Windward Coast Vacation Rentals

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

PRIVATE BEACHFRONT RENTAL
FromCA $666 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
Paradise Bay Resort
FromCA $355 per night
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8.8 (1009 Reviews)
1 Bedroom 2 Guests
Modern Luxury Beach House Kailua
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9.1 (73 Reviews)
3 Bedrooms 7 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
FromCA $170 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 (109 Reviews)
1 Bedroom 2 Guests
Beachfront spectacular Kailua beach
FromCA $1,669 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (105 Reviews)
1 Bedroom 2 Guests
Cozy Custom Vacation Home
FromCA $599 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
FromCA $261 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
BEACHFRONT! Barefoot living on the best spot on Lanikai Beach!
10.0 (77 Reviews)
1 Bedroom 4 Guests
Paradise Bay Resort
FromCA $2,259 per night
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8.3 (502 Reviews)
29 Bedrooms 23 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
Beautiful Kailua Hale Studio
FromCA $294 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromCA $192 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Kailua Beachside home
FromCA $2,576 per night
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New
4 Bedrooms 14 Guests
Footsteps to Hawaii's Best Beach
FromCA $182 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
Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C
10.0 (29 Reviews)
2 Bedrooms 4 Guests
The Banyan Beach Bungalow
FromCA $501 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromCA $553 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 $500 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck
10.0 (12 Reviews)
2 Bedrooms 2 Guests
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
10.0 (10 Reviews)
1 Bedroom 4 Guests
Kalama Room
FromCA $142 per night
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New
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromCA $1,330 per night
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New
1 Bedroom 4 Guests
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
9.6 (142 Reviews)
2 Bedrooms 4 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Oahu Ohana Vans LLC
FromCA $409 per night
New
4 Bedrooms 4 Guests
Paradise Under the Plumeria Tree
FromCA $364 per night
9.6 (49 Reviews)
2 Bedrooms 5 Guests
Kailua Beachside Studio - Monet Room
FromCA $300 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
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 (167 Reviews)
1 Bedroom 2 Guests

About Windward Coast Vacation Rentals

With more than 597 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 1359.29 ft² on average, with prices averaging CA $1,080 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 597 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 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