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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$Kakela Kai, Beachfront Kailua Home, Private, A\/C$

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 granite accents.
Registration Number: 430180100003, TA-083-865-6000-01, GE-083-865-6000-01

4 bedroom
3 bathroom
Sleeps 10

from $987

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3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai

3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai

The Pool House in Kailua offers 3,200 sq ft with 6 bedrooms, 4 baths and one amazing pool. Located in a peaceful and lush neighborhood with views of the Ko’olau Mountain range, it is an easy walk to Kailua Beach, Lanikai Beach and Buzz's Steakhouse.
Registration Number: 420540580000, TA-036-329-7280-01, GE-036-329-7280-01

6 bedroom
4 bathroom
Sleeps 15

from $1,119

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$Hale Ohana: Kailua Retreat w\/hot tub, Tropical Pool, Walk to Beach$

Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to 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.

Hale Ohana meaning Family House is just that!
Registration Number: 430830350000, TA-139-302-3488-01, GE-139-302-3488-01

4 bedroom
3 bathroom
Sleeps 10

from $1,057

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Walker's Lanikai Beach House – Historic Oceanfront Retreat

Walker's Lanikai Beach House – Historic Oceanfront Retreat

Welcome to Walker's Lanikai Beach House. John Walker, was a Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall).
Registration Number: 430080930000, TA-043-470-0288-01, GE-043-470-0288-01

5 bedroom
4 bathroom
Sleeps 14

from $2,976

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Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!

Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!

This Kailua, beachside, pool (heated) home was completely remodeled in 2019 with all new kitchen, bathrooms, pool house, pool surround, landscaping, TV's, furnishings, etc. And NO CLEANING FEE on 30 day bookings!

Each room has an individually controlled AC system.
Registration Number: GE-174-185-2672-01, TA-174-185-2672-01, 430190450000

5 bedroom
1 bathroom
Sleeps 10

from $1,169

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Gorgeous Lankai Villa with Access to Secluded White Sand Beach

Gorgeous Lankai Villa with Access to Secluded White Sand Beach

5 bathroom, gated oceanfront villa was built in 1918 and has just been fully remodeled with an open, contemporary beach house feel while still honoring the original architecture of the home. In the renovation we revealed beautiful arches within, expanded the gourmet kitchen with all new appliances, a coffee bar and wine fridge.
Registration Number: GE-180-925-6448-01, TA-180-925-6448-01

5 bedroom
5 bathroom
Sleeps 15

from $4,262

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OCEANFRONT LANIKAI BEACH ESTATE

Aloha

Relax and unwind at Kai Hale. This beautiful Lanikai ocean front home is directly in front of the Mokulua Islands.

This location is suited for year round living and is ideal for stand-up paddling, kayaking, boogie boarding, snorkeling, and children's activities.
Registration Number: TA-013-232-3328-02, 1430040780002, GE-013-232-3328-02

3 bedroom
3 bathroom
Sleeps 6

from $884

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Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach

Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach

ALOHA! The Kailua Bliss Beach House is a casual and relaxed beach house in the quiet Beachside neighborhood in Kailua, located on a private street, 1 house from the white sands of Kailua beach (Private beach gate is located adjacent to our property and the house is less than 350 feet to the beach).
Registration Number: TA-068-883-0976-01, GE-068-883-0976-01, 143018061000

4 bedroom
4 bathroom
Sleeps 10

from $1,014

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Cool retreat at the entrance to Lanikai. Very Close to Beach. 3 Primary Bedrooms

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 with attention to detail throughout the rental.
Registration Number: GE-164-136-7040-01, TA-164-136-7040-01, 430090180000

3 bedroom
3 bathroom
Sleeps 8

from $583

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Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach

Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near 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.

Unwind at Hale Aloha by Gather, your tranquil retreat just minutes from Kailua’s famous shores.
Registration Number: TA-195-940-3520-01, GE-195-940-3520-01, 420180550000

4 bedroom
2 bathroom
Sleeps 8

from $859

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Beach Studio with private yard in Lanikai - 30 day Minimum Stay

Beach Studio with private yard in Lanikai - 30 day Minimum Stay

Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east side of the island. Designed as your ultimate home away from home, this property offers a unique blend of seclusion and convenience, making it the perfect spot for a truly relaxing and authentic Hawaiian vacation.

Registration Number: TA-200-243-0464-01, GE-200-243-0464-01, 430080730000

1 bedroom
1 bathroom
Sleeps 2

from $157

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Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

Welcome to Lanikai Hale ~ Two Hawaiian style cottages (which can be rented together or separately) on a large fenced-in property in the heart of Lanikai, just 2 miles from Kailua Town on the Windward side of Oahu.
There is plenty of parking and sleeping space for a group of 10 to 12 people.
Registration Number: TA-107-927-8080-01, GE-107-927-8080-01

5 bedroom
3 bathroom
Sleeps 12

from $972

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Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views

Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views

Recently updated with stylish contemporary design, this spacious Kailua home sits on Kailua Beach with nearly 100 linear feet of beach frontage. The home features direct and private access to the white sands with over 2 miles of beach walking at your front doorstep.
Registration Number: 1430200510000, GE-176-489-9328-01, TA-176-489-9328-01

6 bedroom
6 bathroom
Sleeps 14

from $2,392

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$Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w\/Pool, Yard & AC$

Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC

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 Nani Lanikai by Gather, a beautiful three-bedroom, three-bathroom home located in the desirable Lanikai community of Kailua, Oahu.
Registration Number: 430050050000, TA-209-884-5696-01, GE-209-884-5696-01

3 bedroom
3 bathroom
Sleeps 8

from $836

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Koohoo Place - Lanikai, Oahu. From here, you can see forever! NEW LISTING.

Koohoo Place - Lanikai, Oahu. From here, you can see forever! NEW LISTING.

Two bedroom, two bath private residence at the top of Lanikai with spectacular, panoramic views of the Kailua coastline. Feel on top of the world in this truly unique hilltop bungalow. Nestled just beneath the Lanikai Pillboxes, a popular hiking trail, Ko’oho’o provides unobstructed views of the Mokulua Islands and the deep blue Pacific beyond.
Registration Number: N/A, GE-073-725-6960-01, 1430050430000, TA-073-725-6960-01

2 bedroom
2 bathroom
Sleeps 6

from $379

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Villa Frangipani Tropical Beachside Retreat Kailua

Villa Frangipani Tropical Beachside Retreat Kailua

About this space
Once inside our fully gated property you will be immersed in a lush tropical garden with palms surrounding a lagoon style pool. We are just a 2 minute barefoot stroll along a private lane to the soft white sands of Kailua Beach.
Registration Number: 430150140000, TA-172-544-1024-01, GE-172-544-1024-01

4 bedroom
4 bathroom
Sleeps 8

from $609

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3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY DISCOUNT!

3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY DISCOUNT!

E komo mai to Hale Makai, our piece of island paradise in Kailua. Beachside and just three houses from Kailua Beach - you are going to love it here.

Lying alongside a fabulous three-mile stretch of protected beach, Kailua is a small town on the windward side of Oahu.
Registration Number: 1430120060000, GE-203-074-9696-01, TA-203-074-9696-01

3 bedroom
2 bathroom
Sleeps 6

from $372

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La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)

La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)

No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family and close to amenities.

Our luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation.

Registration Number: 440230030000, GE-056-708-4544-01, TA-056-708-4544-01

1 bedroom
1 bathroom
Sleeps 4

from $585

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Happy House on Exquisite Kailua Beachside Property!

Happy House on Exquisite Kailua Beachside Property!

Kailua Beachside: Charming beach house steps from the white sands of beautiful Kailua Beach. Nestled in a large, private garden property, enclosed by stone walls with palms, banana trees and beautiful tropical gardens. Very safe and fun for kids, great for families, with lots of room to roam and hang out.
Registration Number: 1430150090000, TA-210-792-6016-01, GE-210-792-6016-01

3 bedroom
2 bathroom
Sleeps 6

from $524

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$Penthouse View in Lanikai LANIKAI NUC 90\/BB -0108 Most comfortable for 2 or 3.$

Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.

Welcome to the Penthouse in Lanikai! Everyone deserves to experience the Hawaiian lifestyle! Sunrises, moonrises, walks, bike rides, and daily runs on the beach. We have guests from all over the world return year after year. The Penthouse level has the BEST VIEW in the Best neighborhood and is one of the few long term vacation rentals in Lanikai!
Registration Number: 43005029, W00530010-01, GE-136-047-8208-01, TA-136-047-8208-01

2 bedroom
1 bathroom
Sleeps 4

from $421

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Amazing & Large Kailua Beachfront for up to 14 guests

Amazing & Large Kailua Beachfront for up to 14 guests

Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted "Best Beach in the United States" by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu visit.
Registration Number: GE-060-877-8240-01, 430210250000, TA-060-877-8240-01

5 bedroom
5 bathroom
Sleeps 14

from $3,887

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$Kolea Landing Modern Beach House w\/ Double Suite and Third Bedroom Option$

Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option

Aloha and Welcome to Kolea Landing
A short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house is the perfect blend of island and modern living. Our guest house has a master bedroom (king bed) with an en suite bathroom, a second master bedroom (king bed) with an attached bathroom, and for groups (5-6 person) we have a third bedroom (two twin xl beds), for groups of 4 or less our third bedroom will be locked.
Registration Number: 430070230000, GE-082-679-2448-01, TA-082-679-2448-01

3 bedroom
1 bathroom
Sleeps 6

from $644

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Escape & Treat Yourself..Quiet Clean Bright..5 star reviews, Sleeps 4

Escape & Treat Yourself..Quiet Clean Bright..5 star reviews, Sleeps 4

Aloha, this unique Premier Partner property is exclusively available for rental for periods of thirty (30) days or more. ).
5 Bath, treetop location overlooking the world famous Mid Pacific Country Club Golf Course. Where Presidents play.
Registration Number: 420480020000, TA-120-590-3360-01, GE-120-590-3360-01

1 bedroom
0 bathroom
Sleeps 4

from $259

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Lanikai Breeze – Contemporary Comfort Steps from the Shore

Lanikai Breeze – Contemporary Comfort Steps from the 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.

Just steps away from coveted Lanikai Beach, sits our newest luxury home - Lanikai Breeze by Gather.
Registration Number: 430070810000, GE-135-880-0384-01, TA-135-880-0384-01

5 bedroom
4 bathroom
Sleeps 10

from $1,165

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Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores

Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores

This spectacular beachfront home offers two living spaces on the best part of Kailua Beach - known throughout the State as one of the most pristine white sand beaches - the perfect beach home for accommodating groups large and small. Both the main house (5 bedrooms) and the cottage (1 bedroom) have been extensively renovated by professional designers bringing new comforts to even the most discriminating travelers.
Registration Number: 430130010000, TA-137-826-1504-01, GE-137-826-1504-01

6 bedroom
4 bathroom
Sleeps 14

from $2,769

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Beachside Kailua AC 3min walk to beach! Inquire for available dates!

Beachside Kailua AC 3min walk to beach! Inquire for available dates!

CONTACT HOST/RESERVATIONS/DETAILS

This airy, spacious four bedroom Kailua beachside vacation rental home with AC provides the essence of tropical Hawaiian living. Remodeled kitchen and bath(s) finish off this stunning home. Whether you prefer lounging in the sun alongside the very private and enclosed swimming pool, relaxing in the heated spa or watching the sunrise from beautiful Kailua Beach, all are there for your personal enjoyment.
Registration Number: 430190530000, GE-126-659-1744-01, TA-126-659-1744-01

4 bedroom
3 bathroom
Sleeps 8

from $996

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Ohana Beach House - 5 Bedrooms - Steps Away from Kailua Beach

Ohana Beach House - 5 Bedrooms - Steps Away from Kailua Beach

Just steps from one of the most beautiful tourist-free beaches on the island of Oahu, this Hawaiian style home is a perfect peaceful getaway for your extended family. Listen to the waves crashing as you relax on the lanai, or barbeque for your group in true outdoor Hawaiian fashion.
Registration Number: GE-054-032-3840-01, 430180510000, TA-054-032-3840-01

5 bedroom
3 bathroom
Sleeps 10

from $1,213

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Enjoy watching for Sea Turtles off your Ocean Front Deck!

Enjoy watching for Sea Turtles off your Ocean Front Deck!

2 bedroom, 1 bathroom main house and 2 bedroom, 2 bathroom guest cottage. Featuring breathtaking views, a brand new courtyard pool with privacy and manicured yard space, a generous ocean-facing deck for relaxation, beautiful landscaping all around and was air conditioning in all bedrooms.
Registration Number: GE-006-302-3104-01, TA-006-302-3104-01

4 bedroom
3 bathroom
Sleeps 10

from $1,451

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Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning

Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning

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.

One of the original homes on Kailua Beach, this Renovated 1937 five bedroom

Cottage is just one house from the middle of Kailua Beach, the #1 Beach in the

world.
Registration Number: GE-045-319-8848-01, TA-045-319-8848-01, 430160220000

5 bedroom
2 bathroom
Sleeps 10

from $1,278

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Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage

Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage

HALE LANIKAI

Lic# TA-161-257-7280-01
Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations.

Hale Lanikai is BACK!

All new furnishings throughout the property.

Registration Number: 430050500000, GE-161-257-7280-01, TA-161-257-7280-01

4 bedroom
4 bathroom
Sleeps 8

from $2,781

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$Superbly Designed Home w\/ Views of the Mokulua Islands & Ocean: Mokulua Sunrise$

Superbly Designed Home w/ Views of the Mokulua Islands & Ocean: Mokulua Sunrise

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.

Enjoy top-tier luxurious living on your next Hawaiian vacation at the Mokulua Sunrise ocean villa, located in the world famous neighborhood of Lanikai on the eastern shores of the vibrant island of Oahu.
Registration Number: TA-013-318-7072-01, GE-013-318-7072-01, 430040990000

4 bedroom
3 bathroom
Sleeps 8

from $1,075

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1 Bedroom AC Modern 5 Min Walk Beach

Turn key ready for a relaxing stay.

With on site parking, a common use gated entrance leads you down a lava rock pathway to a private gated courtyard that contains a propane BBQ, water feature, patio table & chairs and lighted umbrella to enjoy your garden day or night.
Registration Number: 143024003000, GE-111-409-1520-01, TA-111-409-1520-01

1 bedroom
1 bathroom
Sleeps 2

from $204

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Luxury beachfront villa on a world class beach in Kailua, HI

Luxury beachfront villa on a world class beach in Kailua, HI

As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.
This luxurious Kailua Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises and step onto the beach from your very private and modest oceanfront estate.
Registration Number: GE-048-077-3632-01, TA-048-077-3632-01, 430190500000

6 bedroom
5 bathroom
Sleeps 18

from $4,227

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Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen

Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen

Nestled in the beachside community of Lanikai, Kailua, this fully furnished home is over 1400 square feet of island style living. Beautifully yet simply decorated, this unit is the whole upper half of the main house. The entrance is at mid-floor level with a Brazilian cherry staircase leading to upper and lower levels.
Registration Number: TA-136-919-6544-01, GE-136-919-6544-01

2 bedroom
2 bathroom
Sleeps 4

from $261

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$Lanikai Cottage: Charming Tropical Oasis w\/Private Pool & A\/C, Walk to Beach$

Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to 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.

Charming Lanikai Cottage features two dwellings on the same property, providing a total of three bedrooms and two bathrooms.
Registration Number: TA-111-603-0976-01, GE-111-603-0976-01, 430040320000

3 bedroom
2 bathroom
Sleeps 6

from $731

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Orchid House - Pool and Endless Ocean views!

Orchid House - Pool and Endless Ocean views!

ORCHID HOUSE
TA # 087-311-0016-01

With 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 flooring, gourmet kitchen and appliances, skylights, AC in every room for those rare Kona days, and much more.

Registration Number: GE-087-311-0016-01, TA-087-311-0016-01

3 bedroom
4 bathroom
Sleeps 7

from $1,014

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The Perfect Lanikai Retreat With Direct Access To Secluded White Sand Beach!

The Perfect Lanikai Retreat With Direct Access To Secluded White Sand Beach!

Hale Kainalu is a sweet getaway at the end of Lanikai with exclusive secluded beach used by only 5 houses within a gated drive. This beautiful cottage is literally right on the beach & overlooks the crystal clear, blue and green hued water. Wake up each morning to a glorious sunrise to start your day.
Registration Number: GE-180-925-6448-01, TA-180-925-6448-01

3 bedroom
2 bathroom
Sleeps 6

from $1,130

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$Custom, Renovated Kailua Beach Front w\/pool - Best Location on the Bay!$

Custom, Renovated Kailua Beach Front w/pool - Best Location on the Bay!

9 acres of Kailua Beachfront. The home has been recently refurbished with new furnishings, fixtures, appliances, linen and accessories making it clean, comfortable and refreshed. A beautiful, ocean front lawn separates the home from the ocean, offering quiet and privacy.
Registration Number: TA-148-509-2864-01, 1430150430000, GE-148-509-2864-01

3 bedroom
3 bathroom
Sleeps 10

from $2,784

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$Elegant Home w\/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua$

Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua

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 relaxing atmosphere of Lokomaika’i Kailua (meaning Gracious Kailua) whisk you into vacation mode.
Registration Number: GE-079-127-1936-01, TA-079-127-1936-01, 430830190000

5 bedroom
3 bathroom
Sleeps 11

from $1,259

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Naupaka Hale - Lanikai Beach Home & Cottage

Naupaka Hale - Lanikai Beach Home & Cottage

NAUPAKA HALE
TA-151-566-1312-02
THIS PROPERTY RENTS ONLY MONTHLY FOR 30 DAYS AND LONGER.

Idyllic classic Hawaiian style vacation rental home on large lot with huge sandy beach right in front of your very eyes. This beautiful vacation rental home offers breathtaking views of Lanikai Beach, turquoise water and the Mokulua Islands.
Registration Number: TA-151-566-1312-01, GE-151-566-1312-02

3 bedroom
3 bathroom
Sleeps 6

from $1,268

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Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!

Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!

Indulge in an Unforgettable Stay at Our BRAND-NEW Luxury Beach House at Kailua Beach

Escape to our newly built, luxurious rental home, perfectly nestled in the heart of the most sought-after location by the world-renowned Kailua Beach. This contemporary haven is designed to blend upscale comfort with the breathtaking beauty of Hawaii.
Registration Number: TA-060-008-4480-01, GE-060-008-4480-02, 430150540000

2 bedroom
2 bathroom
Sleeps 4

from $396

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Family friendly Quiet Kailua Beachside lane, steps to lane private beach access

Family friendly Quiet Kailua Beachside lane, steps to lane private beach access

5 mile bike to Kailua town. 2 bedrooms, family room, and kitchen on 2nd floor; laundry, 1 bedroom and bath on 1st floor. Washer/Dryer, Basic Cable, and Wifi includded. Small pets ok.

Monthly rentals only - TLA Approved

Full kitchen, large deck with grill looking out over the Koolau mountains.
Registration Number: 430180410000, TA-199-189-0944-01, GE-199-189-0944-01

3 bedroom
2 bathroom
Sleeps 4

from $340

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Just 40 Steps to the Most Beautiful White Sand Beach in the World

Just 40 Steps to the Most Beautiful White Sand Beach in the World

Tropical Trade Winds and Unsurpassed Views are from our Beach Front Home. Opens up for full enjoyment of Hawaii's Climate. Our rap-around Lanai overlooks the beautiful beach, Kailua Bay, and Offshore Islands.

Kailua is a small upscale town with excellent retail stores.
Registration Number: TA-191-191-0400-01, GE-191-191-0400-01, 430130460000

4 bedroom
3 bathroom
Sleeps 8

from $1,457

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Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking

Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking

Due to local laws we have a rental contract of 30 days.

This beautiful, spacious Kailua home has 3 bedrooms and 2 bathrooms. The house can sleep up to 6. Two bedrooms have a King bed and one bedroom has two twin beds. There is also an attached 1-bedroom, 1 bathroom apartment that rents separately from the main house.
Registration Number: TA-143-873-0240-01, 430750280000, GE-143-873-0240-01

3 bedroom
2 bathroom
Sleeps 6

from $434

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Steps To Kailua Beach

Our beautiful home has been featured in Hawaii Home Magazine and has received a best in class award from the Hawaii Builders Association. The home is within a 2 minute walk to Kailua Beach Park, the Kalapawai Market and Buzz's Steak house. There is ocean, mountain and canal views and a modern open floor plan.
Registration Number: GE-030-384-5376-01, TA-030-384-5376-01

4 bedroom
2 bathroom
Sleeps 7

from $720

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$Large, beautiful, updated home w\/pool, AC,mins from beach in Kailua! Flex stays!$

Large, beautiful, updated home w/pool, AC,mins from beach in Kailua! Flex stays!

Welcome to Holoholo Hale in the beautiful town of Kailua on the island of Oahu. Kailua is the home of two of the best beaches in the world, Kailua Beach Park and Lanikai Beach. The home is a short drive to all the island has to offer including Diamond Head, the pill box hike, the Northshore, and Waikiki.
Registration Number: 420560420000, GE-141-882-0096-01, TA-141-882-0096-01

7 bedroom
3 bathroom
Sleeps 14

from $1,144

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Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room

Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room

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 the allure of Kailua at Villa Hui Hou by Gather!
Registration Number: TA-091-214-0288-01, GE-091-214-0288-01, 430030440000

5 bedroom
4 bathroom
Sleeps 12

from $1,216

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Available and legal for stays less than 30 days.

Available and legal for stays less than 30 days.

Hawaii Sheffield House has been a legal bed and breakfast for over 35 years. We are available and legal for stays of less than 30 days. We provide a unique neighborhood stay in Kailua Hawaii that is just down the street from Kailua Beach.

The Hawaii Sheffield House Ginger Studio has a 'Secret Garden.
Registration Number: TA-137-360-9984-01, GE-137-360-9984-01, 430720040000

1 bedroom
1 bathroom
Sleeps 2

from $336

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Hale Lani – Heavenly Lanikai Hillside Luxury

Hale Lani – Heavenly Lanikai Hillside Luxury

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.

Find your next dream vacation here at Hale Lani, situated on the picturesque northern shores of Oahu, Hawaii.
Registration Number: TA-168-604-3136-01, 430060650000, GE-168-604-3136-01

3 bedroom
4 bathroom
Sleeps 8

from $3,647

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Lovely Private Kailua Cottage

Welcome to our newly renovated 1-bedroom spacious and private cottage that is super centrally located in the heart of Kailua. Our cottage is situated on a beautifully landscaped property which will lead you to a lusciously landscaped garden with outdoor dining & BBQ.
Registration Number: GE-121-728-3584-01, 43071011, TA-121-728-3584-01, 143071110000

1 bedroom
1 bathroom
Sleeps 4

from $425

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