50 Best Kailua Vacation rentals on Holiday Lettings - Beach rentals

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1,074 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

(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 16 minutes

from $130 / night

(11) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $190 / night

$1,300 / week

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from $190 / night

(6) Excellent 

15

Cottage accommodation in Kailua

Oahu / Kailua

4 30 nights min

  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. …see more

from $80 / night

$560 / week

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from $80 / night

6

Studio rental in Kailua

Oahu / Kailua

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
WElCOME TO PARADISE! Kailua is one of the most sought after vacation destinations in Oahu. Kailua is located on the Windward side of Oahu just 12 miles northeast of Honolulu - over Nu'uanu Pali, tallest mountain peak in the Ko'olau mountain range. Kailua offers pictures …see more

from $125 / night

$875 / week

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from $125 / night

(2) Excellent 

13

Vacation cottage in Kailua

Oahu / Kailua

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
This quiet 400-square foot cottage sits by the blue-tiled pool and offers the perfect resting spot after a full day of activities or a sleepy day on the beach. It offers a full bath and kitchenette with full-sized refrigerator, microwave, and toaster oven. The studio i …see more

from $179 / night

$1,200 / week

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avg. 3 hours 11 minutes

from $179 / night

(2) 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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avg. 2 hours 40 minutes

from $145 / 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

15

Kailua Vacation cottage rental

Oahu / Kailua

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • 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

$1,365 / week

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avg. 3 hours 44 minutes

from $195 / night

(2) Excellent 

28

Vacation home with swimming pool in Kailua

Oahu / Kailua

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful four bedroom, two bath, Hawaiian style home is just a short 1 1/2 block walk to the pristine white sands of Kailua Beach and 5 min's from Kailua Town. Newly remodeled with new paint, carpets, drapes, ceiling fans, and furnishings this spacious open floor …see more

from $599 / night

$4,193 / week

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avg. 37 minutes

from $599 / 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

21

Kailua Vacation home rental

Oahu / Kailua

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

$4,200 / week

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Responds fast!
avg. 3 hours 44 minutes

from $600 / night

(1) Excellent 

10

Cottage rental in Kailua

Oahu / Kailua

2 1 night min

  • Sleeps 2
  • 1 night min
  • Car not necessary
  • Ask about pets
  • Private garden
Enjoy the peace and quiet in this quaint, private cottage. The property offers a queen-size bed, kitchenette, lovely tropical yard and covered lanai with outdoor seating to relax in after a day at the beach. Wash the sand off in the private outside shower. Located only …see more

from $105 / night

$660 / week

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avg. 3 hours 47 minutes

from $105 / 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

$1,148 / week

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from $164 / night

(1) Very Good 

8

Vacation cottage in Kailua

Oahu / Kailua

3 3 nights min

  • Sleeps 3
  • 3 nights min
  • Child friendly
Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. Complimentary assigned par …see more

from $139 / night

$910 / week

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from $139 / night

(2) Excellent 

15

Vacation studio rental

Oahu / Kailua

Studio 2 4 nights min

  • Studio
  • Sleeps 2
  • 4 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Air conditioning
Studio with private bath and entrance, air conditioning, internet access, kitchenette, use of pool. Very well equipped kitchenette for light cooking: microwave, refrigerator, coffee machine, electric tea pot, rice cooker, Crock-Pot/Slow Cooker, Convection Steamer, toast …see more

from $85 / night

$560 / week

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avg. 3 hours 26 minutes

from $85 / 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 $495 / night

$3,465 / week

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avg. 3 hours 44 minutes

from $495 / night

9

Kailua Vacation home rental

Oahu / Kailua

3 7 4 nights min

  • 3 bedrooms
  • Sleeps 7
  • 4 nights min
  • Child friendly
The Jungle Waterfall Retreat is tucked into the rainforest of Kailua. Get the quiet relaxation of living surrounded by mountains while only being a 5 minute drive to the beach. Its just 20 minutes to the airport and Waikiki, but you will feel like you are on another isl …see more

from $260 / night

$1,820 / week

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from $260 / 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 $1,050 / night

$7,350 - $12,250 / week

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avg. 22 minutes

from $1,050 / night

23

Vacation home in Kailua

Oahu / Kailua

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • 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 $178 / night

$1,246 / week

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Responds fast!
avg. 2 hours 49 minutes

from $178 / night

(20) Excellent 

Certificate of Excellence

36

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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Responds fast!
avg. 2 hours 27 minutes

from $126 / night

(1) Excellent 

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 $95 / night

$650 / week

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avg. 3 hours 26 minutes

from $95 / night

(14) 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

$1,600 / week

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from $250 / 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

$1,085 / week

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from $165 / night

(3) Very Good 

7

Kailua Vacation b&b rental

Oahu / Kailua

2 1 night min

  • Sleeps 2
  • 1 night min
  • Nearest beach 0.16 mi
  • Ask about children
  • Air conditioning
Hawaii Sheffield House is located only 10 houses to Kailua Beach. The closest beach access is Kaapuni Loop. The address is 131 Kuulei road. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Ginger Studio is a ground floor unit. The …see more

from $144 / night

$1,008 / week

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from $144 / night

14

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 la …see more

from $550 / night

$3,850 / week

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from $550 / night

(36) Very Good 

15

Vacation home in Kailua

Oahu / Kailua

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Car not necessary
Kailua Hale `Ohana is a spacious studio that can accommodate up to 2 guests. The Hale `Ohana is just a five minute walk away from the world famous Kailua Beach. With lots of nearby local activities such as kayaking, kite boarding, wind surfing, paddle boarding, s …see more

from $125 / night

$875 / week

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avg. 3 hours 20 minutes

from $125 / night

(2) Excellent 

29

Vacation home in Kailua

Oahu / Kailua

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This 850 sq ft duplex consists of a master bedroom with a queen bed and a huge walk-in closet. Access to the full bathroom is through the master bedroom. The other bedroom also has a queen bed. All the areas come with ceiling fans and the home is indirectly ventilated w …see more

from $165 / night

$950 - $1,663 / week

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avg. 1 hour 52 minutes

from $165 / night

24

Vacation cottage with swimming pool in Kailua

Oahu / Kailua

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0.8 mi
  • Swimming pool
  • Child friendly
Come bask in the gentle trades of the windward side at the Kailua Palms Estate Guest House, a fabulous two bedroom, two bath vacation guest house located in sleepy Kailua Town near Kailua Beach. The two bedrooms are spacious and comfortable. You will like the relaxed a …see more

from $425 / night

$2,975 / week

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Responds fast!
avg. 1 hour 46 minutes

from $425 / night

(1) Good 

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

$1,183 / week

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avg. 1 hour 55 minutes

from $169 / night

(2) Excellent 

23

Vacation home in Kailua

Oahu / Kailua

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
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 $150 / night

$950 - $1,540 / week

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avg. 1 hour 52 minutes

from $150 / night

(3) Excellent 

21

Cottage rental in Kailua

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Air conditioning
Kailua is first and foremost a beach community. Kailua Beach Park has been named “America's Best Beach”, 'Most Beautiful; Sunrise in the World'; and the world's pre-eminent windsurfing and kitesurfing destinations. Hale Luana, meaning a house to be at leisure and …see more

from $200 / night

$1,400 / week

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avg. 42 minutes

from $200 / 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

$6,825 / week

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avg. 3 hours 44 minutes

from $975 / night

37

Vacation villa with shared pool in Kailua

Oahu / Kailua

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Royal Kailua Estate is the crown jewel of Kailua's beachfront properties. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of over sized stones met with manicured grass provides the driveway that meanders …see more

from $9,500 / night

$66,500 - $140,000 / week

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avg. 22 minutes

from $9,500 / night

26

Vacation villa rental

Oahu / Kailua

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Those who are familiar with Hawaiian history know that pineapples played a crucial role in the island’s development. The sweet fruit were grown out of large plantation estates, which serve as the inspiration for Plantation at Paradise Point whose lavish architecture is …see more

from $4,500 / night

$31,500 / week

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avg. 15 minutes

from $4,500 / night

14

Home rental in Kailua with swimming pool

Oahu / Kailua

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
Your White Sand Beach Awaits... Hale Kimo is located just a beach path away from one of the most beautiful beaches in all of Oahu, Kailua beach! The beach has very limited public access, making for an exclusive beach experience on Oahu! This two story custom home is y …see more

from $750 / night

$5,250 / week

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from $750 / 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 $695 / night

$4,865 / week

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from $695 / 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 …see more

from $475 / night

$3,325 / week

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from $475 / night

(5) 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 $425 / night

$2,500 / week

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Responds fast!
avg. 2 hours 29 minutes

from $425 / night

25

Vacation home in Kailua

Oahu / Kailua

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Peaceful Energy of Maluhia  Let the relaxing atmosphere of Maluhia whisk you into vacation-mode! The tropical pool will make you feel like you are swimming in the middle of your own private lagoon while a heated Jacuzzi will relax your body at the end of the day. The c …see more

from $1,670 / night

$11,690 / week

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from $1,670 / night