Oahu Vacation Rentals – Explore Condos, Villas & Beachfront Homes
Oahu vacation rentals range from oceanfront condos in Waikiki to luxurious resorts in Ko Olina, surfside escapes on the North Shore, and peaceful retreats in towns like Kailua and Waialua. With options for families, couples, long-term visitors, and remote workers, Oahu offers the perfect stay for every traveler.
From world-famous beaches and luxury resorts to quiet towns and hidden coves, Oahu offers a wide range of vacation rentals to match your travel style. Whether you want a high-rise with Diamond Head views or a secluded cottage near the waves, you'll find it here.
In Waikiki, experience vibrant city life, surfing, nightlife, and shopping-all within walking distance. Families and upscale travelers alike love the Ko Olina area in Kapolei, known for its protected lagoons, golf courses, and luxury villas.
The legendary North Shore delivers laid-back beach towns, world-class surf, and open landscapes. Here you'll find spacious rentals near Kuilima Estates and Turtle Bay, perfect for outdoor adventure and ocean lovers.
For a more peaceful setting, head east to the windward side. Kailua and Lanikai are favorites for couples and families seeking calm waters, beach walks, and a more local vibe. On the northwestern shore, Waialua provides a rural escape away from the crowds, ideal for a quiet and reflective stay.
Why Choose Oahu Vacation Rentals?
- Wide variety: from beachfront condos to private villas and family homes
- Full kitchens, lanais, air conditioning, Wi-Fi, and pools
- Convenient access to beaches, hiking, dining, and shopping
- Pet-friendly, extended stay, and snowbird-friendly options available
- Great for couples, groups, digital nomads, and first-time island visitors
Popular Areas for Oahu Rentals
- Waikiki – Iconic beachfront condos, shopping & surf
- Ko Olina – Luxury villas and family-friendly lagoons
- North Shore – Surf culture, remote beaches, and nature
- Kailua – Calm waters and laid-back Windward vibes
- Waialua – Secluded retreats and country charm
Explore all available Oahu vacation rentals below and start planning your perfect island stay today.
Mokulua Sunrise Ocean Villa Lanikai
Experience the ultimate Hawaiian escape at Mokulua Sunrise, a stunning 4-bedroom, 3.5-bath oceanfront villa nestled in the world-famous Lanikai neighborhood of Kailua, Oahu. With sweeping, unobstructed views of the turquoise Pacific and the Mokulua Islands, this...
Luxury Moana Lani: Oceanfront Home with Pool & Jacuzzi
Experience the relaxed elegance of oceanfront living at Moana Lani by Gather, a captivating six-bedroom, six-and-a-half-bath architectural masterpiece designed by renowned architect Philip “Pip” White. Nestled along the tranquil shores of Maunalua Bay between Kahala and...
Orchid House - Pool and Endless Ocean views!
ORCHID HOUSETA # 087-311-0016-01With magical views of the Mokuluas from most rooms, this 3 bedroom, 4 bath custom home was just renovated using exotic hardwoods and stone from around the world. Features include solid hardwood floors, granite countertops, slate stone...
Contemporary Hawaii Living, Calm North Shore Beach
Experience Hawaii in its purest form in this beautifully built custom home, sitting on an exclusive beachfront property on the North Shore of Oahu. Built with the idea of taking in the gorgeous ocean and mountain views, and maximizing the flow of the trade winds, this...
Center of Waikiki - 1 Bedroom 3 Queen Size Beds
THOUGHTFULLY CURATED BY OWNER/ARCHITECT TO CREATE A STRONG SENSE OF BELONGING.YOUR ULTIMATE HAWAIIAN RETREAT IN THE HEART OF WAIKIKI31st-floor corner unit in the Island Colony Aqua hotel building. You are in the CENTER of Waikiki, surrounded by shops and shopping...
Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC
Nestled in the coveted Lanikai community of Kailua, Hale Nani Lanikai invites you to experience authentic island living in a refined, serene setting. This modern retreat accommodates up to eight guests across three spacious bedrooms—each with its own ensuite...
Beachfront top-floor unit on Oahu's north shore!
LOWEST PRICE YET – 25% OFF FOR JULY 13–AUG 10, 2025! ONLY $130/NIGHT.This remodeled condo is on the top floor of a beachfront complex on Oahu's north shore. Experience the North Shore lifestyle, including breathtaking sunsets, world-class surfing, snorkeling, and...
Pili Pono: Elegant Honolulu Retreat with Pool & Private Oasis
Welcome to Pili Pono, a show-stopping 5-bedroom, 6.5-bath luxury estate set within Honolulu’s prestigious Black Point enclave. Spanning 7,470 sq ft of indoor–outdoor living space on a fully enclosed, gated 0.33-acre lot, this custom-designed retreat blends architectural...
Lavish Oceanfront Estate w/Pool, Spa & AC - Close to Beaches: Maunalua Sunset
This expansive oceanfront estate, Maunalua Sunset, sits on a rare double-wide lot along the calm shoreline of Maunalua Bay in Portlock. Multiple standalone structures wrap around a lush courtyard and resort-style pool, creating a private sanctuary designed for extended...
See my other properties #3156864 and #3197017 and #3512192 for more 5-star reviews and to book multiple condos for large groups.Located on a high floor of the Waikiki Sunset with sweeping ocean, coastline, and park views this condo offers enough beds to sleeps 6. 1...
Foster Tower Ocean Front One Bedroom w/direct Ocean Views
Embrace the aloha spirit in this beautifully appointed one-bedroom retreat. Featuring tasteful décor and modern conveniences, this unit provides a true sense of home in Hawaii. The open-concept layout is bathed in natural light, creating an inviting space to unwind...
Poolside Waikiki Retreat w/ AC, surfboard storage, walking distance to beach!
Located in the center of Waikiki with amenities like A/C, on premises laundry, and bike & surfboard storage, this spot is a no brainer. Directly across from the *eight foot deep* outdoor pool and patio, and just blocks from the beach, this apartment is truly a piece of...
Oceanfront Condo W Free Valet Parking & Balcony
This luxury apartment lies in the heart of Waikiki and is the perfect place to relax with friends and family. Sit on the balcony and sip a drink while watching the sun set over the horizon and the surfers ride the endless waves.The apartment comes with FREE valet...
Kakela Kai, Beachfront Kailua Home, Private, A/C
A comfortable beachfront home set in a security-gated neighborhood with central air condition. Decorated with island style rattan furnishings, ceiling fans throughout the house, cool white tile, granite counters and wooden flooring. There is a well stocked kitchen with...
Beautiful Koolina ground floor Villa Bikes, Beach Gear, close walk to beach!
Located in the beautiful Ko Olina Kai Community this beautiful luxury ground floor villa has an excellent location with only a short approx 10min. Walk to the resorts Blue Ocean lagoons and sandy beaches. Relax in tropical island style on our covered lanai which faces a...
"Hale Pohaku" - Waimanalo Beach Front Vacation Rental
This property is a licensed short-term vacation rental Non-Conforming Use Permit #1990/NUC-1689. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, License # TA-059-395-6864-01. TMK 410040420000."Hale Pohaku" - Waimanalo is a...
Ocean View Escape, Walk to Waikiki Beach + Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Three Bedroom Villa at The Beach Villas at Ko' Olina
* Book with confidence! This vacation rental is a LEGAL Oahu vacation Rental Operating in a Resort Zoned District and is not affected by passage of Bill 89. This Luxury Condo is a spacious and beautiful 3 bedroom, 3 bath, professionally decorated Villa with a beautiful...
Luxurious Ocean View Condo - Steps from the beach! sleeps 6- 3 bedroom- 2 bath
Awaiting you in this tropical paradise is a luxurious 3 bedroom 2 bathroom condo that has everything you need to relax and enjoy your time in Hawaii. Nothing was spared in this fully equipped and fabulously appointed condo, whether it be to read a book in comfort and...
Fully Renovated Corner Unit a Block to Waikiki Beach! Parking, AC, Wi-Fi
Ni'ihau Apartments #305 – 247 Beach WalkLocation, location, location! Ni'ihau is a hidden gem found within the hustle and bustle of Waikiki just a block away from world-famous Waikiki Beach where surfers and paddlers spend their days! This beautiful corner unit (673...
BEACH FRONT ESTATE SANDY BEACH Heated Saline Pool/SPA 360 Views: Please Inquire
30 Night Minimum Contract Required: Please InquireWant to share the magic and beauty of the North Shore with your family?Swing open the gate to our Sandy Beach, sink your toes into the warm, soft white sand, and greet the turtles that come in the afternoon. You might...
15% off March & April 2025! Luxury Penthouse - Ocean, Beach & Pool View!
Welcome to our luxurious paradise retreat at Ko Olina Beach Villas, where relaxation meets first-class amenities. This impeccably maintained penthouse in the Beach Tower offers breathtaking views of the ocean, beach, and lagoon pools—a true tropical haven designed for...
Modern Luxury on Spectacular Pipeline Beach
The Highlights: Iconic House | Directly Beachfront on famous Pipeline Beach | Gourmet Kitchen | Sunset Views | WIFI | BBQ | Private Home | Sleeps 10The stunning Blue Wave House sits oceanfront on Pipeline Beach, one of the most desirable beach destinations in the world....
North Shore Bali Style Home on Waialua Beach with Mesmerizing Ocean Views!
. "Hale Ohana", our secluded, luxury beach house has stunning 180 degree views of the breathtaking Haleiwa coastline and tranquil countryside. 45 minutes from Honolulu, but it feels like you're a world away in your own little piece of paradise. Relax on outdoor deck or...
Stunning Fairway Views, Home "E"-Clean-New-Gated, near Jbphh, Cage # Available.
Welcome to Hillside Perfection overlooking the fairways at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, air conditioned executive home located in central Honolulu. Perfect for leisure visitors, temporary military quarters, business travelers, base...
First Class Luxury Beach Front Resort Condominium
Located in the World-Famous Ko Olina Resort and Marina on the 2nd of four lagoons, you’ll enjoy the mile and a half walkway along the four lagoons as you pass the newest 4 Seasons in Hawaii, the Disney Aulani Hotel & Spa, the Marriot Ko Olina Beach Club and us, The Ko...
PERFECT LOCATION BEACH FRONT INQUIRE special discounts reduced rates for march
Experience Haleiwa like a local in this delightful 1-bedroom apartment. Relax in the cozy living room or unwind in the jetted bathtub after a day of exploring. The bedroom features a comfortable king bed for a brilliant night's sleep. With amenities like a washing...
Bright & Cozy Stay Near Waikiki Beach + Parking
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Experience a memorable Hawaiian getaway in this 600 sq ft 1-bedroom condo at Waikiki Banyan (Tower 2 -...
Cool retreat at the entrance to Lanikai-Very Close to Beach-3 Primary Bedrooms
Live your best life! An opportunity for beach living in this renovated and updated luxury rental with views of Kailua Beach and Kailua Beach Park - it's brilliant turquoise blue ocean, sandy beach, large grassy areas and tall ironwood trees. Fine craftsmanship abounds...
Waialua Oceanfront Luxury Home – Secluded North Shore Escape
Featuring Two Master Suites!!!Search no further - this luxurious oceanfront beauty has all the makings of a heaven-sent vacation on one of Oahu's most secluded coastlines. Furnished throughout with hand-picked Balinese furniture and decor, this home is a treat to see...
Ko Olina Kai 1083C: Contemporary 3BR, Private Lanai, Walk to Beach & Dining
Welcome to Ko Olina Kai 1083C by Gather, a beautifully furnished two story townhome in the gated community of Ko Olina Kai Golf Estates. This island contemporary retreat blends modern comfort with effortless indoor outdoor living, creating the perfect environment for an...
Two-story ocean view home with a furnished patio & deck, washer/dryer, & AC
Ka Hale me Ka ike 30 Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in the amazing view from both inside and out at this four-bedroom, family-friendly retreat here...
Malaekahana Beachfront Oasis Steps from Excellent Sandy-Bottom Swimming
Completely restored in 2024, this light-filled, 2,800-sq-ft, open concept home features breathtaking views of Malaekahana Bay. Enjoy the fully equipped modern kitchen, living/dining room for easy entertaining and a recreation room that has a ping-pong table, a game...
Welcome to your slice of paradise in Makaha.This spacious 4-bedroom home on Oʻahu’s west side offers the perfect mix of comfort, nature, and authentic local living. It’s ideal for families, multi-generational groups, or friends traveling together.Step outside and enjoy...
Modern Charm: Renovated 1BR, fast 600Mbps Wifi, W/D in unit, Stunning Views
Welcome to your island paradise! Soak in floor-to-ceiling mountain views with your morning cup of coffee; at night, savor the vista of twinkling city lights. You’ll love whipping up homecooked meals with the full kitchen, working comfortably with the remote work setup,...
Hale Hau'oli ~ House of Happiness
This one bedroom, one bathroom condo was completely renovated in 2020 and has everything you need to relax and enjoy your time on the island. It is the perfect space for solo travel, couples or escaping with your best friend. All of the furnishings are brand new and...
Sunset Beach House in paradise! Inquire for special 30 day rates!
Unit B1 is Ocean Front at Sunset Hale. Split AC units in everyroom. Newly updated 2-bedroom 2.5-bath ground floor oceanfront unit. The Kitchen, living room and dining area are all facing out to beautiful ocean and sunset views! Enjoy these views from inside or hang out...
Welcome! We hope you enjoy the newly renovated and spacious 2 bedroom/2 bathroom. This high-floor unit has an amazing wrap-up lanai deck featuring 180 views of Diamond Head, the ocean, the mountains, the sunrise, sunset, and metro Honolulu. You’ll be a 10-minute walk to...
Luxurious 2-Bdrm, 2.5-Bath Condo with Parking & Fitness Center in Prime Waikiki!
Experience luxury living in this 2 bdrm/2.5 baths/1 parking, corner-end unit at Waikiki Landmark! Located in the Makai Tower, this unit offers breathtaking city and partial ocean views. No detail was overlooked in the thoughtfully designed kitchen renovation, featuring...
Fresh 1 Bedroom with Parking at Waikiki Banyan!!
Freshly Furnished One Bedroom Unit at the Waikiki Banyan with Peakaboo Diamond Head Views! One Free PARKING already included (max 6'), Bedroom with 1 Queen + 1 Full Bed; Living room with 1 Full BedCoin and App Operated washer and dryer on the same floor.Waikiki Banyan...
Ocean and Marina View Suite, Spacious, Quiet and Peaceful with Amazing Sunsets
Discover our waterfront 1BR marina apartment, which features a family-friendly balcony. Unlike typical slivers in the Ilikai marina, this is a true outdoor living space! Imagine breakfasts with marina views, sunset dinners, and Friday fireworks. Inside, find modern...
Oceanfront Luxury Condo Closest to Beach
OCEANFRONT LUXURY CONDO CLOSEST TO BEACH 2br/2ba sleeps (4-6) White Sands Village, Kailua-Kona, Kona Coast, Big Island, Hawaii, USA (20 minutes south of airport overlooking White Sands Beach on Alii Drive 3 1/2 miles south of Historic Kona)This luxury oceanfront condo...
From 185 nt Aloha Summer Sizzle 2025 incl AC, 5 Star Luxury on the Big Island
Island breezes, fragrant blossoms, privacy - Na Hale O Keauhou, Hawaii's Best Kept Secret. This private 2 bedroom, 2-1/2 bath, 2 story town home is located in a 5 star, gated, luxurious resort complex with breathtaking, panoramic views of the ocean and mountains. Within...
Waikiki Shore Beach Front Studio
Large beach front studio (460 sq, ft,) located at the Waikiki Shore, the only condo building in Waikiki that is directly on Waikiki Beach. This unit is located in a building that is within the designated Resort Zone, and therefore eligible for short term vacation...
Modern Luxury Suite at Waikiki Beach Tower w/ Ocean View
Relax in this beautifully renovated unit with ocean views at Waikiki’s finest oceanfront condo building. Wake up to the crystal blue ocean from the luxurious king bed in the master bedroom, entertain family and friends in the open kitchen and living room, and enjoy a...
2 BDRM w/ 4 Beds + 2 Bath + Parking + Partial Ocean View, 2 mins walk to Beach
Legal vacation rental at a fabulous location! This renovated 876 sq ft, 2 bedroom 2 bath with 2 balconies home is across from ‘Alohilani Resort, Steps away from the Waikiki Strip (Kalakaua Ave) and Waikiki beach! There are endless shopping, dining, and activities within...
THE GRAND ISLANDER BY HGVC, 2br Premier Ocean View Condo
This 2-Bedroom, 2-Bathroom partial ocean view Suite with lanai features a primary bedroom with a king-size bed and a 55-inch flat-panel Smart TV. The spa-inspired primary bathroom includes a sleek shower, a deep soaking bathtub, a private water closet with a TOTO...
Waikiki Beach Studio Condo..Minutes to Beaches! Great Value.
Aloha and welcome to the ideal Waikiki studio Condo rental getaway in Waikiki...just a short stroll to incredible beaches! Ideally located at the start of Waikiki, near the marina, we are close to everything for your vacaction getaway. World-class shopping & wonderful...
Simply Beautiful Waikīkī Apartment
*MONTHLY RENTAL* Stay close to Waikīkī Beach, 5 minutes walk to the sand. Our stylish 2-bedroom space is in a secure building with free parking, pool, jacuzzi, sauna and rooftop BBQ area. Highlights include a big balcony, full kitchen, 3 air-conditioners, double shower,...
Deluxe Updated Waikiki Condo - 22nd floor, Free parking & Wi-Fi The pool and all associated amenities will be closed starting April 7, 2025,for an estimated duration of 10 to 14 months to accommodate the RecreationDeck renovation project. Great value. Ideal for groups...