50 Best Kailua Vacation rentals on Holiday Lettings - Beach rentals

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78 Vacation rentals

7

Vacation studio in Kailua

Oahu / Kailua

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Kailua beach is about 1 mile from Kailua town. Kailua Guesthouse is located half-way between. It's about a 10-minute walk to the beach, a 10-minute walk to town. TheBus stop is about 300 feet from our front gate. My father acquired the property in 1947 and b …see more

from $139 / night

$910 / week

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from $139 / night

(8) Excellent 

Certificate of Excellence

23

Kailua Vacation condo rental

Oahu / Kailua

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Sandbar Cottage is an immaculate and beautifully appointed 2 bedroom / 2 bath unit located just a short stroll to one of the most beautiful beaches in the world, Kailua Beach. The unit is fully furnished with A/C in all rooms, cable TV, DVD player, Wi-Fi, washer/dryer, …see more

Certificate of Excellence

from $250 / night

$1600 / week

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Responds fast!
avg. 3 hours 50 minutes

from $250 / night

20

Vacation home with swimming pool in Kailua

Oahu / Kailua

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settl …see more

from $900 / night

$6300 - $9800 / week

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from $900 / night

(1) Very Good 

12

Vacation cottage in Kailua

Oahu / Kailua

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off stree …see more

from $130 / night

$910 / week

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avg. 3 hours 35 minutes

from $130 / night

13

Vacation b&b in Kailua

Oahu / Kailua

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Hawaii Sheffield House is in Kailua Town. is located only 10 houses to Kailua Beach. The address is 131 Kuulei Road. The closest beach access is Ka'apuni Loop.Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite is a ground …see more

from $164 / night

$1148 / week

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from $164 / night

(2) Very Good 

25

Vacation private room in Kailua

Oahu / Kailua

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.18 mi
  • Ask about children
Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) tak …see more

from $165 / night

$1085 / week

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from $165 / night

(2) Excellent 

13

Vacation home in Kailua

Oahu / Kailua

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and …see more

from $350 / night

$2450 - $3850 / week

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from $350 / night

8

Studio accommodation in Kailua

Oahu / Kailua

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 0.3 mi
  • Suitable for children age 5+
  • Air conditioning
Cozy Orchid studio in private home. Private entrance and bathroom. Three blocks from the beach in One Direction and 3 to 5 blocks to Kailua town shopping in the other direction . Air-conditioning and ceiling fan. Small covered patio with table & 2 chairs. Small light …see more

from $66 / night

$450 / week

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from $66 / night

15

Kailua Vacation cottage rental

Oahu / Kailua

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-b …see more

from $195 / night

$1365 / week

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from $195 / night

(1) Very Good 

8

Vacation home in Kailua

Oahu / Kailua

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three mile …see more

from $350 / night

$2450 / week

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from $350 / night

(8) Excellent 

28

Vacation cottage in Kailua

Oahu / Kailua

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach t …see more

from $80 / night

$560 / week

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from $80 / night

20

Cottage rental in Kailua

Oahu / Kailua

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Aloha, come and relax at our tropical Kailua home located in one of Kailua's finest neighborhoods. Kailua Beach hale is located across the street from the beach access (150 feet to the access and about 700 feet to the waters edge) to a quiet sandy section of Kailua beac …see more

from $221 / night

$1547 - $1708 / week

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Responds fast!
avg. 3 hours 58 minutes

from $221 / night

23

Vacation home in Kailua

Oahu / Kailua

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
This 850 sq ft duplex consists of a very spacious living room with a vaulted ceiling, 1 bedroom, 1 full bath and a full kitchen with oven. All the areas come with ceiling fans and the home is indirectly ventilated with a whole house fan. The bedroom has a queen bed and …see more

from $160 / night

$1100 - $1500 / week

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Responds fast!
avg. 31 minutes

from $160 / night

(25) Very Good 

19

Vacation b&b with shared pool in Kailua

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.48 mi
  • Swimming pool
Located in a lovely beachside town, the Garden Studio is a ground floor attached studio with a private entrance and patio. The Studio is designed for relaxing and comes with a queen bed, dining table & chairs, ceiling fan, TV, air-conditioning and WiFi. Enjoy indoor or …see more

from $99 / night

$665 / week

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Responds fast!
avg. 3 hours 44 minutes

from $99 / night

8

Kailua Vacation home accommodation

Oahu / Kailua

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Air conditioning
  • Pet friendly
Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute dri …see more

from $206 / night

$1443 - $1862 / week

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from $206 / night

(1) Excellent 

19

Vacation apartment with shared pool, golf nearby in Kailua

Oahu / Kailua

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
My home is on the hill overlooking Lanikai Bay with 180 degree unobstructed views of the Mokulua Islands. You can observe sun and moon rises from your private patio and whales breaching just offshore in the winter! Trade winds cool the property, but there is also A/C …see more

from $155 / night

$1085 / week

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Responds fast!
avg. 3 hours 44 minutes

from $155 / night

12

Kailua Vacation cottage rental

Oahu / Kailua

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
Cute garden cottage - walking distance to Kailua Beach and Beach Park - private entrance & bath - kitchenette - sleeps 2 adults In your private beach cottage you'll sleep soundly on a firm queen-size bed. A three-step ladder accesses the sleeping loft. Safety bar for th …see more

from $96 / night

$650 / week

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Responds fast!
avg. 3 hours 44 minutes

from $96 / night

(3) Very Good 

23

Kailua Vacation home rental

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It …see more

from $450 / night

$3150 / week

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from $450 / night

13

Vacation cottage in Kailua

Oahu / Kailua

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
Renovated attached cottage, 10 minute walk to Famous Kailua Beach! Perfect location for your Hawaiian get away. Fully renovated 1 bedroom, 650 sqft attached cottage. Private bedroom and pull out sofa bed to sleep two additional guests. There is a full double door refr …see more

from $169 / night

$1183 / week

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Responds fast!
avg. 3 hours 53 minutes

from $169 / night

21

Kailua Vacation home rental

Oahu / Kailua

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life …see more

from $600 / night

$4200 / week

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from $600 / night

24

Kailua Vacation apartment rental

Oahu / Kailua

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Child friendly
This one bedroom has it all! It is in a great neighborhood in Waialae Kahala. Newly renovated and furnished with a comfortable King bed. (Has a day bed for a third person at no extra charge). 2 HD TV's with cable, free internet wifi, and a kitchen with granite counterto …see more

from $150 / night

$1200 / week

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Responds fast!
avg. 3 hours 49 minutes

from $150 / night

23

Vacation home in Kailua

Oahu / Kailua

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Lovely hideaway two bedrooms are attached " Ohana" to the main house with two private entrances. Home provide a lovely the laid-back Kailua beach town and the Hawaiin lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to th …see more

from $123 / night

$835 - $1764 / week

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Responds fast!
avg. 1 hour 23 minutes

from $123 / night

(16) Excellent 

Certificate of Excellence

34

Kailua Vacation home rental

Oahu / Kailua

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Private garden
Come and play at the Beach We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance as well as downtown. And for those of you traveling without a car, a major bus line is just around the corner. Here you will be surrounded by lush …see more

Certificate of Excellence

from $126 / night

$840 / week

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from $126 / night

24

Kailua Vacation home rental

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This beautiful executive home in the wonderful Lanikai community was newly built in 2014. It boasts 3 bedrooms en suite that are generous in size and more than ample in comfort. Guests will find that the spacious living area is open and flows nicely for family gathering …see more

from $696 / night

$4866 / week

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from $696 / night

10

Cottage rental in Kailua

Oahu / Kailua

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.06 mi
  • Child friendly
Enjoy a restful respite in this private cozy cottage. We are in Lanikai, across the street from the ocean and the beautiful Mokulua islands. The cottage is a separate building located on the back corner of a 10,000 sq. ft. lot. It is a comfortable roomy self-contained …see more

from $250 / night

$1750 / week

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from $250 / night

(3) Very Good 

Certificate of Excellence

30

Vacation bungalow with swimming pool in Kailua

Oahu / Kailua

4 7 5 nights min

  • 4 bedrooms
  • Sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This plantation style home is located 3 blocks from Kailua beach and 2 blocks to Kailua town. It has been renovated to have open floor plan to provide comfortable living space without compromising it's Hawaiian charm. Bedrooms with A/C, ceiling fans, fully equipped kit …see more

Certificate of Excellence

from $400 / night

$2500 / week

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Responds fast!
avg. 3 hours 39 minutes

from $400 / night

37

Vacation villa in Kailua

Oahu / Kailua

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Child friendly
Grand Kailua Beachside Estate is the crown jewel of Kailua beachfront property. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of oversized stones met with manicured grass provides the driveway that mea …see more

from $7000 / night

$49000 - $87501 / week

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from $7000 / night

20

Vacation villa in Kailua

Oahu / Kailua

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
This is a beautiful 6 bedroom, 5 bath beachfront home reminiscent of Old Hawaii. Coconut trees abound throughout the spacious lush green lawns which leads directily on to the white sandy beach of Kailua. The home sits on one of the most breath taking beaches in the worl …see more

from $1050 / night

$7350 - $12250 / week

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from $1050 / night

(6) Excellent 

16

Vacation apartment in Kailua

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Child friendly
  • Air conditioning
Very spacious and breezy apartment, a wonderful place to relax and enjoy the beautiful island. It is on a second story above the main house, has a comfortable, welcoming and sunny Lanai. The beach is just a minute walk to the beach. Fully equipped kitchenette with mi …see more

from $191 / night

$1300 / week

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avg. 2 hours 40 minutes

from $191 / night

12

Kailua Vacation studio rental

Oahu / Kailua

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Nearest beach 0.3 mi
  • Suitable for children age 5+
  • Air conditioning
Cozy "Ginger suite" studio in private home. Private entrance and bathroom. Three blocks from the beach. 1 block from the 57 bus stop. 3 blocks to shopping, restaurants and market. Air-conditioning and ceiling fan. Small covered patio. Little kitchenette for light me …see more

from $90 / night

$565 / week

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from $90 / night

34

Vacation home rental

Oahu / Kailua

7 16 10 nights min

  • 7 bedrooms
  • Sleeps 16
  • 10 nights min
  • Child friendly
July & August Special!!! - 15% OFF all Summer Rates when you book this month and next month! No code needed! Discounted rates already applied! Three homes in one! Brand new construction combined with newly remodeled old island charm. Situated at the quiet end of Lanikai …see more

from $2500 / night

$17500 / week

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from $2500 / night

(1) Very Good 

6

Home rental in Kailua with swimming pool

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. …see more

from $975 / night

$6825 / week

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from $975 / night

17

Home rental in Kailua

Oahu / Kailua

6 12 14 nights min

  • 6 bedrooms
  • Sleeps 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
There’s a reason why Kailua is consistently voted as one of the top beach destinations in the world: it’s spectacular. This beautiful home is located on a beachfront paradise within walking distance to Buzz’s Steak House and the quaint Hawaiian town of Kailua. The prop …see more

from $1050 / night

$12250 / week

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from $1050 / night

(1) Excellent 

12

Vacation home rental

Oahu / Kailua

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coole …see more

from $145 / night

$950 / week

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Responds fast!
avg. 3 hours 14 minutes

from $145 / night

24

Vacation villa in Kailua

Oahu / Kailua

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Aloha and welcome to this newly-renovated and very comfortable 5/2 home featuring complete Air Conditioning, perimeter fencing w/ security gates, bamboo flooring, and a 4-person hot tub. This home sleeps 12 people in the 5 bedrooms featuring two king beds, two queen bed …see more

from $606 / night

$4242 - $4767 / week

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Responds fast!
avg. 3 hours 58 minutes

from $606 / night

14

Vacation home rental

Oahu / Kailua

9 20 5 nights min

  • 9 bedrooms
  • Sleeps 20
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Brand New Pool is the gathering spot of this majestic island home. Serene and lush landscape, newly built home offers the perfect floor plan to accommodate large groups boasting 3,300 sf of living space with vaulted ceilings and spacious living areas that can …see more

from $1180 / night

$8260 / week

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from $1180 / night

16

Vacation home in Kailua

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Charming, Private, Hawaiian Style Home Kai Mele cottage has been featured in Coastal Living as guest house of the month, due to this private Kailua beachfront estate being nestled in among 40+ coconut trees and lush tropical gardens. With over 700 feet of an ancient lav …see more

from $550 / night

$3850 / week

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from $550 / night

38

Kailua Vacation home rental

Oahu / Kailua

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Discover a hidden Hawaii at Lanikai Hillside Estate. Part of an exclusive gated community, the villa, whose name means ‘heavenly sea,’ offers access to a semi-private beach and views of uninhabited islands off the coast. Spacious modern Bali-inspired interiors and five …see more

from $6180 / night

$43260 - $50470 / week

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from $6180 / night

20

Vacation home in Kailua

Oahu / Kailua

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Ke'aloha, which means “love,” is certainly appropriate for this cottage. From the moment you step inside this s …see more

from $585 / night

$4095 / week

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from $585 / night

38

Vacation villa with shared pool in Kailua

Oahu / Kailua

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Built by famous stylist Paul Mitchell in the late 1980s. This gated, beachfront, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that's not only beautiful, but also strikes the perfe …see more

from $6250 / night

$43750 / week

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from $6250 / night