House
10.0(236 Reviews)
5 Bedrooms
14 Guests
Oceanfront
Parking
Pool
Ocean View
US $2,876/Night
7 Nights - US $20,131
Windward Coast, HI Holiday Rentals
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Compare Villas, Resorts, & Rentals in Windward Coast
10.0
House
10.0(1 Review)
3 Bedrooms
7 Guests
- Parking
Internet
Child Friendly
Accessibility
US $209/Night
7 Nights - US $1,463
US $2,325/Night
7 Nights - US $16,277
Bed & Breakfast
10.0(185 Reviews)
1 Bedroom
2 Guests
- Parking
Balcony/Terrace
Kitchen- Internet
US $595/Night
7 Nights - US $4,163
House
9.0(10 Reviews)
3 Bedrooms
8 Guests
- Parking
Air Conditioner- Internet
Security/Safety
US $401/Night
7 Nights - US $2,810
House
10.0(149 Reviews)
5 Bedrooms
14 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $3,947/Night
7 Nights - US $27,631
Cottage
10.0(136 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $336/Night
7 Nights - US $2,349
Apartment
10.0(120 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $309/Night
7 Nights - US $2,163
Apartment
10.0(118 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $388/Night
7 Nights - US $2,717
Luxury Holiday Rentals in Windward Coast
Over 582+ Luxury Holiday Rentals in or Near Windward Coast
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
Private Pool- Parking
- Pool
- Ocean View
US $4,986/Night
7 Nights - US $34,902
House
10.0(2 Reviews)
6 Bedrooms
18 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $4,492/Night
7 Nights - US $31,447
House
5 Bedrooms
12 Guests
- Private Pool
- Oceanfront
Hot Tub- Parking
US $4,268/Night
7 Nights - US $29,873
House
9.8(90 Reviews)
6 Bedrooms
16 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,962/Night
7 Nights - US $27,733
New
Villa
5 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $3,408/Night
7 Nights - US $23,854
House
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,345/Night
7 Nights - US $23,415
New
House
9.8(42 Reviews)
5 Bedrooms
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $3,185/Night
7 Nights - US $22,296
House
9.8(59 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $3,111/Night
7 Nights - US $21,774
House
10.0(1 Review)
4 Bedrooms
7 Guests
- Private Pool
- Hot Tub
Breakfast- Parking
US $2,863/Night
7 Nights - US $20,039
Top-Rated Holiday Rentals with a Pool in Windward Coast
Over 163+ The Best Private Villas and Holiday Rentals in Windward Coast with a Pool
House
10.0(117 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $737/Night
7 Nights - US $5,158
House
10.0(104 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,226/Night
7 Nights - US $15,584
House
10.0(99 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $848/Night
7 Nights - US $5,934
House
10.0(63 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,482/Night
7 Nights - US $10,371
House
10.0(43 Reviews)
3 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $2,810/Night
7 Nights - US $19,669
House
10.0(34 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,164/Night
7 Nights - US $8,149
House
10.0(22 Reviews)
5 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,060/Night
7 Nights - US $7,423
Bed & Breakfast
10.0(15 Reviews)
1 Bedroom
4 Guests
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $724/Night
7 Nights - US $5,070
New
House
10.0(13 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,332/Night
7 Nights - US $9,323
Pet-Friendly Holiday Rentals in Windward Coast
Over 58+ Pet-Friendly Holiday Rentals in or Near Windward Coast
House
10.0(31 Reviews)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $295/Night
7 Nights - US $2,064
House
9.0(1 Review)
4 Bedrooms
8 Guests
Private Beach- Oceanfront
- Parking
- Ocean View
US $1,224/Night
7 Nights - US $8,568
House
10.0(26 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $374/Night
7 Nights - US $2,618
US $267/Night
7 Nights - US $1,867
Villa
10.0(6 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $2,044/Night
7 Nights - US $14,306
Apartment
10.0(6 Reviews)
3 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $360/Night
7 Nights - US $2,518
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $276/Night
7 Nights - US $1,931
Apartment
10.0(3 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $585/Night
7 Nights - US $4,097
House
10.0(3 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $416/Night
7 Nights - US $2,910
Large Holiday Rentals and Private Villas in Windward Coast
Over 136+ Large Holiday Rentals and Private Villas in or Near Windward Coast
House
10.0(64 Reviews)
6 Bedrooms
14 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $2,128/Night
7 Nights - US $14,893
House
5 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $2,342/Night
7 Nights - US $16,394
US $3,539/Night
7 Nights - US $24,772
House
10.0(12 Reviews)
4 Bedrooms
18 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $629/Night
7 Nights - US $4,402
Villa
1 Bedroom
4 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $170/Night
7 Nights - US $1,190
Villa
10.0(9 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $977/Night
7 Nights - US $6,842
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $348/Night
7 Nights - US $2,433
House
10.0(6 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,340/Night
7 Nights - US $9,382
House
10.0(6 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $764/Night
7 Nights - US $5,348
Wheelchair Accessible Holiday Homes in Windward Coast
Over 11+ Wheelchair Accessible Holiday Homes in or Near Windward Coast
House
10.0(4 Reviews)
3 Bedrooms
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $281/Night
7 Nights - US $1,970
House
2 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $389/Night
7 Nights - US $2,722
Apartment
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $263/Night
7 Nights - US $1,840
House
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $645/Night
7 Nights - US $4,515
Condo
3 Bedrooms
5 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $365/Night
7 Nights - US $2,557
Apartment
9.8(67 Reviews)
1 Bedroom
2 Guests
- Breakfast
- Kitchen
- Internet
Wheelchair Accessible
US $142/Night
7 Nights - US $991
Cottage
9.6(5 Reviews)
4 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,367/Night
7 Nights - US $9,569
House
5.0(5 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $5,200/Night
7 Nights - US $36,400
House
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $719/Night
7 Nights - US $5,033
Windward Coast Private Villas and Holiday Homes Under $200
Over 108+ Windward Coast Private Villas and Holiday Homes Under $200
House
10.0(88 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $175/Night
7 Nights - US $1,227
Apartment
8.5(57 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $193/Night
7 Nights - US $1,351
Cottage
10.0(56 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $160/Night
7 Nights - US $1,119
US $104/Night
7 Nights - US $728
House
10.0(13 Reviews)
2 Bedrooms
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $187/Night
7 Nights - US $1,306
House
10.0(10 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $124/Night
7 Nights - US $865
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
Laundry
US $176/Night
7 Nights - US $1,229
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Internet
- Child Friendly
US $158/Night
7 Nights - US $1,105
Cottage
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $156/Night
7 Nights - US $1,089
Instantly Bookable Holiday Homes in Windward Coast
Over 258+ Instantly Bookable Holiday Homes in or Near Windward Coast
House
10.0(76 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $684/Night
7 Nights - US $4,790
House
10.0(73 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $521/Night
7 Nights - US $3,648
House
10.0(33 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $740/Night
7 Nights - US $5,178
House
10.0(29 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $300/Night
7 Nights - US $2,102
House
10.0(26 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $359/Night
7 Nights - US $2,514
House
10.0(23 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $436/Night
7 Nights - US $3,054
House
10.0(21 Reviews)
4 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $475/Night
7 Nights - US $3,328
Cottage
10.0(15 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $350/Night
7 Nights - US $2,450
House
10.0(11 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $472/Night
7 Nights - US $3,306
Book a Last Minute Place to Stay in Windward Coast
About Casai's Private Villas and Holiday Rentals in Windward Coast
Discover more than 591 vacation rentals available in Windward Coast. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windward Coast.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windward Coast, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windward Coast. On average, places to stay near Windward Coast offer 1281.82 ft², with nightly prices averaging US $770.
With Casai, finding and comparing holiday rentals in Windward Coast is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Windward Coast, US
There are 591 Windward Coast, US Holiday Rentals
- Prices for a holiday home in Windward Coast start at US $104
- Top rated vacation home in Windward Coast is Place in Paradise-Kailua Beachfront #1990/NUC-1802-FALL SPECIAL
- Most popular short term in Windward Coast is Paradise Bay Resort
- Cheapest place to stay in Windward Coast is Kalama Room
- Most expensive holiday rental in Windward Coast is Hale Lani: Mountainside Ocean View Home | Private Pool & soaking tub with a view
Recently Booked Holiday Rentals in Windward Coast
Frequently Asked Questions About Windward Coast?
What are the top holiday rentals in Windward Coast?
With numerous options available in Windward Coast, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windward Coast:
- Place in Paradise-Kailua Beachfront #1990/NUC-1802-FALL SPECIAL
- PRIVATE BEACHFRONT RENTAL
- Walker Beach House - Lanikai Ocean Front Lic.#1990/NUC-1757
- Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!
- 'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
- Available and legal for stays less than 30 days.
- Steps to Beach-Heated Pool-AC-Gated Community-Minimum Stay 7 Nights-CONTACT HOST
- CHRISTMAS AVAILABILITY! Charming Lanikai Kailua Cottage. Send inquiries to owner
- Oceanfront Paradise in Waimānalo Stunning Views & Hawaiian Sunrises
- Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
How many holiday rentals have private pools in Windward Coast?
Discover a selection of holiday rentals with private pools near Windward Coast with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Windward Coast are best for families?
If you're searching for a family-friendly holiday home in Windward Coast, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windward Coast:
How many Casai.com holiday rentals are available in Windward Coast?
As of 2026, Casai boasts over 591 properties listed in the Windward Coast area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windward Coast.
Nearby Neighborhood (10)
| Neighborhood | Property Count |
|---|---|
| Eastern Honolulu Vacation Rentals in Windward Coast, US | 149 |
| Kalama Tract Vacation Rentals in Windward Coast, US | 106 |
| Lanikai Vacation Rentals in Windward Coast, US | 63 |
| Hawaii Kai Vacation Rentals in Windward Coast, US | 57 |
| Coconut Grove Vacation Rentals in Windward Coast, US | 488 |
| Enchanted Lake Vacation Rentals in Windward Coast, US | 450 |
| Keolu Hills Vacation Rentals in Windward Coast, US | 431 |
| Kuulei Tract Vacation Rentals in Windward Coast, US | 483 |
| Kamehame Ridge Vacation Rentals in Windward Coast, US | 162 |
| Queens Gate Vacation Rentals in Windward Coast, US | 108 |
