Kailua Kona, Big Island

No. 01

Expansive Lanai and Stunning Sunsets - Spectacular Oceanfront Oasis

House

3 bedroom sleeps 8 about $1011 a night

Oceanfront Kona Home. Sandy Beach Access + Walk to Town Wake up to panoramic ocean views and the sound of the waves at this oceanfront home in gated Kona Bay Estates. With sandy beach access and a protected keiki swimming area just steps away, plus a short walk to downtown Kona, this location is hard to beat. Why Guests Love This Home Oceanfront setting with sunset views Sandy beach access with calm swimming area Gated community for privacy Spacious lanai for outdoor dining and relaxing Walk to downtown Kona Beach gear included: 2 chairs, 1 umbrella, 1 cooler Interior Highlights Open-concept living, dining, and kitchen with high ceilings and direct access to the oceanfront lanai.

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No. 02

Stunning Ocean Vistas and Gourmet Kitchen - Luxurious Island Retreat

Villa

3 bedroom sleeps 6 private pool about $1042 a night

From panoramic Pacific, Maui, and Mount Hualalai views to nearly 1,000 square feet of lanais, the details below reveal how this redesigned villa comes together. 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. Access to the resort and amenities will be limited.Access is managed entirely by Hualalai Resort and may change at their discretion. Please contact Hualalai Resort directly for more details. Each January, Hualalai Resort hosts the Mitsubishi Electric Championship.

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No. 03

Oceanfront Kona Home w/ Beach Access & Views!

Entire home

2 bedroom sleeps 6 about $667 a night

Escape to paradise and immerse yourself in the beauty of Kailua-Kona, HI, at this stunning 2-bedroom, 2-bathroom vacation rental house. Just steps away from the picture-perfect beaches, this tropical retreat is your gateway to adventure. Discover the natural wonders of Hawaii at the nearby Magic Sands Beach or venture to the stunning Hawai'i Volcanoes National Park. After a day of exploration, relax on the lanai and soak up the panoramic views as you listen to the waves crashing below. The space STVR-19-360087. TA - -01. GE - -01. Walkable Location Bedroom 1: King Bed.

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No. 04

Kailua Kona Oceanfront Villa in Alii Point a Gated Community

Oceanfront

3 bedroom sleeps 6

Ali'i Point #5 is located at Ali'i Point, a private and gated community of 16 seaside homes with community pool and tennis court.

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No. 05

Oceanfront Lanai and Pool - Stunning Hawaiian Escape

Condo

1 bedroom sleeps 2 private pool about $198 a night

vrKCV - Kona Reef A32, Professionally Managed Top-Floor Oceanfront Kona Condo. Walk to Town. AC. Kona Reef A32 Wake up to panoramic Pacific Ocean views at Kona Reef A32, a beautifully remodeled top-floor oceanfront condo just steps from the shoreline. Watch surfers ride the waves, enjoy breathtaking sunsets from your private lanai, and stroll just minutes to Kona Town for dining, shopping, and island adventures. Perfect for couples or solo travelers seeking a relaxing Kona getaway with incredible views and unbeatable walkability. Why Guests Love This Condo. Top-floor oceanfront location with panoramic views. Private lanai just feet from the water.

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No. 06

50 Feet to Ocean: Kona Deluxe Ground-Floor Unit!

Entire condo

1 bedroom sleeps 4 shared pool about $204 a night

Romantic Retreat. 2 Mi to Shops. Access to 2 Community Pools Savor the spirit of island life at this 1-bedroom, 1-bath Kailua-Kona condo in the oceanfront Casa de Emdeko community. Start your mornings on the private patio with sweeping views, and end your evenings watching the sun set over the Pacific. Whether you're heading out for snorkeling and manta ray night tours or dining in town, you'll find that this Big Island vacation rental makes the ideal base. Pack your swimsuit and book now! The space GE- -01. STVR-19-376491.

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No. 07

Wraparound Lanai and Spectacular Views - Elegant Oceanfront Haven

Condo

1 bedroom sleeps 2 private pool about $257 a night

Hale Kona Kai unit 312 is one of our most popular units at Hale Kona Kai. This 3rd floor corner unit features a wraparound lanai facing west and south for full, unobstructed ocean views and the best possible breeze! The unit has been beautifully updated and has everything you need for a comfortable stay on top of the ocean. Central air conditioning keeps the unit comfortable, especially on those warmer days and nights. The most up-to-date internet/wifi equipment' features high speed wifi, a necessity for "working" remotely where Zoom conference calls may be necessary. Watch never-ending spectacular sunsets from the comfort of your lanai.

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No. 08

Oceanfront Kailua-Kona Islander Studio w/ Lanai!

Entire condo

sleeps 2 shared pool about $179 a night

Switch into island time the second you land on the Big Island of Hawaii and get settled into your tropical home-away-from-home in the Kona Islander Inn. This Kailua-Kona vacation rental studio features 1 bathroom, a well-equipped kitchenette, a private lanai, and a community pool and hot tub.You’ll be right downtown within walking distance of beaches, restaurants, shops and the Farmer’s Market. Plan a sunset cruise, swim with dolphins, go snorkeling or attend a luau during your time in paradise! The space TA- -01. GE- -01. Window A/C Unit. Free WiFi.

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No. 09

Oceanfront Access and Saltwater Pool - Stunning Hawaiian Retreat

House

5 bedroom sleeps 10 private pool about $1660 a night

vrKCV - Kona Bay Estates Hale Kai Olu, Professionally Managed Welcome to Hale Kai Olu - A Classic Oceanfront Retreat Peaceful, private, and truly special, Hale Kai Olu is a custom-built oceanfront home in Kailua-Kona that feels like a real home, not a resort. Set within a gated oceanfront community with 24-hour security, this well-loved property offers generous space, direct shoreline access, and sweeping ocean views toward Kona Village. While the community itself is gated, beaches in Hawaiʻi are public by law. Guests enjoy easy access to the shoreline and can walk along the coast while still benefiting from the privacy, security, and quiet atmosphere of this unique neighborhood.

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No. 10

Oceanfront Retreat with Heated Pool and Kid-Friendly Amenities - Stunning Escape

House

4 bedroom sleeps 14 private pool about $1733 a night

Welcome to Mermaid Cove by the property manager, a vibrant oceanfront estate designed with families in mind. Nestled within a gated community just minutes from Kailua-Kona town, this four-bedroom, four-bathroom retreat sleeps up to fourteen guests and offers direct beach access, a private heated pool with a swim-up bar, and countless kid-friendly amenities, all against the backdrop of stunning Pacific Ocean views. What We Love About Mermaid Cove by the property manager:. Beachfront Bliss - Steps from a gentle, shallow-water beach ideal for kids. Private HEATED Pool and Spa - Complete with swim-up bar, Jacuzzi, and heated outdoor shower.

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No. 11

Oceanfront Lanai and Snorkeling Gear - Stunning Coastal Escape

Condo

1 bedroom sleeps 4 about $187 a night

This newly remodeled oceanfront condo located right in the heart of Kailua Kona has everything you need to make your vacation complete. This one bedroom is fully furnished with snorkeling gear, boogie boards and a kitchen that is a chefs delight. A king size bed in the bedroom and a fold out tempurpedic Queen bed in the living room make this condo a vacationers delight. A lanai that overlooks the bay so you can dine watching the sunsets or enjoy sipping a cup of Kona Coffee while watching dolphins and whales splashing around right in front of you. This unit can be rented with AC at an additional charge of $15 per day, please inquire with a reservation agent.

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No. 12

Oceanfront Oasis with Expansive Lanai - Stunning Coastal Retreat

Condo

1 bedroom sleeps 2 private pool about $209 a night

Welcome to Hale Kona Kai 213, a true and absolute oceanfront Kona vacation condo with large wrap around lanai (balcony), affording almost 4 times the lanai space of other condos at Hale Kona Kai. Year round sunsets can be seen from your condo for the best chance to see our famous Kona Green Flash. This lanai just about hangs over the ocean. View the tide pools and lagoon where turtles like to swim and eat. Let the sounds of the sea lull you to sleep after your day of sightseeing or relaxing. Both bedroom and living room face the sea where you may see dolphins all year and whales when in season. Central air for those warm days after hiking and swimming.

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No. 13

Unobstructed Ocean Views and Wrap Around Lanai - Elegant Oceanfront Retreat

Condo

1 bedroom sleeps 2 private pool about $209 a night

True and absolute top floor oceanfront condo with large wrap around lanai (balcony), affording unobstructive ocean views. The view stretches from the Kaiwi Point and the Kailua Pier to the north, all the way to Ka'awaloa Point at Kealakekua Bay to the south. Watch the sea life in the tide pools and lagoon where turtles like to swim and eat. Let the sounds of the sea lull you to sleep after your day of sightseeing or relaxing. Both bedroom and living room face the ocean where you may see dolphins all year and whales when in season. This unit is elegantly yet simply furnished, decorated, and remodeled with modern materials and easy to clean surfaces.

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No. 14

Oceanfront Serenity and Unobstructed Views - Beautiful Coastal Haven

Condo

1 bedroom sleeps 3 about $212 a night

Honu Haven at Kona Reef - Oceanfront Bliss in Historic Kailua Village Welcome to Honu Haven, your relaxing oceanfront escape at Kona Reef Unit A24 in the heart of historic Kailua-Kona. From the moment you walk through the door, the soothing sound of the Pacific Ocean invites you to slow down, unwind, and embrace island time. Watch the waves roll in, enjoy unforgettable sunsets from your private lanai, and experience the magic of oceanfront living on the Kona Coast. This beautifully updated 1-bedroom, 1-bath condo combines comfort, convenience, and breathtaking views.

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No. 15

Ocean-front sanctuary in Kailua Kona, 2-bedroom retreat with luxury amenities.

Oceanfront

2 bedroom sleeps 4

Welcome to Hale Lula o Nai a House of the Dolphins your oceanfront retreat on scenic Alii Drive!

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No. 16

Private Lanai and Scenic Pool Access - Stunning Oceanfront Retreat

Condo

1 bedroom sleeps 4 shared pool about $122 a night

Ali'i Villas on Hawaiʻi island is home to some of the most pristine waters in the world. With a pool facing epic sunsets, nestled on top of natural volcanic rock, adjacent to the bustling, yet calm Kailua Kona town; Kona Shores awaits. The one bedroom, one bath condo offers a private lanai for outdoor seating and a full kitchen to prepare fresh foods that can be picked up from the local farmers market daily. Come and enjoy scenery that will take your breathe away! The unit has Handicap accessible countertops. A washer and dryer included in the unit. Easy walk out to the pool and oceanfront from the footsteps of your private lanai. Private Community Pool. Key hanging in unit for access.

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No. 17

Oceanfront Kailua-Kona Townhome w/ Pool & Views!

Entire townhouse

2 bedroom sleeps 6 private pool about $205 a night

Snorkel Gear. 0.5 Mi to Honl's Beach Escape to Hawaii at this unbeatable tropical oasis: a beautiful 2-bedroom, 1.5-bath vacation rental townhome. Nestled in the town of Kailua-Kona, this retreat ensures endless opportunities for fun! Snorkel at Magic Sands Beach, find the best local shaved ice stand, or take a day trip to Hawai'i Volcanoes National Park. Endless beauty abounds on The Big Island, evident by the panoramic Pacific views that can be enjoyed from the home's balcony! The space TA- -01. STVR-19-362568.

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No. 18

Oceanfront Pool and Hot Tub - Charming Tropical Escape

Condo

1 bedroom sleeps 2 private pool about $176 a night

Oceanfront Ali'i Drive Condo Steps from Honl's Beach. Kona Reef Wake up just steps from the shoreline at Kona Reef, a popular oceanfront property on scenic Ali'i Drive in Kailua-Kona. Located next to Honl's Beach (Waiʻaha Bay Beach Park) and less than half a mile from downtown Kona, this property places you close to oceanfront dining, shopping, local markets, and Big Island activities. Spend your days exploring the coastline, watching surfers and bodyboarders at the beach next door, or relaxing by the oceanfront pool and hot tub. In the evening, enjoy Kona's famous sunsets and grill dinner at the community BBQ area. Why Guests Love Kona Reef. Oceanfront location on Ali'i Drive.

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No. 19

Oceanfront Pool and Charming Amenities - Stunning Coastal Retreat

Condo

1 bedroom sleeps 4 private pool about $128 a night

Kona Reef unit #B33: This 758 sq. ft. vacation rental places you right next to one of the few white sand beaches in Kona, Honl’s Beach, and just a short walk to charming Kailua-Kona town. Unit B33 includes a flat screen TV, DVD player, washer/dryer, and full kitchen with 4-burner stove/oven, microwave, dishwasher, coffee maker, refrigerator, and more. Sleeps up to 4 in 1 king bed and 1 sofa bed. Fringing a sandy beach park and within easy walking distance of Kailua-Kona, Kona Reef Resort welcomes you to sunny days and gorgeous sunsets on Hawaii Island’s west shore. It’s the easy life with an oceanfront swimming pool, jet spa, and poolside cabana with grills.

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No. 20

Private Lanai and Poolside Cabana - Gorgeous Oceanfront Escape

Condo

1 bedroom sleeps 4 private pool about $128 a night

Located just a short walk from historic Kailua-Kona washer/dryer, flat screen TV, WiFi, and fully furnished private lanai add a touch of extra comfort for your stay. Sleeps up to four guests in one king and one sofa bed. Town, this spacious 630 sq. ft. vacation condo offers all the comforts of home for your vacation. Take in relaxing views of adjacent Honl’s Beach Park from your fully furnished lanai and enjoy our unit’s many conveniences including air conditioning and ceiling fans, washer/dryer, WiFi, flat screen TV, fully equipped kitchen with microwave, full-sized refrigerator, range/oven, appliances, and dishwasher. Sleeps up to four guests in one king and one sofa bed.

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No. 21

Oceanfront Pool and Expansive Lanai - Stunning Hawaiian Retreat

Condo

1 bedroom sleeps 3 private pool about $193 a night

Welcome to Hale Kona Kai 412, a stunning oceanfront condo at the top corner of the building that promises an unforgettable getaway in the heart of Kailua Kona. This completely remodeled modern unit is perched on the top floor, offering breathtaking views of the Pacific Ocean from its expansive wraparound lanai, where you can soak in the beauty of the Hawaiian sunsets. This one-bedroom, one-bathroom retreat comfortably accommodates two guests. The spacious bedroom features a luxurious king-sized bed, ensuring a restful night's sleep after a day of adventure. POOL NOTICE: The pool will be closed from June 21 - July 2, due to exterior work being completed close to the pool area.

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No. 22

Oceanfront Swimming Pool and Gourmet Kitchen - Stunning Island Retreat

Condo

1 bedroom sleeps 4 private pool about $173 a night

Kona Reef unit #D01 on the ground-floor: Walk from the private lanai to the ocean’s edge for a beautiful Kona sunset. This open-design, air-conditioned 758 sq. ft. retreat invites you to prep meals in the gourmet kitchen with breakfast bar. Other touches include ceiling fans, a washer/dryer, and WiFi. Sleeps 4 in 1 King and 1 Sofa bed. Fringing a sandy beach park and within easy walking distance of Kailua-Kona, Kona Reef Resort welcomes you to sunny days and gorgeous sunsets on Hawaii Island’s west shore. It’s the easy life with an oceanfront swimming pool, jet spa, and poolside cabana with grills. Minimum age to book this property is: 18

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No. 23

Oceanfront Lanai and Resort Amenities - Stunning Island Escape

Condo

2 bedroom sleeps 5 private pool about $273 a night

vrKCV - Kanaloa at Keauhou 2002, Professionally Managed Oceanfront Kanaloa Condo. 2BR w/ Central A/C, 3 Pools & Sunset Lanai Wake up to sweeping ocean views and the sound of waves at Kanaloa at Keauhou 2002, a comfortable oceanfront 2-bedroom condo perfect for couples and families. Located along the beautiful Keauhou coastline, this spacious condo offers central air conditioning, a covered lanai for outdoor dining, and easy access to pools, tennis courts, and nearby snorkeling beaches. Spend mornings sipping coffee on the lanai, explore the reefs at Kahalu'u Beach Park, or head to Keauhou Bay for kayaking, manta ray experiences, and boat tours.

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No. 24

4BD Ka'Ulu Estate (102A) at Hualalai Resort

House

4 bedroom sleeps 8 private pool about $5840 a night

From the infinity-edge pool overlooking the reflective pond and 5th fairway, the details below show how this newly completed estate brings everyone together. 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. Access to the resort and amenities will be limited.Access is managed entirely by Hualalai Resort and may change at their discretion. Please contact Hualalai Resort directly for more details. Each January, Hualalai Resort hosts the Mitsubishi Electric Championship.

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No. 25

2BD Hillside Villa (6102) at Hualalai Resort

Villa

2 bedroom sleeps 4 private pool about $899 a night

From sweeping ocean, golf course, and sunset views to the ground-floor villa's direct lawn access, the details below show how 2BD Hillside Villa (6102) lives. 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. Access to the resort and amenities will be limited.Access is managed entirely by Hualalai Resort and may change at their discretion. Please contact Hualalai Resort directly for more details. Each January, Hualalai Resort hosts the Mitsubishi Electric Championship.

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