Owner Direct Vacation Rentals in Sherwood Beach

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  6.  Sherwood Beach

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335 Sherwood Beach Vacation Homes From $170

Looking for the ideal vacation rental in Sherwood Beach? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

All Inclusive Waimanalo Beachlots, Sleeps 8
All Inclusive Waimanalo Beachlots, Sleeps 8
House
Waimanalo, HI, USA
0.7k from Sherwood Beach center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Jacuzzis

2 Bedrooms8 Guests
New to Booking
$325
Average price / night
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House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more
House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more
House
Waimanalo, HI, 96795, United States
0.6k from Sherwood Beach center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Hot Tub, Internet

2 Bedrooms9 Guests
9.0

Fabulous

94 reviews

$346
Average price / night
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Waimanalo Beach Cottages
Waimanalo Beach Cottages
Cabin
Waimanalo, HI, USA
1.5k from Sherwood Beach center

Accommodations, Parking, Lodges, Cabins, Pet-friendly, Lodgings, Places to stay, Self-catering

39 Bedrooms50 Guests
8.8

Fabulous

51 reviews

$507
Average price / night
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Wonderful executive home steps from a gorgeous beach 30 night stay required!
Wonderful executive home steps from a gorgeous beach 30 night stay required!
House
Waimanalo, HI, 96795, United States
0.7k from Sherwood Beach center

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

4 Bedrooms6 Guests
10.0

Exceptional

31 reviews

$295
Average price / night
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Newly Upgraded Private Home in Kailua
Newly Upgraded Private Home in Kailua
Villa
Sherwood Beach, Waimanalo, Hawaii, USA
4.2k from Sherwood Beach center

Pet Friendly, Internet, Air Conditioner, Parking, Child Friendly

1 Bedroom4 Guests
New to Booking
$170
Average price / night
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Great Price! 1000sf Gated New House Steps from Waimanalo Beach
Great Price! 1000sf Gated New House Steps from Waimanalo Beach
House
Waimanalo, HI, 96795, United States
0.7k from Sherwood Beach center

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

2 Bedrooms4 Guests
New to Booking
$184
Average price / night
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Seabreeze Hawaii Kai
Seabreeze Hawaii Kai
House
Honolulu, HI, USA
4.2k from Sherwood Beach center

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

3 Bedrooms6 Guests
New to Booking
$231
Average price / night
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Great Price! 2600sf 5 bedroom 3 bath Gated New House Steps from Waimanalo Beach
Great Price! 2600sf 5 bedroom 3 bath Gated New House Steps from Waimanalo Beach
House
Waimanalo, HI, 96795, United States
0.7k from Sherwood Beach center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

5 Bedrooms8 Guests
New to Booking
$341
Average price / night
Check Availability
Lanikai Ohana Hale
Lanikai Ohana Hale
House
Kailua, HI, USA
4.5k from Sherwood Beach center

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

1 Bedroom4 Guests
New to Booking
$976
Average price / night
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4 Bedroom/ 3 Bathroom Private Home
4 Bedroom/ 3 Bathroom Private Home
House
Waimanalo, HI, 96795, United States
0.8k from Sherwood Beach center

AC, Free Parking, Internet, Pool

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$842
Average price / night
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Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Relax at Kapakai Cottage 2-Bedroom Comfort with Full Kitchen & WD
Apartment
Kailua, HI, USA
4.7k from Sherwood Beach center

Apartments, Accommodations, Parking, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$219
Average price / night
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Waimanalo Beach Cottage
Waimanalo Beach Cottage
House
Waimanalo, HI, 96795, United States
0.8k from Sherwood Beach center

AC, Extra Bed, Free Parking, Internet, Kitchen, No Smoking

2 Bedrooms5 Guests
New to Booking
$316
Average price / night
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A Place of Peace Where Heaven Meets the Ocean
A Place of Peace Where Heaven Meets the Ocean
House
Kailua, HI, USA
4.7k from Sherwood Beach center

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

2 Bedrooms4 Guests
New to Booking
$662
Average price / night
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Beachfront Executive Retreat - The Waimanalo Villa
Beachfront Executive Retreat - The Waimanalo Villa
House
Waimanalo, HI, 96795, United States
0.9k from Sherwood Beach center

AC, Balcony, Crib, Dryer, Free Parking, Internet, Kitchen, Microwave, No Smoking

1 Bedroom8 Guests
New to Booking
$583
Average price / night
Check Availability
Upscale Kailua Getaway Steps to Swim Beach!
Upscale Kailua Getaway Steps to Swim Beach!
House
Kailua, HI, USA
5.5k from Sherwood Beach center

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

3 Bedrooms6 Guests
New to Booking
$936
Average price / night
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Waimanalo Beach Family Home,  2 Bed, 2 Bath, Steps to Beach
Waimanalo Beach Family Home, 2 Bed, 2 Bath, Steps to Beach
House
Waimanalo, HI, 96795, United States
0.9k from Sherwood Beach center

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

2 Bedrooms6 Guests
8.8

Fabulous

50 reviews

$279
Average price / night
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2 Bedroom Cottage With Hot Tub
2 Bedroom Cottage With Hot Tub
Cottage
Waimanalo, HI, 96795, United States
0.9k from Sherwood Beach center

AC, Barbecue, Crib, Free Parking, Internet, Kitchen, Microwave, Outdoor Space, Patio

2 Bedrooms5 Guests
New to Booking
$404
Average price / night
Check Availability
Bright 3-bedroom tropical house in Waimanalo Beach Lots
Bright 3-bedroom tropical house in Waimanalo Beach Lots
House
Waimanalo, HI, 96795, United States
1.0k from Sherwood Beach center

Barbecue, Dryer, Free Parking, Internet, Laundry, Microwave, No Smoking, TV, Washer

3 Bedrooms6 Guests
New to Booking
$332
Average price / night
Check Availability
BEACHFRONT with Hot Tub! White Sand Beach with Sandy Bottom Bay Sleeps 8-18
BEACHFRONT with Hot Tub! White Sand Beach with Sandy Bottom Bay Sleeps 8-18
House
Waimanalo, HI, 96795, United States
1.0k from Sherwood Beach center

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

4 Bedrooms18 Guests
10.0

Exceptional

12 reviews

$945
Average price / night
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Oceanfront Gem! Private 4 bdr beach home on long white sandy Waimanalo Beach.
Oceanfront Gem! Private 4 bdr beach home on long white sandy Waimanalo Beach.
House
waimanalo, HI, 96795, United States
1.1k from Sherwood Beach center

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

4 Bedrooms8 Guests
9.8

Exceptional

124 reviews

$2334
Average price / night
Check Availability
Great Price! 3800sf 7 rooms 4 baths Huge Gated House Steps from Waimanalo Beach
Great Price! 3800sf 7 rooms 4 baths Huge Gated House Steps from Waimanalo Beach
House
Waimanalo, HI, 96795, United States
1.1k from Sherwood Beach center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

7 Bedrooms10 Guests
8.0

Good

4 reviews

$440
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental 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 Vacation Rentals in Sherwood Beach.

Sherwood Beach Vacation Rentals on the Map

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Frequently Asked Questions

There are a lot of options in Sherwood Beach. If you plan on staying in the Sherwood Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Sherwood Beach

You can explore 335 verified vacation rentals in Sherwood Beach. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Sherwood Beach vary depending on the season, property size, and location. Rates typically start from around $170 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Sherwood Beach include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Sherwood Beach welcome pets. Currently, 6 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Sherwood Beach often include amenities such as View, Oceanfront, and Ocean View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.