Vacation rentals in Holualoa, HI with a pool

Explore 58 vacation rentals, homes, and villas with pools in Holualoa, HI for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Air Condition Homes, Homes with Free Parking and Homes with hot tub. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $107 per night and homes offering up to 15 bedrooms and 12 bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

58 Homes with Pools in Holualoa

Kona Dreams

Kailua Kona, Hawaii, US
3 Bedrooms 6 Guests
Aug 27 - 30
$737 night

Kona Dreams by Gather invites you to experience the charm of island living from a peaceful Kailua-Kona neighborhood. With sweeping ocean views, a private pool, and beautifully maintained tropical landscaping, this 3-bedroom, 2.5-bath retreat offers 1,748 square feet of comfort—perfect for families or groups seeking a relaxing Big Island getaway. From vibrant sunsets over the Pacific to cooling breezes drifting through the lanais, every moment at Kona Dreams feels like stepping into your own slice of paradise. What You’ll Love About Kona Dreams • Private pool surrounded by lush tropical gardens • Expansive ocean views from the primary suite, living areas, and lanais • Bright open-concept living, dining, and kitchen layout • Chef-ready kitchen with central island and stainless steel appliances • Multiple lanais offering shade, sun, and unforgettable sunset vistas • Convenient location just minutes from downtown Kona and Ali‘i Drive Living & Dining The main level features a spacious great room with high ceilings and an open layout that encourages gathering and conversation. Large windows bring in abundant natural light and ocean blues, while the adjacent dining area and breakfast nook make mealtimes effortless. Enjoy family movie nights on the plush seating or step outside for lanai dining with a view. Chef-Ready Kitchen With stainless steel appliances, beautiful countertops, and a central island, the kitchen is designed for everything from quick breakfasts to full family dinners. Ample prep space and quality cookware make it easy to embrace your inner chef. Outdoor Oasis Outdoors, Kona Dreams offers a private pool framed by tropical landscaping—plumeria trees, vibrant flowers, and swaying palms. The pool deck provides both shaded and sun-splashed seating for lounging, reading, and grilling. The upper and lower lanais invite you to enjoy morning coffee, whale-watching with the provided binoculars, or a sunset meal as the sky glows over the Pacific. Sleeping Quarters • Primary Suite (Upper Level) – California King bed, ensuite full bath, private lanai with sweeping ocean views, space for crib/Pack & Play • Guest Bedroom 2 (Lower Level) – Queen bed, partial ocean and garden views, private lanai access, shared full bath • Guest Bedroom 3 (Lower Level) – Queen bed, partial ocean and garden views, private lanai access, shared full bath • Powder Room – Half bath located on main living level Extras • Air conditioning (split/room units) • High-speed Wi-Fi • Washer and dryer • Beach gear (towels, chairs, cooler) • Binoculars for whale watching • Parking available Community Highlights Kona Dreams is located in a tranquil residential neighborhood just minutes from Kona’s best attractions—beaches, snorkeling, shopping, dining, golf, and scenic coastal drives. Enjoy the peace of a private home with easy access to Big Island adventures. Nearby • Walk or short drive – Shopping, cafés, and local dining • Short drive – Kona beaches, surf spots, historic sites, and coastal parks Good to Know Good to Know • This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. • Tax ID: TA-205-114-4192-01 • STVR-19-357729 / NUC-19-0959 / PL-NUCR-2025-002849 • TMK: 760220350000 Kona Dreams by Gather offers the ideal blend of comfort, scenery, and authentic Big Island charm. Reserve your preferred dates and experience the beauty of Hawaii from this peaceful ocean-view retreat.

Papala Place at Kahakai Estates

Kailua Kona, HI, US
4 Bedrooms 8 Guests
Sep 7 - 10
$1,276 night

This private four-bedroom retreat within the gated Kahakai Estates blends elegance, space, and island charm. With partial ocean views, lush gardens, and a resort-style pool area, Papala Place offers a serene escape just minutes from Kailua Kona’s beaches, shopping, and dining. What You’ll Love About Papala Place at Kahakai Estates * Expansive backyard with sparkling pool, spa, shaded lounges, and sunset views * Tropical landscaping with private lawn, volleyball net, and cornhole for family fun * Bright, airy interiors with high ceilings and seamless indoor-outdoor living * Fully equipped gourmet kitchen with island seating * Covered lanais and outdoor dining spaces for every time of day Living & Dining A grand gated entrance leads to airy living spaces finished in warm tones and coastal accents. Multiple sitting areas flow toward the outdoors, framed by large windows and sliding doors that open to the pool terrace. The main living room features plush sectional seating, ceiling fans, and a smart TV for evening gatherings. An adjacent dining area seats eight at a rustic-style table, ideal for shared meals. Chef-Ready Kitchen The open kitchen is anchored by a central island with bar seating, surrounded by rich wood cabinetry and granite countertops. Stainless steel appliances, a gas range, and abundant prep space make it easy to create everything from fresh poke bowls to gourmet dinners. Outdoor Oasis Set against manicured greenery and swaying palms, the backyard centers around a sparkling pool and raised spa. Multiple lounge zones—some shaded, others in full sun—invite you to relax any time of day. Enjoy breakfast poolside, watch the sky glow at sunset from the upper terrace, or fire up the built-in grill in the outdoor kitchen for an alfresco feast. Sleeping Quarters * Primary Suite – King bed, ensuite bath with soaking tub & walk-in shower, ocean view balcony, central A/C, ceiling fan * Guest Bedroom 2 – King bed & double bed, ensuite bath, central A/C, ceiling fan * Guest Bedroom 3 – Two twin beds, ensuite bath, central A/C, ceiling fan * Guest Bedroom 4 – King bed, central A/C, ceiling fan Extras High-speed Wi-Fi, washer/dryer, smart lock entry, beach towels, and ample parking. The home’s private gated setting offers tranquility while keeping you close to Kona’s highlights. Nearby – Walk Stroll to local markets, coffee spots, and casual eateries. Beach access and shoreline paths are close for morning walks or sunset photos. Nearby – Short Drive Reach golf courses, hiking trails, historical sites, shopping districts, spas, tennis courts, and water sports outfitters within minutes. Good to Know * This property is fully air-conditioned and designed for family comfort. Pets and smoking are not permitted. * This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. * STVR-19-360748 * PL-NUCR-2025-003515/NUC-19-1246 * TAT ID: TA-114-043-0336-01 * TMK: 3750400240000 Reserve your dates now and experience the best of island life at Papala Place at Kahakai Estates.

Kona’s Shangri La

Kailua Kona, HI, US
5 Bedrooms 14 Guests
Aug 30 - Sep 2
$1,482 night

Perched directly above the blue curve of Lyman’s Bay, Kona’s Shangri La is a custom tri-level oceanfront retreat designed for families and groups seeking space, comfort, and effortless island living. Set along the iconic Ali‘i Drive coastline in Kailua-Kona, this 5-bedroom, 5-bathroom home brings everyone together with expansive glass walls, multiple indoor living areas, and inviting outdoor spaces anchored by a solar-heated pool, ocean-view hot tub, and dining at the water’s edge. What You’ll Love About Kona’s Shangri La • Tri-level oceanfront home with sweeping views of Lyman’s Bay • Solar-heated pool, ocean-view hot tub, and outdoor shower • Three full living areas and two complete kitchens for ultimate flexibility • Outdoor dining for 10 at the coastline • Steps to snorkeling, surf spots, beaches, and Ali‘i Drive attractions Living & Dining Across all three levels, floor-to-ceiling windows frame the ocean, bringing in natural light and gentle breezes. The living rooms on the second and third floors are designed for gathering, each offering plush seating, queen sleeper sofas, split A/C, ceiling fans, and seamless lanai access. Large glass panels open toward the coastline, creating uninterrupted sightlines to the water. Dining options are plentiful: indoors with panoramic views or outside beside the shoreline, where the sound of the surf becomes your backdrop. The eight-seat dining table on the second floor and the beachfront table for ten offer comfortable, view-rich places to share meals. Chef-Ready Kitchen Two fully equipped kitchens, located on the second and third levels, feature stainless steel appliances, full-size refrigerators, electric cooktops, microwaves, dishwashers, and cabinets stocked with kitchen essentials. With additional kitchenettes in the home, preparing group meals or simple beach-day snacks is easy and convenient. Outdoor Oasis Swaying palms and peaceful ocean sounds set the tone for this private outdoor space. Relax in the solar-heated pool, soothe in the ocean-view hot tub, or unwind on a lounge chair while taking in the colors of the Kona coast. Rinse off under the outdoor shower after a shoreline swim or surf session. The coastline-front dining terrace provides one of the home’s standout experiences: sharing meals just steps from the water as waves break along the lava rock. Sleeping Quarters • Primary Suite – Second Floor King bed, split A/C, ceiling fan, ensuite bathroom with dual vanities • Guest Bedroom 2 – Second Floor Queen bed, split A/C, ceiling fan, ensuite bathroom • Guest Bedroom 3 – Third Floor King bed, mountain view, split A/C, ceiling fan • Guest Bedroom 4 – Third Floor Queen bed, mountain view, split A/C, ceiling fan • Guest Bedroom 5 – First Floor Studio King bed and twin daybed, ocean view, lanai access, split A/C, ceiling fan, ensuite bathroom • Second Floor Living Room Queen sleeper sofa, ocean view, lanai access, split A/C, ceiling fan • Third Floor Living Room – Penthouse Level Queen sleeper sofa, ocean view, lanai access, split A/C, ceiling fan Extras • Elevator access to second and third floors • Private entrance on each level • Beach chairs and towels • Commercial-size washer/dryer • Smart TVs and high-speed Wi-Fi • Outdoor seating terraces on multiple levels • Pack and Play available • Jet tub, soaking tubs, and walk-in showers • Security cameras and enhanced safety features Nearby • Walk: Magic Sands Beach, Cafés and shops along Ali‘i Drive, Local farmers’ markets Hulihe‘e Palace • Short Drive: Pu‘uhonua O Hōnaunau National Historical Park, Two Step snorkeling Kona dining and shopping district, Golf courses and hiking trails Good to Know • This home is oceanfront. Always observe ocean safety and supervise children near the water. • Parking on-site. • This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. • Tax ID: TA-103697715201 • Hawaii STVR Registration: STVR-19-364715 • TMK: 760140070002 Reserve your dates now and experience oceanfront living at Kona’s Shangri La.

Kona Sunset House at Walua

Kailua Kona, HI, US
3 Bedrooms 6 Guests
Aug 26 - 29
$463 night

"Kona Sunset House" on the Famous Walua Road Running Trail is a spectacular property for the perfect Hawaii Vacation. First and Foremost, the property has unsurpassed Ocean Sunset views. Located in a quiet upscale neighborhood on the Walua bike and walking path just minutes from Downtown Kona. Above the heat at approximately five hundred foot elevation where the cool breezes create a perfect climate. The center of the home features a great open space of living and dining with bedrooms located at both ends of the common area, great for multiple couples wanting privacy. Fantastic views are seen from kitchen, living room, master and Bedroom two, adjacent to the Lanai. The Fully Equipped kitchen includes: bamboo cabinets, granite counters, tile floors and excellent appliances. The Full Length lanai is wonderfully furnished with additional table and chairs for out-door dining, futon, deck chairs and bistro set for all day enjoyment. A Master Bedroom with island decor that connects to the Lanai, includes a solid mahogany four post king size bed, flat screen tv, A large custom tile walk-in shower and granite counter sink. Bedroom#2 has a solid teak queen size opium bed and private entrance to the lanai too. Bedroom#3 has the option of 2 twin beds that can be made into one King upon request! There is a Safe now available for guests to use! The owners appreciate guest feedback! The Large private pool has fully landscaped grounds really makes this property feel like paradise. This is a very clean and comfortable home. Sit back and watch the palms sway in the sunset or take a snooze to the sound of exotic birds singing. ***All Reservation Requests greater than 12 months in Advance MUST be approved in advance by the Broker In Charge. Rates are subject to change.*** **All guests are required to sign a rental agreement with Property Manager Property Management** STVR#19-345615 NUCR-21-0297 TA# TA-163-304-0896-01 Please note this home does not have Air Conditioning.

❤️PiH❤️ PACIFIC VISTA RETREAT ★ Luxury Retreat w/ Ocean Views ★ Heated Pool

Holualoa, HI, US
5 Bedrooms 11 Guests
Aug 26 - 30
$989 night

Brought to you by Paradise in Hawaii Luxury Homes. Welcome to Pacific Vista Retreat, a part of our Hawaiian Luxury Collection. Pacific Vista Retreat in Kahakai Estates is a wonderful 5-bedroom home, minutes away from downtown Kailua-Kona. It has some of the most amazing views of the Pacific Ocean and coastline of any vacation rental on the Big Island. We pride ourselves on providing some of the most sought after homes on the Big Island of Hawaii, and our guest reviews on our other homes give you a sense of our focus on customer service, and how our goal is to ensure our guests have the finest vacations possible.  We have now partnered with the wonderful homeowners of Pacific Vista Retreat to provide a very similarly well-equipped home for your entire family or group to enjoy.  Pacific Vista Retreat, on its one-acre lot provides a perfect setting for your private Big Island getaway and is designed for large groups of up to 11 people in 5 separate bedrooms. Pacific Vista Retreat is an inviting, relaxing, scenic and luxurious home for your Hawaiian vacation. The spacious outdoor lanai, gazebo and private heated saltwater pool all have majestic views of the Ocean. The entire home is designed to be open and take advantage of outdoor living and ocean breezes. The home is wheelchair-friendly too. Fast WiFi with great coverage included! We know our Guests look forward to an exceptional experience from the moment you start planning your Big Island vacation. We’ve incorporated all of our vacationing experiences from Hawaii and around the world, to ensure you have an exceptional stay.  We love friends & families  The Big Island is such a spectacular place to spend with your friends and family, children and grandchildren. Vacations create such wonderful memories; our hope is this trip will be one of your fondest family memories and that you’ll return year after year.  This 5-bedroom home is fully furnished with two Primary Suites, each with a private ensuite bathroom and king size bed and lanai. The third bedroom has a queen and a twin daybed. The fourth bedroom is furnished with two twin XL beds that can be converted into a king with a 4" mattress topper. The 5th bedroom has a queen size bed. The airy, open concept main floor includes kitchen, dining area, great room. The great room is perfect for relaxing, playing games, listening to music on the sound-bar, watching the game, or relaxing with a movie.  This home does not have AC, and instead has a QuietCool whole house ventilation system.  The open design of the house provides good air flow. There are large ceiling fans in each room. ​​​​​​​Floor and personal fans are available and provided as well. Outdoor living at its best, the expansive main lanai has seating areas complete with outdoor large 75" screen TV, outdoor BBQ and dining area and a stunning pool with an outdoor shower too. WiFi is available throughout the home and lanais.  County Law requires alarms on all ground-level sliding doors that lead to pool area, in order to prevent doors from being left open indefinitely. Whether you’re celebrating a birthday, anniversary, a new job, retirement, or simply celebrating the sunshine, this home is sure to have you fall in love with the Big Island.  Beyond building an elegant, yet comfortably furnished home, we know it’s often the small surprises and conveniences that make all the difference.  Examples include: • High-end luxury mattresses in all bedrooms for your comfort and enjoyment  • Luxurious high-end bedding for all beds  • Luxurious towels  • A fully equipped kitchen for all of your cooking and baking needs • Brand new high-end Weber Gas Grill for outdoor grilling or cooking • High-end Ninja blender for making great smoothies and other tropical drinks • Large selection of vinegars, oils and spices  • Starter pack of Kona coffee & a collection of teas  • Popcorn  For your day at the Beach: We love building really big sand castles. Kona sand is exceptional for this and we have the tools for kids and adults alike. For your day at the beach, you’ll find: • Comfortable beach chairs, beach mats, umbrellas, sand toys and sandcastle making equipment • Large collection of snorkel gear in multiple sizes so you can share the wonders of the ocean • Boogie boards to enjoy playing in the waves  • Life jackets for the younger ones  • Large wheeled cooler and Tupperware containers for your beach picnic For those with children: Having traveled with our kids when they were young we know how difficult it is to lug all the baby equipment. Our goal is to make your life easier so we have equipped our vacation home with: • Pack ’n Play • High chair • Baby monitors • Bed safety rails Things to do: There’s no chance of running out of things to do on the Big Island! Here’s a small sample. Check out Paradise in Hawaii Luxury Homes website for even more great ideas on things to do while on the Big Island.  Whale Watching: Each winter the Big Island is host to the incredible Humpback whales. Pour your coffee and grab the binoculars (provided) and look for whale spouts, breeches and fin slapping.  Beaches: The Big Island has a variety of exceptional beaches for snorkeling, surfing, boogie boarding and scuba diving. Black Sand, green Sand, and white sand for perfect sandcastles can all be found on the Big Island  Golfing: Home to the PGA Men’s and Women’s tours, there are incredible golf courses found all around the island. Visit our webpage to find out more about golf on the Big Island.  Volcano National Park: Take a day trip to the Volcano, walk through a lava tube, and in the evening you may even see the orange glow of Lava in the crater.  Telescopes and Stargazing: See the telescopes at Mauna Kea or at the Observatory and learn about the stars and our universe  Sea Horses: See the Sea Horse Aquarium Hikes: The Big Island has hikes for all skill levels  Coffee Tours: Fresh Kona Coffee and Coffee tours. There is nothing in the world like Kona Coffee.  Contact us today to book your stay at this spectacular home! GET TAX ID: GE-202-720-0512-01 TAT TAX ID: TA-202-720-0512-01 Hawaii County: STVR-19-350669 / PL-NUCR-2022-000944 Licence number: STVR-19-350669

Ho’o Maluhia

Kailua Kona, HI, US
3 Bedrooms 8 Guests
Aug 26 - 30
$595 night

Hoʻo Maluhia – Ocean View Luxury Retreat with Pool, A/C & Sunset Lanais Above Kailua-Kona Experience Big Island paradise at Hoʻo Maluhia, a luxurious hillside retreat perched 700 feet above Kailua-Kona. This spacious two-level home offers breathtaking 180° ocean views, a private pool, and brand-new split A/C systems in all sleeping areas for ultimate comfort. Located just minutes from beaches, Ali‘i Drive, dining, and top attractions, Hoʻo Maluhia blends indoor-outdoor island living with elevated tranquility. Why Guests Love Hoʻo Maluhia • Panoramic 180° Pacific Ocean views — from Kailua Bay to endless sunsets • Split air conditioning in every bedroom for restful sleep in any season • Private pool with sun loungers, outdoor shower, and tropical landscaping • Expansive lanais on both levels with al fresco dining and lounge seating • California King primary suite with ocean views and spa-inspired ensuite • Fully equipped gourmet kitchen with BBQ grill and multiple dining spaces • Quiet hillside location with cool breezes, just minutes to town and beaches • Fast Wi-Fi, smart TVs, beach gear, garage parking, and more Living, Dining & Outdoor Living The upper-level great room welcomes you with vaulted ceilings, a large sectional sofa, and uninterrupted ocean views from every angle. Dine indoors or on the lanai while watching colorful sunsets fade into starry skies. Sliding glass doors connect the interior seamlessly to the lanais, creating the ultimate indoor-outdoor lifestyle. Chef’s Kitchen & BBQ Ready Cook like a local in the fully stocked gourmet kitchen featuring stainless steel appliances, ample counter space, and a center island for casual breakfasts. A BBQ grill just steps away makes grilling at sunset a breeze. Serve meals poolside, on the lanai, or in the elegant dining room with an ocean backdrop. Pool & Outdoor Retreat Your private pool area offers a sun-drenched oasis surrounded by lush greenery. Relax on a lounge chair, rinse off in the outdoor shower, or enjoy a quiet morning coffee in the secluded lower lanai. Coastline views, swaying palms, and evening breezes complete this tropical sanctuary. Sleeping Arrangements – All with A/C • Primary Suite – California King bed, split A/C, ensuite bath with dual vanities and walk-in shower, lounge seating, and ocean views • Guest Bedroom 2 – Queen bed, split A/C, ensuite bath, ocean views, and lanai access • Guest Bedroom 3 – Queen bed, split A/C, ensuite bath, private outdoor shower and breakfast nook • Bonus Room – Sofa bed and twin trundle (2 twin beds), split A/C, ocean views Additional Amenities • New Split A/C Systems in All Bedrooms (2025) • Ceiling fans throughout for added ventilation • High-speed Wi-Fi and Smart TVs for streaming and remote work • Full laundry room with washer and dryer • Garage plus driveway parking • Beach towels and gear rentals available nearby Prime Location – Minutes to Everything • Ali‘i Drive – 5 minutes to shops, restaurants, farmers markets, and nightlife • Kahaluʻu Beach Park – Excellent snorkeling with turtles and reef fish • Keauhou Bay – Snorkel, manta ray night dives, boat tours • Kailua Pier – Ironman World Championship site and sunset strolls • Day trips – Mauna Kea Observatory, Volcanoes National Park, Hōnaunau, and Kona coffee farms Good to Know • Split air conditioning added to all sleeping areas in 2025 • Upstairs portion designed with mobility in mind: 42-inch doorways and seamless shower in the primary • Quiet residential area – please respect quiet hours • This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. • Hawaiian Tax ID: TA-022-569-1648-01 • STVR-19-365043 / NUC-19-1732 / PL-NUCR-2024-002425 • TMK: 770200780000 Book Your Stay at Hoʻo Maluhia Relax, recharge, and reconnect at Hoʻo Maluhia — your private ocean-view oasis above Kailua-Kona. Perfect for families, couples, and groups seeking comfort, beauty, and location. Reserve your dates today and experience the best of Hawaiʻi Island from this unforgettable retreat.

Honu Hale

Kailua-Kona, HI, US
5 Bedrooms 16 Guests
Aug 26 - 29
$1,116 night

Set above the Kona coastline with sweeping views of Lyman’s Bay and Holualoa Bay, Honu Hale is a spacious, view-drenched retreat designed for families and groups seeking comfort, privacy, and effortless indoor-outdoor living. With five bedrooms, multiple lanais, a private saltwater pool, and sleeping for up to sixteen, this hillside estate blends generous gathering spaces with peaceful corners to unwind and reconnect. What You’ll Love About Honu Hale • Nearly 180-degree ocean and coastline views from multiple rooms • Large private saltwater pool, hot tub, and oversized outdoor chess set • Spacious great room with vaulted ceilings and ocean-facing bay windows • Private office with half bath, AC, and lanai access • Upgraded kitchen with ocean-view windows, double ovens, and breakfast seating • Multiple lanais connecting the home to warm breezes and vibrant sunsets Living & Dining High vaulted ceilings, exposed beams, and wide ocean-view windows set the tone for relaxed coastal living. Sink into the plush sofas for movie nights, gather for game time, or enjoy long, slow mornings watching the light change over the water. A formal indoor dining space seats six comfortably and opens directly to the pool terrace. Downstairs, an additional media room with a queen sleeper sofa and Smart TV provides extra flexibility for larger groups. Chef-Ready Kitchen The upgraded kitchen is bright, organized, and designed for easy meal preparation. Stainless steel appliances, double ovens, ample counter space, and an ocean-facing window make cooking a joy. A breakfast bar for three and an attached kitchen nook offer casual dining spots. Steps away, a poolside BBQ invites outdoor meals framed by swaying palms and wide-open coastal views. Outdoor Oasis A private saltwater pool anchors the outdoor living space, surrounded by loungers, lush landscaping, and space to watch little ones play. A bubbling hot tub sits at the edge of the terrace with panoramic ocean views. Enjoy oversized outdoor chess, multiple shaded seating areas, and dining options perfect for sunset meals. From morning coffee to the last glow of the day, the outdoor spaces at Honu Hale embrace the warmth and beauty of the Kona Coast. Sleeping Quarters • Primary Bedroom – King bed, garden view, ensuite bath, lanai access, window AC, ceiling fan • Guest Bedroom 2 – King bed, ocean view, window AC, ceiling fan, shared Jack & Jill bath • Guest Bedroom 3 – Four twin beds, garden view, ceiling fan, shared Jack & Jill bath • Guest Bedroom 4 – Queen bed, ocean view, private lanai, separate entrance, window AC, ceiling fan, shared Jack & Jill bath • Guest Bedroom 5 – King bed, ocean view, private lanai, window AC, ceiling fan, shared Jack & Jill bath • Office – Queen sleeper sofa, AC, desk, private lanai • Bonus Room – Queen sleeper sofa, AC, TV Bathrooms • Primary Ensuite – Dual vanities, soaking tub, walk-in shower • Jack & Jill Bath (BR 2 & 3) – Dual vanities, tub/shower combo • Jack & Jill Bath (BR 4 & 5) – Dual vanities, tub/shower combo • Guest Half Bath – Off the entry near the office Extras • Beach chairs and towels • Crib and additional bedding • Private garage • Smart TVs and cable • Washer and dryer • Hot tub • Outdoor chess • Beach equipment rentals available ($) • Smart lock • Laptop-friendly spaces Nearby • Walk: Quiet residential streets with coastline overlooks • Short Drive: Magic Sands Beach, Kahaluu Beach Park, Downtown Kona shops and dining, Keauhou Shopping Center, Snorkeling, surfing, SUP, horseback riding, and helicopter tours, Historic sites and scenic beaches Good to Know • AC is available only in sleeping areas. • The driveway is steep; full-size vehicles recommended. • This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. • Licensed short-term rental. • Exterior stairs connect levels of the home. • No pets allowed. • No smoking allowed. • Tax ID: TA-102-287-6160-01 • TMK: 770200620000 • Permit: STVR-19-365866 / NUC-19-1874 / PL-NUCR-2025-002994 Reserve Your Stay! Experience wide-open coastal views, resort-style amenities, and the ease of island living at Honu Hale. Your Kona getaway awaits.

Hale Joli

Kailua-Kona, Hawaii, US
4 Bedrooms 8 Guests
Aug 28 - 31
$977 night

Welcome to Hale Joli, a private hillside retreat in Kailua-Kona where panoramic ocean views, warm wood architecture, and the natural beauty of the Big Island come together. Set on historic royal lands once belonging to King Lunalilo, this single-level home blends old Hawaii charm with modern comfort, offering a peaceful escape surrounded by tropical gardens, birdsong, and endless blue horizons. What You’ll Love About Hale Joli • Historic setting on former royal grounds with a true sense of place • Heated infinity pool with panoramic ocean and sunset views • Private road location with lush botanical surroundings and serene quiet • Tropical orchard of 30+ fruit trees and a mini Kona coffee farm • Unique layout with each bedroom accessed via covered outdoor pathways Living & Dining The great room anchors the home with soaring vaulted ceilings, natural wood finishes, and a full wall of sliding glass doors that invite breezes and sunlight inside. The living area offers comfortable seating for quiet mornings or relaxed evenings, complemented by Smart TV entertainment. A spacious dining table seats eight for memorable meals shared indoors, while the open layout makes it easy for everyone to connect whether cooking, relaxing, or planning the day’s adventures. Chef-Ready Kitchen Designed for effortless cooking, the kitchen features stainless steel appliances, a gas stove, double ovens, wine fridge, generous prep space, and essentials from blender and kettle to coffee grinder and rice cooker. Enjoy ocean-facing meal prep or step directly out to the lanai for al fresco dining. Outdoor Oasis Hale Joli’s outdoor spaces offer the atmosphere of a private resort. The heated infinity pool stretches toward the ocean, framed by a wide sundeck with loungers and shaded seating. An outdoor shower provides a refreshing post-swim rinse, while the barbecue area and firepit create beautiful settings for sunset grilling or stargazing. Explore the grounds to find tropical plantings, a flourishing orchard, and the beginnings of a mini Kona coffee farm. Mornings here are peaceful, and evenings glow with breathtaking colors across the horizon. Sleeping Quarters • Primary Bedroom: King bed, ensuite bath with tub and shower combo, ocean view, ceiling fan, lanai access • Guest Bedroom 2: King bed, shared Jack-and-Jill bath with tub and shower combo, ocean view, ceiling fan, lanai access • Guest Bedroom 3: Two double beds, shared Jack-and-Jill bath, ocean view, ceiling fan, lanai access • Detached Ohana Suite: King bed, private ensuite bathroom, located in a separate detached guest suite for added privacy Each room opens to the lanai and is accessed via covered outdoor walkways, enhancing privacy and elevating the indoor-outdoor lifestyle. Extras • Washer and dryer • Beach towels • Additional bedding • Smartlock entry • Free parking • Laptop-friendly workspace • Emergency contact information provided • Suitable for children and elderly • Single-level home • Outdoor lighting and safety equipment • Heated private pool • Lanai and private yard Nearby Short Drive: • Kailua-Kona town for dining, shopping, and oceanfront strolls • Kona International Airport • Local beaches and snorkeling spots • Golf courses • Hiking trails • Museums and cultural attractions • Spa and wellness centers Good to Know • Listing Update Notice (07/1/2026) Beginning July 1, the property will feature four bedrooms instead of three with the addition of a detached Ohana suite located adjacent to the main home. The Ohana suite will include a king bed, ensuite bathroom, seating area, workspace, and a private outdoor dining area for four. Interior photos will be added to the listing once they become available. • This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. • This property is not equipped with A/C • Licensed short-term vacation rental • TA-175-028-7872-01 • TMK: 760100200000 • This property is a licensed short term vacation rental. NUC-19-1678 / STVR-19-364639 / PL-NUCR-2026-003596 Reserve your dates now and experience Hale Joli’s rare blend of Hawaiian heritage, beautiful design, and peaceful oceanview living.

Ono Oasis

Kailua Kona, HI, US
3 Bedrooms 6 Guests
Aug 28 - Sep 1
$649 night

Ono Oasis is a striking retreat in Kailua Kona, HI, offering a private heated pool, lush tropical landscaping, and serene indoor–outdoor living for an unforgettable Hawaiian getaway. Spanning 2,800 square feet, this elegantly crafted home accommodates up to six guests across three beautifully appointed bedroom suites—perfect for families or groups seeking tranquility, comfort, and island adventure. What You’ll Love About Ono Oasis • Private solar heated saltwater pool ideal for sunlit afternoons • Expansive open-air living room filled with natural light • Quick access to local beaches, dining, and hiking trails • Thoughtfully outfitted with essential comforts for a worry-free stay • Surrounded by lush gardens and tropical foliage for enhanced relaxation Living & Dining The spacious living room flows seamlessly into the indoor dining area, inviting relaxation and connection. High ceilings and abundant natural light create an airy, welcoming atmosphere, while comfortable seating ensures everyone feels at home. Elegant touches throughout complement the home’s tropical surroundings. Chef-Ready Kitchen The fully equipped kitchen includes a refrigerator, stove, microwave, dishwasher, and generous counter space—perfect for preparing island-inspired meals. A breakfast bar provides additional seating for casual bites or morning coffee chats. Outdoor Oasis Step outside to a peaceful lanai where you can enjoy morning tea, afternoon lounging, or sunset cocktails. The private pool area offers ample seating, outdoor dining space, and a relaxing environment surrounded by swaying palms and lush greenery. Sleeping Quarters • Primary Bedroom – King bed, ensuite bath, direct backyard access • Guest Bedroom 2 – Queen bed, ensuite bath • Guest Bedroom 3 – Queen bed, ensuite bath Extras • High-speed Wi-Fi • Smart TV • Washer & dryer • Household essentials available • Central A/C not necessary due to cool elevation and breezy airflow Resort / Community Highlights Explore a variety of nearby activities including spa services, shopping, watersports, golf, and local hiking trails. From fishing to snorkeling to scenic drives, adventure is always within easy reach. Nearby • Beaches – Just a short drive away • Dining & shopping – Minutes from Kona Town • Attractions – Museums, scenic hiking trails, and Big Island adventures Good to Know • Parking is free, and essential supplies—including coffee, bottled water, and household basics—are provided to help you settle in effortlessly. • This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. • Tax ID: TA-209-864-3968-01 • TMK 770130630000 • STVR-19-361566 / NUC-19-1651 / PL-NUCR-2025-002948 Reserve your dates now while your preferred week is available. Discover the comfort, charm, and tropical serenity of Ono Oasis—your private Hawaiian sanctuary awaits.

Honu O Kai (Turtle of the Sea)

Kailua Kona, HI, US
3 Bedrooms 8 Guests
Sep 16 - 21
$686 night

Honu O Kai (Turtle of the Sea) – Kailua Kona, HI A serene coastal retreat designed for family gatherings and relaxing getaways, Honu O Kai offers 2,928 sq. ft. of indoor-outdoor living space with panoramic ocean views and upscale amenities—all just moments from the beach. What Sets Honu O Kai Apart • Brand-new split system A/C in every sleeping area – each guest can set their own ideal temperature for a personalized and restful stay • Unmatched ocean views from multiple rooms • Private pool with plenty of lounge space • Gourmet kitchen with stainless steel appliances • Comfortable living area with plush seating • Kid-friendly bonus room with bunk beds Living & Dining Designed for connection and comfort, the open-concept living and dining area is filled with natural light and framed by ocean and garden views. A spacious dining table for eight invites memorable meals and relaxed conversation. Chef-Ready Kitchen This well-equipped kitchen features premium stainless steel appliances, a large center island with bar seating, and all the cookware needed for home-style meals or island-inspired feasts. Outdoor Oasis Enjoy your morning coffee or evening cocktails on the wrap-around lanai with unobstructed views of the Pacific. The lush backyard includes a private pool surrounded by lounge chairs—perfect for sunbathing, swimming, or unwinding after island adventures. Sleeping Quarters All bedrooms now feature newly installed split system A/C, ensuring that every guest can sleep in total comfort—cool, quiet, and just the way they like it. • Primary Suite – King bed, ensuite bath, ocean view, lanai access • Guest Bedroom 2 – Queen bed, garden and ocean views • Guest Bedroom 3 – Two Queen beds, perfect for families • Bonus Room – Twin bunk bed, ideal for younger guests • Three Full Bathrooms + One Half Bath – Modern and well-stocked Extras & Amenities Stay cool, connected, and entertained with: • Split system A/C in all bedrooms • High-speed Wi-Fi • Pool table • Full laundry room with washer & dryer • Kitchen essentials, and children’s amenities Location Highlights • Walk to beaches, local shops, and trails • Easy access to museums, historic sites, and markets • Short drive to world-class dining and entertainment Good to Know • Starter supplies provided: coffee, toiletries, paper products, and more • Daily resort fee may apply – please inquire for details • This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. • HAWAII TAX ID #TA-029-452-2880-01 • Licensed Short-Term Vacation Rental: STVR-19-355698 / NUC-19-0809 / PL-NUCR-2026-003539 Now Featuring Individual Climate Control in Every Bedroom Reserve your dates now and enjoy tailored comfort, modern amenities, and the peaceful beauty of Hawaii at Honu O Kai.

Hale Pua

Kailua Kona, HI, US
5 Bedrooms 16 Guests
Aug 26 - 29
$2,161 night

Hale Pua is an oceanfront sanctuary blending elegance, comfort, and the natural beauty of Kailua Kona’s rugged coastline. Located along scenic Alii Drive, this expansive 5-bedroom, 6-bath estate offers 5,140 square feet of luxurious living space and accommodates up to 16 guests. From sweeping ocean views and cool sea breezes to a private saltwater pool and multiple outdoor lounging areas, Hale Pua delivers the quintessential Hawai‘i retreat. What You’ll Love About Hale Pua • Private saltwater pool with spa and water feature • Game room with foosball and home theater • Multiple outdoor dining areas ideal for sunset meals • Ocean-facing walls of glass that bring in light, breezes, and spectacular views • Vibrant artwork and thoughtful finishes throughout • Every bedroom features a king bed, ensuite bathroom, air conditioning, and ceiling fans, ensuring ultimate comfort for all guests. • The home also features a dedicated media room with an 80-inch TV, nine reclining theater seats, and a large Blu-Ray collection. Living & Dining Designed to maximize indoor–outdoor living, Hale Pua features walls of glass that open to the sound of waves and glistening ocean views. The living area offers abundant seating and a Smart TV, creating a comfortable space to unwind. The light-filled dining area transitions seamlessly to the lanai, making it easy to enjoy meals with ocean breezes and postcard-worthy sunsets. Chef-Ready Kitchen The fully upgraded kitchen makes cooking effortless with state-of-the-art appliances, two large islands, and generous counter space ideal for group meal prep. A spacious pantry, refrigerator, dishwasher, oven, and essential cookware ensure you have everything needed for home-style dining. Natural light and views of both the pool and ocean enhance every culinary moment. Outdoor Oasis Your private backyard retreat includes a sparkling saltwater pool, hot tub, lush gardens, and a dining area for eight—perfect for romantic dinners or family gatherings under the stars. Relax on the loungers, enjoy yoga by the pool, or watch surfers, turtles, and even seasonal Humpback whales from the comfort of your oceanfront haven. Sleeping Quarters • Primary Bedroom – King bed + Twin bed, oceanfront lanai, ensuite with double sinks & walk-in shower • Kona Coffee Room – King bed, ensuite • Pua Room – King bed, ensuite • Surf Room – King bed, ensuite • Ohana Room – King bed + Queen sleeper sofa, ensuite, loft-style layout • Office – Two twin beds, access to nearby bathroom • Game Room – Sofa bed, exterior access Extras • Air conditioning in all sleeping areas • Two full-size washers and dryers • Beach towels • Free onsite parking • High-speed Wi-Fi throughout Resort / Community Highlights Enjoy easy access to hiking trails, golfing, water sports, spa experiences, and nearby dining. Whether you crave adventure or serenity, Hale Pua places the best of the Big Island at your doorstep. Nearby Walk: Tide pools at Turtle Cove, shoreline access, local cafés Short Drive: Kailua Village, beaches, boutiques, golf courses, cultural sites Good to Know • Daily resort fees for external amenities are not included • This home offers A/C only in the sleeping areas • This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. • Hawaii Tax ID: TA-078-702-0288-01 • Licensed Short-Term Vacation Rental: STVR-19-346902 / NUC-19-0315, PL-NUCR-2025-003102 • TMK: 760170430000 Reserve your stay at Hale Pua and experience an oceanfront retreat that offers both luxury and the soul-soothing rhythm of island life. From unforgettable sunsets to spacious gathering areas, this spectacular home promises a vacation filled with comfort, beauty, and lasting memories.

Ali’i Point #9

Kailua Kona, HI, US
3 Bedrooms 6 Guests
Aug 26 - 29
$3,023 night

Ali’i Drive runs a quiet stretch of coastline south of Kailua Bay, where the lava shelf meets the Pacific and the trade winds carry the sound of surf through open windows. Ali’i Point #9 sits along that stretch, a 3,190-square-foot home with three bedrooms, three and a half baths, and a private infinity edge solar heated pool overlooking the ocean. A pod-style layout gives the home its rhythm. Living and kitchen open to the lanai on one level, bedrooms resting above, each connected by a covered walkway allowing nature to seep in. What You’ll Love About Ali’i Point #9 • 3,190 square feet across two levels, with ocean views from the primary suite and guest room equipped with Queen bed • Private pool and jacuzzi, outdoor shower, and a lanai built for long afternoons • Koa-wood kitchen with a full chef’s setup • Community tennis and a second heated pool within the gated community • Walkable to Ali’i Drive beaches, coffee, and casual dining The Main Level Vaulted ceilings carry the breeze through the living and dining area, where sliding doors open to the lanai and the pool beyond. The kitchen anchors the space. Koa-wood cabinetry the color of dark honey, a full suite of appliances, and counter space enough for two cooks and a conversation. This is the floor where the day gathers. Breakfast at the counter, lunch under the lanai cover, a long dinner with the sliders pulled wide and the sound of water moving somewhere close. Due to this open flow layout, this space does not feature air conditioning. Outdoor Living The lower level opens directly to the water, with the pool set into lava rock just above the shoreline. Lounge seating lines the edge, with shaded areas for midday and open sun closer to the water. An outdoor shower sits just off the pool for easy rinses after the beach. The lanai ties it all together; pool, lounge, and dining in one continuous space. Mornings start here, afternoons drift between sun and shade, and evenings settle in as the light softens over the coast. Sleeping Quarters All bedrooms occupy the upper level, linked by a covered open-air walkway. Given the oceanfront proximity and the separation between floors, the layout suits adult guests and older children. • Primary suite: king bed with ocean views, en-suite bath with a jacuzzi tub • Second bedroom: king bed, en-suite bath, mountain views toward the slopes of Hualalai • Third bedroom: queen bed, en-suite bath, ocean views just outside the shutters Extras Air conditioning in the bedrooms, ceiling fans and cross breezes everywhere else. High-speed Wi-Fi, smart TVs, and full laundry. Resort & Community The Ali’i Point community offers a lap pool and tennis courts shared across the neighborhood. Beyond the gate, Ali’i Drive is the Kona coast in short form. Snorkeling, surf-watching, waterfront restaurants, and a steady stream of outriggers and paddleboards heading out at dawn. Nearby • A short walk to Ali’i Drive beaches, coffee shops, and casual dining • A short drive to Kona Country Club, hiking trails above the coast, and the cultural sites around Hulihe’e Palace Good to Know • Air conditioning is installed in the sleeping areas only. The main level stays cool through vaulted ceilings, ceiling fans, and trade winds off the water. • All bedrooms are on the upper level, connected by a covered outdoor walkway. • The pod-style design embraces the outdoors. Guests with small children should review the layout carefully before booking. • No EV charging on-site. Guests with electric vehicles should plan charging elsewhere during the stay. • A starter kit of basic supplies is provided. Please replenish as needed for longer stays. • Hawaii Tax ID: TA 166-655-4368-01 • STVR License: STVR-19-363491 / NUC-19-1388 / PL-NUCR-2026-003582 • TAT ID: TA 166-655-4368-01 Reserve while your week is still open. The Kona coast keeps its own time, and Ali’i Point #9 is a fine place to learn its rhythm. Mornings on the lanai, afternoons in the pool, evenings as the light turns copper over the water.

Kona Beach Bungalows**

Kailua Kona, Hawaii, US
15 Bedrooms 30 Guests
Aug 26 - 31
$9,189 night

Welcome to Kona Beach Bungalows by Gather! Dive into an unparalleled Hawaiian escape at our prestigious oceanfront estate, nestled right in the heart of Kailua Kona. Experience island luxury as it was meant to be! The moment you step onto the property, Kona Beach Bungalows welcomes you with a radiant embrace of Aloha. Spanning a vast oceanfront expanse, this Award-winning, 12-bedroom, 9-bathroom haven is masterfully crafted to provide up to 24 guests with an immaculate blend of opulence, comfort, and the enchanting spirit of Hawaii. Moana Makai, the jewel of the estate, is a living testament to the grandeur of Hamlet (Lucky) Bennett’s design. Stroll through the serene koi ponds marking the main entrance and enter a realm of sheer luxury. Indulge in the cool embrace of air-conditioned interiors, the gleam of granite black countertops, and the rich hues of Koa cabinets. Take a moment to challenge friends or family to a game on the state-of-the-art billiard table, or perhaps raise a glass at one of the two wet bar areas. Then, as day transforms into a vibrant Hawaiian evening, step onto the breathtaking lanai. Perch on the plush sofa, surrounded by majestic Koa chairs, and witness nature’s magic – the magnificent sunsets, playful spinner dolphins, and majestic humpback whales. Memories aren’t just made here; they are cherished. But that’s just half of it. Moana Mauka, an equally splendid oceanview estate, stands proudly next to Moana Makai. Designed with the same refined touch of Hamlet Bennett, it boasts spacious interiors highlighted by Koa kitchen cabinets, a sweeping slate and hardwood floor, and an enviable lanai that offers ocean views to die for. Its six bedrooms, donned mostly in Tommy Bahama Lexington furnishings, offer unparalleled comfort. And in its amenity garage, a treasure trove awaits: snorkeling gear, surf boards, boogie boards, and even toddler gear for the little ones. Beyond the walls of these estates, the adventures continue. Dive into the resort-style saltwater pool, unwind in the hot tub, or wander through the scenic oceanfront yard. And for the explorers among you, the prime location ensures you’re minutes away from Hawaii’s most sought-after activities – from snorkeling and surfing to exploring the wonders of the Volcanoes National Park and the Mauna Kea Observatory. For the foodies and shoppers, the Alii Gardens Marketplace across the street and nearby restaurants promise a treat. Yet, what truly sets Kona Beach Bungalows apart isn’t just the luxury or location; it’s the feeling of home it provides. A place where families gather, adventures are embarked upon, and memories are woven into the very fabric of the estate. As we always say, come for the sunsets, stay for the Aloha. So, why wait? Book your slice of Hawaiian paradise at Kona Beach Bungalows and let the Aloha spirit embrace you. In compliance with Hawai’i County Ordinance Number 2018-114, this property is a Hosted Rental Unit wherein the Property Owner has contracted with an onsite Caretaker who resides at the property. The Caretaker may assist with certain duties on the Property but is not an employee of or in anyway affiliated with Elite Pacific Properties, LLC powered by Gather. TA-004-988-1088-01 TMK 750200380000

Ono Hale 3 Bedroom Home

Kailua Kona, HI, US
3 Bedrooms 8 Guests
Aug 26 - 30
$593 night

We welcome you to stay at our private luxury home (Ono Hale) in the lush hills above historic Kailua Kona. Located just minutes from town and Kona’s beautiful sandy beaches. Cool and quiet. Ono Hale is situated on a very private lot on a quiet street at a perfect 750 ft elevation for ideal warm days and cool nights year round! At nearly 2800 finished sqft, the house sits on just over 1/3 acre that is fabulously landscaped with blossoming tropical flora. This 3 bedroom (2 King, 1 Queen) 2.5 bath home enjoys drop dead gorgeous panoramic ocean views with a 6 ft deep pool. Ono Hale is decorated with Brazilian cherry hardwood floors, quartzite stone tile, granite countertops, travertine tile and teak cabinetry. The high end finishes, open floor plan and tongue and groove vaulted wood ceilings create the environment for an incredible vacation getaway. If that sounds good, wait until you see the amazing covered lanai that stretches the whole length of the house! There is also a separate private lanai off the Master suite, the perfect place to enjoy your morning Kona coffee. There is a fully equipped kitchen which opens up to the main living space and the stunning lanai. The kitchen is stocked with basic necessities, large fridge/freezer, gas stove, oven, microwave and dishwasher. The closet is stocked with snorkel gear, beach chairs, beach towels and a cooler for relaxing at the beach. The home has cable television and also offers free wireless internet. Watch the ships arrive and depart and enjoy those magnificent Kona Sunsets! Hawaiian style comfort, Million dollar views, and just minutes from downtown Kona for shopping, restaurants, and beaches. An Air Mattress is available for 2 guest upon request. TAT tax ID # TA-094-136-5248-01 STVR#19-364955 NCU#19-1712 **All guests are required to sign a rental agreement with Property Manager Property Management** **All Reservation Requests greater than 12 months in Advance MUST be approved in advance by the Broker In Charge. Rates are subject to change.** Please note this home does not have Air Conditioning. Hosted by RedAwning Vacation Rentals, over 1,000,000 Guests Served Welcome to RedAwning, a whole new way to travel. We make staying in a unique home or apartment easier than staying at a hotel. By partnering with local hosts throughout North America, we provide you with the broadest collection of homes in the most destinations. Every stay includes our experienced 24/7 customer assistance, our free mobile app, and accidental damage protection for your trip with no security deposits. Wherever you want to go, RedAwning is here to make your journey easier! Want your own property to be included here and in the RedAwning Collection? Join Us and we will instantly promote your property everywhere guests shop for travel.

Dolphin Manor

Kailua Kona, Hawaii, US
5 Bedrooms 18 Guests
Sep 30 - Oct 5
$1,522 night

Perched directly on the lava-rock shoreline of Kailua-Kona, Dolphin Manor offers a front-row seat to the Pacific’s ever-changing beauty. This two-story, 3,667-square-foot oceanfront estate combines refined comfort with a walkable location just steps from downtown Kona and Honl’s Beach. With panoramic views, a private pool and spa, and sleeping space for up to 18 guests, it’s ideal for multigenerational escapes, milestone celebrations, or gathering friends in one unforgettable setting. What You’ll Love About Dolphin Manor * Oceanfront luxury estate with daily dolphin sightings * Private pool, spa, BBQ area, and wrap-around lanai with endless views * Five ensuite bedrooms, each with lanai access, A/C, and TV * Multiple living spaces including media room and office * Walkable to downtown Kona dining, shops, and Honl’s Beach Living & Dining A grand, gated entry leads into sun-filled interiors framed by vaulted ceilings and sliding glass doors to the sea. Two oceanview living rooms offer plush seating and coastal breezes, while the media room provides a cozy, air-conditioned retreat for movie nights. The dining area, set beside large windows, seats eight comfortably, with additional spots at the breakfast bar. Chef-Ready Kitchen A fully renovated kitchen shines with stainless steel appliances, a gas cooktop, wine fridge, and granite counters. Ocean views from the sink and prep spaces turn cooking into a pleasure, whether you’re brewing Kona coffee or preparing a fresh island feast. Outdoor Oasis Step onto the wrap-around lanai and breathe in the salt air. Lounge by the pool and spa, fire up the BBQ for an alfresco dinner, or watch spinner dolphins and wintertime whales from your private oceanfront perch. Lava outcroppings in front of the home add drama to the endless blue horizon. Sleeping Quarters * Downstairs Primary Suite – King bed, sleeper sofa, ensuite with soaking tub, dual vanities, walk-in shower, lanai access, ocean view * Upstairs Primary Suite – King bed, ensuite with tub/shower combo, lanai access, ocean view * Guest Bedroom 3 – King bed, ensuite with tub/shower combo, lanai access * Guest Bedroom 4 – King bed, ensuite with tub/shower combo, lanai access * Guest Bedroom 5 – King bed, ensuite with tub/shower combo, lanai access * Media Room – Queen sleeper sofa, ensuite bath with walk-in shower * Living Room – Two queen sleeper sofas, access to shared bath, lanai access Extras * Dual washers and dryers * Ceiling fans throughout * Private gated parking for four vehicles * Beach towels, BBQ grill, Wi-Fi Nearby Activities Downtown Kailua-Kona’s shops, cafes, Honl’s Beach, seaside bars, and art galleries Short Drive: Kahalu‘u Beach Park, Keauhou Harbor, Kona Farmers Market, multiple golf courses, Puʻuohonua o Hōnaunau National Historical Park, secluded Big Island beaches Good to Know ***Note that this home does not feature air conditioning in the living room, dining room or kitchen, however the nano door that opens all the way across allows for the ocean breezes to enter and keep guests comfortable in these spaces.*** * This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. * Licensed STVR 21-562958 * TA-039-641-1904-01 * TMK 750190280000 Reserve your dates now and experience Kona’s oceanfront living at its most inviting.

Hale Kope Kai

Kailua-Kona, HI, US
3 Bedrooms 7 Guests
Aug 26 - 29
$1,009 night

Hale Kope Kai delivers true oceanfront living on Hawaii’s Big Island. Nestled into the lava rock coastline of Kailua-Kona, this 3-bedroom, 3.5-bath luxury home with a bonus office loft blends modern comfort with unobstructed Pacific views. Whether you’re here for a romantic retreat, family gathering, or remote-work getaway, the home’s private pool, open-air lanai, and walk-to-beach location make it an unforgettable base for exploring the Kona Coast. What You’ll Love About Hale Kope Kai * Direct oceanfront location with spectacular sunsets & wave views from nearly every room * Private oceanview pool & BBQ lanai for outdoor dining and island-style entertaining * Dedicated office loft with printer & twin bed—perfect for remote work or flexible sleeping * Air-conditioned throughout the home * Minutes from Magic Sands Beach, Ali‘i Drive, shops, dining & historic Kona sites Living & Dining Step into the vaulted great room, where wall-to-wall pocket doors frame the ocean just beyond. Neutral-toned furnishings, coastal artwork, and cool tile floors set a relaxed tone, while the open layout flows to a covered lanai with a dining table and lounge seating just feet from the surf. Chef-Ready Kitchen The gourmet kitchen features granite countertops, rich wood cabinetry, and stainless steel appliances, including double ovens and a wine fridge. A breakfast bar overlooks the main living area, making it easy to stay connected while cooking. Outdoor Oasis From sunrise coffee to sunset cocktails, the lanai offers uninterrupted views of waves crashing against the lava rock shore. Take a dip in your private pool, grill fresh catch for dinner, or watch dolphins glide by from your lounge chair. Sleeping Quarters * Primary Suite – King bed, vaulted ceilings, A/C, ceiling fan, lanai access, ensuite bath with soaking tub & walk-in shower, ocean views * Guest Suite – Queen bed, A/C, ceiling fan, lanai access, ensuite bath with walk-in shower; detached from main house via covered stairway for privacy * Additional Sleeping Area -- King bed, A/C, ceiling fan, ensuite bath with walk-in shower; detached from main house via covered stairway for privacy * Office Loft – Twin bed, dedicated desk with printer, half bath, and ocean views Extras A/C throughout, laundry, high-speed Wi-Fi, streaming-ready TVs, beach towels, and outdoor shower. Nearby * Magic Sands Beach – 5 mins * Keauhou Shopping Center – 10 mins * Kailua Pier & Ali‘i Drive – 10 mins * Hulihe‘e Palace & Mokuaikaua Church * Kona coffee farms, snorkeling tours, manta ray night dives Good to Know * This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. * Licensed Short-Term Vacation Rental: PL-STVR-2022-000481 * Hawaii Tax ID: TA-008-330-5472-01 * TMK: 750190320000 Reserve your stay at Hale Kope Kai and experience Kona’s coastline like never before—where your backyard is the Pacific and every evening ends with a sunset show.

77-6386 Hale Alii Honu Kai

Kailua Kona, HI, US
3 Bedrooms 9 Guests
Aug 26 - Sep 2
$3,706 night

*Inquiry Only* Hale Ali‘i Honu Kai is a stunning 5,000 sq. ft. retreat designed for ultimate relaxation and connection with nature. Soaring ceilings, panoramic ocean views, elegant shoji screens, and telescoping glass doors dissolve the line between indoor luxury and the natural world. Surrounded by lush tropical gardens, the home features a 50-foot lanai, a tranquil oceanside infinity pool, and multiple open-air gathering spaces—all leading to a rare 300-foot stretch of private oceanfront, offering breathtaking views at every turn. Escape to your own peaceful sanctuary, perfectly situated in the heart of Kona. Space Primary bedroom: Cal King / Office / Indoor, outdoor bath Bamboo studio: Cal King / Kitchen / Air- conditioning Ohana 2nd floor:  1 bedroom: Cal King, living room: Queen bed & Single day bed, 1 bathroom Expansive open-air dining and lounging space Japanese-inspired estate infused with rich Hawaiian heritage Lush, park-like grounds with the soothing soundtrack of the ocean Amenities: Gated, private Washer/dryer Security system Gourmet kitchen with commercial appliances Imu pit / prep area Park-like setting garden with a pavilion Outdoor dining 4 televisions including 56 inch HDTV media room Wall safe High speed wireless internet Secure gated parking Oceanside infinity pool Fully equipped Kitchen equipped with basic appliances, kitchenware, tableware, and much more. Grill on lanai Cleaning products Linens: bedding, kitchen and bathroom Beach accessories - Beach towels, beach chairs, umbrella, cooler and some sand toys Air conditioning (in Bamboo Studio) Free internet, WiFi Private Pool Experience Within walking distance - Snorkeling, Magic Sands Beach & Magic’s restaurant. Just 3 miles south is Kona Country Club, Golf, restaurant and lounge. Dramatic volcanoes only a short helicopter ride away. Stargazing on Mauna Kea is a favorite! Area Kailua-Kona / Keauhou Located just 8 miles south of Keahole-Kona Airport, the sunny Kona district is known for its crystal-clear waters and rich cultural heritage. Explore historic landmarks like Huliheʻe Palace, Mokuʻaikaua Church, and Ahuʻena Heiau, or immerse yourself in local traditions at signature events such as the International Billfish Tournament (August), Ironman World Championship Triathlon (October), and the Kona Coffee Cultural Festival (November). Spend your days snorkeling, diving, paddle boarding, or simply watching spinner dolphins and Hawaiian sea turtles glide along the shoreline. Stroll down scenic Ali‘i Drive for oceanfront dining, cocktails, and stunning sunsets. For a deeper taste of the island, tour Kona’s renowned coffee farms, vanilla farms, or even visit a unique seahorse farm. At the southern end of Kailua-Kona lies Keauhou Bay, the historic birthplace of King Kamehameha III. This coastal gem offers ideal conditions for swimming, kayaking, canoeing, snorkeling, and spotting graceful manta rays—perfect for those seeking adventure or peaceful connection with the ocean. Other things to note: All LUVA Vacation Rentals are professionally cleaned, with enhanced cleaning protocols in place to ensure our guests can relax and vacation with confidence. Personal greeting and orientation of Hale Alii Honu Kai on arrival day. Guests are required to sign a rental agreement with LUVA Real Estate. LUVA provides the basic household conveniences for the kitchen, bathrooms, and laundry room. A complimentary welcome gift awaits our guests upon arrival. Concierge services: upon request Parties, receptions, weddings, luaus, events and gatherings of any kind are strictly prohibited. Holiday Booking Policy: -->Please note; we can not accept or confirm "Instant Bookings" for our holiday seasons, December 15 - January 7, all years. Please email our Management team for availability and holiday season requirements and/or restrictions// Festive Seasons is non-refundable, non-changeable. To ensure a seamless holiday experience, we have the following booking requirements for Christmas and New Year’s stays: - If booking over both Christmas and New Year’s, a 10 night stay is required. - If not staying for both holidays, check-in and check-out must fall between December 26–29. Thank you for your understanding—we look forward to hosting you for a festive and memorable stay! . *60 days cancelation policy. STVR-19-357217 GET / TAT : W26343683-01

Kona Kanewa Home

Kailua-Kona, HI, US
4 Bedrooms 10 Guests
Aug 26 - 31
$1,076 night

Walk to Magic Sands Large Home w/ Private Pool, Hot Tub, Terrace & 2 W/Ds You need never leave this four-bedroom home to have a memorable vacation in Kailua-Kona, as you’ll have your very own outdoor pool, a private hot tub, and a picnic and grilling area on the terrace to enjoy in the Big Island sunshine. Yet this property also boasts an ideal location for beach-going and exploring, with Magic Sands Beach Park less than half a mile up the road. Scenically set among the palms and a few houses back from the ocean, this two-level home was designed to accommodate a crowd. There are small comforts and conveniences everywhere you look, from the two washers and two dryers on the back patio to the six TVs positioned throughout the house. Make yourself at home in the main living space on the second floor, offering exposed-beam ceilings, windows on three sides that frame tropical greenery, and an airy layout that’s only enhanced by opening the balcony doors. The living room has a pair of sofas and a big-screen TV and entertainment system, while the dining room table sits in the light and the breeze of the sliding glass doors. The kitchen has every essential appliance (including a double-door refrigerator and a dishwasher) and a peninsula breakfast bar for four. An additional kitchenette - with a refrigerator and a microwave - awaits downstairs in the family room. You’ll be able to spend your days or nights swimming in the outdoor pool, soaking in the hot tub, rinsing off in the outdoor shower, and manning the gas grill for barbecues on the terrace. Cap your evenings with DVD, Blu-ray, or Netflix favorites before retiring to one of the four bedrooms, each of which has blissful air conditioning for a restful night’s sleep. <b>Things to Know</b> Please be advised that the free WiFi can be spotty Full kitchen upstairs and a kitchenette (with a full-size refrigerator and a microwave) downstairs AC in each bedroom Two washers and two dryers on the back lanai Outdoor shower This property is managed by Heavenly Vacations by Casago. License number: 770170270000

Kona Alii 707

KAILUA KONA, HI, US
1 Bedrooms 4 Guests
Aug 26 - 29
$174 night

Beautifully remodeled spacious 1 bedroom, 2 bath that includes AC in the living room, modernized kitchen, large lanai, and 7th story viewing sundeck where you can bask in the Hawaii sunshine or under the shade of the outdoor umbrella, enjoy sunsets, & stargaze at night! It is in the best location overlooking downtown Kailua-Kona! Kona Ali’i 707 is a top floor, penthouse condo in the heart of Kona by the ocean, restaurants, night life, and gift shops! Stay at this retreat and home away from home. The primary suite offers a comfortable King-Sized Bed with an en-suite bathroom with a rain shower head with bathtub/shower combo. A Queen-sized Murphy bed with Firm Sealy Mattress is located in the living room. The large sectional couch can also sleep 2 kids comfortably. The modernized guest bathroom includes a vanity, glass enclosures, and a front-load washer and dryer as well. The kitchen is fully equipped with quartz counters and stainless steel appliances. The living area provides a grand gathering space with high ceilings, dining set, large sectional couch, smart TV, and various seating areas for you to relax and enjoy quality time. There is one covered parking space. Beach supplies included! The pool is pristine and excellently maintained. There is a BBQ for your convenience at the complex and access to a common area rooftop deck on the 7th floor with a stunning ocean view. There are cooling trade winds and gorgeous sunsets. This is a secured complex, with elevator access. Start your day at a nearby coffee shop then bring home fresh flowers from the flea market. Spend the afternoon by the Pool or grab some sun on your own deck. Late afternoon, cross Alii Dr. to join the others on the Seawall enjoying a spectacular Kona sunset. Then pick from a dozen great restaurants, watch a bit of volleyball and stop for Gelato or Shave Ice. TAT#TA-022-597-3760-01 STVR#19-360814 **All guests are required to sign a rental agreement with Property Manager Property Management** ***All Reservation Requests greater than 12 months in Advance MUST be approved in advance by the Broker In Charge. Rates are subject to change.***

Kailua Kona Estate**

Kailua Kona, Hawaii, US
6 Bedrooms 16 Guests
Sep 14 - 17
$4,083 night

Welcome to Kailua Kona Estate by Gather, where luxury meets the laid-back charm of Hawaii. Just 5 minutes from downtown Kona, this 9,452 sqft private mansion sits on five beautifully manicured acres, offering the perfect blend of upscale living and island ease for up to 16 guests. Step into this sunlit haven and feel the warmth. The estate’s skylights flood the space with Kona’s natural glow, highlighting the elegant mahogany details and a cozy stacked stone fireplace. It’s the perfect setting for both relaxing and entertaining, complete with a wet bar for those evening get-togethers. With five officially listed bedrooms and two additional flex rooms (showcased in our photos with a king bed and three full beds), the house adapts to your group’s needs, whether it’s a large family gathering or a getaway with friends. The heart of the home is the chef’s kitchen, decked out with triple refrigerators and spacious quartz counters. It’s where culinary magic happens, and memories are made. Upstairs, the lanai is your front-row seat to some of the most stunning ocean views and sunsets Kona has to offer. Outside, the 100ft infinity pool and a jacuzzi tub await for those moments of pure relaxation. Every bedroom, designed for comfort, features top-quality mattresses and linens, ensuring peaceful sleep after your island adventures. Located in a secure, gated community, the estate not only promises tranquility but also a connection with the surrounding nature. We’re all about sustainability and respecting the beautiful land we call home. This space is perfect for families looking to make lasting memories. We observe quiet hours past 9:30 PM to keep the peace with our neighbors (making the 16-seater movie room your go-to spot for late-night entertainment). Please note, the pool, pickleball court, and lanai close at 10 PM nightly. While we love celebrations, the estate isn’t set up for parties or events. If you need help finding a spot for your event, just reach out. Our on-site hosts have their own private space, so they’re there if you need them but out of sight for your stay. Kailua Kona Estate is more than just a stay. It’s a luxury experience wrapped in the easy-going spirit of the Big Island. Ready to make some memories? Book your stay today and discover why Kona is a little slice of paradise! In compliance with Hawai’i County Ordinance Number 2018-114, this property is a Hosted Rental Unit wherein the Property Owner has contracted with an onsite Caretaker who resides at the property. The Caretaker may assist with certain duties on the Property but is not an employee of or in anyway affiliated with Elite Pacific Properties, LLC powered by Gather. TA-025-660-4672-01 750110140000

Ho’oka’ana Hale

Kailua-Kona, HI, US
3 Bedrooms 6 Guests
Sep 8 - Oct 8
$408 night

Stunning tropical retreat near the beach with pool, views & spacious lanai Live the luxe life at the top of Alii Heights! Surrounded by colorful blooms and palm trees, find yourself waking up every day in paradise. Located in gorgeous Kailua-Kona this custom home boasts a great central location to many tropical amusements such as; Magic Sands Beach Park, Black Sand Beach, the Kona Country Club, Kaloko-Honokōhau National Historical Park, and of course, delicious, authentic Hawaiian food, and shopping! At your retreat, you’ll be mesmerized by the effortless flow between indoor and outdoor living. Inside, discover a sprawling open floor plan. The main living area, dining area, and kitchen, all seamlessly blend together as one. Here, you can relax in the home’s central air-conditioning on the plush seating. Or, you can practice your culinary skills in the gleaming dark-wood kitchen. Utilize the suite of stainless steel appliances and ample meal prep space before serving your creations at the breakfast bar or dining table. In the primary bedroom, you will discover an oasis in itself. With bright pool views, tasteful decorations, a California King-sized bed, and an impressive en suite bathroom, this space is ready to welcome you with open arms. Unwind in the comfort of one of the two walk-in showers within the primary bathroom each morning, starting your day off right. (In another one of the magazine-worthy bathrooms, an official Jacuzzi brand jetted tub awaits peaceful soaks if that is more your style.) The second bedroom also boasts a California King-sized bed, and the third, a bunk bed with two twin-sized beds. After a day spent out in the sand and surf, wash your clothes in the private washer/dryer. And as an additional interior perk, appreciate a large air-conditioned garage. Outside, a stunning swimming pool with solar heating and a sprawling ocean-view lanai are prepared to become staples of your vacation. From the enclosed backyard, you will be able to watch the sunset come nightfall. Lounge on one of the many plush seats, dine alfresco on the spacious outdoor dining table, practice your barbecuing skills on the grill, and rinse off in the outdoor shower. Memories curated in this home will be beautiful, full of sunshine, and life-long. <b>THINGS TO KNOW</b> • 30+ night rental. • This home may not be rented for commercial purposes. • This property is managed by Heavenly Vacations. License number: 770290670000

Hale Pahukoa

Kailua Kona, HI, US
3 Bedrooms 8 Guests
Aug 28 - 31
$528 night

This charming property has been kept the same since the original build to keep the "sugar plantation" style of the old Hawaii days. No major upgrades have been made to keep an old Hawaii days feel. The RATES REFLECT the style accordingly. This home is perfect for LOCATION LOCATION LOCATION & FOR A DEAL! Other homes in this area run 3x the going rates for this vintage Hawaiian beach house. Please be aware this is an older home and the owners and repeat guests adore this home exactly the way it is. Ideally nestled in Kona Bay Estates Community located min from center of downtown. The simple seaside style will melt all of your cares away as you sip on your Mai Tai in the cool shade of the deep, covered lanai. Experience the feel of being in another place in another time. All beds are fitted with comfy mattress toppers & the master bed has a 2 inch memory foam topper for a peaceful, cozy nights sleep! Close to Kailua Pier where the fishing is fine and the canoe races begin! IronMan start and finish is nearby. Property has a 7 night minimum all year round, unless arrangements have been approved by the owner of the Property. This property does NOT have any Air Conditioning. **TA-023-091-6096-01 STVR#19-363825 NCU#19-1595 **All guests are required to sign a rental agreement with Property Manager Property Management** ***All Reservation Requests greater than 12 months in Advance MUST be approved in advance by the Broker In Charge. Rates are subject to change. *** Disclosure about Pool: There is some algae on the pool floor/sides that is not fixable until owners replaster pool. It’s not harmful, and the pool guy is very good with chemical balance and keeping water clear. Hosted by RedAwning Vacation Rentals, over 1,000,000 Guests Served Welcome to RedAwning, a whole new way to travel. We make staying in a unique home or apartment easier than staying at a hotel. By partnering with local hosts throughout North America, we provide you with the broadest collection of homes in the most destinations. Every stay includes our experienced 24/7 customer assistance, our free mobile app, and accidental damage protection for your trip with no security deposits. Wherever you want to go, RedAwning is here to make your journey easier! Want your own property to be included here and in the RedAwning Collection? Join Us and we will instantly promote your property everywhere guests shop for travel.

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Vacation Rentals Near Holualoa

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