Vacation Rentals with Private Pool in Windward Coast, USA: Compare 10+ Sites & Save

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  3.  USA

  4.  Windward Coast

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56 Best Vacation Rentals with Private Pool in Windward Coast (Starting from $347)

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.
House
Kailua, HI, 96734, United States
2.6k from Windward Coast center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

89 reviews

$1720
Average price / night
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Kailua Palms Guest House with Pool and Views!  Parking and wi-fi included
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
Cottage
Kailua, HI, 96734, United States
2.7k from Windward Coast center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
9.6

Exceptional

13 reviews

$591
Average price / night
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Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen
Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen
House
Kailua, HI, 96734, United States
3.0k from Windward Coast center

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

4 Bedrooms8 Guests
New to Booking
$686
Average price / 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
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

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

4 Bedrooms8 Guests
9.8

Exceptional

45 reviews

$426
Average price / night
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Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1122
Average price / night
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Maluhia: Luxurious Kailua Home w/Pool Oasis, A/C, Near Beaches and Shopping!
Maluhia: Luxurious Kailua Home w/Pool Oasis, A/C, Near Beaches and Shopping!
House
Kailua, HI, 96734, United States
3.3k from Windward Coast center

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

4 Bedrooms9 Guests
9.0

Fabulous

2 reviews

$1317
Average price / night
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Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua
Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua
House
Kailua, HI, 96734, United States
3.3k from Windward Coast center

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

5 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$818
Average price / night
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Waterfront, pool/spa Home with amazing views! NO CLEANING FEE!
Waterfront, pool/spa Home with amazing views! NO CLEANING FEE!
House
Kaneohe, HI, 96744, United States
3.4k from Windward Coast center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.6

Exceptional

22 reviews

$1223
Average price / night
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Kailua Beachside by Gather: Beachfront Villa w/ Heated Pool & Ocean Views
Kailua Beachside by Gather: Beachfront Villa w/ Heated Pool & Ocean Views
Villa
Kailua, HI, 96734, United States
3.5k from Windward Coast center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
New to Booking
$1878
Average price / night
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Spacious Waterfront with Gorgeous View & Pool
Spacious Waterfront with Gorgeous View & Pool
Villa
Kaneohe, HI, 96744, United States
3.5k from Windward Coast center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet

5 Bedrooms10 Guests
10.0

Exceptional

9 reviews

$937
Average price / night
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 Steps to Beach- Heated Pool- AC-Minimum Stay 7 Nights-CONTACT HOST
Steps to Beach- Heated Pool- AC-Minimum Stay 7 Nights-CONTACT HOST
House
Kailua, HI, 96734, United States
3.7k from Windward Coast center

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

3 Bedrooms6 Guests
10.0

Exceptional

57 reviews

$676
Average price / night
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Luxury beachfront villa on a world class beach in Kailua, HI
Luxury beachfront villa on a world class beach in Kailua, HI
House
Kailua, HI, 96734, United States
3.7k from Windward Coast center

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

6 Bedrooms18 Guests
10.0

Exceptional

2 reviews

$4253
Average price / night
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Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
House
Kailua, HI, 96734, United States
3.8k from Windward Coast center

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

7 Bedrooms14 Guests
New to Booking
$4187
Average price / night
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Beachside Kailua AC 3min to beach - DATES AVAIL! Min Stay 7 Nights-CONTACT HOST
Beachside Kailua AC 3min to beach - DATES AVAIL! Min Stay 7 Nights-CONTACT HOST
House
Kailua, HI, 96734, United States
3.9k from Windward Coast center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

98 reviews

$777
Average price / night
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Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
House
Kailua, HI, 96734, United States
3.9k from Windward Coast center

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

5 Bedrooms10 Guests
10.0

Exceptional

9 reviews

$1354
Average price / night
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★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the Beach
★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the Beach
House
Kailua, HI, 96734, United States
3.9k from Windward Coast center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

34 reviews

$1084
Average price / night
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Huge House, Heated Pool, AC, Steps to Kailua Beach
Huge House, Heated Pool, AC, Steps to Kailua Beach
House
Kailua, HI, 96734, United States
4.1k from Windward Coast center

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

8 Bedrooms20 Guests
9.6

Exceptional

80 reviews

$1380
Average price / night
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Zen Home with AC, Pool, Near Kailua Beach
Zen Home with AC, Pool, Near Kailua Beach
House
Kailua, HI, 96734, United States
4.2k from Windward Coast center

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

4 Bedrooms12 Guests
9.8

Exceptional

77 reviews

$1067
Average price / night
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KAILUA BEACH VILLA - 1990/NUC-1798
KAILUA BEACH VILLA - 1990/NUC-1798
House
Kailua, HI, 96734, United States
4.2k from Windward Coast center

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

8 Bedrooms14 Guests
9.4

Superb

86 reviews

$2894
Average price / night
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Kailua Beach Hideaway TA-189-305-8560-01
Kailua Beach Hideaway TA-189-305-8560-01
House
Kailua, HI, 96734, United States
4.4k from Windward Coast center

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

4 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$1187
Average price / night
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Pilipu Palms 2
Pilipu Palms 2
House
Kailua, HI, 96734, United States
4.4k from Windward Coast center

AC, Free Parking, Internet, Kitchen, No Smoking, Pool

3 Bedrooms5 Guests
New to Booking
$385
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
4.5k from Windward Coast 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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Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
Kailua Sands | Oceanfront Pool Retreat with Gym | Sleeps 7
House
Kailua, HI, 96734, United States
4.6k from Windward Coast 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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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
4.8k from Windward Coast 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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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
4.9k from Windward Coast 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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'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
5.0k from Windward Coast 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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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
5.1k from Windward Coast center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$347
Average price / night
Check Availability

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 Windward Coast.

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Windward Coast Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 56 verified vacation rentals with a private pool in Windward Coast. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Windward Coast 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 Windward Coast 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 Windward Coast often include additional features such as Pool, Private Pool, and Ocean View. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Windward Coast 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.