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.

Kailua vacation rentals offer a laid-back, beachy escape on Oahu's windward coast, known for powdery white sands, turquoise waters, and a local town vibe that's both relaxed and refined. Just 30 minutes from Honolulu, Kailua feels like a hidden paradise, ideal for travelers seeking peace, beauty, and authentic island living.

Choose from charming beach cottages, modern island homes, and spacious family retreats - all within walking distance to world-famous Kailua Beach and Lanikai. Many rentals include private yards, lanais, outdoor showers, and beach gear, making it easy to live like a local from the moment you arrive.

Spend your days kayaking to the Mokulua Islands, hiking the Lanikai pillbox trail for panoramic views, or browsing Kailua's boutiques and farmers markets. With its calm waters, friendly community, and scenic charm, Kailua is perfect for couples, families, and extended stays alike.

Whether you're here to relax, explore, or work remotely, Kailua vacation rentals offer the comfort of home with the beauty of Hawaii just outside your door.

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Luxury Lanikai Oceanfront Home – Secluded Beachside Elegance

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 will love.
Registration Number: TA-127-965-6960-01, GE-127-965-6960-01, 1430010120001

4 bedroom
3 bathroom
Sleeps 6

from $2,009

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Charming 3-bedroom house with a pool and AC in beautiful Kailua

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 brilliant property offers 2 queen beds and 2 twin beds for a peaceful night's sleep. With amenities like AC, WiFi, pool, and a washing machine, guests can relax in the bathtub or shower after a day of exploring.
Registration Number: 44013049, TA-173-947-0848-01, GE-173-947-0848-01

3 bedroom
2 bathroom
Sleeps 8

from $490

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$Relaxing 5bd\/3ba Kailua Home Just Steps from Kailua Beach with Wifi and A\/C$

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.
Registration Number: GE-161-351-8336-01, TA-161-351-8336-01, 430270250000

5 bedroom
3 bathroom
Sleeps 12

from $470

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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 - providing both ample privacy and on property parking.
Registration Number: 43003076, GE-164-517-2736-01, TA-164-517-2736-01

3 bedroom
4 bathroom
Sleeps 6

from $2,354

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$Leaf House: Lux Retreat w\/ Pool, Ocean Views & Outdoor Living Near Lanikai$

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 five-bedroom, four-and-a-half-bathroom retreat in the picturesque neighborhood of Lanikai, Kailua, Hawaii.
Registration Number: TA-032-430-3360-01, GE-032-430-3360-01, 430020420000

5 bedroom
4 bathroom
Sleeps 10

from $1,163

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

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 luxury Hawaiian home for your next beachfront getaway.
Registration Number: TA-200-559-6160-01, GE-200-559-6160-01, 430160130000

5 bedroom
5 bathroom
Sleeps 12

from $2,709

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Suite By the Sea - a bright and sparkling Apartment

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 in a paradise of your own.

Registration Number: TA-155-463-6800-02, GE-155-463-6800-02

1 bedroom
1 bathroom
Sleeps 2

from $176

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Centrally located, pet-friendly, 1 bedroom in Kailua

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 both long or short stays to make your holiday one to remember.
Registration Number: TA-185-831-1680-01, 1430520420000, GE-185-831-1680-01

1 bedroom
1 bathroom
Sleeps 4

from $166

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$Kailua Beachside: Lux Beachfront Villa w\/ Heated Pool, Ocean Views & Modern Amen$

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 five-bedroom, five-bathroom two-story villa in Kailua, Hawaii, perfect for up to ten guests.
Registration Number: 430200630000, GE-028-490-7520-02, TA-028-490-7520-01

5 bedroom
5 bathroom
Sleeps 10

from $2,118

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Spectacular Lanikai Oceanfront Home with Pool

Spectacular Lanikai Oceanfront Home with Pool

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 furnishings including all beds and linens and a re-modeled kitchen that includes new stainless steel appliances, new dish ware, and everything needed for those who love to cook.
Registration Number: GE-191-501-7728-01, TA-191-501-7728-01

6 bedroom
6 bathroom
Sleeps 18

from $1,441

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$Seahorse Beach House: Calm Oasis w\/ Private Yard Just Steps from Kailua Beach$

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, just steps away from Kailua’s powder white sand beaches.
Registration Number: 430130190000, TA-129-806-1824-01, GE-129-806-1824-01

2 bedroom
2 bathroom
Sleeps 4

from $625

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

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 updated 4BR/4BA retreat, ideal for 8 guests seeking tranquility, steps to the sands and calm waters of Lanikai Beach.

Registration Number: 430060440000, GE-053-385-4720-01, TA-053-385-4720-01

4 bedroom
4 bathroom
Sleeps 8

from $758

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🚐 Skip the hotel — 🏕️ Camping Experience — 🤑 Budget Friendly Vacation! 🏝️

🚐 Skip the hotel — 🏕️ Camping Experience — 🤑 Budget Friendly Vacation! 🏝️

Embark on a camping experience in Hawaii with our minivan camper perfect for individuals or couples.
It's a 25 minute Uber/Lyft from the airport.

CAMPING GEAR INCLUDED:
► 8" Memory Foam Mattress with CLEAN FRESH sheets
► Solar Powered Rechargeable Battery with 120 volts AC and plenty of USB ports
► Extra USB C and Lightning Cables
► Mobile Wifi Internet Hotspot
► Sink with Running Water
► Propane Gas Grill with 2 Burners
► Metal Pot and Frying Pan
► Coffee Maker and 2 Metal Mugs
► Cooking and Eating Utensils
► Plates, Bowels and Cups
► Refrigerator / Freezer Adjustable
► Beach Chairs
► Beach Towels
► Hammock
► Clothes Line
► Portable Flashlights

Immerse yourself in the beauty of Hawaii in luxury with our specially customized minivan camper designed for solo travelers or couples looking for an exceptional camping adventure.
Registration Number: TA-304-451-9023-02, GE-223-011-9008-16, 99981440

1 bedroom
0 bathroom
Sleeps 2

from $333

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$Peaceful Oceanfront Home Near Downtown Kailua w\/ BBQ & AC: Kai Mele$

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 beachfront getaway filled with all the historic charm and character.
Registration Number: 430130320000, TA-160-294-7072-01, GE-160-294-7072-01

3 bedroom
2 bathroom
Sleeps 6

from $890

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Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi

Steps to beach! Beachside 4-bedroom house in Kailua with AC & WiFi

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 been completely renovated with new kitchen and bathrooms, hardwood floors throughout main house and all brand new furniture and bedding.
Registration Number: GE-100-709-7344-01, TA-100-709-7344-01, 143015028000

4 bedroom
2 bathroom
Sleeps 6

from $488

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Lanikai Hillside Estate – Panoramic Luxury Above the Sea

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 vacation rental nestled on the world’s most isolated chain of islands.
Registration Number: 430010090000, GE-053-605-3248-01, TA-053-605-3248-01

7 bedroom
6 bathroom
Sleeps 10

from $4,165

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Hale Alapi'i Lanikai Getaway by Gather: Newly Renovated Near Beach & Hiking

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 Gather, a serene four-bedroom, three-bathroom home nestled in the heart of Kailua’s iconic Lanikai neighborhood.
Registration Number: 430030350000, GE-150-218-4960-01, TA-150-218-4960-01

4 bedroom
3 bathroom
Sleeps 6

from $666

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$Lanikai Hideaway: Modern Luxe Indoor-Outdoor Living\/Walk to Lanikai Beach$

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 four-bedroom, three-bathroom private retreat nestled in the idyllic town of Kailua, Hawaii.
Registration Number: GE-093-106-8416-01, TA-093-106-8416-01, 430030430000

4 bedroom
3 bathroom
Sleeps 9

from $834

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Short walk to Kailua Beach across the street-Quiet AC's-Lg. Kitchen-Patio-Grill

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 home.
Registration Number: TA-164-136-7040-01, GE-164-136-7040-01, 430090180000

1 bedroom
2 bathroom
Sleeps 4

from $306

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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 additional optional bed/bath), 4 bathrooms and sleeps up to 11 guests.
Registration Number: TA-123-605-1968-01, 430180070002, GE-123-605-1968-01

6 bedroom
5 bathroom
Sleeps 11

from $2,387

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$4BR Mokulua Seaside w\/ Private Studio, Steps to the Beach$

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 splendid retreat that harmonizes luxury living with the tranquil beauty of Kailua's oceanside.
Registration Number: TA-013-318-7072-01, GE-013-318-7072-01, 430040990000

4 bedroom
4 bathroom
Sleeps 10

from $951

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Cozy Aloha Suite with AC in charming Kailua

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.

Registration Number: 420200220000, TA-188-004-1472-01, 90/BB-0102, GE-188-004-1472-01

1 bedroom
1 bathroom
Sleeps 2

from $185

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Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool

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 breeze off of Kailua Bay this quiet home is the perfect place to relax and unwind

Enjoy island living at its best in this fully furnished bright and breezy home with in ground pool and spacious Lanai.
Registration Number: 43067102, TA-143-675-2896-01, GE-143-675-2896-01

3 bedroom
2 bathroom
Sleeps 7

from $193

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

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 Lanikai Beachside Retreat

Nestled just a block from the world-famous white sands of Lanikai Beach, Nohie Lanikai by Gather offers the perfect blend of island charm and modern comfort.
Registration Number: 430060920000, TA-139-353-0368-01, GE-139-353-0368-01

4 bedroom
3 bathroom
Sleeps 8

from $595

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

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 Kahakai whisk you away into vacation mode!
Registration Number: 430130020000, GE-039-143-1168-01, TA-039-143-1168-01

6 bedroom
5 bathroom
Sleeps 12

from $1,288

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