Kailua Vacation Rentals – Beachfront Homes and Island Cottages
Kailua vacation rentals deliver an authentic island experience on Oahu's scenic windward coast. Stay steps from world-famous beaches like Kailua Beach and Lanikai, with cozy cottages, modern family homes, and tropical escapes perfect for kayaking, hiking, and relaxing in paradise.
Island Living on Oahu's Windward Side
Kailua offers one of Oahu's most peaceful and picturesque vacation settings. Located just 30 minutes from Honolulu, this seaside town is known for its soft white sands, turquoise waters, and small-town charm. With no high-rises in sight, Kailua maintains a residential, beach-friendly vibe ideal for extended stays, family retreats, and romantic escapes.
Popular Activities in Kailua
From your vacation rental, enjoy quick access to outdoor adventures like:
- Kayaking to the Mokulua Islands
- Hiking the scenic Lanikai Pillbox Trail
- Swimming and sunbathing at Kailua Beach Park
- Shopping local boutiques and farmers markets
Key Features of Kailua Vacation Rentals
- Steps from Kailua or Lanikai Beach
- Private lanais, gardens, and outdoor showers
- Beach gear often included (chairs, boogie boards, bikes)
- Quiet neighborhoods perfect for remote work or extended stays
- Local eateries, cafés, and groceries within walking distance
Perfect For:
- Families needing space and beach access
- Couples seeking a romantic, secluded getaway
- Remote workers looking for inspiration and tranquility
- Visitors planning longer-term stays in a residential setting
Kailua is more than a beach destination-it's a lifestyle. Book a stay in one of our handpicked Kailua vacation homes and discover why travelers return to this corner of Oahu year after year.
Downtown Kailua | Steps to shops | W/D | Parking
New Listing Special!Welcome to this charming 2-bed, 1.5-bath condo in a prime downtown Kailua location, just a short stroll from world-famous Kailua Beach. This updated home features a fully equipped and stocked kitchen, 2 comfortable queen beds, and modern amenities...
Beautifully remodeled Lanikai house,spacious inside alot of green space outside
In the quaint exclusive neighborhood of Lanikai, our quiet place sets back off the road. It’s a beautifully remodeled house. Beautiful Lanikai Beachhouse newly remodeled December 2022. Rarely available. New fresh paint, new floors, new beds, new mattress, new kitchen...
Charming 3-bedroom house with a pool and AC in beautiful Kailua
This 3-bedroom house is perfect for your escape to Kailua. Nestled in a soothing neighborhood, this beautiful property offers 2 queen beds, 2 twin beds, and a queen-sized pull-out couch to ensure a peaceful night’s sleep for everyone. With amenities like AC, WiFi, a...
Relaxing 5bd/3ba Kailua Home Just Steps from Kailua Beach with Wifi and A/C
Just four homes away from the Kailua Beach pristine white sands, this spacious retreat combines a stunning 4-bedroom home with a separate private studio cottage. Your perfect Hawaiian getaway awaits with a thoughtful blend of comfort and island living. Sleep in...
3 BR Oceanfront Private Lanikai Beach House
Lanikai Beach Oceanfront. This home is a tastefully updated beachfront getaway on what is often cited as one of the world's best beaches. There are 3 bedrooms, 4 bathrooms and an open concept living area. The lot is just under 1/2 of an acre - large for the area -...
Awesome 5-bedroom house in Lanikai overlooking the Mokulua islands
Experience that perfect Hawaiian getaway with breathtaking ocean and Mokulua Island views from this exquisite Lanikai hillside residence. The home is ideal for a long extended family vacation with 5 bedrooms, two of them with king-sized beds and four with their own...
Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai
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 Leaf House by Gather, your serene...
Kailua Beach Luxury Villa – Coastal Elegance on Oahu’s Windward Shore
Welcome to Kailua Beach Villa, a spacious and contemporary oceanfront retreat on Oʻahu’s Eastern Shore. With 5 bedrooms, 5 baths, and 4,000 square feet of airy living space, this private villa blends modern design with barefoot luxury. Step outside to direct beach...
Suite By the Sea - a bright and sparkling Apartment
Welcome to our new private studio apartment, where comfort and convenience await you. This hidden gem boasts a well-equipped kitchenette, perfect for preparing your favorite meals. Nestled just a short stroll away from the breathtaking Kailua Beach, you'll find yourself...
Kailua vacation rental wih stunning views - 5 min to beach
The studio is an overlooking Mid Pac country club, and has 180* views of the Ko'olau mountains and also the popular Pill Box hike peak which has views of the coast line. From the studio you may feel like you are in a birds nest , since there are birds singing ,and the...
Castle Point Estate by Gather: Oceanfront w/ Pool, Spa & Lanais
At Castle Point Estate in Kailua, panoramic views of Kailua Bay and the Mokulua Islands unfold from a nearly 33,000-square-foot parcel with over 110 feet of ocean frontage. This Balinese-Hawaiian-inspired single-level estate blends exclusivity with resort-style living,...
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern Amen
Welcome to Kailua Beachside, a five-bedroom, five-bath beachfront villa where modern design meets the relaxed rhythm of island life. Located on the peaceful north end of world-famous Kailua Beach, this two-story residence offers a seamless connection between indoor and...
Lanikai Oceanfront Home with Pool and Japanese-Style Hot Tub
Six bedroom ocean front home with pool and Japanese-style onsen (hot tub) is ideally suited for multi-family or multi-generational accommodation. Recent renovations and 2021 upgrades include split-air conditioning throughout the home, updated landscaping, new...
1 Mi to Beach, Remote Work Hub: Modern Kailua Gem!
Walk to Shopping & Dining | Furnished Lanai | Home Gym | Community Pool AccessFind your slice of Oahu paradise at this luxury Windward Harbour vacation rental! The 3-bedroom, 2-bath condo boasts inviting indoor and outdoor living spaces, making it easy to recharge after...
Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach
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.Seahorse Beach House is a hidden Hawaiian gem,...
Lanikai Ola Nani: Majestic Retreat, Close to Beach, Designer Details, Views!
Lanikai Ola Nani by Gather is a refined island sanctuary just steps from the sands of world-famous Lanikai Beach. This four-bedroom, four-bathroom retreat combines designer renovations with indoor-outdoor flow, creating a private haven for monthly stays in Kailua’s...
🚐 Skip the hotel — 🏕️ Camping Experience — 🤑 Budget Friendly Vacation! 🏝️
Embark on a camping experience in Hawaii with our minivan camper perfect for individuals or couples.**Located in Kailua!! It's a 25 minute Uber/Lyft from the airport.CAMPING GEAR INCLUDED:► 8" Memory Foam Mattress with CLEAN FRESH sheets ► Solar Powered Rechargeable...
Lanikai Hillside Estate – Panoramic Luxury Above the Sea
Perched above the crystalline waters of Lanikai Beach, Lanikai Hillside Estate by Gather is a newly designed 7-bedroom, 6.5-bath luxury retreat with 6,295 sq ft of interior living plus expansive lanai spaces. Floor-to-ceiling glass, an infinity-edge pool, and panoramic...
Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
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...
Hale Alapi'i Lanikai Getaway: Newly Renovated Near Beach & Hiking
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...
Lanikai Hideaway: 4 BR Luxury Retreat near Lanikai Beach
Tucked into the sought-after Lanikai neighborhood of Kailua, Lanikai Hideaway is a 4-bedroom, 3-bath luxury retreat designed for those who want space, privacy, and a true island connection. Just a 10-minute walk from the world-famous sands of Lanikai Beach, this...
Waterfront Lanikai Beach Compound
Sprawling oceanfront 5BR/5BA compound, steps to Lanikai beach.Share meals and play games in the oceanside backyard. Walk 5 minutes to gorgeous days on Kailua Beach Park or just steps to iconic Lanikai Beach.Furnished fully-equipped kitchen. Two parking spaces.The...
Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill
Live the beach life! An opportunity to live across the street from Kailua Beach Park, with the perfect combination of sandy beach, large grassy areas, tall ironwood trees, and turquoise-blue waters. You will love this generous ground-level one-bedroom, one-bathroom...
Hoʻonānea I Loko Kailua
If you're looking to work remotely, travel for work, remodel your home & have a place to live while it's worked on then this is the perfect home. This is a redesigned and remodel home that was originally built in the 1960's. The home is tastefully designed with a...
Kailua Luxury Beachfront House
Prices start at $36,000/month and will not be pro-rated based on the length of stay. Please inquire for an accurate quote.Welcome to Kailua Beach Villa. This luxury beachfront home is perfect for your next Hawaiian vacation. This spacious 2 level home has 5 bedrooms (1...
Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen
Just a short stroll from the turquoise waters and powder-soft sands of Kailua Beach, Kailua Beach House is a light-filled 4-bedroom, 2.5-bath island retreat designed for laid-back luxury. This single-level residence blends open-concept living with a private outdoor...
Sunlit Island Escape in Kailua
Welcome to your island getaway! Nestled in the heart of Kailua, this bright and inviting home is perfectly located just minutes from Kailua Beach, where you can soak up the sun, enjoy crystal-clear waters, or try your hand at paddleboarding.This property combines modern...
4BR Mokulua Seaside w/ Private Studio, Steps to the Beach
Mokulua Seaside by Gather is a refined oceanside escape that brings together luxury, space, and the beauty of Lanikai. Just one house from the sand on Kailua’s coveted Mokulua Drive, this four-bedroom, four-bathroom retreat spans 3,316 square feet of interior living...
Tropical Bliss in Kailua
Welcome to your dream retreat in Kailua, a sun-drenched haven where tranquility meets convenience. This charming unit is part of a thoughtfully designed duplex, offering a perfect balance of privacy and community. Whether you’re here to relax, explore, or work, this...
Cozy Aloha Suite with AC in charming Kailua
Welcome to our home! We are a legal vacation rental (TA-188-004-1472-01, 90/BB-0102) hosting guests for more than 30 years. We are an environmentally-conscious family doing our share to "Live Lightly" so our natural resources are protected.**PLEASE NOTE: As of November...
Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool
Nestled in a quiet neighborhood, this charming home is located just one mile from the heart of Kailua town's shopping and resturants. It is also just a bike ride away from the world famous Kailua and Lanikai Beaches. With stunning views of the Ko'olau Mountains and the...
Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.
Kick back and relax in this calm, stylish beach getaway. This recently updated apartment features a living space with an ocean view from the balcony. Bright and airy, you’ll enjoy ocean breezes and fall asleep to the sound of waves. Have your pick from the gorgeous...
Charming apartment with AC and WiFi in serene Kailua.
New charming studio rental located on the owner's property in beautiful Kailua, Hawaii. Perfectly situated just moments away from stunning beaches, lush landscapes, and quaint town. This cozy retreat offers a unique blend of comfort, convenience, and island charm. The...
Kailua Hale Kahakai by Gather: Lux Oceanview Villa w/ Beach, Walk to Attractions
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...