Short-Term Rentals in Windward Coast, USA: Compare 10+ Sites & Save

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224 Best Short-Term Rentals in Windward Coast (Starting from $104)

@ Marbella Lane - Sunshine Seascape Ocean View
@ Marbella Lane - Sunshine Seascape Ocean View
House
Kaneohe, HI, USA
3.3k from Windward Coast center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$573
Average price / night
Check Availability
Kailua Condo / Townhouse on Oahu 30 day period 7 day min
Kailua Condo / Townhouse on Oahu 30 day period 7 day min
Apartment
Kailua, HI, 96734, United States
2.3k from Windward Coast center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$383
Average price / night
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Kalama Room
Kalama Room
Apartment
Kailua, HI, USA
4.2k from Windward Coast center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

1 Bedroom2 Guests
New to Booking
$104
Average price / night
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Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
House
Kailua, HI, 96734, United States
2.6k from Windward Coast center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

89 reviews

$1720
Average price / night
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Your Perfect Home Charming 2BR2BA Apartment with Full Kitchen WD & AC
Your Perfect Home Charming 2BR2BA Apartment with Full Kitchen WD & AC
Apartment
Kailua, HI, USA
4.2k from Windward Coast center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

2 Bedrooms6 Guests
New to Booking
$261
Average price / night
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Kailua Palms Guest House with Pool and Views!  Parking and wi-fi included
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
Cottage
Kailua, HI, 96734, United States
2.7k from Windward Coast center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
9.6

Exceptional

13 reviews

$591
Average price / night
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Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
4.3k from Windward Coast center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms14 Guests
New to Booking
$1890
Average price / night
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Hoʻonānea I Loko Kailua
Hoʻonānea I Loko Kailua
House
Kailua, HI, 96734, United States
2.8k from Windward Coast center

AC, Dryer, Fitness Equipment, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
New to Booking
$520
Average price / night
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Sunny Kailua Home with Covered Lanai 1 Mi to Beach!
Sunny Kailua Home with Covered Lanai 1 Mi to Beach!
House
Kailua, HI, USA
4.7k from Windward Coast center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms7 Guests
New to Booking
$209
Average price / night
Check Availability
Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches
Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches
House
Kailua, HI, 96734, United States
2.8k from Windward Coast center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
9.0

Fabulous

89 reviews

$372
Average price / night
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Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps to the Center of the Beach home
House
Kailua, HI, USA
4.8k from Windward Coast center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

5 Bedrooms10 Guests
New to Booking
$2342
Average price / night
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Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen
Beachside Kailua Beach House by Gather w/ Pool & Gourmet Kitchen
House
Kailua, HI, 96734, United States
3.0k from Windward Coast center

AC, Balcony, Dryer, Fireplace, Free Parking, Hot Tub, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
New to Booking
$686
Average price / night
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Cottage in Kailua Town
Cottage in Kailua Town
Apartment
Kailua, HI, USA
5.0k from Windward Coast center

Air Conditioner, Security/Safety, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$252
Average price / night
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Luxurious, Private Hilltop Retreat with Postcard View -- minutes to Kailua Beach
Luxurious, Private Hilltop Retreat with Postcard View -- minutes to Kailua Beach
House
Kaneohe, HI, 96744, United States
3.0k from Windward Coast center

AC, Free Parking, Internet, No Smoking

2 Bedrooms4 Guests
New to Booking
$590
Average price / night
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Modern Luxury Beach House Kailua
Modern Luxury Beach House Kailua
House
Windward Coast, USA
5.0k from Windward Coast center

Luxury, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms7 Guests
9.1

Superb

73 reviews

$275
Average price / night
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Close to Kailua Beach-AC's-Renovated/Upgraded-Fenced Backyard-Patio-Laundry
Close to Kailua Beach-AC's-Renovated/Upgraded-Fenced Backyard-Patio-Laundry
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
9.0

Fabulous

2 reviews

$373
Average price / night
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Cozy Custom Vacation Home
Cozy Custom Vacation Home
House
Kaneohe, HI, USA
5.0k from Windward Coast center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
8.9

Fabulous

8 reviews

$376
Average price / night
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Absolutely Oceanfront - 60' Waterfall Lap Pool
Absolutely Oceanfront - 60' Waterfall Lap Pool
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
9.4

Superb

168 reviews

$686
Average price / night
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Private One Bedroom Side House close to Kailua
Private One Bedroom Side House close to Kailua
House
Kailua, HI, USA
5.2k from Windward Coast center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
3.5

Review score

2 reviews

$235
Average price / night
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Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
Apartment
Kailua, HI, 96734, United States
3.1k from Windward Coast center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
9.4

Superb

163 reviews

$633
Average price / night
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Kailani Loft, Kailua Coconut Grove 1-bedroom
Kailani Loft, Kailua Coconut Grove 1-bedroom
Apartment
Kailua, HI, USA
5.2k from Windward Coast center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering

1 Bedroom3 Guests
9.3

Superb

47 reviews

$193
Average price / night
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Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Laundry
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
9.8

Exceptional

76 reviews

$240
Average price / night
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Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua
Tropical Gardens,4 Bdr, Large Yard, Pool, 5 min Walk to Beach,Koi Pond, Kailua
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

Barbecue, Crib, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.8

Exceptional

45 reviews

$426
Average price / night
Check Availability
 New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach
New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach
Apartment
Kailua, HI, 96734, United States
3.1k from Windward Coast center

Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.8

Exceptional

30 reviews

$240
Average price / night
Check Availability
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
Hale Ohana: Kailua Retreat w/hot tub, Tropical Pool, Walk to Beach
House
Kailua, HI, 96734, United States
3.1k from Windward Coast center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1122
Average price / night
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Hale Maluhia - Gorgeous Kaneohe Bay Home
Hale Maluhia - Gorgeous Kaneohe Bay Home
House
Kaneohe, HI, 96744, United States
3.2k from Windward Coast center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

24 reviews

$354
Average price / night
Check Availability
KAILUA-STEPS TO THE BEACH
KAILUA-STEPS TO THE BEACH
House
Kailua Beach, HI, 96734, United States
3.3k from Windward Coast center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

87 reviews

$182
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Windward Coast.

Where to stay in Windward Coast? Best neighborhoods & areas

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VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Windward Coast Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 224 verified short-term rentals in Windward Coast, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Windward Coast vary depending on location, property size, and travel dates. Rates typically start from around $104 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Windward Coast include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Windward Coast, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Windward Coast often include amenities such as Internet, View, and Ocean View, providing a comfortable and convenient stay.

Short-term rentals in Windward Coast are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.