Windward Coast Holiday Rentals

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

PRIVATE BEACHFRONT RENTAL
FromGB £351 per night
10.0 (166 Reviews)
1 Bedroom 2 Guests
Modern Luxury Beach House Kailua
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9.1 (85 Reviews)
3 Bedrooms 7 Guests
Paradise Bay Resort
FromGB £203 per night
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8.8 (1005 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
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
10.0 (120 Reviews)
1 Bedroom 2 Guests
Oahu Camper Adventures
FromGB £93 per night
9.1 (65 Reviews)
1 Bedroom 4 Guests
Hawaii's Hidden Hideaway Bed & Breakfast
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8.4 (67 Reviews)
1 Bedroom 2 Guests
Available and legal for stays less than 30 days.
10.0 (112 Reviews)
1 Bedroom 2 Guests
Beachfront spectacular Kailua beach
9.0 (1 Review)
4 Bedrooms 8 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (107 Reviews)
1 Bedroom 2 Guests
Cozy Custom Vacation Home
FromGB £327 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
FromGB £143 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
FromGB £315 per night
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8.2 (478 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
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage
10.0 (61 Reviews)
2 Bedrooms 4 Guests
Kailua Beachside home
FromGB £1,408 per night
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New
4 Bedrooms 14 Guests
Beautiful Kailua Hale Studio
FromGB £284 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromGB £105 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Upscale Kailua Getaway Steps to Swim Beach!
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New
3 Bedrooms 6 Guests
Footsteps to Hawaii's Best Beach
FromGB £99 per night
10.0 (45 Reviews)
1 Bedroom 2 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
FromGB £274 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromGB £293 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
FromGB £273 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
Kalama Room
FromGB £77 per night
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New
1 Bedroom 2 Guests
Gorgeous 2 bedroom bayside house on Windward side of Oahu
9.8 (72 Reviews)
2 Bedrooms 6 Guests
Lanikai Ohana Hale
FromGB £727 per night
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New
1 Bedroom 4 Guests
Beautiful Kailua Hale 1 Bedroom
FromGB £258 per night
9.8 (29 Reviews)
1 Bedroom 4 Guests
Cozy Kaaawa Studio with Mountain Views - 30 Day Min
9.8 (25 Reviews)
1 Bedroom 2 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Oahu Ohana Vans LLC
FromGB £223 per night
New
4 Bedrooms 4 Guests
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
9.6 (149 Reviews)
1 Bedroom 3 Guests
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
9.6 (142 Reviews)
2 Bedrooms 4 Guests
Paradise Under the Plumeria Tree
FromGB £199 per night
9.6 (49 Reviews)
2 Bedrooms 5 Guests
Kailua Beachside Studio - Monet Room
FromGB £159 per night
9.6 (36 Reviews)
1 Bedroom 2 Guests
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
9.6 (13 Reviews)
2 Bedrooms 4 Guests

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

Discover more than 600 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 1360.69 ft², with nightly prices averaging GB £594.

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.uk holiday rentals are available in Windward Coast?

As of 2026, Casai boasts over 600 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 171
Kalama Tract Vacation Rentals in Windward Coast, US 124
Lanikai Vacation Rentals in Windward Coast, US 80
Hawaii Kai Vacation Rentals in Windward Coast, US 71
Coconut Grove Vacation Rentals in Windward Coast, US 498
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