Kailua, Hawaii

Vacation Rentals in Kailua, Hawaii

Discover 257 vacation rental properties in Kailua. From 1 to 8 bedrooms. Average $609/night. 100% have pools.

257 verified listings Book securely on VRBO Prices updated March 2026

257 properties available

Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood- Legal

Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood- Legal

1 bath
PoolA/CWiFiBalcony
$399/night
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Ocean View Guest Cottage - 90/TVU-0287

Ocean View Guest Cottage - 90/TVU-0287

2 beds 1 bath
PoolA/CWiFiBalcony
$450/night
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Beautiful Beachside Bungalow

Beautiful Beachside Bungalow

1 bed 1 bath
PoolA/CWiFiBalcony
$448/night
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Direct Ocean Front, fantastic view, Kona Bali Kai

Direct Ocean Front, fantastic view, Kona Bali Kai

2 beds 2 baths
PoolA/CWiFiBalcony
$246/night
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Oceanfront Condo with Breath Taking Views

Oceanfront Condo with Breath Taking Views

2 beds 1 bath
PoolA/CWiFiBalcony
$295/night
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🌴Lovely garden unit ocean view from the lanai. Well equipped with AC and WiFi🌴

🌴Lovely garden unit ocean view from the lanai. Well equipped with AC and WiFi🌴

1 bed 1 bath
PoolA/CWiFiBalcony
$122/night
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Ocean View Condo with Large Lanai

Ocean View Condo with Large Lanai

1 bed 1 bath
PoolA/CWiFiBalcony
$149/night
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🏖️Ocean View | Close to Pool & BBQ Area | WIFI | vrKCV🏖️

🏖️Ocean View | Close to Pool & BBQ Area | WIFI | vrKCV🏖️

1 bed 1 bath
PoolA/CWiFiBalcony
$131/night
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PRIVATE BEACHFRONT RENTAL

PRIVATE BEACHFRONT RENTAL

1 bed
PoolA/CWiFiBalcony
$331/night
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Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.

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

2 beds 1 bath
PoolA/CWiFiBalcony
$352/night
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Come relax on the lake! Beautiful lake and mountain views. Kayaks included.

Come relax on the lake! Beautiful lake and mountain views. Kayaks included.

1 bed 1 bath
PoolA/CWiFiBalcony
$136/night
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Charming Kailua Studio Retreat: Your Tranquil Oasis Awaits

Charming Kailua Studio Retreat: Your Tranquil Oasis Awaits

1 bed 1 bath
PoolA/CWiFiBalcony
$156/night
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Entire Fantastic Kailua Cottage.. waiting for you!

Entire Fantastic Kailua Cottage.. waiting for you!

1 bath
PoolA/CWiFiBalcony
$121/night
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Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking

Walk to beach, 3 bd, 2 bth private house, heated pool, yard, AC, WIFI, parking

3 beds 2 baths
PoolA/CWiFiBalcony
$321/night
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Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views

Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views

2 beds 1 bath
PoolA/CWiFiBalcony
$390/night
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Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua

Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua

4 beds 2 baths
PoolA/CWiFiBalcony
$301/night
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Koohoo Place - Lanikai, Oahu. From here, you can see forever! NEW LISTING.

Koohoo Place - Lanikai, Oahu. From here, you can see forever! NEW LISTING.

2 beds 2 baths
PoolA/CWiFiBalcony
$250/night
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250 Steps to the Beach! MONTHLY DISCOUNT!

250 Steps to the Beach! MONTHLY DISCOUNT!

3 beds 2 baths
PoolA/CWiFiBalcony
$291/night
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Kahela - Paradise for Rent

Kahela - Paradise for Rent

4 beds 4 baths
PoolA/CWiFiBalcony
$542/night
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Kailua Private Place in Paradise. Sleeps 2 to 4! Full Kitchen, AC, lanai w/BBQ

Kailua Private Place in Paradise. Sleeps 2 to 4! Full Kitchen, AC, lanai w/BBQ

1 bed 1 bath
PoolA/CWiFiBalcony
$140/night
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Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!

Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$263/night
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Kailua Beach "The Pink House" 100 Yards from Ocean

Kailua Beach "The Pink House" 100 Yards from Ocean

4 beds 2 baths
PoolA/CWiFiBalcony
$596/night
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Kailua Beachfront - SHORT TERM LICENSED RENTAL #90/TVU-0141

Kailua Beachfront - SHORT TERM LICENSED RENTAL #90/TVU-0141

4 beds 4 baths
PoolA/CWiFiBalcony
$1,652/night
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Kailua Oceanfront - Contact host for Thanksgiving Week Special

Kailua Oceanfront - Contact host for Thanksgiving Week Special

3 beds 4 baths
PoolA/CWiFiBalcony
$812/night
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Licensed Lanikai Beach Tree House since 1985 - Just 100 Yards to Lanikai Beach!

Licensed Lanikai Beach Tree House since 1985 - Just 100 Yards to Lanikai Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$351/night
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Kailua Beach Home

Kailua Beach Home

1 bed 2 baths
PoolA/CWiFiBalcony
$175/night
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La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)

La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)

1 bed 1 bath
PoolA/CWiFiBalcony
$538/night
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Beachfront Cottage - Steps to beach, AC

Beachfront Cottage - Steps to beach, AC

4 beds 3 baths
PoolA/CWiFiBalcony
$1,302/night
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Kailua Cottage 3 bedroom 2 bath with an office room. Minimum 30 consecutive days

Kailua Cottage 3 bedroom 2 bath with an office room. Minimum 30 consecutive days

4 beds 2 baths
PoolA/CWiFiBalcony
$281/night
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Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC

Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC

3 beds 3 baths
PoolA/CWiFiBalcony
$718/night
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Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach

Hale Aloha: Luxe Waterfront Home, Island Vibe, Private Pool, Near Kailua Beach

4 beds 2 baths
PoolA/CWiFiBalcony
$954/night
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Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach

Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$457/night
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Kailua Beachfront SHORT-TERM LICENSED RENTAL - Amazing Views, Spacious Home

Kailua Beachfront SHORT-TERM LICENSED RENTAL - Amazing Views, Spacious Home

5 beds 5 baths
PoolA/CWiFiBalcony
$1,902/night
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KAILUA BEACH VILLA - 90/TVU-0286

KAILUA BEACH VILLA - 90/TVU-0286

8 beds 4 baths
PoolA/CWiFiBalcony
$1,763/night
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Huge House, Heated Pool, AC, Steps to Kailua Beach

Huge House, Heated Pool, AC, Steps to Kailua Beach

8 beds 5 baths
PoolA/CWiFiBalcony
$1,135/night
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Coconut Grove Kailua Vacation Home

Coconut Grove Kailua Vacation Home

3 beds 1 bath
PoolA/CWiFiBalcony
$234/night
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Kailua Beachfront w/Pool - Licensed Short-Term Rental - Steps to Kailua Beach

Kailua Beachfront w/Pool - Licensed Short-Term Rental - Steps to Kailua Beach

3 beds 3 baths
PoolA/CWiFiBalcony
$2,604/night
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Perfect Kailua Vacation at Ka Hale Lai-House of Serenity- pool and spa

Perfect Kailua Vacation at Ka Hale Lai-House of Serenity- pool and spa

4 beds 3 baths
PoolA/CWiFiBalcony
$1,416/night
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Newly REMODELED AND the best access to sandy Lanikai Beach! NUC # 90/TVU-0031

Newly REMODELED AND the best access to sandy Lanikai Beach! NUC # 90/TVU-0031

4 beds 4 baths
PoolA/CWiFiBalcony
$1,974/night
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La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)

La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)

1 bed
PoolA/CWiFiBalcony
$518/night
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Kailua Town & Kailua Beach

Kailua Town & Kailua Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$367/night
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Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach

Amazing 🌺 Kailua Beach House 🌺 Pool! Game Room! 1 House from Beach

4 beds 4 baths
PoolA/CWiFiBalcony
$808/night
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Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

Lanikai Hale - 2 cottages to rent together or separately - sleeps up to 12

5 beds 3 baths
PoolA/CWiFiBalcony
$997/night
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Licensed Short-Term Rental - Hale Oahu Estate - Kailua BeachFront #90/TVU0022

Licensed Short-Term Rental - Hale Oahu Estate - Kailua BeachFront #90/TVU0022

6 beds 4 baths
PoolA/CWiFiBalcony
$2,203/night
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Lanikai Beach Front-Lic #90/TVU-0042 - Views, Beach, Legal Short-term Rental

Lanikai Beach Front-Lic #90/TVU-0042 - Views, Beach, Legal Short-term Rental

5 beds 4 baths
PoolA/CWiFiBalcony
$1,902/night
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Family friendly Quiet Kailua Beachside lane, steps to lane private beach access

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

3 beds 2 baths
PoolA/CWiFiBalcony
$281/night
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Steps to Kailua Beach-Heated Pool-A/C-Gated Community- ASK OWNER Availability

Steps to Kailua Beach-Heated Pool-A/C-Gated Community- ASK OWNER Availability

4 beds 4 baths
PoolA/CWiFiBalcony
$851/night
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Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning

Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach by RedAwning

5 beds 2 baths
PoolA/CWiFiBalcony
$2,267/night
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Showing 48 of 257 properties

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