Windward Coast Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Windward Coast, USA

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
Makani Moana~Lanikai ~ Spectacular Ocean+Mokulua Islands Views + A/C
10.0 (33 Reviews)
4 Bedrooms 8 Guests
Modern Luxury Beach House Kailua
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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
1 bedroom steps to white sand beach
10.0 (4 Reviews)
1 Bedroom 2 Guests
Beautiful Guest House Kailua Beach
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9.1 (70 Reviews)
1 Bedroom 2 Guests
Kailua Kai/Beach Front Licensed Rental #1990/NUC-1780
9.6 (138 Reviews)
4 Bedrooms 10 Guests
Cozy Custom Vacation Home
FromUS $439 per night
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9.0 (10 Reviews)
3 Bedrooms 8 Guests
Beachfront spectacular Kailua beach
FromUS $1,224 per night
9.0 (1 Review)
4 Bedrooms 8 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
Paradise Bay Resort
FromUS $423 per night
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8.0 (458 Reviews)
29 Bedrooms 23 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
PRIVATE BEACHFRONT RENTAL
FromUS $527 per night
10.0 (173 Reviews)
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromUS $976 per night
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New
1 Bedroom 4 Guests
Upscale Kailua Getaway: Steps to Swim Beach!
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New
3 Bedrooms 6 Guests
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
10.0 (120 Reviews)
1 Bedroom 2 Guests
A Place of Peace - where heaven meets the Ocean
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New
2 Bedrooms 4 Guests
Available and legal for stays less than 30 days.
10.0 (114 Reviews)
1 Bedroom 2 Guests
@ Marbella Lane - Sunshine Seascape Ocean View
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New
4 Bedrooms 8 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (108 Reviews)
1 Bedroom 2 Guests
Kalama Room
FromUS $104 per night
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New
1 Bedroom 2 Guests
KAILUA-STEPS TO THE BEACH
FromUS $175 per night
10.0 (87 Reviews)
2 Bedrooms 5 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
BEACHFRONT! Barefoot living on the best spot on Lanikai Beach!
10.0 (77 Reviews)
1 Bedroom 4 Guests
Footsteps to Hawaii's Best Beach
FromUS $153 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromUS $145 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
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
9.6 (144 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 (169 Reviews)
1 Bedroom 2 Guests
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
9.4 (164 Reviews)
1 Bedroom 2 Guests
Ocean View Guest Cottage - 1990/NUC-1797
9.4 (101 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 (161 Reviews)
2 Bedrooms 5 Guests
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
9.2 (106 Reviews)
2 Bedrooms 3 Guests
60 second walk to Lanikai Beach. 2 Bedrooms w/AC
9.0 (13 Reviews)
2 Bedrooms 4 Guests
Light and breezy Kailua apartment
9.0 (2 Reviews)
1 Bedroom 2 Guests
Private Luxury Home, Steps from the Beach w/AC, Ranch Beach House
8.0 (1 Review)
2 Bedrooms 4 Guests

About Windward Coast Vacation Rentals

With more than 577 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 1345.54 ft² on average, with prices averaging US $792 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.

Windward Coast Vacation Rental Frequently Asked Questions

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 577 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 145
Kalama Tract Vacation Rentals in Windward Coast, US 104
Lanikai Vacation Rentals in Windward Coast, US 64
Hawaii Kai Vacation Rentals in Windward Coast, US 51
Coconut Grove Vacation Rentals in Windward Coast, US 494
Enchanted Lake Vacation Rentals in Windward Coast, US 442
Keolu Hills Vacation Rentals in Windward Coast, US 423
Kuulei Tract Vacation Rentals in Windward Coast, US 483
Kamehame Ridge Vacation Rentals in Windward Coast, US 162
Queens Gate Vacation Rentals in Windward Coast, US 108