Windward Coast Vacation Rentals

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

New Serene 2-bedroom bungalow in Waimanalo
Oahu Camper Adventures
FromUS $125 per night
9.4 (63 Reviews)
1 Bedroom 4 Guests
Paradise Bay Resort
FromUS $271 per night
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8.8 (1012 Reviews)
1 Bedroom 2 Guests
PRIVATE BEACHFRONT RENTAL
FromUS $489 per night
10.0 (158 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
Modern Luxury Beach House Kailua
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9.1 (73 Reviews)
3 Bedrooms 7 Guests
Hawaii's Hidden Hideaway Bed & Breakfast
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8.4 (67 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
Beachfront spectacular Kailua beach
FromUS $1,224 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Available and legal for stays less than 30 days.
10.0 (108 Reviews)
1 Bedroom 2 Guests
Cozy Custom Vacation Home
FromUS $376 per night
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8.9 (8 Reviews)
3 Bedrooms 8 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (105 Reviews)
1 Bedroom 2 Guests
Waimanalo Beach Cottages
8.8 (37 Reviews)
39 Bedrooms 50 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
KAILUA-STEPS TO THE BEACH
FromUS $192 per night
10.0 (86 Reviews)
2 Bedrooms 5 Guests
Paradise Bay Resort
FromUS $1,657 per night
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8.3 (502 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
Kailua Beachside home
FromUS $1,890 per night
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New
4 Bedrooms 14 Guests
Beautiful Kailua Hale Studio
FromUS $216 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 $427 per night
10.0 (22 Reviews)
1 Bedroom 4 Guests
Entire Fantastic Kailua Cottage. waiting for you!
10.0 (16 Reviews)
1 Bedroom 3 Guests
Beautiful Beachside Bungalow
FromUS $367 per night
10.0 (14 Reviews)
1 Bedroom 2 Guests
Cozy Kaaawa Studio with Mountain Views - 30 Day Min
9.8 (25 Reviews)
1 Bedroom 2 Guests
Peaceful Hawaii Paradise three minutes from Beautiful Beach
9.8 (20 Reviews)
1 Bedroom 2 Guests
Kalama Room
FromUS $104 per night
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New
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromUS $976 per night
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New
1 Bedroom 4 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
Paradise Under the Plumeria Tree
FromUS $267 per night
9.6 (49 Reviews)
2 Bedrooms 5 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 (164 Reviews)
1 Bedroom 2 Guests
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
9.4 (162 Reviews)
1 Bedroom 2 Guests

About Windward Coast Vacation Rentals

With more than 596 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 1355.19 ft² on average, with prices averaging US $795 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 596 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