Oceanfront Rentals in Sleeping Giant Trailhead, HI: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
  3.  USA

  4.  Hawaii

  5.  Kapaa

  6.  Sleeping Giant Trailhead

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625 Best Oceanfront Rentals in Sleeping Giant Trailhead (Starting from $144)

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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Tranquil Shores | 2BR Condo | Walk to Beach & Dining
Tranquil Shores | 2BR Condo | Walk to Beach & Dining
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

2 Bedrooms4 Guests
9.6

Exceptional

5 reviews

$413
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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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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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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Oceanview Studio with private lanai, outdoor pool, BBQ area & beach access
Oceanview Studio with private lanai, outdoor pool, BBQ area & beach access
Apartment
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

Balcony, Barbecue, Dryer, Free Parking, Kitchen, Microwave, No Smoking, Outdoor Space, Pool

1 Bedroom2 Guests
9.6

Exceptional

4 reviews

$282
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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\"Ocean View Oasis\" Wailua Bay View 104 Overlooking the Beautiful Bay
\"Ocean View Oasis\" Wailua Bay View 104 Overlooking the Beautiful Bay
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom4 Guests
9.2

Superb

157 reviews

$363
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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\"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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Charming Wailua Bay View Oceanfront Top Floor with an Amazing View!
Charming Wailua Bay View Oceanfront Top Floor with an Amazing View!
House
HI, USA
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.0

Fabulous

3 reviews

$304
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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Spectacular Oceanfront View Top Floor Corner Condo at Wailua Bay View
Spectacular Oceanfront View Top Floor Corner Condo at Wailua Bay View
House
HI, USA
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
7.0

Good

1 reviews

$191
Average price / night
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Fern Grotto Inn - Lonely Planet Recommends our Cottages! VRBO Bear Stayed Here!
Fern Grotto Inn - Lonely Planet Recommends our Cottages! VRBO Bear Stayed Here!
House
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

3 Bedrooms6 Guests
9.8

Exceptional

21 reviews

$624
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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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
Wailua Bay View
Apartment
Sleeping Giant Trailhead, Kapaa, Hawaii, USA
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$144
Average price / night
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Paradise Found | 2BR Condo | Ocean  Front Views | With AC
Paradise Found | 2BR Condo | Ocean Front Views | With AC
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

2 Bedrooms6 Guests
10.0

Exceptional

101 reviews

$796
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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Oceanfront Top Floor Luxury Condo for 2 with AC - Wailua Bay View 312
Oceanfront Top Floor Luxury Condo for 2 with AC - Wailua Bay View 312
Condo
Kapaa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

1 Bedroom2 Guests
9.8

Exceptional

140 reviews

$384
Average price / night
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Aloha Manor is Elegant Gated Oceanfront Living!
Aloha Manor is Elegant Gated Oceanfront Living!
Condo
Kapaʻa, HI, 96746, United States
1.8k from Sleeping Giant Trailhead center

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

2 Bedrooms6 Guests
9.8

Exceptional

49 reviews

$536
Average price / night
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Oceanfront Top Floor Luxury Condo for 2 - Wailua Bay View 306
Oceanfront Top Floor Luxury Condo for 2 - Wailua Bay View 306
Condo
Kapaʻa, 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
9.8

Exceptional

83 reviews

$384
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 Oceanfront Rentals in Sleeping Giant Trailhead.

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

Sleeping Giant Trailhead Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 625 verified oceanfront rentals in Sleeping Giant Trailhead. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Sleeping Giant Trailhead vary depending on the property size, exact beachfront location, and season. Rates typically start from around $144 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Sleeping Giant Trailhead offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Sleeping Giant Trailhead welcome pets. Currently, 1 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Sleeping Giant Trailhead often include features designed for a comfortable coastal stay, such as View, Ocean View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.