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.
Luxury Beach Vacation House in Kailua Beach
Additional guest fee of $98 per person per day applies to parties over 10 people. Additional service fee and tax will apply.A private home with eight bedrooms on Kailua Beach (Voted Number One Beach in America). (Adjacent 2-bedroom Guest Cottage also available to...
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
Hawaii's Hidden Hideaway is an AWARD WINNING Bed and Breakfast. Recipient for two years in a row the MOST ROMANTIC HIDEAWAY AWARD, voted by it's guests. Featured in the TRAVEL magazine and other international publications. We have free parking, free WiFi and NO RESORT...
Steps to beach, pool, garden. April/May Cancellation Special. CALL NOW!
Minimum 30 day rental, this 3 bedroom, 3 bath with a private pool is the perfect location to relax and unwind. The entire property is surrounded by lush landscaping, beautiful palm trees and tropical flowers. The spacious yard is perfect for sun bathing, barbecuing or...
Kailua Beach Estate: Historic Property with Large Yard & Ocean View
October 2024 updates: Newly constructed upstairs deck, Brand new window ac unit in master bedroom, new patio furniture, new sectional couch in living room. Our beach estate is located on over an acre of land, just one house back (a quick 30 second walk down a sandy...
Lanikai Paradise across the street from the beach with AC and Parking!
Welcome to your tropical escape in the heart of Lanikai, across the street from one of the most breathtaking beaches in all of world. This licensed short-term rental offers comfort, style, and space. Additional bedrooms are available to sleep up to 16 guests!- 4...
Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches
Min 30 days requiredLush tropical gardens make this private home into a quiet, comfortable retreat. Large enough for six adults, plus a couple of keiki (children), this home was designed by the late Vladimir Ossipoff, award-winning Hawaii architect. Mr. Ossipoff's...
Close to Kailua Beach-AC's-Renovated/Upgraded-Fenced Backyard-Patio-Laundry
For questions, to verify availability dates or to check the availability of other furnished rentals we manage, please contact the owner. This is a fully furnished & renovated/updated 3/2 rental with a big, fenced & shady yard with tropical trees and plants, including...
Maluhia: Luxurious Kailua Home w/Pool Oasis, A/C, Near Beaches and Shopping!
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.Let the tranquil atmosphere of Maluhia by...
Cozy Lanikai Cottage Walking Distance to the Beach-Near Shops & Restaurants
This property is a 30-day minimum rental and is professionally managed by Ali'i Beach Rentals.ENHANCED PROTOCOLS : We have revised our protocols to include contactless check-in & check-out, professional EPA approved non-toxic undetectable antimicrobial electrostatic...
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
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.Ranch Beach Estate is a hidden Hawaiian gem,...
Luxurious five-bedroom modern retreat
This five-bedroom home inHonolulu offers a blend of modern design and tranquil vibes. The spacious interior features an open-concept living area .The kitchen is modern and functional, with sleek finishes and ample storage. The master suite provides a serene retreat....
Luxury Lanikai Oceanfront Home – Secluded Beachside Elegance
LUXURY Lanikai oceanfront home built in 2006, charming board and batten home, concrete floors throughout with the charm of old Hawaii. Beautiful gardens, outside dining and entertainment areas, large pool, big yard spaces, and awesome private outdoor showers that you...
Kai Moena Estate - Kailua Luxury Beachfront Compound with Pool, Spa, AC, Sauna, Tennis Court & More!
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.Property is currently for sale. The property...
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...
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...
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 -...
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, a luxurious...
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...
Charming 1-Bedroom Kailua Cottage with AC, Walk to the Best Part of the Beach
Welcome to Alohawaii Properties by the Sea, a licensed transient accommodations operator (License 1990/NUC-1760), Registration Numbers GE-039-001-2928-01, TA-039-001-2928-01). We are delighted to share that we have been named the winner of the 2021 Best of Kailua Awards...
Pilipu Palms 2
Large 3 BR, 2.5 Bath on quiet family friendly beachside street, steps to private street access to beautiful Kailua Beach! Bamboo floor throughout, new kitchen and baths.Split AC in all bedrooms.Large covered lanai, pool, and hot tub. Open floor plan allows for fourth...
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...
Stunning Oceanfront Beach House w/AC & Mokulua Isle Views at Lanikai Oceanside
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.With front row seats to the ocean and the...
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern Amen
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.Stay at Kailua Beachside by Gather, a...
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...
Loft In Kailua - Spacious with Parking, Internet and minutes to Kailua Beach!
MINUTES TO KAILUA BEACH AND TOWN!!This well appointed one bedroom split level loft apartment is beautifully furnished with high ceilings and open floor plan. The upstairs has a shuttered master suite with queen bed, a huge en-suite full bath that has a soaking tub and...
Beautiful 3 Bedroom home near Lanikai beach available September 20-October 20
This is a Beautiful home available only from September 20th-October 20th. Situated just 1/2 block to Lanikai beach and with access to hiking the Lanikai Pill Boxes just one block away. Just a short walk to Kailua Beach and a restaurant as well. Large Lanai with a very...
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,...
Serene Lanikai House Near the Beach w/Full Kitchen and Great Outdoor Space
This property is a 30-day minimum rental and is professionally managed by Ali'i Beach Rentals.ENHANCED PROTOCOLS : We have revised our protocols to include contactless check-in & check-out, professional EPA approved non-toxic undetectable antimicrobial electrostatic...
Lanikai Ola Nani: Majestic Retreat, Close to Bch, 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...
Luxurious 4BR Kailua Home with Panoramic Ocean and City Views
PERFECT FOR:Large families | Multi-generational trips | Beach lovers | Remote workers | Corporate retreatsPrime Kailua Location:- Panoramic ocean & city views from your windows- Walking distance to world-famous Kailua Beach- Minutes to Lanikai Beach & town center- Quiet...
Peaceful Oceanfront Home Near Downtown Kailua w/ BBQ & AC: Kai Mele
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 Kai Mele, your next charming...
Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi
**Please note--beginning Sept. 25, 2025 only 90 Day rentals and longer will be accepted.Welcome to paradise! Discover this adorable 4-bedroom gem in Kailua only 4 houses from magnificent Kailua beach. We are on a private lane with path to beach.This charming house has...
Comfy 1 bedroom steps to white sand beach
Experience Windward Hawaii at this beautiful 1 bedroom in the heart of Lanikai. You'll be within a short walking distance of one of the best beaches on the island and close to Kailua town with many unique shops and restaurants. You'll enjoy beautiful views of the...
Lanikai Hillside Estate – Panoramic Luxury Above the Sea
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 Lanikai Hillside Estate, a premier...
Hale Alapi'i Lanikai Getaway by Gather: Newly Renovated Near Beach & Hiking
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 Hale Alapi'i Lanikai Getaway by...
Lanikai Hideaway: Modern Luxe Indoor-Outdoor Living/Walk to Lanikai 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.Welcome to Lanikai Hideaway, an exquisite...
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...
The Perfect Escape
Bring your swimsuit, everything else you need is already here. Our guest house is the perfect location, close to the beach and Kailua town. A large one bedroom guest house with its own private entrance, secure parking, kitchenette and washer & dryer. Enjoy the priceless...
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
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 Kailua Beach House by Gather, a...
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
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 Mokulua Seaside by Gather, a...
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...
Kailua Beach Bop
Discover Kailua's island charm while staying in our Hawaiian style home. Wake up to chirping birds on a quiet treelined street. Enjoy your breakfast in the sun room overlooking the lush green backyard filled with fruit trees. The living spaces are open & flooded w/...
New! Lanikai Beach Cottage - 5min walk to the best beach!
Located in the most private and peaceful locations on Oahu, our Lanikai cottage is only 5 min from one of the most beautiful beaches in the world. Welcome to Lanikai Oasis, Tax ID GE-159-110-0416-01 and TA-159-110-0416-01. Just a10min drive to many restaurants and...