50 Best Kailua Vacation rentals on Holiday Lettings - Beach rentals

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1,051 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. 2 hours 58 minutes

from $130 / 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 58 minutes

from $195 / 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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avg. 3 hours 51 minutes

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

(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

(4) Excellent 

14

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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Responds fast!
avg. 3 hours 17 minutes

from $179 / night

(22) 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 20 minutes

from $126 / 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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avg. 3 hours 58 minutes

from $600 / 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. 3 hours 6 minutes

from $145 / night

(8) Excellent 

32

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

24

Vacation home in Kailua

Oahu / Kailua

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
*Please note the homeowner lives on site, in a completely separate unit, and may be present during your stay* Your next Hawaiian getaway eagerly awaits at this 3-bedroom, 1-bath vacation rental house, just a 5 minute-drive from Kailua Beach. This home sleeps 5 guests a …see more

from $179 / night

$1,253 - $1,603 / week

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avg. 52 minutes

from $179 / 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 58 minutes

from $975 / night

(3) Excellent 

21

Vacation studio rental

Oahu / Kailua

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This air-conditioned Studio is a private retreat away from home. Very well equipped kitchenette for light cooking: microwave, refrigerator, coffee machine, electric tea pot, rice cooker, Crock-Pot/Slow Cooker, Convection Steamer, toaster, vegetable steamer, electric f …see more

from $84 / night

$588 - $612 / week

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from $84 / night

40

Vacation home in Kailua

Oahu / Kailua

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Kailani Villa  Nestled on a lush mountainside in Lanikai, just one block from Lanikai Beach, you will find Kailani Villa: a two-story modern and luxurious masterpiece.    Kailani Villa embodies modern elegance, punctuated by Hawaiian touches throughout.  Set behind gat …see more

from $900 / night

$6,300 / week

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from $900 / 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

(1) Excellent 

15

Kailua Vacation cottage rental

Oahu / Kailua

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Private and tropical cottage within easy walking distance to Kailua Beach, Beach Park and Kailua Town. Private entrance & bath, kitchenette. My place is close to public transport and the city center. You’ll love my place because of the location, the people, and the amb …see more

from $108 / night

$757 - $787 / week

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from $108 / 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. 2 hours 28 minutes

from $150 / night

39

Vacation villa with shared pool in Kailua

Oahu / Kailua

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • 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 $7,500 / night

$52,500 / week

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from $7,500 / 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

(3) Very Good 

7

Kailua Vacation b&b rental

Oahu / Kailua

2 Min stay varies

  • Sleeps 2
  • Min stay varies
  • 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 $134 / night

$973 - $1,078 / week

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from $134 / 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

(1) Very Good 

16

Vacation apartment in Kailua

Oahu / Kailua

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
This charming 2 bedroom, 1 bath vacation rental, located in a quaint part of Kailua town, is just a quick 15 minute walk or a 2 minute drive to the world famous Kailua beach. Kailua Apartment is an upstairs unit, with over 1100 square feet of living space. This rental …see more

from $195 / night

$1,365 / week

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from $195 / night

(37) 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 44 minutes

from $125 / 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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avg. 3 hours 6 minutes

from $178 / night

20

Vacation home with swimming pool in Kailua

Oahu / Kailua

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

$6,300 / week

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Responds fast!
avg. 3 hours 58 minutes

from $900 / 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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from $200 / 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

(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

$2,450 / week

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avg. 3 hours 58 minutes

from $350 / 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. 2 minutes

from $4,500 / night

(4) 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 58 minutes

from $495 / night

19

Vacation home in Kailua

Oahu / Kailua

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Beautiful beachfront home set in a security gated neighborhood. Decorated with island style rattan furnishings, ceiling fans throughout, cool white tile and wooden floorings. Central A/C, gourmet kitchen with granite flooring and countertops. Enjoy the ocean view fro …see more

from $950 / night

$6,650 / week

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from $950 / night

6

Studio rental in Kailua

Oahu / Kailua

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Private entry and bathroom, so no breakfast . Small meal prep are with small Refrig, coffee maker, hot plate, microwave, pots, dishes , utensils. Linens. Towels. Very small outside area, table & 2 chairs. Residential family home. Quiet, mellow owner prefer like minded …see more

from $70 / night

$505 / week

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from $70 / 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 $585 / night

$4,095 / week

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from $585 / 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 $172 / night

$1,085 / week

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from $172 / 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. 2 hours 28 minutes

from $165 / 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

45

Kailua Vacation home rental

Oahu / Kailua

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
The Envy of All Paradises In the middle of the great Pacific, on the world's most isolated chain of island, lies a small coastal community that is blessed with heaven-like beauty. LANIKAI, the “heavenly sea”. The envy of all paradises.   It's crystal clear waters, white …see more

from $7,000 / night

$49,000 / week

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from $7,000 / night

44

Vacation home in Kailua

Oahu / Kailua

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
The Essence of Kailua Beach Living Castle Point Estate is an estate built to embody the essence of luxury Kailua Beach living. Bringing in the elements of the ocean, bold colors bounce off soft hues and simplicity offers a space where natural beauty can be enjoyed. Buil …see more

from $9,500 / night

$66,500 / week

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from $9,500 / 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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from $105 / night