Windward Coast Cottage Rentals

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

PRIVATE BEACHFRONT RENTAL
FromUS $489 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
FromUS $272 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
FromUS $125 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
FromUS $1,224 per night
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
FromUS $439 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 $423 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
FromUS $1,890 per night
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New
4 Bedrooms 14 Guests
Beautiful Kailua Hale Studio
FromUS $381 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromUS $141 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
FromUS $134 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
FromUS $368 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromUS $402 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
Kalama Room
FromUS $104 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
FromUS $976 per night
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New
1 Bedroom 4 Guests
Beautiful Kailua Hale 1 Bedroom
FromUS $354 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
FromUS $300 per night
New
4 Bedrooms 4 Guests
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
9.6 (142 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 $214 per night
9.6 (36 Reviews)
1 Bedroom 2 Guests

About Windward Coast Vacation Rentals

There are over 600 amazing vacation rentals available in Windward Coast. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Windward Coast.

Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Windward Coast, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Windward Coast. The average size of places to stay near Windward Coast is approximately 1360.69 ft², with prices averaging US $797 per night.

Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Windward Coast. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.

Frequently Asked Questions About Windward Coast?

What are the top cottages, summer homes, and lake houses in Windward Coast?

How many rentals, hotels, or resorts are available in Windward Coast?

Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 600 properties listed by Vacation Cottage in the Windward Coast area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Windward Coast.

Nearby Neighborhood (10)

NeighborhoodProperty Count
Eastern Honolulu Rental Cottages and Private Getaways in Windward Coast, US 171
Kalama Tract Rental Cottages and Private Getaways in Windward Coast, US 124
Lanikai Rental Cottages and Private Getaways in Windward Coast, US 79
Hawaii Kai Rental Cottages and Private Getaways in Windward Coast, US 71
Coconut Grove Rental Cottages and Private Getaways in Windward Coast, US 498
Enchanted Lake Rental Cottages and Private Getaways in Windward Coast, US 452
Keolu Hills Rental Cottages and Private Getaways in Windward Coast, US 434
Kuulei Tract Rental Cottages and Private Getaways in Windward Coast, US 475
Kamehame Ridge Rental Cottages and Private Getaways in Windward Coast, US 163
Queens Gate Rental Cottages and Private Getaways in Windward Coast, US 107