Windward Coast Vacation Rentals with Pools
House
10.0(29 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
Pool
Ocean View
Balcony/Terrace
View
US $273/Night
7 Nights - US $1,911
Resort
8.0(458 Reviews)
9 Baths
23 Guests
377.93 ft²
Oceanfront
Hot Tub- Pool
- Ocean View
US $423/Night
7 Nights - US $2,963
Condo
1 Bedroom
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
US $2,892/Night
7 Nights - US $20,244
Apartment
10.0(17 Reviews)
1 Bedroom
1 Bath
3 Guests
400 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $143/Night
7 Nights - US $1,002
House
5 Bedrooms
2 Baths
10 Guests
1797.57 ft²
- Pool
- Balcony/Terrace
- View
Parking
US $2,342/Night
7 Nights - US $16,394
Apartment
10.0(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
1095 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $383/Night
7 Nights - US $2,683
US $976/Night
7 Nights - US $6,832
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
900 ft²
Private Pool- Oceanfront
- Hot Tub
Fireplace/Heating
US $404/Night
7 Nights - US $2,826
House
3 Bedrooms
3 Baths
6 Guests
2055.91 ft²
- Pool
- Balcony/Terrace
- View
- Parking
US $936/Night
7 Nights - US $6,552
House
9.6(142 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $906/Night
7 Nights - US $6,343
Apartment
1 Bedroom
1 Bath
4 Guests
796.53 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $173/Night
7 Nights - US $1,211
House
9.6(45 Reviews)
1 Bedroom
1 Bath
4 Guests
416 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $686/Night
7 Nights - US $4,805
Why Choose Rent By Owner for your Windward Coast Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windward Coast
How to Book Your Windward Coast Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windward Coast
Common Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Windward Coast, HI
Coconut Grove
Enchanted Lake
Keolu Hills
Maunawili
Kailua
Waimanalo
Waimanalo Beach
Kalama Tract
Kahalu u
Lanikai
Ka'a'awa
Kaneohe
Frequently Asked Questions About Windward Coast Rentals with Pools
1. What are the top Rentals With Pools in Windward Coast?
There are a lot of options in Windward Coast. If you plan on staying in the Windward Coast area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Rentals With Pools in Windward Coast:
- Kailua Oceanfront Villa with Heated Pool & Spa
- Beachside Kailua AC - DATES AVAIL incl Christmas! Min Stay 7 Nights-CONTACT HOST
- Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
- Luxury Estate~Spectacular Location~Heated Pool~Private Beach Access!
- Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783
- Large, beautiful, updated home w/pool, AC,mins from beach in Kailua!
- Hale Mokulua - Lanikai, Oahu/pools, spa, beach!
- Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach
- Spacious Waterfront with Gorgeous View & Pool
- Lanikai Breeze: Beautiful Private Home w/Pool, Yard & AC - Walk to the Beach
2. How many Rentals With Pools are available in Windward Coast?
Currently, the total number of properties listed by RBO in 2026 is over 180 in the Windward Coast area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Windward Coast.
More Rentals You May Like Near Windward Coast
Cottage
9.6(13 Reviews)
2 Bedrooms
2 Baths
4 Guests
828 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $621/Night
7 Nights - US $4,345
House
9.6(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
2900 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $461/Night
7 Nights - US $3,227
House
9.4(168 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $716/Night
7 Nights - US $5,010
Apartment
9.4(164 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $681/Night
7 Nights - US $4,770
Bed & Breakfast
9.2(105 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $380/Night
7 Nights - US $2,659
House
9.0(94 Reviews)
2 Bedrooms
1 Bath
9 Guests
1250 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $339/Night
7 Nights - US $2,375
Cottage
2 Bedrooms
1 Bath
5 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $378/Night
7 Nights - US $2,649
Apartment
2 Bedrooms
1 Bath
3 Guests
- Pool
Kitchen- Parking
Air Conditioner
US $282/Night
7 Nights - US $1,977
Cottage
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $250/Night
7 Nights - US $1,750
Apartment
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $155/Night
7 Nights - US $1,088
House
10.0(229 Reviews)
5 Bedrooms
5 Baths
14 Guests
4400 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $3,047/Night
7 Nights - US $21,326
House
10.0(116 Reviews)
4 Bedrooms
4 Baths
8 Guests
3200 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $679/Night
7 Nights - US $4,750
