Vacation Rentals with Pool in Sleeping Giant Trailhead, HI: Compare 10+ Sites & Save

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  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Hawaii

  5.  Kapaa

  6.  Sleeping Giant Trailhead

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527 Best Vacation Rentals with Pool in Sleeping Giant Trailhead (Starting from $188)

Worldmark Kapaa Shore
Worldmark Kapaa Shore
Apartment
Kapaa, HI, USA
1.7k from Sleeping Giant Trailhead center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Self-catering

3 Bedrooms10 Guests
7.4

Good

33 reviews

$188
Average price / night
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Wailua Bay View 105 Oceanfront Condo
Wailua Bay View 105 Oceanfront Condo
Condo
Kapaʻa, HI, 96746, United States
1.4k from Sleeping Giant Trailhead center

AC, Barbecue, Dryer, Free Parking, Internet, Laundry, Microwave, No Smoking, Pool

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$533
Average price / night
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Wailua Bay View 115
Wailua Bay View 115
Apartment
Kapaa, HI, USA
1.7k from Sleeping Giant Trailhead center

Apartments, Accommodations, Pools, Lodgings, Beach, Places to stay, Family

2 Bedrooms4 Guests
8.8

Fabulous

4 reviews

$341
Average price / night
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Wailua Bay View 215 Oceanfront condo
Wailua Bay View 215 Oceanfront condo
Condo
Kapaʻa, HI, 96746, United States
1.5k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.2

Superb

5 reviews

$496
Average price / night
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Luxury Oceanfront ground floor condo
Luxury Oceanfront ground floor condo
House
Kapaa, HI, USA
1.8k from Sleeping Giant Trailhead center

Luxury, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Beach, Jacuzzis

2 Bedrooms6 Guests
New to Booking
$1339
Average price / night
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Bamboo Suite - Beachfront Ground Floor Condo - Lae Nani 316
Bamboo Suite - Beachfront Ground Floor Condo - Lae Nani 316
Condo
Kapaʻa, HI, 96746, United States
1.7k from Sleeping Giant Trailhead center

Barbecue, Free Parking, Internet, Laundry, Microwave, No Smoking, Outdoor Space, Pool, TV

2 Bedrooms4 Guests
9.4

Superb

20 reviews

$523
Average price / night
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Gardenfront Escape with Ocean Views at Kapa’a Sands 24
Gardenfront Escape with Ocean Views at Kapa’a Sands 24
House
Kapaa, HI, USA
1.8k from Sleeping Giant Trailhead center

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

2 Bedrooms4 Guests
8.7

Fabulous

13 reviews

$258
Average price / night
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Blue Hawaii - Top Floor Lae Nani 334 - Beachfront Condo with AC & WD
Blue Hawaii - Top Floor Lae Nani 334 - Beachfront Condo with AC & WD
Condo
Kapaʻa, HI, 96746, United States
1.7k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
10.0

Exceptional

80 reviews

$478
Average price / night
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Hale Kai at Kapaa Sands 15
Hale Kai at Kapaa Sands 15
House
Kapaa, HI, USA
1.8k from Sleeping Giant Trailhead center

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

2 Bedrooms4 Guests
8.4

Very Good

5 reviews

$381
Average price / night
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Luxury Gated Oceanfront Condo on Ground Floor
Luxury Gated Oceanfront Condo on Ground Floor
Condo
Kauai County, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

2 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$1040
Average price / night
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"Sea Haven" at the Wailua Bay View 305
"Sea Haven" at the Wailua Bay View 305
Apartment
Kapaa, HI, USA
1.8k from Sleeping Giant Trailhead center

Apartments, Cheap, Accommodations, Pools, Lodgings, Beach, Places to stay

1 Bedroom2 Guests
8.0

Good

1 reviews

$304
Average price / night
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Spectacular Oceanfront Corner Condo with Expansive Top Floor Views at Wailua Bay View!
Spectacular Oceanfront Corner Condo with Expansive Top Floor Views at Wailua Bay View!
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.6

Exceptional

127 reviews

$347
Average price / night
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Stunning Oceanfront Condo - The Seashore Hideaway, Wailua Bay View, Unit 208, Kapaa
Stunning Oceanfront Condo - The Seashore Hideaway, Wailua Bay View, Unit 208, Kapaa
Apartment
HI, USA
1.8k from Sleeping Giant Trailhead center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Beach, Places to stay, Condos

1 Bedroom2 Guests
New to Booking
$280
Average price / night
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\"Picture Perfect\" Oceanfront on the Top Floor at Wailua Bay View!
\"Picture Perfect\" Oceanfront on the Top Floor at Wailua Bay View!
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.2

Superb

135 reviews

$352
Average price / night
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"Picture Perfect" Oceanfront Beauty Top Floor at Wailua Bay View!
"Picture Perfect" Oceanfront Beauty Top Floor at Wailua Bay View!
House
HI, USA
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom4 Guests
8.0

Good

1 reviews

$326
Average price / night
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Breathtaking Oceanfront Views from Top Floor Condo at Wailua Bay View – A Coastal Paradise!
Breathtaking Oceanfront Views from Top Floor Condo at Wailua Bay View – A Coastal Paradise!
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.2

Superb

55 reviews

$344
Average price / night
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Stunning Oceanfront View Top Floor Condo at Wailua Bay View
Stunning Oceanfront View Top Floor Condo at Wailua Bay View
House
HI, USA
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.7

Exceptional

3 reviews

$326
Average price / night
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Charming Oceanfront Top Floor Condo at Wailua Bay with Stunning Views and Local Fisherman Sightings!
Charming Oceanfront Top Floor Condo at Wailua Bay with Stunning Views and Local Fisherman Sightings!
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.0

Fabulous

88 reviews

$349
Average price / night
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Coastal Charm Hideaway Oceanfront 2 Bedroom
Coastal Charm Hideaway Oceanfront 2 Bedroom
House
Kapaa, HI, USA
1.8k from Sleeping Giant Trailhead center

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

2 Bedrooms4 Guests
New to Booking
$306
Average price / night
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Breathtaking Sunrise View Oasis 3 Bedroom Sleeps 6, Oceanfront Luxury, Pool & AC
Breathtaking Sunrise View Oasis 3 Bedroom Sleeps 6, Oceanfront Luxury, Pool & AC
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

3 Bedrooms6 Guests
9.6

Exceptional

87 reviews

$1309
Average price / night
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Wailua Bay View 103
Wailua Bay View 103
Apartment
Kapaa, HI, USA
1.8k from Sleeping Giant Trailhead center

Apartments, Cheap, Accommodations, Pools, Serviced apartments, 3-star, Lodgings, Vacation rentals, Beach

3 Bedrooms10 Guests
8.3

Very Good

16 reviews

$240
Average price / night
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Wailua Bay View 108 Oceanfront, Ground floor condo centrally located
Wailua Bay View 108 Oceanfront, Ground floor condo centrally located
Condo
Wailua, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.6

Exceptional

71 reviews

$306
Average price / night
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Oceanfront!  Watch the surf from your private lanai! No hidden fees.  Book now!
Oceanfront! Watch the surf from your private lanai! No hidden fees. Book now!
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.4

Superb

183 reviews

$286
Average price / night
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Sunrise Oceanfront Luxury - 3BR Sleeps 6 - AC, 180° Ocean Views, Steps to Ocean!
Sunrise Oceanfront Luxury - 3BR Sleeps 6 - AC, 180° Ocean Views, Steps to Ocean!
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

3 Bedrooms6 Guests
9.0

Fabulous

57 reviews

$745
Average price / night
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Just finished complete renovation in March, 2025
Just finished complete renovation in March, 2025
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom4 Guests
9.4

Superb

120 reviews

$428
Average price / night
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Just renovated and right on the ocean!  No hidden fees.
Just renovated and right on the ocean! No hidden fees.
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.8

Exceptional

228 reviews

$300
Average price / night
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Ocean Front at Lae Nani Resort -  #234
Ocean Front at Lae Nani Resort - #234
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom4 Guests
9.4

Superb

113 reviews

$388
Average price / night
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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 Sleeping Giant Trailhead.

Where to stay in Sleeping Giant Trailhead? Best neighborhoods & areas

Sleeping Giant Trailhead Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 527 verified vacation rentals with a pool in Sleeping Giant Trailhead. 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 Sleeping Giant Trailhead vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $188 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Sleeping Giant Trailhead 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 Sleeping Giant Trailhead welcome pets. Currently, 1 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 Sleeping Giant Trailhead 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 Sleeping Giant Trailhead 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.