Vacation Rentals with Private Pool in Kailua Beach, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Hawaii

  5.  Kailua
  6.  Kailua Beach

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59 Best Vacation Rentals with Private Pool in Kailua Beach (Starting from $347)

Kahela - Paradise for Rent
Kahela - Paradise for Rent
House
Kailua, HI, 96734, United States
0.3k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.8

Exceptional

51 reviews

$665
Average price / night
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Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio

4 Bedrooms8 Guests
10.0

Exceptional

115 reviews

$678
Average price / 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
House
Kailua, HI, 96734, United States
0.4k from Kailua Beach center

AC, Barbecue, Crib, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$1641
Average price / night
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3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai
3,200 sq ft House with Pool, 6 Bedrooms, walking distance to Kailua and Lanikai
House
Kailua, HI, 96734, United States
0.5k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

6 Bedrooms15 Guests
10.0

Exceptional

4 reviews

$1206
Average price / night
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Steps from Kailua Beach, heated pool, gazebo, AC,  NO CLEANING FEE!
Steps from Kailua Beach, heated pool, gazebo, AC, NO CLEANING FEE!
House
Kailua, HI, 96734, United States
0.5k from Kailua Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1013
Average price / night
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Wow!   Home just steps from the Beach with Private Salt Water Pool
Wow! Home just steps from the Beach with Private Salt Water Pool
House
Kailua, HI, 96734, United States
0.8k from Kailua Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
9.6

Exceptional

43 reviews

$1281
Average price / night
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BEACHSIDE LUXURY HOME, AC, HEATED POOL, INQUIRE WITH OWNER FOR DESIRED DATES
BEACHSIDE LUXURY HOME, AC, HEATED POOL, INQUIRE WITH OWNER FOR DESIRED DATES
House
Kailua, HI, 96734, United States
0.8k from Kailua Beach center

AC, Arcade, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
10.0

Exceptional

62 reviews

$1339
Average price / night
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Enjoy watching for Sea Turtles off your Ocean Front Deck!
Enjoy watching for Sea Turtles off your Ocean Front Deck!
House
Kailua, HI, 96734, United States
0.9k from Kailua Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1460
Average price / night
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Spectacular Lanikai Ocean Front w/Pool - newly remodeled, sleeps up to 18!
Spectacular Lanikai Ocean Front w/Pool - newly remodeled, sleeps up to 18!
House
Kailua, HI, 96734, United States
0.9k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

6 Bedrooms18 Guests
New to Booking
$1806
Average price / night
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Upscale Kailua Getaway: Steps to Swim Beach!
Upscale Kailua Getaway: Steps to Swim Beach!
House
Kailua, HI, 96734-3109, United States
1.0k from Kailua Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$1593
Average price / night
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Lanikai Breeze: Beautiful Private Home w/Pool, Yard & AC - Walk to the Beach
Lanikai Breeze: Beautiful Private Home w/Pool, Yard & AC - Walk to the Beach
House
Kailua, HI, 96734, United States
1.1k from Kailua Beach center

AC, Balcony, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$1133
Average price / night
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Naupaka Hale & Cottage
Naupaka Hale & Cottage
House
Lanikai, HI, 96734, United States
1.2k from Kailua Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$1276
Average price / night
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Hale Lani: Mountainside Ocean View Home | Private Pool & soaking tub with a view
Hale Lani: Mountainside Ocean View Home | Private Pool & soaking tub with a view
House
Kailua, HI, 96734, United States
1.3k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$4136
Average price / night
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Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783
Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783
House
Kailua, HI, 96734, United States
1.4k from Kailua Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms10 Guests
10.0

Exceptional

34 reviews

$3308
Average price / night
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MINUTES TO KAILUA BEACH-FABULOUS POOL  great indoor/ outdoor living
MINUTES TO KAILUA BEACH-FABULOUS POOL great indoor/ outdoor living
House
Kailua, HI, 96734, United States
1.5k from Kailua Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.6

Exceptional

8 reviews

$461
Average price / night
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Steps to beach, tropical garden and private pool
Steps to beach, tropical garden and private pool
House
Kailua, HI, 96734, United States
1.6k from Kailua Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.2

Superb

20 reviews

$650
Average price / night
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Resort-like, Kailua Beach, Lanikai Beach, Private Pool, AC, Tropical Retreat
Resort-like, Kailua Beach, Lanikai Beach, Private Pool, AC, Tropical Retreat
House
Kailua, HI, 96734, United States
1.6k from Kailua Beach center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

73 reviews

$592
Average price / night
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Kailua Beach Villa: Stunning Beachfront Estate Private Pool/Spa, Ocean View & AC
Kailua Beach Villa: Stunning Beachfront Estate Private Pool/Spa, Ocean View & AC
Villa
Kailua, HI, 96734, United States
1.6k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Laundry, Microwave

5 Bedrooms12 Guests
New to Booking
$2363
Average price / night
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Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access! 30+ Nights
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access! 30+ Nights
House
Kailua, HI, 96734, United States
1.6k from Kailua Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$347
Average price / 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
House
Kailua, HI, 96734, United States
1.7k from Kailua Beach center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$591
Average price / night
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Orchid House - Pool and Endless Ocean views!
Orchid House - Pool and Endless Ocean views!
House
Kailua, HI, 96734, United States
1.7k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$1020
Average price / 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
House
Kailua, HI, 96734, United States
1.7k from Kailua Beach center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Laundry, Microwave, No Smoking

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$1142
Average price / night
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'Star of Hawaii'  Beachside, Pool, Steps to Beach - Great for Families
'Star of Hawaii' Beachside, Pool, Steps to Beach - Great for Families
House
Kailua, HI, 96734, United States
1.8k from Kailua Beach center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
9.4

Superb

98 reviews

$669
Average price / night
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Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
House
Kailua, HI, 96734, United States
1.9k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Microwave, No Smoking

3 Bedrooms7 Guests
New to Booking
$2750
Average price / night
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Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
House
Kailua, HI, 96734, United States
1.9k from Kailua Beach center

AC, Barbecue, Crib, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom4 Guests
9.6

Exceptional

44 reviews

$751
Average price / night
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Kailua Luxury Estate: Licensed Rental #1990/NUC-1787
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787
House
Kailua, HI, 96734, United States
2.0k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

6 Bedrooms16 Guests
9.8

Exceptional

76 reviews

$4216
Average price / 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
House
Kailua, HI, 96734, United States
2.0k from Kailua Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$734
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Kailua Beach.

Where to stay in Kailua Beach? Best neighborhoods & areas

Kailua Beach Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 59 verified vacation rentals with a private pool in Kailua Beach. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Kailua Beach vary depending on the property size, location, and travel season. Rates typically start from around $347 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Kailua Beach also welcome pets. Currently, 2 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Kailua Beach often include additional features such as Wellness Facilities, Ocean View, and View. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Kailua Beach include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.