Windward Coast Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes 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
Luxurious five-bedroom modern retreat
10.0 (1 Review)
5 Bedrooms 18 Guests
PRIVATE BEACHFRONT RENTAL
FromCA $656 per night
10.0 (175 Reviews)
1 Bedroom 2 Guests
Modern Luxury Beach House Kailua
|
9.2 (88 Reviews)
3 Bedrooms 7 Guests
Hawaii's Hidden Hideaway Bed & Breakfast
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8.4 (67 Reviews)
1 Bedroom 2 Guests
Beautiful Guest House Kailua Beach
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9.1 (70 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
Cozy Custom Vacation Home
FromCA $614 per night
|
9.0 (10 Reviews)
3 Bedrooms 8 Guests
Available and legal for stays less than 30 days.
10.0 (114 Reviews)
1 Bedroom 2 Guests
Beachfront spectacular Kailua beach
FromCA $1,711 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (108 Reviews)
1 Bedroom 2 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
Waimanalo Beach Cottages
8.4 (30 Reviews)
39 Bedrooms 50 Guests
KAILUA-STEPS TO THE BEACH
FromCA $261 per night
10.0 (87 Reviews)
2 Bedrooms 5 Guests
Paradise Bay Resort
FromCA $592 per night
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8.0 (458 Reviews)
29 Bedrooms 23 Guests
Enchanting Beach Bungalow with Private Garden
10.0 (80 Reviews)
1 Bedroom 2 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 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
Beautiful Kailua Hale Studio
FromCA $322 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
A Place of Peace - where heaven meets the Ocean
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New
2 Bedrooms 4 Guests
Footsteps to Hawaii's Best Beach
FromCA $197 per night
10.0 (55 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
FromCA $187 per night
10.0 (46 Reviews)
1 Bedroom 2 Guests
Charming Apartment in Prime Location – Steps from Kailua Beach & Town
10.0 (35 Reviews)
1 Bedroom 3 Guests
Kalama Room
FromCA $145 per night
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New
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromCA $1,365 per night
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New
1 Bedroom 4 Guests
Secluded Beach Bungalow with Private Garden
10.0 (33 Reviews)
1 Bedroom 2 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C
10.0 (29 Reviews)
2 Bedrooms 4 Guests
The Banyan Beach Bungalow
FromCA $513 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromCA $655 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
FromCA $513 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 (105 Reviews)
2 Bedrooms 3 Guests

About Windward Coast Vacation Rentals

With more than 598 Windward Coast vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Windward Coast.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windward Coast, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Windward Coast. Places to stay near Windward Coast are 1361.33 ft² on average, with prices averaging CA $1,126 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Windward Coast with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Windward Coast?

What are the top vacation rentals in Windward Coast?

How many Rentbyowner vacation rentals are available in Windward Coast?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 598 in the Windward Coast area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windward Coast. 

Nearby Neighborhood (10)

NeighborhoodProperty Count
Eastern Honolulu Vacation Rentals in Windward Coast, US 165
Kalama Tract Vacation Rentals in Windward Coast, US 114
Hawaii Kai Vacation Rentals in Windward Coast, US 69
Lanikai Vacation Rentals in Windward Coast, US 66
Coconut Grove Vacation Rentals in Windward Coast, US 498
Enchanted Lake Vacation Rentals in Windward Coast, US 455
Keolu Hills Vacation Rentals in Windward Coast, US 437
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