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

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  4.  Windward Coast

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80 Best Vacation Rentals with Pool in Windward Coast (Starting from $173)

Your Perfect Home Charming 2BR2BA Apartment with Full Kitchen WD & AC
Your Perfect Home Charming 2BR2BA Apartment with Full Kitchen WD & AC
Apartment
Kailua, HI, USA
4.2k from Windward Coast center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

2 Bedrooms6 Guests
New to Booking
$261
Average price / night
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Kailua Condo / Townhouse on Oahu 30 day period 7 day min
Kailua Condo / Townhouse on Oahu 30 day period 7 day min
Apartment
Kailua, HI, 96734, United States
2.3k from Windward Coast center

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

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$383
Average price / night
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Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
4.3k from Windward Coast center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms14 Guests
New to Booking
$1890
Average price / 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.
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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Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
House
Kailua, HI, USA
4.8k from Windward Coast center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
New to Booking
$2342
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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Stylish 1BR Apartment with AC Full Kitchen & WD - Just Steps to the Beach
Stylish 1BR Apartment with AC Full Kitchen & WD - Just Steps to the Beach
Apartment
Kailua, HI, USA
5.7k from Windward Coast center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom4 Guests
New to Booking
$173
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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Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Apartment
Kailua, HI, USA
5.7k from Windward Coast center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms4 Guests
New to Booking
$273
Average price / night
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Absolutely Oceanfront - 60' Waterfall Lap Pool
Absolutely Oceanfront - 60' Waterfall Lap Pool
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

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

1 Bedroom2 Guests
9.4

Superb

168 reviews

$686
Average price / night
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Upscale Kailua Getaway Steps to Swim Beach!
Upscale Kailua Getaway Steps to Swim Beach!
House
Kailua, HI, USA
7.3k from Windward Coast center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$936
Average price / night
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Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
Apartment
Kailua, HI, 96734, United States
3.1k from Windward Coast center

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

1 Bedroom2 Guests
9.4

Superb

163 reviews

$633
Average price / night
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Paradise Bay Resort
Paradise Bay Resort
Resort
Windward Coast, USA
7.5k from Windward Coast center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 4-star, Lodgings, Hot tubs

29 Bedrooms23 Guests
8.4

Very Good

517 reviews

$1657
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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Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Apartment
Kailua, HI, USA
7.9k from Windward Coast center

Apartments, Accommodations, Parking, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$219
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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Lanikai Ohana Hale
Lanikai Ohana Hale
House
Kailua, HI, USA
8.3k from Windward Coast center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
New to Booking
$976
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
Check Availability
 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
Check Availability
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
House
Kaneohe, HI, 96744, United States
3.9k from Windward Coast center

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

2 Bedrooms4 Guests
9.6

Exceptional

142 reviews

$765
Average price / night
Check Availability
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
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 Pool in Windward Coast.

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VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Windward Coast Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 80 verified vacation rentals with a pool in Windward Coast. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Windward Coast vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $173 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Windward Coast offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Windward Coast welcome pets. Currently, 5 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Windward Coast often include additional outdoor features such as View, Pool, and Ocean View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Windward Coast offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.