Windward Coast Vacation Rentals

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

Modern Luxury Beach House Kailua
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9.1 (85 Reviews)
3 Bedrooms 7 Guests
Paradise Bay Resort
FromZA R4,413 per night
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8.8 (1009 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
PRIVATE BEACHFRONT RENTAL
FromZA R7,949 per night
10.0 (163 Reviews)
1 Bedroom 2 Guests
Oahu Camper Adventures
FromZA R2,119 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
Beachfront spectacular Kailua beach
FromZA R20,748 per night
9.0 (1 Review)
4 Bedrooms 8 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
FromZA R7,448 per night
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8.9 (8 Reviews)
3 Bedrooms 8 Guests
Available and legal for stays less than 30 days.
10.0 (109 Reviews)
1 Bedroom 2 Guests
Waimanalo Beach Cottages
FromZA R8,594 per night
8.8 (31 Reviews)
39 Bedrooms 50 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (106 Reviews)
1 Bedroom 2 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
Paradise Bay Resort
FromZA R28,088 per night
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8.3 (502 Reviews)
29 Bedrooms 23 Guests
KAILUA-STEPS TO THE BEACH
FromZA R3,246 per night
10.0 (87 Reviews)
2 Bedrooms 5 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
FromZA R32,037 per night
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New
4 Bedrooms 14 Guests
Beautiful Kailua Hale Studio
FromZA R6,458 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromZA R2,385 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
FromZA R2,264 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
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow
10.0 (29 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
FromZA R6,234 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromZA R6,998 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
FromZA R6,219 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
Beautiful Kailua Hale 1 Bedroom
FromZA R5,859 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
Kalama Room
FromZA R1,763 per night
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New
1 Bedroom 2 Guests
Peaceful Hawaii Paradise three minutes from Beautiful Beach
9.8 (20 Reviews)
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromZA R16,544 per night
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New
1 Bedroom 4 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
9.6 (148 Reviews)
1 Bedroom 3 Guests
Oahu Ohana Vans LLC
FromZA R5,085 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
FromZA R4,528 per night
9.6 (49 Reviews)
2 Bedrooms 5 Guests
Kailua Beachside Studio - Monet Room
FromZA R3,644 per night
9.6 (36 Reviews)
1 Bedroom 2 Guests
Lanikai Studio with Stunning Ocean View looking out at the Mokulua Islands
9.6 (35 Reviews)
1 Bedroom 2 Guests
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
9.6 (13 Reviews)
2 Bedrooms 4 Guests
La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)
9.6 (10 Reviews)
1 Bedroom 3 Guests

About Windward Coast Vacation Rentals

With more than 599 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 1361.76 ft² on average, with prices averaging ZA R13,589 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 599 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