Oceanfront Rentals in Kaupo Bay, HI: Compare 10+ Sites & Save

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  6.  Kaupo Bay

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107 Best Oceanfront Rentals in Kaupo Bay (Starting from $124)

Cozy Honolulu Retreat with Pool Access, Near Beaches
Cozy Honolulu Retreat with Pool Access, Near Beaches
Apartment
Waimanalo, HI, USA
2.4k from Kaupo Bay center

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

1 Bedroom2 Guests
New to Booking
$147
Average price / night
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Honu Cottage:  Quiet, Oceanfront Comfort +  EPIC VIEWS!
Honu Cottage: Quiet, Oceanfront Comfort + EPIC VIEWS!
Cottage
Waimanalo, HI, 96795, United States
1.2k from Kaupo Bay center

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

1 Bedroom4 Guests
9.4

Superb

100 reviews

$299
Average price / night
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Waimanalo Beach Cottages
Waimanalo Beach Cottages
Cabin
Waimanalo, HI, USA
3.8k from Kaupo Bay 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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Makapu’u Hale, Literally oceanfront! VIEWS! A/C, 2 bedroom/2 bath
Makapu’u Hale, Literally oceanfront! VIEWS! A/C, 2 bedroom/2 bath
House
Waimanalo, HI, 96795, United States
1.3k from Kaupo Bay center

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

3 Bedrooms6 Guests
10.0

Exceptional

107 reviews

$629
Average price / night
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All Inclusive Waimanalo Beachlots, Sleeps 8
All Inclusive Waimanalo Beachlots, Sleeps 8
House
Waimanalo, HI, USA
4.7k from Kaupo Bay 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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Mana Kai at Waimanalo: Beachfront Luxury & Tranquility w/  Stunning Ocean Views
Mana Kai at Waimanalo: Beachfront Luxury & Tranquility w/ Stunning Ocean Views
House
Waimanalo, HI, 96795, United States
1.8k from Kaupo Bay center

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

4 Bedrooms10 Guests
New to Booking
$749
Average price / night
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Hale Maunalua
Hale Maunalua
House
Honolulu, HI, USA
6.1k from Kaupo Bay center

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

4 Bedrooms10 Guests
New to Booking
$628
Average price / night
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BEACH FRONT ESTATE - WHITE SANDY BEACH AND BLUE LAGOON /3 HOUSES/GATED/HOT TUB
BEACH FRONT ESTATE - WHITE SANDY BEACH AND BLUE LAGOON /3 HOUSES/GATED/HOT TUB
House
Waimanalo, HI, 96795, United States
2.0k from Kaupo Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

22 reviews

$1464
Average price / night
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Home with Sweeping Views, Pool & Yard
Home with Sweeping Views, Pool & Yard
House
Kaupo Bay, Waimanalo, Hawaii, USA
6.9k from Kaupo Bay center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$536
Average price / night
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Luxury Estate~Spectacular Location~Heated Pool~Private Beach Access!
Luxury Estate~Spectacular Location~Heated Pool~Private Beach Access!
House
Waimanalo, HI, 96795, United States
2.1k from Kaupo Bay 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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Lanikai Ohana Hale
Lanikai Ohana Hale
House
Kailua, HI, USA
9.1k from Kaupo Bay 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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Villa Luana – Saltwater Pool Retreat with Mountain Views , Near Sandy Beach
Villa Luana – Saltwater Pool Retreat with Mountain Views , Near Sandy Beach
Villa
Honolulu, HI, 96825, United States
2.2k from Kaupo Bay center

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

4 Bedrooms12 Guests
5.0

Review score

4 reviews

$427
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
9.5k from Kaupo Bay 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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Cozy Honolulu Retreat w/ Pool Access, Near Beaches
Cozy Honolulu Retreat w/ Pool Access, Near Beaches
Apartment
Honolulu, HI, 96825, United States
2.4k from Kaupo Bay center

Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Patio, Pool, TV, Washer

1 Bedroom2 Guests
9.8

Exceptional

9 reviews

$124
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
9.8k from Kaupo Bay 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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Newly Renovated and Listed 3 Bedroom 2 bathroom Home
Newly Renovated and Listed 3 Bedroom 2 bathroom Home
House
Honolulu, HI, 96825, United States
2.5k from Kaupo Bay center

Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms8 Guests
8.0

Good

5 reviews

$724
Average price / night
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Serene Sandy Beach Golf Course Home
Serene Sandy Beach Golf Course Home
House
Honolulu, HI, 96825, United States
2.6k from Kaupo Bay center

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

3 Bedrooms6 Guests
New to Booking
$347
Average price / night
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Executive Balinese Vacation Home in Hawaii Kai
Executive Balinese Vacation Home in Hawaii Kai
House
Honolulu, HI, 96825, United States
3.0k from Kaupo Bay center

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

6 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1042
Average price / night
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Honolulu Waterfront Oasis
Honolulu Waterfront Oasis
House
Honolulu, HI, 96825, United States
3.6k from Kaupo Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

31 reviews

$523
Average price / night
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Hale Pohaku, Waimanalo - Lic.#1990/NUC-1689
Hale Pohaku, Waimanalo - Lic.#1990/NUC-1689
House
Waimanalo, HI, 96795, United States
3.8k from Kaupo Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

61 reviews

$1432
Average price / night
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Beach Paradise Hawaiian Vacation Home: 300 feet From White Sand Beach, A/C
Beach Paradise Hawaiian Vacation Home: 300 feet From White Sand Beach, A/C
House
Waimanalo, HI, 96795, United States
3.8k from Kaupo Bay center

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

3 Bedrooms6 Guests
9.8

Exceptional

13 reviews

$367
Average price / night
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Island Beach Cottage with a deck !! Gated, Air Conditioning,steps to beach
Island Beach Cottage with a deck !! Gated, Air Conditioning,steps to beach
Cottage
Waimanalo, HI, 96795, United States
4.1k from Kaupo Bay center

AC, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms4 Guests
9.8

Exceptional

83 reviews

$203
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
4.2k from Kaupo Bay center

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

4 Bedrooms8 Guests
9.8

Exceptional

122 reviews

$2016
Average price / night
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Very Private, Peaceful,& Prestigious - Beautiful Ocean, Other Islands &Mtn Views
Very Private, Peaceful,& Prestigious - Beautiful Ocean, Other Islands &Mtn Views
House
Honolulu, HI, 96825, United States
4.3k from Kaupo Bay center

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

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$233
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
4.6k from Kaupo Bay center

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

2 Bedrooms9 Guests
9.0

Fabulous

94 reviews

$376
Average price / night
Check Availability
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
4.7k from Kaupo Bay center

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

2 Bedrooms6 Guests
8.8

Fabulous

50 reviews

$317
Average price / night
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Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool
Ohana Kai: Modern Water Front Condo w/Gorgeous Views, A/C, Yard, & Shared Pool
Condo
Honolulu, HI, 96825, United States
4.7k from Kaupo Bay center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$422
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 Kaupo Bay.

Where to stay in Kaupo Bay? Best neighborhoods & areas

Kaupo Bay Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 107 verified oceanfront rentals in Kaupo Bay. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Kaupo Bay vary depending on the property size, exact beachfront location, and season. Rates typically start from around $124 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 Kaupo Bay 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 Kaupo Bay welcome pets. Currently, 5 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 Kaupo Bay often include features designed for a comfortable coastal stay, such as Oceanfront, Ocean View, and View. 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.