Vacation Rentals with Pool in Sherwood Beach, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Hawaii

  5.  Waimanalo
  6.  Sherwood Beach

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133 Best Vacation Rentals with Pool in Sherwood Beach (Starting from $120)

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
Check Availability
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

$832
Average price / night
Check Availability
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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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
$378
Average price / night
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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
Check Availability
Luxury Estate~Spectacular Location~Heated Pool~Private Beach Access!
Luxury Estate~Spectacular Location~Heated Pool~Private Beach Access!
House
Waimanalo, HI, 96795, United States
3.1k from Sherwood Beach center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Elevator, Fitness Equipment

9 Bedrooms20 Guests
10.0

Exceptional

37 reviews

$10719
Average price / night
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Cozy Honolulu Retreat with Pool Access, Near Beaches
Cozy Honolulu Retreat with Pool Access, Near Beaches
Apartment
Waimanalo, HI, USA
5.9k from Sherwood Beach center

Apartments, Accommodations, Pools, Parking, Spa, Lodgings, Vacation rentals, Places to stay

1 Bedroom2 Guests
New to Booking
$147
Average price / night
Check Availability
Kailua Home Pool & Spa with amazing views
Kailua Home Pool & Spa with amazing views
House
Kailua, HI, 96734, United States
3.5k from Sherwood Beach center

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

3 Bedrooms7 Guests
9.8

Exceptional

29 reviews

$339
Average price / night
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Ocean View Hawaii Kai Studio
Ocean View Hawaii Kai Studio
Apartment
Sherwood Beach, Waimanalo, Hawaii, USA
6.5k from Sherwood Beach center

Wheelchair Accessible, Internet, Parking, Balcony/Terrace, Kitchen, Pool, Air Conditioner

1 Bedroom2 Guests
New to Booking
$120
Average price / night
Check Availability
Lavish Lanikai Hillside Estate: Oceanview w/Pool/Spa, AC & Mokulua Isle Views
Lavish Lanikai Hillside Estate: Oceanview w/Pool/Spa, AC & Mokulua Isle Views
House
Kailua, HI, 96734, United States
4.0k from Sherwood Beach center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Kitchen, Laundry

5 Bedrooms10 Guests
New to Booking
$3655
Average price / night
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Tranquil Marina Front Pool House Resort
Tranquil Marina Front Pool House Resort
House
Honolulu, HI, USA
6.6k from Sherwood Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

1 Bedroom8 Guests
New to Booking
$299
Average price / night
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Lanikai 5 star LUXURY PRIVATE OCEANFRONT, steps into the sea, pool, spa!
Lanikai 5 star LUXURY PRIVATE OCEANFRONT, steps into the sea, pool, spa!
House
Kailua, HI, 96734, United States
4.0k from Sherwood Beach center

AC, Barbecue, Breakfast Available, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$3007
Average price / night
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Kuapa Isle Gem Unit 419
Kuapa Isle Gem Unit 419
House
Honolulu, HI, USA
6.6k from Sherwood Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$233
Average price / night
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Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach!
Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach!
House
Kailua, HI, 96734, United States
4.3k from Sherwood Beach center

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

5 Bedrooms14 Guests
10.0

Exceptional

21 reviews

$1121
Average price / night
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Stylish 1BR Apartment with AC Full Kitchen & WD - Just Steps to the Beach
Stylish 1BR Apartment with AC Full Kitchen & WD - Just Steps to the Beach
Apartment
Kailua, HI, USA
6.9k from Sherwood Beach center

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

1 Bedroom4 Guests
New to Booking
$173
Average price / night
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Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai
Leaf House: Lux Retreat w/ Pool, Ocean Views & Outdoor Living Near Lanikai
House
Kailua, HI, 96734, United States
4.3k from Sherwood Beach center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Kitchen, Laundry

5 Bedrooms10 Guests
New to Booking
$1263
Average price / night
Check Availability
Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Charming Hale Mokolea in Lanikai 2BR 2BA Full Kitchen
Apartment
Kailua, HI, USA
6.9k from Sherwood Beach center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms4 Guests
New to Booking
$273
Average price / night
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Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
Villa Hui Hou: Luxe O'ahu Villa Private Oasis! Gourmet Kitchen & Media Room
House
Kailua, HI, 96734, United States
4.3k from Sherwood Beach center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Kitchen, Laundry, Microwave

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1110
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
7.7k from Sherwood Beach 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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Luxury Lanikai Oceanfront Home!
Luxury Lanikai Oceanfront Home!
House
Kailua, HI, 96734, United States
4.4k from Sherwood Beach center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
New to Booking
$2017
Average price / night
Check Availability
Kailua Beachside home
Kailua Beachside home
House
Kailua, HI, USA
8.2k from Sherwood Beach 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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Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach
Lanikai Cottage: Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach
House
Kailua, HI, 96734, United States
4.4k from Sherwood Beach center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$734
Average price / night
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Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
House
Kailua, HI, 96734, United States
4.5k from Sherwood Beach center

AC, Barbecue, Crib, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom4 Guests
9.6

Exceptional

44 reviews

$751
Average price / night
Check Availability
Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC
Hale Nani Lanikai: Beautiful Tropical Home Close to Beach w/Pool, Yard & AC
House
Kailua, HI, 96734, United States
4.7k from Sherwood Beach center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$591
Average price / night
Check Availability
Orchid House - Pool and Endless Ocean views!
Orchid House - Pool and Endless Ocean views!
House
Kailua, HI, 96734, United States
4.7k from Sherwood Beach center

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

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$1020
Average price / night
Check Availability
Resort-like, Kailua Beach, Lanikai Beach, Private Pool, AC, Tropical Retreat
Resort-like, Kailua Beach, Lanikai Beach, Private Pool, AC, Tropical Retreat
House
Kailua, HI, 96734, United States
4.8k from Sherwood Beach center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

73 reviews

$592
Average price / night
Check Availability
Steps to beach, tropical garden and private pool
Steps to beach, tropical garden and private pool
House
Kailua, HI, 96734, United States
4.9k from Sherwood Beach center

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

3 Bedrooms6 Guests
9.2

Superb

20 reviews

$650
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 Vacation Rentals with Pool in Sherwood Beach.

Where to stay in Sherwood Beach? Best neighborhoods & areas

Sherwood Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 133 verified vacation rentals with a pool in Sherwood Beach. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Sherwood Beach vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $120 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Sherwood Beach offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Sherwood Beach welcome pets. Currently, 2 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Sherwood Beach often include additional outdoor features such as Pool, View, and Ocean View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Sherwood Beach offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.