Kailua Vacation Rentals

Kailua vacation rentals offer beachside comfort on Oahu's windward coast. Choose from cozy cottages and ocean-view homes near Kailua and Lanikai Beach, perfect for kayaking, hiking, or simply relaxing in this peaceful island town.

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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...

🛏 5 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 12
📍 Kailua, Hawaii

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 -...

🛏 3 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii

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...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii

Kailua Beach Luxury Villa – Coastal Elegance on Oahu’s Windward Shore

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 Villa, the perfect...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 12
📍 Kailua, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii

Kailua Shores Estate by Gather: Expansive Home w/ Pool, Spa, AC & Scenic Views

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 Shores Estate by Gather, one...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii

Centrally located, pet-friendly, 1 bedroom in Kailua

This Kailua bed & breakfast boasts 1 inviting bedroom. The nice living room with a cozy sofa bed provides extra space for guests to relax. Enjoy the peaceful surroundings and take advantage of amenities like WiFi, AC, and a washing machine. Our place is equipped for...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua, Hawaii

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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii

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...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii

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...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 18
📍 Kailua, Hawaii

Steps to the Beach Guesthouse

A private setting in a detached home on a wonderful street! The longer the reservation the better, please contact for details. To answer the most common question, yes, we are 'steps' away: 80 medium sized steps for me! The beach is down a sandy path and is a one of the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii

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,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua, Hawaii

Lanikai Ola Nani: Majestic Retreat, Close to Bch, Designer Details, Views!

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.Discover Lanikai Ola Nani, an exquisitely...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii

🚐 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...

🛏 1 Bedroom
🛁 0 Bathrooms
👤 Sleeps 2
📍 Kailua, Hawaii

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...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii

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...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii

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...

🛏 7 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii

Your Beach House-Ocean/Mtn Views-Steps from the beach

Aloha! E Komo Mai to our Hale (House).We will be on vacation, and our home will be available Dec. 13, 2022 - Jan 5, 2023. We are looking for a wonderful family to enjoy our home while we are out. If you would like to rent our home during these specific dates, we could...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Kailua, Hawaii

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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii

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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 9
📍 Kailua, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua, Hawaii

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...

🛏 6 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 11
📍 Kailua, Hawaii

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...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii

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...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Kailua, Hawaii

Nohie Lanikai by Gather: 4BR Beachside Retreat w/ Lanai & Private Yard

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 Nohie Lanikai by Gather – A...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii

Kailua Hale Kahakai by Gather: Lux Oceanview Villa w/ Beach, Walk to Attractions

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 Kailua Hale...

🛏 6 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 12
📍 Kailua, Hawaii

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