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Vacation Rentals in Kailua: Beach Rentals, Houses and Condos

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about Kailua

Kailua, Hawaii Vacation Rentals and Tourism

If you’re planning the ultimate beach vacation, then make sure you consider staying in one of the amazing Kailua beach rentals listed here. After all, the shores of Kailua, Oahu have time and time again, been rated the best in the world! And unlike popular tourist destinations like Honolulu, you can find a Kailua private beach rental that will allow you to genuinely get away from it all.

Luckily, it’s really easy to find a Kailua beach house for rent! If you want to discover what’s so special about this secluded community, then the best way to do so is to book one of the charming Kailua vacation rentals found here. A trip to Hawaii promises to be delightful and memorable, but do you really want to spend all of your time bumping in to fellow tourists?

A Kailua private beach rental really is a dream! Honolulu is just a short drive away, and yet many vacationers do not venture to Kailua. Why not enjoy the same views of nature, exotic plants and animals, and beach activities of Honolulu, without the crowds? A Kailua beach house for rent is close to, and yet far enough away from Honolulu to make it a very unique accommodation.

Kailua arguably features the best wind surfing on the planet, and of course all the tropical fun in the sun and beauty that Hawaii is known for – but without the stress that comes with busy vacation spots like Honolulu. But remember that for those who do stay in Kailua vacation rentals, Honolulu’s attractions are still only 15 minutes away!

Booking one of the Kailua beach rentals found here should be the very first step you take as you gear up for your Hawaii getaway.

Kailua Vacation Rental Deals

Don't be intimidated by hotel prices—if you want to take a vacation to Kailua, check out Kailua discount vacation rentals for last minute deals and all around good prices on homey, luxurious Kailua rental condos, town homes, and beach houses. Choose from a wide variety of roomy but still budget-friendly options for a way to enjoy your Kailua home away from home. Affordable Kailua vacation rentals accommodate groups of any size so none of you family will miss out on Kailua's beauty and adventure. Spacious but cheap Kailua vacation rentals will help you stress less by saving more. 

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Family Friends Reconnect Relax Recharge -Pool Spa Near Beach
Kailua House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $529 /nt
 
 
 
 
 

66 reviews write a review

Comfortable Kailua Home
Kailua House Rental Picture
  • bedrooms 2
  • community Coconut grove Kailua
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $250 - $285 /nt
    $1,750 - $1,995 /wk
    $5,100 - $5,500 /mth
 
 
 
 
 

18 reviews write a review

Ohana House - Walk to Kailua Beach
Kailua Cottage Rental Picture
  • bedrooms 1
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $140 /nt
 
 
 
 
 

12 reviews write a review

Tropical beach Hale
Kailua Studio Rental Picture
  • bedrooms 1
  • community Kalama
  • rental type Studio
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $160 - $180 /nt
    $1,120 - $1,260 /wk
    $4,700 - $5,200 /mth
 
 
 
 
 

17 reviews write a review

"Hale Nalu Palekaiko" Surf Paradise Hale
Kailua House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $100 - $585 /nt
    $700 - $3,900 /wk
    $11,500 /mth
 
 
 
 
 

37 reviews write a review

Luna's House, Saltwater pool, 1 block to beach
Kailua House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $345 - $400 /nt
    $2,415 - $2,950 /wk
    $7,500 - $8,500 /mth
 
 
 
 
 

3 reviews write a review

Hale Kai Vacation Rental
Kailua House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $2,065 /wk
 
 
 
 
 

13 reviews write a review

Hawaiian-Adventure-Get-A-Way
Kailua House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $195 - $199 /nt
    $1,265 - $1,293 /wk
    $3,600 - $3,800 /mth
 
 
 
 
 

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KaiStudioAloha2- studio vacation rental
Kailua Studio Rental Picture
  • bedrooms 0
  • community Enchanted Lake
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $63 - $69 /nt
    $427 - $477 /wk
    $1,430 - $1,580 /mth
 
 
 
 
 

21 reviews write a review

Cozy Studio Suite
Kailua Studio Rental Picture
  • bedrooms 0
  • community
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $74 - $79 /nt
    $515 - $550 /wk
    $2,150 - $2,300 /mth
 
 
 
 
 

9 reviews write a review

Rest, Relax and Enjoy the Beautiful Waters of Lanikai
Kailua Studio Rental Picture
  • bedrooms 1
  • community
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $150 /nt
 
 
 
 
 

2 reviews write a review

Newly Renovated Quaint Kailua Cottage
Kailua House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $250 /nt
    $1,500 /wk
 
 
 
 
 

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88
Kailua House Rental Picture
  • bedrooms 8
  • community
  • rental type House
  • sleeps 16
  • baths 4
  • rates (USD) $995 - $1,500 /nt
    $5,600 - $10,500 /wk
    $16,000 - $19,000 /mth
 
 
 
 
 

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Comfy Cozy, Nice, Mellow, ks3 - Special $496/wk., Best Value
Kailua Studio Rental Picture
  • bedrooms 0
  • community Kailua Enchantd Lake
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $63 - $73 /nt
    $427 - $477 /wk
    $1,440 - $1,540 /mth
 
 
 
 
 

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Peter's Place
Kailua Apartment Rental Picture
  • bedrooms 2
  • community
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,600 - $1,950 /wk
 
 
 
 
 

6 reviews write a review

Absolutely Oceanfront -60 ft Nat Salt Pool/Waterfalls-$220
Kailua House Rental Picture
  • bedrooms 1
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $220 /nt
    $1,540 /wk
    $5,500 /mth
 
 
 
 
 

6 reviews write a review

Comfy Beachside Hideaway in a Lush Tropical Garden!
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

13 reviews write a review

1 Beautiful Island Getaway ~ Kuu Home Uluwehi
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $495 - $700 /nt
    $3,465 /wk
 
 
 
 
 

5 reviews write a review

Happy House on Exquisite Kailua Beachside Property!
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD)
 
 
 
 
 

19 reviews write a review

Kailua- 300 Steps to Beach- Tropical & Spacious Beach
Kailua Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $269 - $289 /nt
    $1,813 /wk
    $7,000 /mth
 
 
 
 
 

43 reviews write a review

Beachfront Honu Heaven offers solar heated pool, hot tub & steps to Lanikai beach
Kailua Villa Rental Picture
  • bedrooms 4
  • rental type Villa
  • sleeps 10
  • baths 3
  • rates (USD) $1,750 - $3,500 /nt
    $12,250 - $24,500 /wk
    $49,000 - $98,000 /mth
 
 
 
 
 

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Stunning Kailua Oceanfront House with Beach Walk Right Outside
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $4,900 - $7,700 /wk
 
 
 
 
 

43 reviews write a review

Modern Beach House On Pristine Kailua Beach- In Town & Surrounded by Nature
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $399 - $600 /nt
    $2,099 - $4,199 /wk
    $8,400 /mth
 
 
 
 
 

5 reviews write a review

Stunning Beach Front Kailua Residence, Architectual Island Design.
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $8,400 - $11,200 /wk
    $48,000 /mth
 
 
 
 
 

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Ensconce yourself in unpretentious luxury.
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths
  • rates (USD) $12,600 - $30,625 /wk
    $88,500 - $131,250 /mth
 
 
 
 
 

3 reviews write a review

Lanikai Oceanfront, Pool, Luxury Amenities, Yard, Parking.
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $66,750 - $90,000 /mth
 
 
 
 
 

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Walk Across The Street To Kailua's White Sand Beach!
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $4,515 - $9,800 /wk
 
 
 
 
 

2 reviews write a review

Sandcastle - Peaceful Beach House
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $7,700 - $15,575 /wk
    $50,250 /mth
 
 
 
 
 

2 reviews write a review

Striking, Contemporary Executive Beachfront Estate
Kailua House Rental Picture
  • bedrooms 8
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $3,500 - $9,000 /nt
    $24,500 /wk
 
 
 
 
 

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Gorgeous sandy beachfront! Yard, Sunrise Views
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 13
  • baths 4
  • rates (USD) $6,300 - $12,075 /wk
    $38,400 - $51,750 /mth
 
 
 
 
 

1 reviews write a review

Swaying Palms Luxury Kailua Beachfront
Kailua House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 12
  • baths 6
  • rates (USD) $15,750 - $21,875 /wk
    $50,000 /mth
 
 
 
 
 

3 reviews write a review

Hale Nani- Steps to Beach, Spacious Yard, ~AC~, 4 Bedrooms, 3 Baths
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $450 - $795 /nt
    $3,150 - $4,165 /wk
 
 
 
 
 

14 reviews write a review

Villa Lanikai Alii- Luxury Beachfront w/Pool, Spacious Yard, More
Kailua Villa Rental Picture
  • bedrooms 5
  • rental type Villa
  • sleeps 10
  • baths 4
  • rates (USD) $4,200 - $6,250 /nt
    $126,000 /mth
 
 
 
 
 

1 reviews write a review

Kailani Beach House Stunning Beachfront!
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 6
  • rates (USD) $6,965 - $12,075 /wk
 
 
 
 
 

8 reviews write a review

Lanikai-Resort-Like Estate, Spa, Pool, Tropical yard, 2 Min. walk to Beach
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $495 - $595 /nt
 
 
 
 
 

14 reviews write a review

Location, location!! Short Walk To Beach
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $325 - $450 /nt
    $2,275 - $3,150 /wk
 
 
 
 
 

7 reviews write a review

Kailua Beachfront - Spacious Family Home in Kailua's Best Location
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD) $1,200 - $1,950 /nt
    $8,400 - $21,000 /wk
    $36,000 - $54,000 /mth
 
 
 
 
 

30 reviews write a review

Royal Kailua Estate - Upscale Private Beachfront Resort with Stunning Courtyard
Kailua Villa Rental Picture
  • bedrooms 7
  • rental type Villa
  • sleeps 14
  • baths 7
  • rates (USD) $6,000 - $12,000 /nt
    $42,000 - $84,000 /wk
    $168,000 - $336,000 /mth
 
 
 
 
 

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Aloha Tropical Hideaway
Kailua Studio Rental Picture
  • bedrooms 1
  • rental type Studio
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $149 /nt
 
 
 
 
 

34 reviews write a review

Experience Complete Tranquility In Paradise
Kailua House Rental Picture
  • bedrooms 8
  • rental type House
  • sleeps 18
  • baths 4
  • rates (USD) $5,600 - $6,300 /wk
    $20,000 /mth
 
 
 
 
 

7 reviews write a review

Happy Kailua Beachside Home 1/2 Block from Kalama Beach Park
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $300 - $400 /nt
    $2,100 /wk
 
 
 
 
 

47 reviews write a review

Luxury private home with the convenience of Kailua Beach just steps away.
Kailua House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $4,550 - $17,500 /wk
    $19,500 - $48,000 /mth
 
 
 
 
 

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Beautiful Private Hawaiian Style Home - 3 MIN walk to Beach, Pool, New Hot Tub
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $529 /nt
 
 
 
 
 

66 reviews write a review

Coconut Hideaway - Spacious & what a view! - Sept stay special $165/nt sleeps 4
Kailua House Rental Picture
  • bedrooms 1
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $185 /nt
 
 
 
 
 

21 reviews write a review

Quiet, Intimate One Bedroom Short Walk to Kailua Beach
Kailua Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $125 - $150 /nt
 
 
 
 
 

16 reviews write a review

Kailua Beach Cottage, Steps Away From The Best Beach In Hawaii!!
Kailua House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths 1
  • rates (USD) $265 - $325 /nt
    $1,855 - $2,030 /wk
 
 
 
 
 

27 reviews write a review

5 minute walk to Beach, A/C, WiFi, BEST VALUE!
Kailua Studio Rental Picture
  • bedrooms 0
  • rental type Studio
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $145 /nt
    $945 /wk
    $3,500 /mth
 
 
 
 
 

22 reviews write a review

Kailua Beach-Tropical Sands Luxury Suite-Walk to Kailua Beach
Kailua Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $170 /nt
    $1,085 /wk
    $4,200 /mth
 
 
 
 
 

21 reviews write a review

Oahu Lani a child-friendly, family-oriented beachfront villa
Kailua Villa Rental Picture
  • bedrooms 10
  • rental type Villa
  • sleeps 18
  • baths 3
  • rates (USD) $5,500 - $7,500 /nt
    $38,500 - $40,250 /wk
 
 
 
 
 

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Elegant Studio-Cottage, Tropical, Pool, Spa, Kayaks, Beach 2 min/walk
Kailua Studio Rental Picture
  • bedrooms 0
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $195 /nt
    $1,365 /wk
 
 
 
 
 

8 reviews write a review

Award Winner Hawaii's Hidden Hideaway - Bed and Breakfast
Kailua House Rental Picture
  • bedrooms 0
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $165 /nt
 
 
 
 
 

4 reviews write a review

Stunning Kailua Beachside 3 BR Home with Lagoon Pool
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $575 - $675 /nt
    $4,025 /wk
    $12,000 /mth
 
 
 
 
 

17 reviews write a review

Close To Kailua Beach, Kailua Town And Easy Access To Several Island Highways.
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $250 /nt
 
 
 
 
 

3 reviews write a review

Enchanted Lake Villa
Kailua Studio Rental Picture
  • bedrooms 0
  • rental type Studio
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $100 - $130 /nt
    $665 - $850 /wk
 
 
 
 
 

51 reviews write a review

6br/4.25ba Oceanfront Luxury Villa/Kailua Beach/Pool/Spa 25 steps to the Beach
Kailua House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 17
  • baths
  • rates (USD) $995 /nt
    $6,965 /wk
    $25,000 /mth
 
 
 
 
 

15 reviews write a review

Kailua Beachside 'Host With the Most' - 5-Bedroom/6-Bath Newer Home (Sleeps 10)
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 6
  • rates (USD) $495 - $595 /nt
    $3,465 - $4,165 /wk
 
 
 
 
 

16 reviews write a review

Absolutely Oceanfront-60 ft lap pool w/ waterfalls- Licensed
Kailua House Rental Picture
  • bedrooms 0
  • rental type House
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $220 /nt
    $1,540 /wk
    $6,000 /mth
 
 
 
 
 

26 reviews write a review

New Modern Island Style Beachside Apartment
Kailua Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $235 - $300 /nt
    $1,603 - $2,100 /wk
 
 
 
 
 

8 reviews write a review

Beautiful Home ~ Sleeps 2-4 people ~ Ask about discounted rates for 2 people!
Kailua House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $275 /nt
 
 
 
 
 

4 reviews write a review

5 Minute Walk to Kailua Beach - Kailua Hale `Ohana, Air Conditioning.
Kailua Studio Rental Picture
  • bedrooms 1
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $115 /nt
    $800 /wk
    $2,600 /mth
 
 
 
 
 

57 reviews write a review

Lofty Studio with Stunning Panoramic Mountain Views Near Beach
Kailua Studio Rental Picture
  • bedrooms 1
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $150 /nt
    $900 /wk
 
 
 
 
 

27 reviews write a review

Beachfront Rental
Kailua Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $190 - $200 /nt
 
 
 
 
 

28 reviews write a review

Beautiful Beach House- Walk to Kailua Beach!!
Kailua Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $275 - $325 /nt
 
 
 
 
 

12 reviews write a review

Ocean View House With Large Patio Courtyard Area.
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $450 - $800 /nt
    $3,850 /wk
 
 
 
 
 

6 reviews write a review

Beautiful Ocean Front Home on Kailua Bay!
Kailua Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • sleeps 12
  • baths 4
  • rates (USD)
 
 
 
 
 

15 reviews write a review

Bali Hai Kailua -Incredible Plantation Home- 1.5 Blocks 2beach
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $6,500 - $8,000 /mth
 
 
 
 
 

4 reviews write a review

'E komo mai. Nou ka hale.' 'Come inside, the house is yours.'
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $2,450 /wk
 
 
 
 
 

23 reviews write a review

The Windsurfer Cottage Hawaii - Kaimakani - 'The Sea Wind'
Kailua Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $150 - $200 /nt
 
 
 
 
 

4 reviews write a review

New 2B/2B, Steps To Beach Luxury Kitchen,bathroom, Living Room And Pool! Sleep4
Kailua Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 2
  • rates (USD) $350 - $400 /nt
    $2,350 - $2,800 /wk
    $7,500 - $9,900 /mth
 
 
 
 
 

4 reviews write a review

Play, Rest, Relax And Enjoy The Island From The Kailua Garden Inn
Kailua Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $110 /nt
 
 
 
 
 

6 reviews write a review

Tropical Beach Hale, 1 bedroom, A/C, across street from beach access
Kailua Studio Rental Picture
  • bedrooms 1
  • rental type Studio
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $170 /nt
    $1,120 - $1,190 /wk
    $4,500 - $4,800 /mth
 
 
 
 
 

17 reviews write a review

Beautiful Vacation Rental Home At The Beginning Of Oahu's Famous Lanikai Beach!
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $8,750 - $19,250 /wk
 
 
 
 
 

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'Savannah's Cabana, Wireless Internet, Block to Kailua Beach!
Kailua Studio Rental Picture
  • bedrooms 1
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $150 /nt
    $1,050 /wk
 
 
 
 
 

48 reviews write a review

'Hale Nalu Palekaiko' Pool, Walk to Kailua Beach
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $500 /nt
 
 
 
 
 

37 reviews write a review

Beautiful Kailua Home - Walk to Beach
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $255 - $399 /nt
    $1,785 - $2,065 /wk
    $4,389 - $6,385 /mth
 
 
 
 
 

11 reviews write a review

Beautiful Home For Relaxation....
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $6,300 - $9,800 /wk
 
 
 
 
 

1 reviews write a review

Just Steps Away From Kailua Beach! Or Just Stay At Your Private Pool!
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $800 - $1,275 /nt
    $8,925 /wk
 
 
 
 
 

2 reviews write a review

Beachfront 3bd/2ba House - Kailua Beach
Kailua Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $450 - $650 /nt
 
 
 
 
 

3 reviews write a review

Beachside Kailua Island Living at its Best
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

23 reviews write a review

Kailua, Oahu Beachfront
Kailua House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $10,020 /mth
 
 
 
 
 

7 reviews write a review

Great Value + Great Location= Great Vacation!
Kailua Studio Rental Picture
  • bedrooms 0
  • rental type Studio
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD)
 
 
 
 
 

30 reviews write a review

$575. Last min deal in Air Conditioning & Ocean Views Pool, gym, indoor playroom
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths 5
  • rates (USD) $675 - $950 /nt
    $4,725 - $6,650 /wk
 
 
 
 
 

20 reviews write a review

Kailua Beachfront - All New Apartment!
Kailua Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 3
  • baths 1
  • rates (USD) $1,743 - $2,303 /wk
    $5,900 - $6,900 /mth
 
 
 
 
 

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SEPTEMBER-NOVEMBER DISCOUNTS! Your Island Beach Side Home Away From Home
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $575 - $875 /nt
 
 
 
 
 

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Charming Kailua Apartment, a/C, Wifi Available
Kailua Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $225 - $300 /nt
    $2,100 /wk
 
 
 
 
 

8 reviews write a review

Beautiful Ocean Views in 3 Bedroom Home W/Hot Tub & Game Room
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $349 - $549 /nt
    $2,443 /wk
 
 
 
 
 

7 reviews write a review

7 bd 4.5 ba Beachside Retreat - Steps from Kailua Beach.
Kailua House Rental Picture
  • bedrooms 7
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $950 - $1,750 /nt
    $6,650 /wk
    $25,000 - $35,000 /mth
 
 
 
 
 

1 reviews write a review

Gorgeous 'Green' Home on a Quiet Beach side Lane
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD)
 
 
 
 
 

20 reviews write a review

Hawaii Quaint! Local Comfort! New!!
Kailua Studio Rental Picture
  • bedrooms 1
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $90 /nt
    $630 /wk
    $2,550 /mth
 
 
 
 
 

21 reviews write a review

Kailua Guesthouse Palm Cabana - Walk to Kailua Beach
Kailua Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 3
  • baths 1
  • rates (USD) $159 - $169 /nt
    $1,050 - $1,120 /wk
 
 
 
 
 

1 reviews write a review

Beachside getaway!!!
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 2
  • rates (USD) $700 - $750 /nt
 
 
 
 
 

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Hotel Like Surroundings... Steps To The Beach
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $975 - $2,000 /nt
 
 
 
 
 

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Pikake Hale - Beachside Comfort - Check Specials
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 13
  • baths 4
  • rates (USD) $600 - $975 /nt
    $6,825 /wk
 
 
 
 
 

33 reviews write a review

Pool, Spa, Waterfront, View Home
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $899 - $1,599 /nt
    $6,293 - $9,093 /wk
 
 
 
 
 

6 reviews write a review

Charming Cottage On A Private Lane, Beachside Kailua
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $4,900 /wk
    $8,000 /mth
 
 
 
 
 

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Luxurious, Family Friendly, & Fully Stocked Camper Van
Kailua Recreational_vehicle Rental Picture
  • bedrooms 1
  • rental type Recreational vehicle
  • sleeps 4
  • baths 1
  • rates (USD) $99 /nt
    $799 /wk
    $2,500 /mth
 
 
 
 
 

7 reviews write a review

FALL SPECIALS.....AVAILABLE THROUGH THE HOLIDAYS
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $7,000 - $14,000 /wk
    $22,000 - $40,000 /mth
 
 
 
 
 

20 reviews write a review

Location, Location! Beachside Hawaiian Home with solar heated pool
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $4,900 - $5,250 /wk
    $15,000 - $16,500 /mth
 
 
 
 
 

10 reviews write a review

Beautifully designed Kailua Home - Close to the beach and town!
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $7,500 /mth
 
 
 
 
 

13 reviews write a review

Spectacular Beachside Home with Salt Water Pool and Full A/C
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $12,900 /mth
 
 
 
 
 

4 reviews write a review

Kailua Beach House, comfortable beach home with private pool
Kailua House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $9,275 /wk
 
 
 
 
 

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Located on Famous Kailua Beach
Kailua House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $1,750 /nt
 
 
 
 
 

1 reviews write a review

Honu Kai, Kailua Beachfront, Private Jacuzzi, Shared Pool
Kailua House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $30,000 /mth
 
 
 
 
 

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The Ginger Hale Beachfront Retreat
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $5,460 /wk
 
 
 
 
 

5 reviews write a review

Spacious & Affordable 2 Bedroom in Kailua
Kailua House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

1 reviews write a review

AC, Mountain Views, Wi-fi, 5 Minutes to Kailua Beach
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $295 - $425 /nt
 
 
 
 
 

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Kailua Beachside Perfect Vacation: One House from Beach
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $3,850 /wk
 
 
 
 
 

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Spacious Kailua Beachfront Home
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

4 reviews write a review

Stop! Must See Kailua Beachside Villa
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 4
  • rates (USD)
 
 
 
 
 

4 reviews write a review

Minutes Walk to World Famous Kailua Beach
Kailua House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

3 reviews write a review

Honey Stop. You Gotta See This House!
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

1 reviews write a review

Windward Hawaii Beachfront Paradise - Kailua Beach
Kailua House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD)
 
 
 
 
 

18 reviews write a review

'Star of Hawaii' - Family Living, Pool, Walk to Beach
Kailua House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD)
 
 
 
 
 

34 reviews write a review