Windward Coast Holiday Rentals

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

New Serene 2-bedroom bungalow in Waimanalo
Oahu Camper Adventures
FromUS $125 per night
9.4 (63 Reviews)
1 Bedroom 4 Guests
Paradise Bay Resort
FromUS $271 per night
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8.8 (1012 Reviews)
1 Bedroom 2 Guests
PRIVATE BEACHFRONT RENTAL
FromUS $489 per night
10.0 (162 Reviews)
1 Bedroom 2 Guests
Beautiful Guest House Kailua Beach
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9.1 (75 Reviews)
1 Bedroom 2 Guests
Luxurious five-bedroom modern retreat
10.0 (1 Review)
5 Bedrooms 18 Guests
Modern Luxury Beach House Kailua
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9.1 (73 Reviews)
3 Bedrooms 7 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 (109 Reviews)
1 Bedroom 2 Guests
Cozy Custom Vacation Home
FromUS $376 per night
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8.9 (8 Reviews)
3 Bedrooms 8 Guests
Waimanalo Beach Cottages
8.8 (31 Reviews)
39 Bedrooms 50 Guests
KAILUA-STEPS TO THE BEACH
FromUS $192 per night
10.0 (87 Reviews)
2 Bedrooms 5 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
Enchanting Beach Bungalow with Private Garden
10.0 (80 Reviews)
1 Bedroom 2 Guests
Paradise Bay Resort
FromUS $1,657 per night
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8.3 (502 Reviews)
29 Bedrooms 23 Guests
BEACHFRONT! Barefoot living on the best spot on Lanikai Beach!
10.0 (77 Reviews)
1 Bedroom 4 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
Beautiful Kailua Hale Studio
FromUS $216 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
Kailua Beachside home
FromUS $1,890 per night
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New
4 Bedrooms 14 Guests
Footsteps to Hawaii's Best Beach
FromUS $141 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromUS $134 per night
10.0 (45 Reviews)
1 Bedroom 2 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
@ Marbella Lane - Sunshine Seascape Ocean View
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New
4 Bedrooms 8 Guests
Secluded Beach Bungalow with Private Garden
10.0 (32 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 $368 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromUS $406 per night
10.0 (22 Reviews)
1 Bedroom 4 Guests
Entire Fantastic Kailua Cottage. waiting for you!
10.0 (16 Reviews)
1 Bedroom 3 Guests
Beautiful Beachside Bungalow
FromUS $367 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
Cozy Kaaawa Studio with Mountain Views - 30 Day Min
9.8 (25 Reviews)
1 Bedroom 2 Guests
Peaceful Hawaii Paradise three minutes from Beautiful Beach
9.8 (20 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
Oahu Ohana Vans LLC
FromUS $300 per night
New
4 Bedrooms 4 Guests
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
9.6 (141 Reviews)
2 Bedrooms 4 Guests
Paradise Under the Plumeria Tree
FromUS $267 per night
9.6 (49 Reviews)
2 Bedrooms 5 Guests
Kailua Beachside Studio - Monet Room
FromUS $227 per night
9.6 (36 Reviews)
1 Bedroom 2 Guests
La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)
9.6 (9 Reviews)
1 Bedroom 3 Guests
Cozy Island Home! Short Drive to MCBH & the beach.
9.6 (9 Reviews)
1 Bedroom 4 Guests

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

Discover more than 597 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 1353.43 ft², with nightly prices averaging US $795.

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 597 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 177
Kalama Tract Vacation Rentals in Windward Coast, US 136
Lanikai Vacation Rentals in Windward Coast, US 79
Hawaii Kai Vacation Rentals in Windward Coast, US 77
Coconut Grove Vacation Rentals in Windward Coast, US 495
Enchanted Lake Vacation Rentals in Windward Coast, US 452
Keolu Hills Vacation Rentals in Windward Coast, US 434
Kuulei Tract Vacation Rentals in Windward Coast, US 475
Kamehame Ridge Vacation Rentals in Windward Coast, US 163
Queens Gate Vacation Rentals in Windward Coast, US 107