Windward Coast Holiday Rentals

Compare Villas, Resorts, & Rentals in Windward Coast, USA

Relaxed Kaneohe Retreat | Carport, AC, W/D
New
1 Bedroom 7 Guests
Sunny Kailua Home w/Covered Lanai 1 Mi to Beach!
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10.0 (1 Review)
3 Bedrooms 7 Guests
Paradise Bay Resort
FromUS $284 per night
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8.8 (1006 Reviews)
1 Bedroom 2 Guests
PRIVATE BEACHFRONT RENTAL
FromUS $469 per night
10.0 (175 Reviews)
1 Bedroom 2 Guests
Beautiful Guest House Kailua Beach
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9.1 (70 Reviews)
1 Bedroom 2 Guests
Luxurious five-bedroom modern retreat
10.0 (1 Review)
5 Bedrooms 18 Guests
Cozy Custom Vacation Home
FromUS $439 per night
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9.0 (10 Reviews)
3 Bedrooms 8 Guests
Hawaii's Hidden Hideaway Bed & Breakfast
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8.4 (67 Reviews)
1 Bedroom 2 Guests
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
10.0 (120 Reviews)
1 Bedroom 2 Guests
Beachfront spectacular Kailua beach
FromUS $1,224 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Available and legal for stays less than 30 days.
10.0 (114 Reviews)
1 Bedroom 2 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (108 Reviews)
1 Bedroom 2 Guests
Waimanalo Beach Cottages
8.4 (30 Reviews)
39 Bedrooms 50 Guests
Paradise Bay Resort
FromUS $423 per night
|
8.0 (458 Reviews)
29 Bedrooms 23 Guests
KAILUA-STEPS TO THE BEACH
FromUS $192 per night
10.0 (87 Reviews)
2 Bedrooms 5 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
Enchanting Beach Bungalow with Private Garden
10.0 (80 Reviews)
1 Bedroom 2 Guests
BEACHFRONT! Barefoot living on the best spot on Lanikai Beach!
10.0 (77 Reviews)
1 Bedroom 4 Guests
Upscale Kailua Getaway: Steps to Swim Beach!
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New
3 Bedrooms 6 Guests
A Place of Peace - where heaven meets the Ocean
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New
2 Bedrooms 4 Guests
Beautiful Kailua Hale Studio
FromUS $230 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
@ Marbella Lane - Sunshine Seascape Ocean View
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New
4 Bedrooms 8 Guests
Footsteps to Hawaii's Best Beach
FromUS $258 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromUS $134 per night
10.0 (46 Reviews)
1 Bedroom 2 Guests
Kalama Room
FromUS $104 per night
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New
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromUS $976 per night
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New
1 Bedroom 4 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Secluded Beach Bungalow with Private Garden
10.0 (33 Reviews)
1 Bedroom 2 Guests
Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C
10.0 (29 Reviews)
2 Bedrooms 4 Guests
The Banyan Beach Bungalow
FromUS $367 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromUS $477 per night
10.0 (22 Reviews)
1 Bedroom 4 Guests
Entire Fantastic Kailua Cottage. waiting for you!
10.0 (17 Reviews)
1 Bedroom 3 Guests
Beautiful Beachside Bungalow
FromUS $367 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)
9.8 (11 Reviews)
1 Bedroom 3 Guests
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
9.6 (142 Reviews)
2 Bedrooms 4 Guests
Heavenly Hale Best monthly Vacation rental - walk to beach!
9.6 (4 Reviews)
2 Bedrooms 4 Guests
Absolutely Oceanfront - 60' Waterfall Lap Pool
9.4 (168 Reviews)
1 Bedroom 2 Guests
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
9.4 (164 Reviews)
1 Bedroom 2 Guests
Honu Cottage: Quiet, Oceanfront Comfort + EPIC VIEWS!
9.4 (100 Reviews)
1 Bedroom 4 Guests
Ocean View Guest Cottage - 1990/NUC-1797
9.4 (99 Reviews)
2 Bedrooms 4 Guests
Little Yellow Cottage: Steps to Lanikai Beach
9.4 (57 Reviews)
2 Bedrooms 4 Guests
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
9.2 (157 Reviews)
2 Bedrooms 5 Guests
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
9.2 (104 Reviews)
2 Bedrooms 3 Guests

About Casai's Private Villas and Holiday Rentals in Windward Coast

Discover more than 598 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 1358.32 ft², with nightly prices averaging US $808.

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.

Frequently Asked Questions About Windward Coast?

What are the top holiday rentals in Windward Coast?

How many Casai.com holiday rentals are available in Windward Coast?

As of 2026, Casai boasts over 598 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)

NeighborhoodProperty Count
Eastern Honolulu Vacation Rentals in Windward Coast, US 162
Kalama Tract Vacation Rentals in Windward Coast, US 113
Hawaii Kai Vacation Rentals in Windward Coast, US 70
Lanikai Vacation Rentals in Windward Coast, US 62
Coconut Grove Vacation Rentals in Windward Coast, US 499
Enchanted Lake Vacation Rentals in Windward Coast, US 456
Keolu Hills Vacation Rentals in Windward Coast, US 438
Kuulei Tract Vacation Rentals in Windward Coast, US 483
Kamehame Ridge Vacation Rentals in Windward Coast, US 164
Queens Gate Vacation Rentals in Windward Coast, US 108