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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Kakela Kai, Beachfront Kailua Home, Private, A/C
From $987/night

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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii
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3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai
From $1,119/night

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. The home offers a...

🛏 6 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 15
📍 Kailua, Hawaii
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Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
From $1,057/night

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!...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii
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Walker's Lanikai Beach House – Historic Oceanfront Retreat
From $2,976/night

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). Mr....

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii
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Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
From $1,169/night

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. The...

🛏 5 Bedrooms
🛁 1 Bathroom
👤 Sleeps 10
📍 Kailua, Hawaii
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Gorgeous Lankai Villa with Access to Secluded White Sand Beach
From $4,262/night

Gorgeous Lankai Villa with Access to Secluded White Sand Beach

This gorgeous 5 bedroom, 4.5 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...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 15
📍 Kailua, Hawaii
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OCEANFRONT LANIKAI BEACH ESTATE
From $884/night

OCEANFRONT LANIKAI BEACH ESTATE

AlohaRelax 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. A...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii
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Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach
From $1,014/night

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...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii
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Cool retreat at the entrance to Lanikai. Very Close to Beach. 3 Primary Bedrooms
From $583/night

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii
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Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach
From $859/night

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...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii
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Beach Studio with private yard in Lanikai - 30 day Minimum Stay
From $157/night

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii
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Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12
From $972/night

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...

🛏 5 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 12
📍 Kailua, Hawaii
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Kailua Beachfront Luxury Home – Expansive Elegance with Ocean Views
From $2,392/night

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. 6...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii
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Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC
From $836/night

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii
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Koohoo Place - Lanikai, Oahu. From here, you can see forever! NEW LISTING.
From $379/night

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii
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Villa Frangipani Tropical Beachside Retreat Kailua
From $609/night

Villa Frangipani Tropical Beachside Retreat Kailua

About this spaceOnce 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. Built in 1938, our home...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii
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3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY DISCOUNT!
From $372/night

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....

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii
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La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
From $585/night

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua, Hawaii
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Happy House on Exquisite Kailua Beachside Property!
From $524/night

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,...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii
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Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.
From $421/night

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

Welcome to the Penthouse in Lanikai! We have been sharing our piece of paradise for over 20 years.! 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...

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Kailua, Hawaii
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Place in Paradise - Kailua Beach Oceanfront Vacation Home
From $3,887/night

Place in Paradise - Kailua Beach Oceanfront Vacation Home

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...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii
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Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option
From $644/night

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

Aloha and Welcome to Kolea LandingA 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...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Kailua, Hawaii
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Lanikai Breeze – Contemporary Comfort Steps from the Shore
From $1,165/night

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,...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii
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Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
From $2,769/night

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...

🛏 6 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii
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Beachside Kailua AC 3min walk to beach! Inquire for available dates!
From $996/night

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

CONTACT HOST/RESERVATIONS/DETAILSThis 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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii
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Ohana Beach House - 5 Bedrooms - Steps Away from Kailua Beach
From $1,213/night

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...

🛏 5 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii
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Oceanfront Lanikai Beach Vacation Home
From $1,451/night

Oceanfront Lanikai Beach Vacation Home

TA-006-302-3104-01Beautiful ocean front home at the beginning of Oahu's famous Lanikai Beach!. 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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii
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Kailua Beach Historic Renovated Cottage
From $1,278/night

Kailua Beach Historic Renovated Cottage

This property is offered as a monthly rental. Although full-month occupancy isnot required, the monthly rate remains fixed and applies in full, regardlessof the number of nights stayed, as prorated rates are not available.One of the original homes on Kailua Beach, this...

🛏 5 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii
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Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage
From $2,781/night

Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage

HALE LANIKAILic# TA-161-257-7280-01Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations.Hale Lanikai is BACK! Better than ever!!All new furnishings throughout the property.Original Koa...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii
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Mokulua Sunrise Ocean Villa Lanikai
From $1,075/night

Mokulua Sunrise Ocean Villa 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.Enjoy top-tier luxurious living on your next...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii
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1 Bedroom AC Modern 5 Min Walk Beach
From $204/night

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....

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii
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Luxury beachfront villa on a world class beach in Kailua, HI
From $4,227/night

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...

🛏 6 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 18
📍 Kailua, Hawaii
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Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen
From $261/night

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua, Hawaii
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Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach
From $731/night

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...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii
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Orchid House - Pool and Endless Ocean views!
From $1,014/night

Orchid House - Pool and Endless Ocean views!

ORCHID HOUSETA # 087-311-0016-01With 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...

🛏 3 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 7
📍 Kailua, Hawaii
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The Perfect Lanikai Retreat With Direct Access To Secluded White Sand Beach!
From $1,130/night

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...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii
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Kailua Beachfront Vacation Home with Pool
From $2,784/night

Kailua Beachfront Vacation Home with Pool

One of the few Licensed Short-Term Vacation Rentals on the Windward side of Oahu, this three bedroom, three bath home with large swimming pool sits on .9 acres of Kailua Beachfront. The home has been recently refurbished with new furnishings, fixtures, appliances, linen...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Kailua, Hawaii
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Bright and airy 1-bedroom cottage in charming Kailua, 1 block to beach. WiFi, AC
From $269/night

Bright and airy 1-bedroom cottage in charming Kailua, 1 block to beach. WiFi, AC

This sunny cottage in Kailua is a perfect choice for guests seeking a quiet retreat in a fantastic location, so conveniently close to all that Kailua has to offer, including sandy beaches, popular restaurants and eateries, all kinds of great boutique shops, Whole Foods,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii
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Kai Moena Estate - Kailua Luxury Beachfront Estate with Pool, Spa, AC, Sauna, Fitness Center & More!
From $6,286/night

Kai Moena Estate - Kailua Luxury Beachfront Estate with Pool, Spa, AC, Sauna, Fitness Center & More!

Prices start at $100,000/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.Property is currently for sale. The property manager will contact you to make arrangements to schedule showings at a convenient time. This luxury...

🛏 7 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii
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Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua
From $1,259/night

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...

🛏 5 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 11
📍 Kailua, Hawaii
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Naupaka Hale - Lanikai Beach Home & Cottage
From $1,268/night

Naupaka Hale - Lanikai Beach Home & Cottage

NAUPAKA HALETA-151-566-1312-02THIS 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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Lanikai, Hawaii
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Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!
From $396/night

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

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

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua, Hawaii
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Family friendly Quiet Kailua Beachside lane, steps to lane private beach access
From $340/night

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

Only steps to beach through private street gate, and a short 1.5 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 -...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Kailua, Hawaii
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Just 40 Steps to the Most Beautiful White Sand Beach in the World
From $1,457/night

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....

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Kailua, Hawaii
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Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking
From $434/night

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...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Kailua, Hawaii
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Steps To Kailua Beach
From $720/night

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...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Kailua, Hawaii
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Large, beautiful, updated home w/pool, AC,mins from beach in Kailua! Flex stays!
From $1,144/night

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...

🛏 7 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 14
📍 Kailua, Hawaii
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Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
From $1,216/night

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...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 12
📍 Kailua, Hawaii
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Available and legal for stays less than 30 days.
From $336/night

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Kailua, Hawaii
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Hale Lani – Heavenly Lanikai Hillside Luxury
From $3,647/night

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...

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