Large group vacation rentals in O‘ahu, HI

Explore 168 large group vacation rentals, homes, and villas in O‘ahu, HI for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Air Condition Homes, Homes with Free Parking and Homes with hot tub. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $131 per night and homes offering up to 9 bedrooms and 10 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

168 Great for Groups in O‘ahu

Luminous Seascape | Ocean View

Kaneohe, HI, US
4 Bedrooms 8 Guests
Aug 31 - Sep 30
$253 night

Immerse yourself to our contemporary haven boasting tranquil ocean views! This getaway offers all the essentials for a perfect stay. Wake up to breathtaking scenery through sunlit windows, unwind on the spacious terrace surrounded by lush greenery, and let the soothing sound of the waves melt your stress away. With convenient highway access & just moments from the island’s stunning beaches, this is the escape you’ve been dreaming of. Create unforgettable memories in your own slice of paradise! • 1,950 sqft • sanitized, self-check-in (contact-free) • free parking • full kitchen • fast & stable wifi • desk for remote work • Gas BBQ grill and outdoor dining Managed by | Marbella Lane | full-service vacation rental property management | Top performer by AirDNA 4 bedrooms • 3 baths • 1 kitchen THINGS TO KNOW: • Streaming is available using your own accounts. • Please note that the driveway is uneven. • No pets are allowed at this vacation rental. • Security camera details: 1 at driveway; 1 facing out toward the courtyard. PARKING NOTES: Designated parking for one vehicle is available on the right side of the bottom of the driveway. Guests will have access to the entire home except for a closet that we have locked. Car is highly recommended. CANCELLATION POLICY: Specific Cancellation policy applies to each platform. No refund within 30 days of check-in, if you book on our website. Security Deposit ($500 USD) — Note: We have a NO-pet policy. Also, an extra guest fee applies after 6 guests, $50 per person, per night.

Wailupe Beachfront Getaway

Honolulu, Hawaii, US
5 Bedrooms 12 Guests
Aug 31 - Sep 30
$987 night

Where Oʻahu’s south shore meets crystalline waters, Wailupe Beachfront Getaway welcomes up to twelve guests to experience effortless island living. This 4,291‑square‑foot, five‑bedroom retreat unfolds across two spacious levels with sweeping oceanfront views, private pool and spa, and seamless indoor‑outdoor design. What You’ll Love About Wailupe Beachfront Getaway * Direct beach frontage with kayaks and paddleboards ready for sunrise sessions * Private pool, hot tub, and fire‑pit lounge framed by swaying palms * Two spacious living rooms that disappear to the ocean via pocket doors * Separate game‑room suite with kitchenette, sofa bed, and private entry * Pet‑friendly residence with EV charger, smart tech, and high‑speed Wi‑Fi Living & Dining Floor‑to‑ceiling glass walls open to the trade winds, creating a breezy flow between the lounges and lanais. Two living rooms feature plush seating and smart TVs, ideal for family movie nights or quiet reading by the sea. A generous dining table for eight overlooks the shoreline, inviting guests to linger over island‑inspired meals. Chef‑Ready Kitchen With a Viking range, dual ovens, wine fridge, and expansive prep space, the kitchen is designed for both gourmet chefs and casual family cooking. An adjacent wet bar and outdoor BBQ station make entertaining effortless. Outdoor Oasis Lounge on the expansive hardwood deck, soak in the bubbling hot tub, or float in the sun‑lit pool as palms sway overhead. A stone fire pit anchors evening gatherings, while two kayaks and paddleboards wait at the water’s edge. From sunrise paddles to starlit conversations, the lanai offers an endless stage for island moments. Sleeping Quarters * Primary Suite – King bed, three walk‑in closets, spa bath with soaking tub, dual vanities, ocean‑view balcony, split A/C * Guest Suite 2 – King bed, ensuite bath, ocean‑view balcony, split A/C * Guest Suite 3 – Queen bed + Twin with trundle, ensuite bath, ocean‑view balcony, split A/C * Guest Suite 4 – King bed, ensuite bath, blackout drapes, ocean‑view balcony, split A/C * Guest Suite 5 (Studio/Game Room) – Queen bed + sofa bed, half bath ensuite, full bath steps away, kitchenette, smart TV, private entrance, pool & ocean view Extras * Central A/C * High-speed Wi-Fi * Washer/dryer * Pool table * Beach gear * Outdoor shower * Garage parking * EV charger * Pet-friendly policy for extended stays Nearby Reach Aina Haina Shopping Center (5 min), Kahala Mall (10 min), and Waikiki’s dining and nightlife (20 min) with ease. Legendary hikes at Diamond Head, Koko Crater, and the dramatic cliffs of China Walls are just minutes away. HNL airport is a straightforward 25‑minute drive. Good to Know * Available for exclusive 30‑day rental periods only; rates reflect a full 30‑day stay * Dog‑friendly with prior approval; additional fee applies * TA‑148‑851‑7632‑01 * TMK 350220050000 Reserve your dates now and immerse yourself in the rhythm of oceanfront island life.

Hillside Villas 1534-2

Kapolei, Hawaii, US
3 Bedrooms 6 Guests
Oct 31 - Nov 29
$252 night

Welcome to Hillside Villas 1534-2, a peaceful 3-bedroom, 2.5-bath retreat in Ko Olina, offering garden serenity, breezy indoor–outdoor living, and quick access to lagoons, dining, and resort-style amenities. Located in the heart of Kapolei’s sought-after resort community, this 1,173 sq ft villa accommodates up to 6 guests and delivers a relaxing home base for beach days, sunset strolls, and unforgettable Oʻahu adventures. With natural light, tropical landscaping, and a private garden lanai, Hillside Villas 1534-2 blends comfort with an easygoing island lifestyle. What You’ll Love About Hillside Villas 1534-2 • Spacious, light-filled layout designed for comfort and gathering • Private garden lanai—perfect for morning Kona coffee or sunset cocktails • Granite-top kitchen with stainless-steel appliances & breakfast bar • Chic coastal décor that enhances the island ambiance • Resort-style pool, whirlpool & BBQ cabana just a short stroll away Living and Dining Step into the open-concept living area where natural light fills the space and stylish coastal decor sets a serene mood. Relax on comfortable seating after a day at the lagoons, or gather around the dining table for family meals and game nights. Sliding glass doors blend indoor living with the lush outdoors, inviting island breezes throughout the home. Chef-Ready Kitchen Perfectly designed for home-cooked meals, the kitchen features stainless-steel appliances, granite countertops, a spacious island, and ample cookware. Whether preparing quick beach snacks or a full island-inspired meal, the kitchen keeps everyone connected with its open layout and adjacent dining area. Outdoor Oasis Your private garden lanai offers a tranquil spot framed by palms and tropical landscaping. Enjoy alfresco dining, sip something refreshing under the warm Hawaiian sun, or unwind in the shade as cooling trade winds flow through. It’s the ideal setting for quiet mornings, relaxing afternoons, and sunset happy hours. Sleeping Quarters • Primary Bedroom – King bed, ensuite bath, smart TV, generous closet • Guest Bedroom 2 – Queen bed, natural light, ceiling fan • Guest Bedroom 3 – Double bed; versatile space for work, rest, or kids Extras Central A/C • High-speed Wi-Fi • Washer & dryer • Smart TVs • Designated parking stall • Beach towels • Starter amenities (shampoo, dish soap, detergents) Hillside Villas Community Highlights Enjoy Ko Olina’s private gated setting with access to a resort-style lagoon-style pool, bubbling whirlpool, shaded BBQ cabana, and lush walking paths. Nearby, explore the renowned Ko Olina Golf Course, marina charters, four postcard-worthy lagoons, boutique shopping, and popular restaurants like Monkeypod Kitchen. Nearby You can walk to Ko Olina Station’s shops and dining, enjoy the beaches and water activities at Lagoon Two, or explore the garden-lined walking paths throughout the resort. A short drive brings you to Kapolei Commons for additional shopping and dining, the family-friendly Wet’n’Wild Hawaiʻi waterpark, and a variety of scenic hiking trails and outdoor adventures. Good to Know • Assigned parking is for standard or compact vehicles only. We cannot accommodate oversized vehicles or large SUVs. Public parking or street parking is not available in this community. If you arrive with a vehicle that does not fit into the assigned parking space, you might be turned away and not allowed to check in. This unit has 2 parking spaces available for guest use. • Ola No Smoking Clause for all Residential Vacation Rentals: Smoking is strictly prohibited within the premises of the vacation rental property. This includes, but is not limited to, the interior of the accommodation, balconies, patios, and any common areas within the property. The policy extends to the use of cigarettes, cigars, pipes, electronic cigarettes, marijuana and any other form of smoking or vaping. Guests are required to respect this no-smoking policy to maintain a healthy and comfortable environment for all occupants and neighbors. Any violation of this policy will result in a penalty, and the cost of any necessary cleaning, deodorizing, or damage repair will be charged to the guest. It is the responsibility of the guest to inform all members of their party and any visitors about the no-smoking policy. Failure to comply with this policy may lead to eviction from the property without refund. The property owner/manager reserves the right to enforce this policy and take appropriate action against any guest or visitor found smoking on the premises. • Quiet hours 10 pm – 8 am per HOA rules • No resort or parking fees at this time (subject to change) • All bedding configurations are as noted; please inquire if you need alternate setups • TA-190-899-1488-01 • TMK 910560130098 Exclusively offered by Gather, Hillside Villas 1534-2 provides a relaxing blend of comfort, convenience, and resort-style amenities in one of Oʻahu’s most desirable coastal communities. Reserve your stay today, and enjoy a refreshing Ko Olina escape that feels both welcoming and wonderfully effortless.

Watermark Waikiki Unit 901

Honolulu, Hawaii, US
2 Bedrooms 4 Guests
Sep 30 - Oct 30
$335 night

Step into refined island living at Watermark Waikiki Unit 901, a spacious two-bedroom, two-bathroom corner residence in Honolulu’s iconic resort district. From the ninth floor, your lanai frames sweeping views of the ocean, marina, city, mountains, and fiery sunsets—a daily spectacle of Hawai‘i’s natural beauty. Designed with comfort and ease in mind, this home balances open-plan living with private retreats, creating an inviting base for extended stays in Waikiki. What You’ll Love About Watermark Waikiki Unit 901 * Panoramic ocean, city, mountain, and sunset views from the lanai * Open-concept living and dining area with abundant natural light * Gourmet kitchen with Viking appliances, granite countertops, and island seating * Two serene king bedrooms, each with dedicated bath access * Resort-style amenities including pool, hot tub, gym, sauna, and tropical gardens Living & Dining The corner positioning floods the home with light and frames city-to-mountain views. Relax in the chic living room with plush sofas, a ceiling fan, and smart TV, or gather around the dining table set against wide windows. Sliding glass doors lead to the lanai, where coffee at sunrise and cocktails at dusk are unforgettable. Chef-Ready Kitchen Anchoring the living space, the kitchen is fitted with rich African Mahogany cabinetry, granite counters, and stainless Viking appliances. An island with bar seating invites casual meals or conversation while cooking. Outdoor Oasis Your private lanai is the highlight: lounge seating and a café table make it the perfect perch for morning breezes, evening lights, and a constant sense of place in the heart of Honolulu. Sleeping Quarters * Primary Suite – King bed, ensuite bath with dual vanity, walk-in shower, and soaking tub; mountain views * Guest Bedroom – King bed, workspace, closet, and flat-screen TV; adjacent bath with walk-in shower Extras * In-unit laundry and private storage * One covered parking stall * High-speed Wi-Fi and smart lock entry * Central A/C for comfort throughout Resort / Community Highlights The Watermark community surrounds you with thoughtful amenities: a lagoon-style pool with hot tub, fully equipped fitness center, sauna, BBQ grills, lush tropical landscaping, koi ponds, and peaceful garden paths. Secure entry, a stylish lobby, and meeting rooms add to the sense of comfort. Nearby * Walk: Waikiki’s beaches, Ala Moana Center shopping, dining, and green parks * Short Drive: Golf courses, hiking trails, cultural attractions, and Honolulu International Airport (HNL) Good to Know * This residence is available exclusively as a monthly rental. Full-month occupancy is not required, but the fixed monthly rate applies regardless of length of stay. The property will be occupied solely by the renter for the reserved period. Please inquire for details. * Tax ID: TA-208-202-2912-02 * TMK: 260110010044 Reserve your dates now and embrace effortless island living at Watermark Waikiki Unit 901.

Ilikai Hotel | 2 Ocean view Studios, Sleeps 10 | ML-4142

Honolulu, HI, US
2 Bedrooms 10 Guests
Aug 31 - Sep 2
$634 night

NEW 2 Ocean View studio villas at Ilikai Resort & Suites with Free Parking ** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and drop-off is included and you’ll only be responsible for a $15/day airport tax. Upgrades to larger vehicles are available upon request.Please note: Holiday periods may result in limited rental car availability. We recommend booking as early as possible. Welcome to your dream Honolulu retreat - an exclusive 2-bedroom, 2-bath residence created by including 2 separate yet nearby premium villas within the coveted Ilikai Hotel & Luxury Suites Resort. Please note these villas are not connected, however, they are located at the same resort within walking distance of each other on two separate floors. Perfect for families or groups, this expansive configuration comfortably accommodates up to 10 guests with plenty of room to gather or enjoy private moments in luxurious surroundings. Both the units within this listing feature air conditioning for comfort and partial ocean views to enjoy incredible Oahu sunsets. Plus 2 FREE parking stalls in the Ilikai garage. ILK-732 is a beautifully upgraded 1 bedroom/studio style 1 bath villa, perfectly situated on the 7 floor at Ilikai Hotel & Luxury Suites Resort. This villa seamlessly blends comfort & style, offering an additional 127 square feet of Lanai space to soak in the Honolulu landscapes and refreshing island breezes. The property includes 1 bedrooms. BD1 features a King, and a pull-out sofa-accommodating up to 4 guests. ILK-437 is a beautifully upgraded studio 1 bath villa, perfectly situated on the 4 floor at Ilikai Hotel & Luxury Suites Resort. This villa seamlessly blends comfort & style, offering an additional 127 square feet of Lanai space to soak in the Honolulu landscapes and refreshing island breezes. The property includes 0 bedrooms. BD1 features two double beds and a pull-out sofa-accommodating up to 6 guests. Parking Information: The suites comes with 1 free parking space each in the garage. The placards and FOB access cards will be available in your rooms upon arrival. #TA-001-489-4592-01 #TA-061-406-1568-01 Perfectly positioned between Waikiki’s world famous white sand beaches and the vibrant energy of downtown Honolulu, the Ilikai Hotel & Luxury Suites offers the best of Oahu in one iconic oceanfront setting. This legendary landmark blends relaxed island elegance with modern resort comfort, creating an unforgettable home base for your Hawaii escape. Wake up to breathtaking panoramic views of the Pacific Ocean, sparkling marina waters, and Oahu’s stunning south shore, where every sunrise and sunset paints the sky in brilliant color. With more than five decades of warm Hawaiian hospitality, the Ilikai welcomes you with an atmosphere that feels both timeless and effortlessly luxurious. From the moment you arrive, you are greeted by fragrant tropical blooms and gentle trade winds in the open air lobby, setting the tone for a true resort experience. Spend your days lounging on the expansive sun deck, taking a refreshing dip in the swimming pool, or staying energized in the on site fitness center. The Ilikai is also home to convenient dining options, boutique shops, and easy access to Waikiki Beach, Ala Moana Center, and Honolulu’s best restaurants and nightlife. Whether you are here to relax by the water, explore the island, or enjoy the excitement of the city, the Ilikai Hotel & Luxury Suites delivers the ultimate blend of comfort, location, and resort style amenities for an extraordinary Hawaii getaway. Licence number: TA-001-489-4592-01

Hale Alapi’i Lanikai Getaway

Kailua, HI, US
4 Bedrooms 6 Guests
Dec 31 - Jan 30
$634 night

Just a short stroll from turquoise water and powder-soft sand, Hale Alapi‘i Lanikai Getaway by Gather is a serene 4-bedroom, 3-bath retreat set in Kailua’s coveted Lanikai neighborhood. Recently renovated interiors meet breezy outdoor living, surrounded by tropical greenery and views of the famous Lanikai Pillbox ridge. Perfect for families and longer stays, the home includes a separate studio for added privacy. What You’ll Love About Hale Alapi‘i Lanikai Getaway • Three-minute walk to a secluded swimming cove and ten minutes to Lanikai Beach • Main house plus an optional private studio, ideal for extended family or couples • Bright open-plan living with modern finishes and abundant natural light • Split A/C cooling all areas of the home for easy comfort • Lush yard, furnished lanai seating, and a peaceful residential setting Living & Dining The main house gathers everyone in a light-filled, open-concept space. Large windows frame palms and greenery, while comfortable seating invites relaxed conversation after a day on the sand. The adjacent dining area seats the crew for family meals, board games, and planning tomorrow’s adventures. Chef-Ready Kitchen A renovated, fully equipped kitchen keeps cooking simple and social. Stone-look counters, generous storage, and a functional island make prep a breeze, from sunrise smoothies to casual island-style dinners. Outdoor Oasis Step outside to a private, tropical setting designed for unhurried days. Settle into cushioned lounge seating on the lanai, sip morning coffee as birdsong fills the air, and watch the light change over the Lanikai Pillbox. After the beach, rinse off, grill your favorites, and dine under the palms. Sleeping Quarters • Primary Bedroom – King bed, ensuite bath, Split A/C • Guest Bedroom 2 – Queen bed, shared bath, Split A/C • Guest Bedroom 3 – Two twin beds, shared bath, Split A/C • Guest Studio – Queen bed, ensuite bath, private entrance, Split A/C Extras Approximately 1,750 sq ft of interior space across the main house and studio, Smart TV, high-speed Wi-Fi, laptop-friendly setup, washer and dryer, ceiling fans, and free driveway parking. The separate studio adds flexibility for multi-generational travel or guests who want their own quiet space. Resort / Community Highlights Set within a peaceful residential neighborhood in Lanikai. Private home, no shared resort amenities, with easy pedestrian access to beaches and the Pillbox Trailhead two blocks away. Nearby Walk to a calm swimming cove for snorkeling and paddling, or take a ten-minute stroll to world-famous Lanikai Beach. Launch kayaks toward the Mokulua Islets when conditions allow, hike the Lanikai Pillbox Trail for sweeping Windward views, and explore Kailua Town’s cafés, boutiques, and Whole Foods. HNL is the nearest major airport. Good to Know • This property is offered as a monthly rental • The monthly rate applies in full regardless of the number of nights stayed • Minimum 30-day booking period required • Optional studio available for an additional fee, confirm pricing at inquiry • Free parking in the driveway • Exclusive use for the duration of the rental period • TAT ID: TA-150-218-4960-01 • TMK: 430030350000 Reserve your dates at Hale Alapi‘i Lanikai Getaway by Gather and enjoy easy island living between the beach, the Pillbox trail, and the relaxed charm of Kailua.

Kailua Sands

Kailua, HI, US
4 Bedrooms 7 Guests
Dec 31 - Jan 30
$3,212 night

Kailua Sands sits directly on the golden curve of Kailua Beach, where turquoise waters meet soft sand just steps from your lanai. This single-level, 3,360-square-foot home embraces a seamless indoor-outdoor flow, centered around a private pool courtyard framed by swaying palms and the sound of the surf. What You’ll Love About Kailua Sands • Direct beachfront location with panoramic ocean views • Private pool courtyard at the heart of the home, perfect for a morning swim or a relaxing evening in the jacuzzi • Separate pool house with Murphy bed and gym equipment • Fully equipped chef’s kitchen with breakfast bar • Spacious yard leading straight to the sand • Filtered water throughout the home Living & Dining Sliding glass walls open the living areas to both ocean breezes and poolside lounging. Two seating zones make it easy for groups to spread out or gather together. The dining table, framed by wood-beamed ceilings, offers views of both the courtyard and the water beyond. Chef-Ready Kitchen A curved breakfast bar anchors the open kitchen, equipped with high-end appliances, abundant prep space, and ocean views to keep the cook inspired. Outdoor Oasis The pool courtyard is the soul of the home with a stunning jacuzzi, with sun loungers, shaded decks, and the gentle lull of nearby waves. Just beyond the lawn, a private path takes you directly to Kailua Beach. Sleeping Quarters • Primary Suite – Cal king bed, ensuite bath, ocean view, central AC, ceiling fan, blackout drapes • Guest Bedroom 2 – King bed, ensuite bath, central AC, ceiling fan, blackout drapes • Guest Bedroom 3 – Queen bed, central AC, ceiling fan, blackout drapes • Pool House – Murphy bed, ensuite bath, pool view, central AC, ceiling fan, gym equipment Extras Central AC throughout, high-speed Wi-Fi, washer/dryer, gas BBQ grill, dedicated workspace, elliptical machine, yoga mat. Nearby A short drive brings you to Lanikai Beach, the Lanikai Pillbox Trail, boutique shopping, and golf courses. Good to Know * Pool heat fee to 85–88°F: $2,000/month. Utility fee: $1,000/month. Driveway parking. 30-day minimum rental; exclusive use during your stay. * Property is currently for sale. The property manager will contact you to make arrangements to schedule showings at a convenient time. * TAT: TA-132-806-7584-01 * TMK: 1430170330000 Reserve your dates now to experience beachfront living at Kailua Sands — where every day begins and ends with the ocean. The property will be made exclusively available to the renter for a full period of 30-days and no one else may occupy the property during that period. Rates based on a 30 day rental period. Please Inquire.

Kailua Hale Kahakai

Kailua, HI, US
6 Bedrooms 12 Guests
Aug 31 - Sep 30
$988 night

Welcome to Kailua Hale Kahakai, a serene beachfront estate set along one of the most breathtaking stretches of Kailua Beach. With six bedrooms, five bathrooms, and over 4,300 sq. ft. of breezy living space, this expansive retreat blends open-air island design, panoramic ocean views, and peaceful privacy on a quiet flag lot surrounded by swaying palms. Ideal for family gatherings, reunions, group travel, and extended stays, this home delivers a true Hawaiian beachfront experience. What You’ll Love About Kailua Hale Kahakai • Direct beachfront access to Kailua Beach • Four ocean-view bedrooms on the upper level • Expansive shaded lanai and lush oceanfront backyard • Large chef-ready kitchen with stainless appliances and center island • Two living rooms, formal dining room, and multiple indoor/outdoor gathering spaces • Natural tradewinds and ceiling fans throughout (home is not air-conditioned) Living & Dining Designed for families and groups, the spacious living areas invite relaxation with coastal décor, sliding glass doors, and sweeping views of the turquoise shoreline. The formal living room overlooks Kailua Beach, while the adjacent TV room features a Smart TV for movie nights or quiet downtime. The bright, window-wrapped dining room seats your group comfortably and opens to the oceanfront backyard. Chef-Ready Kitchen The fully equipped kitchen includes stainless-steel appliances, a large center island, microwave, mixer, blender, toaster oven, coffee maker, grinder, and ample cookware. Whether preparing meals or crafting island cocktails, this kitchen is ready for every occasion. Outdoor Oasis Step onto the shaded lanai overlooking a private, palm-framed lawn that stretches toward the shoreline. Enjoy covered outdoor lounging and dining, oceanview seating areas, and a direct pathway to Kailua’s soft sandy beach. It’s the perfect setting for sunrise coffee, sunbathing, or sunset unwinding. Sleeping Quarters • Main Bedroom Suite (Upper Level) – King bed, balcony with ocean and bay views, ensuite with soaking tub and dual vanities • Guest Bedroom 2 (Upper Level) – King bed, ocean view, shared full bath with tub • Guest Bedroom 3 (Upper Level) – King bed, garden view, shared full bath with tub • Guest Bedroom 4 (Upper Level) – King bed, ocean view, shared full bath with shower/tub combo • Guest Bedroom 5 (Upper Level) – Queen bed, ocean view, shared full bath with shower/tub combo • Guest Bedroom 6 (Main Level) – King bed, garden view, private ensuite bath with walk-in shower Additional full bath on the ground level. Extras • Beach chairs, mats, umbrella, boogie boards, coolers • Insulated cooler bag and beach bag • Full-size washer/dryer • Additional bedding • On-site parking • Smart TVs and cable • Ceiling fans and natural breezes • Secure smartlock entry Nearby • Walk: Kailua Beach, Kalama Beach, Kailua Beach Park, Kailua Town shops and restaurants, Island Snow, Lanikai Bike Path • Short Drive: Lanikai Beach, Lanikai Pillbox Hike, Downtown Honolulu, Ala Moana Center, Kahala Mall, Koʻolau Golf Course, Maunawili Falls Trail, Whole Foods Kailua, Target Kailua Good to Know • Monthly rental; full monthly rate applies regardless of number of nights stayed • Home does not have air conditioning; cooled by trade winds and ceiling fans • Exclusive to renter for the full 30-day period • Tax ID: TA-039-143-1168-01 • TMK: 430130020000 Reserve your dates now and experience the beauty, privacy, and beachfront serenity of Kailua Hale Kahakai.

Coconut Plantation 1110-3

Kapolei, HI, US
2 Bedrooms 4 Guests
Aug 31 - Sep 29
$235 night

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available. Welcome to Coconut Plantation 1110-3 by Gather, where a blend of comfort and elegance awaits. Nestled in the serene Coconut Plantation at Ko Olina Resort, this stunning two-bedroom, two-bathroom downstairs unit offers an idyllic escape with modern conveniences and timeless charm. Step into a freshly updated space where contemporary wood plank flooring harmonizes with the tropical outdoor surroundings. The heart of this home, a fully upgraded kitchen, shines with new appliances and eye-catching gray, white, and silver natural quartz countertops, creating an inviting space for culinary creativity and social gatherings. Experience tranquility on the airy and open lanai. Encircled by verdant vegetation and the sweet scent of plumeria trees, this private sanctuary features deep seating lounge furniture and a ceiling fan, crafting a perfect spot for unwinding or intimate conversations. Each bedroom is an oasis of relaxation with flatscreen smart TVs for leisurely entertainment and high-end mattresses for ultimate comfort. This home provides top-notch beach gear like high-end island beach chairs and a generous supply of luxurious beach towels. For your convenience, the home includes a residential-grade side-by-side washer and dryer, and offers parking with a private compact garage for one vehicle and a second assigned exterior spot. Please note, per community guidelines, driveway parking is no longer permitted. Coconut Plantation’s location is unbeatable. Spend your days on the Ko Olina Championship Golf Course, at one of Ko Olina’s four breathtaking beach lagoons, or exploring the island’s rich culture and beauty. Indulge in world-class dining and nightlife just minutes away, or embrace the excitement of city life with a drive to Honolulu. Public transportation and limousine service offer easy access to and from the resort. Immerse yourself in the luxury and allure of island living at Coconut Plantation 1110-3 by Gather. Book your Hawaii escape today and embrace the beauty and tranquility of Ko Olina! NOTES Electricity usage is capped at $400/month; guests are responsible for excess usage. Overnight parking of commercially registered vehicles is not permitted. Per Oahu Ordinance, this home has a minimum 29-night rental period. (The nightly rental rate advertised would be multiplied by the number of nights rented; with a minimum of 29 nights). 1 Assigned parking stall for standard or compact vehicles only. We cannot accommodate oversized vehicles or large SUVs. Public parking or street parking is not available in this community. If you arrive with a vehicle that does not fit into the assigned parking space, you might be turned away and not allowed to check in. Ola No Smoking Clause for all Residential Vacation Rentals: Smoking is strictly prohibited within the premises of the vacation rental property. This includes, but is not limited to, the interior of the accommodation, balconies, patios, and any common areas within the property. The policy extends to the use of cigarettes, cigars, pipes, electronic cigarettes, marijuana and any other form of smoking or vaping. Guests are required to respect this no-smoking policy to maintain a healthy and comfortable environment for all occupants and neighbors. Any violation of this policy will result in a penalty, and the cost of any necessary cleaning, deodorizing, or damage repair will be charged to the guest. It is the responsibility of the guest to inform all members of their party and any visitors about the no-smoking policy. Failure to comply with this policy may lead to eviction from the property without refund. The property owner/manager reserves the right to enforce this policy and take appropriate action against any guest or visitor found smoking on the premises. By booking and accepting these terms and conditions, the guest acknowledges and agrees to abide by the no-smoking policy outlined above. As of 07/15/2025 - October 20–31, 2025: Annual dryer vent cleaning (external only). No unit entry required, but roof noise may be heard. For more details, please refer to the official schedule or contact management. HI Registration: TA-129-868-8512-01 TMK 910560040126

Coconut Plantation 1074-1

Kapolei, HI, US
4 Bedrooms 8 Guests
Sep 30 - Oct 29
$373 night

Welcome to Coconut Plantation 1074-1 by Gather, a beautifully upgraded four-bedroom, three-bath villa in the coveted Coconut Plantation at Ko Olina Resort. Offering 1,715 square feet across two stories, this furnished home combines resort-style amenities with everyday convenience, making it ideal for families, business travelers, or extended stays in Hawaiʻi. What You’ll Love About Coconut Plantation 1074-1 * Spacious four-bedroom, three-bath villa in Coconut Plantation community * Gourmet kitchen fully stocked with utensils and linens * Primary suite with king bed, soaking tub, and separate shower * First-floor guest bedroom with queen bed and lanai access * Free high-speed WiFi, three TVs, and full-size washer/dryer * Walkable to Ko Olina Golf Course, marina, lagoons, Four Seasons, and Disney Aulani Living & Dining Step inside to an open floor plan filled with natural light and warm décor. The living room invites relaxation with plush seating and a flat-screen TV, while the dining area offers space for six—perfect for meals, board games, or planning tomorrow’s adventures. Chef-Ready Kitchen The upgraded kitchen is fully equipped with stainless steel appliances, utensils, and linens, making meal preparation effortless. Granite counters and an island breakfast bar add both function and style. Outdoor Oasis Unwind on the lanai, surrounded by tropical landscaping and views of the Coconut Plantation community. With outdoor dining and lounge seating, it’s the perfect setting for morning coffee or sunset cocktails. Sleeping Quarters * Primary Bedroom (Upstairs) – King bed, ensuite bath with dual sinks, soaking tub, walk-in shower, private lanai, TV, ceiling fan * Guest Bedroom (First Floor) – Queen bed, full bath nearby, lanai access, ceiling fan * Guest Bedroom 2 (Upstairs) – Queen bed, ceiling fan * Guest Bedroom 3 (Upstairs) – Two twin beds, TV, ceiling fan * Bathrooms – Three full baths (two upstairs, one on first floor) Extras * Free high-speed WiFi and three televisions * Full-size washer and dryer * Compact two-car garage (standard/compact vehicles only) Resort / Community Highlights * Ko Olina Championship Golf Course * Ko Olina Marina for sailing and water sports * Four sandy lagoons with scenic walking paths * Four Seasons Resort and Aulani Disney Resort nearby * Shops, dining, spas, luaus, and community pools and hot tubs within walking distance Nearby Stroll to Ko Olina lagoons, marinas, and resort dining. A short drive brings you to Honolulu (30 minutes), Hanauma Bay, Sea Life Park, the Polynesian Cultural Center, and the North Shore’s iconic beaches. Good to Know * Monthly rental only: minimum 29 nights; no prorated stays * Scheduled Maintenance: Oct 20–31, 2025 – annual dryer vent cleaning (roof noise possible, no entry) * Guest responsible for electricity usage above $500/month * No overnight parking of commercial vehicles * Two assigned parking stalls: compact/standard vehicles only (no oversized SUVs/trucks; no public/street parking) * Strict no-smoking/vaping policy: Smoking is prohibited inside the villa, on balconies, patios, and in all community/common areas. This applies to cigarettes, cigars, pipes, electronic cigarettes, marijuana, and vaping. * Guest responsibility: Guests must inform all members of their party and any visitors about this no-smoking policy. * Enforcement: Failure to comply may lead to penalties, cleaning charges, or eviction without refund. The property owner/manager reserves the right to enforce this policy and take action against any guest or visitor found smoking. * Agreement: By booking and accepting these terms, the guest acknowledges and agrees to abide by the no-smoking policy. * Hawaii Tax ID: TA-212-795-8016-01 * TMK: 910560040049 Reserve your extended stay at Coconut Plantation 1074-1 by Gather, where resort convenience, spacious comfort, and the beauty of Ko Olina come together.

Posh 4BR with Spectacular Views

Kapolei, HI, US
4 Bedrooms 8 Guests
Aug 30 - Sep 30
$244 night

Welcome to this posh corner lot 4-bedroom house, located in a private gated community. This stylish home features a modern interior design with top-notch appliances. Boasting the glorious mountain and coastline views from the lanai of this home. Perfect for the getaway that you truly deserve! • 1,815 sqft • sanitized, self-check-in (contact-free) • Free driveway parking on premises - 2 spaces • full kitchen • desk for remote working • fast & stable wifi Managed by | Marbella Lane | full-service vacation rental property management | Top performer by AirDNA 4 bedrooms • 3 baths • 1 kitchen QUIET TIME: This is in a gated residential community, please be mindful of our neighbors, no parties, no events, or large gatherings, HOA requires quiet hours 9:00 pm - 8:00 am. MONTHLY RENTAL ONLY PARKING: Driveway parking. No parking allowed on the street and road. Guests will have access to the entire home except for a few closets, and cabinets that we have locked. CANCELLATION POLICY: Specific Cancellation policy applies to each platform. No refund within 30 days of check-in, if you book on our website. Security Deposit ($500 USD) — As a friendly reminder, if you’ve any issues during your stay, please bring them to our attention. We would love to fix the issues for you right away. Any refunds on cleaning or nightly rate will not be authorized after checkout, and we have a very strict no-smoking policy. Any traces of smoking inside the unit will result in a penalty of $500 USD. — Note: We have a NO-PETS policy, we’ll appreciate your kind understanding. Also, extra guest fee applies after 6 guests, $50 per person, per night.

Sky Ala Moana 3509

Honolulu, HI, US
2 Bedrooms 4 Guests
Aug 30 - Sep 29
$232 night

Indulge in luxury living within this exquisite condo at Sky Ala Moana. With two bedrooms, two baths, and two parking spots, this residence epitomizes contemporary elegance fused with timeless charm. Upon entering, you’re greeted by a meticulously designed space adorned with tasteful accents that create an ambiance perfect for both relaxation and entertainment. The fully equipped kitchen boasts modern appliances and elegant quartz countertops, harmonizing functionality with style seamlessly. Luxury extends into the bedrooms, where a plush bed, split-mounted AC, and ample closet space await, ensuring a tranquil night’s sleep infused with classic opulence. One bedroom providing sweeping ocean views! The full bathrooms is adorned with high-quality finishes, reflecting the refined taste that defines the entire unit. Convenience is paramount, with an in-unit washer/dryer combo ensuring effortless living. Step out onto the private balcony to behold breathtaking views, embracing the fusion of modern sophistication and timeless allure. And don’t forget the lanai, offering a stunning vantage point for both sunrise and sunset vistas. Sky Ala Moana offers a plethora of amenities, including a state-of-the-art fitness center, a sparkling swimming pool, a soothing sauna, and a beautiful rooftop terrace with panoramic views of the city and the ocean. Your safety and comfort are paramount with 24-hour security and concierge services. Additionally, it is located across the street from Ala Moana Center, walking distance to various stores (including Walmart, Sam’s, Target, Don Quijote (Japanese supermarket), Palama Market (Korean supermarket) as well as a bank (Bank of Hawaii) conveniently located across the street. It is also easily accessible to public transportation, providing a gateway to explore the rest of the island effortlessly. Elevate your lifestyle with this unparalleled penthouse experience at Sky Ala Moana. Features and Amenities * Washer/Dryer in the unit * Pool * Gym * Common BBQ area * Parking (2 assigned parking stalls) * WiFi * TV Outdoor * Lanai - 2 chairs and table Living * Linens * Cable TV/Smart TV * Split-mounted ac Kitchen * Full kitchen * Refrigerator/Freezer * Coffee maker (Keurig) * Dishwasher * Oven Range * Microwave * Dishes/Utensils/Cookware Master Bedroom * Queen size bed * Split mounted AC Second Bedroom * Queen size bed * Split mounted AC Living Room * Queen Size Sofa Bed * Split mounted AC Private Bathroom * Fully-Upgraded Finishes throughout. * Hair dryer * Extra towels and tissue *All stays will require a mandatory mid-stay cleaning* TA-048-722-0736-01 Hawaii Life Rentals is a locally owned, licensed real estate company with rentals on Kauai, Maui, Oahu, and Hawaii. We offer on-island personal assistance and Concierge services. Rates do not include taxes, cleaning and applicable fees. VRBO/Hawaii Life bookings: Guests must sign a rental contract within 48 hours of booking to confirm the reservation. In compliance with the Ordinances of the City & County of Honolulu, the Property will be made available to you for your use and occupancy for a minimum period of thirty (30) days.

2 master suites | MT+Ocean Views

Waianae, HI, US
4 Bedrooms 10 Guests
Aug 29 - 31
$372 night

Make beautiful memories in this spacious 4 BR home with 2 master suites, located in a gated community with 24 hours security. It is within the greater Waianae area, right in the heart of the Makaha Valley. On the Leeward side of Hawaii where the Ocean Trade Winds keep you refreshed. This lovely home is situated to enjoy sweeping views of the ocean and the magnificent Pu’ukea’ au Mountain Range from the windows throughout this home. Easy access to tropical beaches, surf spots, & hiking trails. • Built in 2022 • 1,935 sqft Wood floor throughout the house • On Rim Lot with ultimate privacy • Sanitized, self-check-in (contact-free) • Free driveway parking on premises - 2 spaces • Full kitchen • Fast & stable wifi (Business grade) • Dedicated workspace in each bedroom • Community Pool • GYM Area • BBQ Grill Professional landscaping with native plants, fruits, and outdoor seatings. Managed by | Marbella Lane | full-service vacation rental property management | Top performer by AirDNA 4 bedrooms • 3.5 baths • 1 kitchen Additional notes: Two master suites - one on each floor. Suite 1 on 1st floor - king bed (master suites) Suite 2 on 2nd floor -2 Queen beds (master suites) Bedroom 3 on 2nd floor - king bed Bedroom 4 on 2nd floor - bunk beds (1 full size & 1 twin size) The garage-converted game room provides fun for all, it is stocked with shot board game / Foosball / Arcade Basketball/ portable Cornhole. LOCATION The property is located in a gated community on the western side of Oahu (Cottages at Mauna Olu), with 24 hours security. The community has parks, and is close to the golf course. There is plenty to do in this sunny town, all within 10 mins drive, including swimming, snorkeling, diving, hiking, and so much more. Depending on the seasons, You could catch sightings of whales, dolphins, and turtles in the ocean. Waianae is 40 minutes from the airport (HNL), 45 minutes from the heart of Waikiki, and an hour from the North Shore. It’s the perfect place to relax after a day of exploration. QUIET TIME: This is in a gated residential community, please be respectful of our neighbors; no parties, no events, or large gatherings. HOA requires quiet hours 9:00 pm - 8:00 am. PARKING: No parking allowed on the street. Guests will have access to the entire home except for a few closets, and cabinets that we have locked. A car is highly recommended CANCELLATION POLICY: Specific Cancellation policy applies to each platform. No refund within 30 days of check-in, if you book on our website. Security Deposit ($500 USD) — Note: We have a NO-PETS policy, we’ll appreciate your kind understanding. Also, extra guest fee applies after 6 guests, $50 per person, per night. License number: STR# 2466

Glam 2 Master suites|MT+Ocean Views

Waianae, HI, US
4 Bedrooms 10 Guests
Aug 29 - 31
$378 night

Welcome to your dream island retreat! This spacious 4BR home with two Luxe master suites invites you to unwind in comfort and style. Nestled in a gated community with 24-hour security in Makaha Valley, this lavish home offers sweeping of the majestic ocean and Puʻukeaʻau Mountain views from nearly every room. Enjoy Hawaii’s serene Leeward side, where the Ocean Trade Winds keep you cool, with easy access to pristine beaches, surf spots, and scenic trails. Your perfect island getaway awaits! • Built in 2022 • 1,935 sqft Wood floor throughout the house • On Rim Lot with ultimate privacy • Sanitized, self-check-in (contact-free) • Free driveway parking on premises - 2 spaces • Full kitchen • Fast & stable wifi (Business grade) • Dedicated workspace in each bedroom • Community Pool • GYM Area • Shared hot tub Professional landscaping with native plants, fruits, and outdoor seatings. Managed by | Marbella Lane | full-service vacation rental property management | Top performer by AirDNA 4 bedrooms • 3.5 baths • 1 kitchen Additional notes: Two master suites - one on each floor. Suite 1 on 1st floor - king bed (master suites) Suite 2 on 2nd floor -2 Queen beds (master suites) Bedroom 3 on 2nd floor - king bed Bedroom 4 on 2nd floor - bunk beds (1 full size & 1 twin size) The garage-converted game room provides fun for all, it is stocked with Foosball / Arcade Basketball/ portable Cornhole. LOCATION The property is located in a gated community on the western side of Oahu (Cottages at Mauna Olu), with 24 hours security. The community has parks, and is close to the golf course. There is plenty to do in this sunny town, all within 10 mins drive, including swimming, snorkeling, diving, hiking, and so much more. Depending on the seasons, You could catch sightings of whales, dolphins, and turtles in the ocean. Waianae is 40 minutes from the airport (HNL), 45 minutes from the heart of Waikiki, and an hour from the North Shore. It’s the perfect place to relax after a day of exploration. QUIET TIME: This is in a gated residential community, please be respectful of our neighbors; no parties, no events, or large gatherings. HOA requires quiet hours 9:00 pm - 8:00 am. PARKING: No parking allowed on the street. Guests will have access to the entire home except for a few closets, and cabinets that we have locked. A car is highly recommended CANCELLATION POLICY: Specific Cancellation policy applies to each platform. No refund within 30 days of check-in, if you book on our website. Security Deposit ($500 USD) — Note: We have a NO-PETS policy, we’ll appreciate your kind understanding. Also, extra guest fee applies after 6 guests, $50 per person, per night. License number: STR # 2466

Hillside Villas 1496-3

Kapolei, HI, US
2 Bedrooms 4 Guests
Aug 30 - Sep 28
$168 night

Tucked into the peaceful hills of Ko Olina, Hillside Villas 1496-3 is a beautifully designed two-story villa that blends relaxed island living with elevated comfort. From the private lanai, take in ocean and pool views framed by palms and glowing sunsets. Inside, airy interiors and thoughtful touches make this an inviting home base for extended stays on Oʻahu’s leeward coast. What You’ll Love About Hillside Villas 1496-3 • Ocean, pool, and sunset views from the private lanai • Open-concept living with plantation shutters and ceiling fans • Well-equipped kitchen designed for easy everyday cooking • Comfortable king and queen bedrooms ideal for couples or small families • Prime Ko Olina location near lagoons, golf, and world-class resorts Living & Dining The main living space feels bright and welcoming, with plantation shutters filtering in natural light and ceiling fans keeping the air moving. Settle in for movie nights with the smart TV or slide open the doors to the lanai and let the outdoors become part of your day. The adjacent dining area is perfectly sized for shared meals or relaxed evenings in. Chef-Ready Kitchen The kitchen is fully equipped with modern appliances and generous counter space, making everything from quick breakfasts to home-cooked dinners feel effortless. With the dining area just steps away, it is easy to stay connected while cooking. Outdoor Oasis Step outside to your private lanai and unwind with morning coffee or an evening drink as the sky shifts through shades of gold and blue. Overlooking lush landscaping with ocean and pool views beyond, it is a quiet spot to slow down and savor island life. Sleeping Quarters • Primary Suite: King bed, flat-screen TV, large window, ensuite bath with walk-in shower • Guest Bedroom: Queen bed, ceiling fan, TV • Guest Bath: Tub and shower combination • Half Bath: Conveniently located on the first floor Extras • Washer and dryer in unit • Assigned parking stalls • Gated community entry • Beach towels provided • Private entrance Resort / Community Highlights Set within the Ko Olina Resort area, Hillside Villas offers a peaceful residential setting close to sandy lagoons, coastal walking paths, and the Ko Olina Championship Golf Course. World-class dining, spas, and family attractions are all within easy reach. Nearby • Walk: Ko Olina lagoons, scenic resort pathways, select dining options • Short Drive: Four Seasons Resort and Spa, Aulani Disney Resort, Ko Olina Golf Course, Waikele Premium Outlets, Pearl Harbor, North Shore beaches Good to Know • This property is offered as a monthly rental. The monthly rate applies in full regardless of length of stay. • Minimum rental period is 29 nights. • Electricity usage is capped at $500 per month. Guests are responsible for any excess. • Grills are not permitted on private lanais. • Two assigned parking stalls for standard or compact vehicles only. Oversized vehicles cannot be accommodated. • Smoking and vaping are strictly prohibited anywhere on the property, including lanais and common areas. • Long-term stays of 6 months or more require guests to cover electric, cable, phone, and internet costs. • Tax ID: TA-196-713-0112-02 • TMK: 910560130011 Reserve your dates at Hillside Villas 1496-3 and settle into an extended Ko Olina stay defined by comfort, sunsets, and easy island living.

Vacation Rentals in O‘ahu by Amenities & Features

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Vacation Rentals Near O‘ahu

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