manicured grounds with unobstructed ocean views. The kitchen has concrete countertops and top-end appliances....

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua-Kona, Hawaii

Private Pool. Fully Air-conditioned .

This home is new on the rental market. Previously, it was reserved for our family use only. It has been completely refurbished this year. It is the perfect getaway for those that would like their private pool and is located in a peaceful subdivision close to all the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua-Kona, Hawaii

Permitted Luxury Home, Stunning Views, Heated Pool, Perfect Location!

Luxury Home with the Best Views on the Kona Coast (Big Island of Hawaii). We have a STVR (short term vacation rental) permit issued by the County of Hawaii. You'll love our large, heated pool with travertine decking around the pool for the ultimate luxury. Cooks dream...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 10
📍 Kailua-Kona, Hawaii

Keauhou Gardens - Top Floor Hideaway

Spacious top floor condo offering a nearly 180 degree ocean view from a large private lanai overlooking a free form pool and spa tub with lava waterfall.This roomy 1600 square foot unit is newly air conditioned and features a condo wide glass wall opening the generous...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Private home at Hualalai Resort, near Four Seasons. Pool, Spa, Exclusive!

This beautiful and meticulously maintained home situated on the 9th hole of Hualalai's Jack Nicklaus golf course with Pacific Ocean views is available for private rentals. Perfectly located, the home is just a short walk or golf cart ride (two golf carts provided) to...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Kailua-Kona, Hawaii

Stunning Pool with Ocean View From Private Lanai 1200' Above Sea Level!

Relax and unwind in this NEW 2 bedroom, 1 bath property in the lower, self contained level of a two story home.Your complete privacy is assured as you have the entire lower level to yourself with your own private lanai (400 sq ft) and no internal stairway to the unit...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Kailua-Kona, Hawaii

Waiulu Tropical Sanctuary: A Luxury Oceanview Estate at Hualalai

Imagine waking in the primary suite of Waiulu Tropical Sanctuary, where collapsible walls vanish to reveal ocean breezes and poolside serenity—a magical start to your Hualalai escape. Masterfully redesigned by Henderson Design Group, this 4-bedroom estate, with a...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Stunning Ocean View In Luxury Home In Keauhou Estates

Enjoy spectacular 180-degree ocean views from this 3 bedroom, 3700 square foot luxury home in Keauhou Estates on the Big Island of Hawaii. The house has an open floor plan, marble floors throughout most of the main living spaces, and large rooms with tasteful and...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

Large 3-bedroom condo in Kona Coast Resort with AC, WiFi, fitness room - NEW!

Kona Coast Resort #1-301 is a 3 bedroom, 2 bath condo with fantastic ocean views and all of the amazing amenities of a 5-Star Resort! Enjoy two swimming pools, three spas, a sauna, a playground, tennis/pickle-ball courts, volleyball courts, and two fitness centers.Relax...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua-Kona, Hawaii

Experience luxury near golf courses, 4 mins to Four Seasons Resort

STVR-19-357988 https://tours.spaces.808.com/1759448 Luxury living can be found at this spectacular 4 bedroom, 4.5 bath, resort home. Located within the Four Seasons Resort Hualalai on the Big Island of Hawaii. The gourmet kitchen is fully equipped with high-end...

🛏 4 Bedrooms
🛁 1 Bathroom
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

View of Mauna Kea in Gated Community across from Golf Course

Quiet & Private 1 King bed/1 Twin daybed/1 bath kitchenette (attached to main house) w/ separate entrance & patio ~600 sqft in secluded & gated community at a cool 2400 ft elevation. Wake up to beautiful views of Mauna Kea. Located 30 min by car from Kona Airport,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 3
📍 Kailua-Kona, Hawaii

Kona Lighthouse Hawaii - FAMILY BEACH HOUSE

The Kona Lighthouse is centrally located in a peaceful neighborhood along the Gold Coast of the Big Island, a 5-mile scenic, oceanfront drive between the towns of Kailua-Kona and Keauhou-Kona. —- Ideal for family and small group vacations. A block from White Sands...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kailua-Kona, Hawaii

119 night April disc Alii Dr Fully Equipped, Pool, Jacuzzi, BBQ, High-Speed WiFi

Welcome to Kona Bali Kai Ocean and Surf location! Your dream vacation awaits at our beautiful condo located in a prime spot close to downtown, Magic Sands Beach, and Kahalu'u Bay. Picture yourself opening the slider and listening to the soothing waves at night. Our...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua-Kona, Hawaii

Gorgeous Keauhou Resort Condo!

1B/1b Short distance to beautiful Keauhou Bay (5 min walk)Please read completely, so that there are no surprises upon your arrival! ❤■ We love the open air lifestyle and find it comfortable with the doors and windows open and the fans going. The breeze on the island...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

Keokis Kona Oceanfront Rental

Aloha! This is Casa De Emdeko's premiere unit. It has been remodeled down to the studs. Everything is brand new and sparkling. Plus this is the only unit that literally is perched on the edge of the Ocean Front Salt Water Pool! No other unit has views like this one....

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 kailua-Kona, Hawaii

OCEANFRONT TWO BEDROOM CONDO at SEA VILLAGE with A/C in ALL ROOMS!

Imagine - warm tropical climate, views and sounds of the ocean just out your door, panoramic views, and the perfect accommodations - is there anyway else to experience Hawaii? This two-bedroom, two-bath condominium gives you all of that and more! Comfortable set up with...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua-Kona, Hawaii

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