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Vacation Rentals in Kaupulehu, Hawaii

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about Kaupulehu

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Kaupulehu, Hawaii vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Kaupulehu are added and updated every week!

Compared to hotels, Kaupulehu vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Kaupulehu, Hawaii Vacation Rentals and Tourism

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Kaupulehu things to do

 

Ocean Sports

We took the Sunset Dinner Cruise. We were picked up promptly on time from the hotel with a few stops to pick up other people and then driven to the pier to...read more

 

Kekaha Kai State Park

Don't miss the turn to get in. Keep going down for 1.5 or so... Pretty bumpy but if you have a Jeep it's not so bad. Restrooms and BBQ. The beach is...read more

 

Anaeho'omalu Bay

Anaeho'omalu Bay is off Waikoloa Beach Drive and is home to the Waikoloa Canoe Club, and the Lava Lava Beach Club (restaurant, and beachfront bar, open to...read more

 

Blue Wilderness Dive Adventures

Great trip with these guys! Went scuba diving with my son. Did a two tank dive last week and my wife and other two boys snorkelers. Guides were Kevin and...read more

 

Ocean Rider Seahorse Farm

For starters, the tour is pricey. (Current price is $40/adult and $30/child ($26/toddler). Discount for kama'aina is 10% off; 24 hour advance reservation on...read more

 

Atlantis Submarines Kona

Friendly staff and clean boat and sub although this tour is not for those who are claustrophobic- even just a little. I'm not but when they close the hatch,...read more

 

Bikeworks Beach and Sports

Easy, friendly and fast! Super kind and knowledgable staff that take the time to set up the bike to make it feel as if it was tailor made for you. A...read more

 

Kuki'o Beach

This is where I found my "happy place" on the Big island! It is attached to a resort, but since all beaches are public in Hawaii, if you go fairly early,...read more

 

Hualalai Golf Club

Nice course with some spectacular views. Course is fairly open but the greens are tough. In the summer you will be beat down by the sun. It is hot, very...read more

 

Kua Bay

This is a beautiful beach with great waves for boogie boarding. That said, it is also very crowded with lots of rocks and not a lot of the soft, white,...read more

 

Jack's Diving Locker

My husband and I just returned from a week of excellent diving with Jack's. We did a combination of basic and advanced boat dives, and enjoyed all of them....read more

 

King's Trail - Malama Petroglyph Trail

King's Trail (or Ala Kahakai), is located at the entrance to Waikoloa Fairway Villas, off Waikoloa Beach Dr. Just make a right turn when you see the Kings...read more

 

Kikaua Point Park

Great spot to get married. How do I know? Because I got married here.... The "wedding area" is a grassy knoll by the beach - perfect setting for a small...read more

 

Kona Hawaii Fishing with Captain Jeff Rogers

Folks, I have fished all over the world and Capt'n Jeff is a very knowledgeable fisherman and a willing teacher. Of course, if you think you know it all,...read more

 

Kona Coast State Park

This area is also known as Kekaha Kai State Park. This is one of the best beach parks in Kona, if not on the entire island or in the whole state. I have...read more

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Oceanfront and exclusive 6 bedroom Estate near Mauna Kea Beach
Kaupulehu House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 8
  • rates (USD) $2,850 - $3,500 /nt
    $19,950 - $42,000 /wk
    $85,500 - $105,000 /mth
 
 
 
 
 

5 reviews write a review

Luxury 3bdrm w/Ocean View @ Four Seasons Resort Hualalai
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,000 - $1,300 /nt
    $7,000 - $19,600 /wk
    $32,900 - $39,000 /mth
 
 
 
 
 

5 reviews write a review

3 Bdrm 3.5 Bath Luxury Ocean View Suites, Hualalai Golf Villas at Four Seasons
Kaupulehu Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $9,800 /wk
    $35,000 /mth
 
 
 
 
 

4 reviews write a review

Hualalai's Best Location - Near the Ocean and the Four Seasons!
Kaupulehu Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $1,100 - $1,300 /nt
    $7,700 - $16,800 /wk
    $33,000 - $39,000 /mth
 
 
 
 
 

11 reviews write a review

Four Seasons Resort Hualalai / Hualalai Resort
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,100 /nt
 
 
 
 
 

4 reviews write a review

Four Seasons Hualalai Luxury Villa, 3+ Bedrooms, 2 Golf Carts
Kaupulehu Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $950 - $1,895 /nt
 
 
 
 
 

2 reviews write a review

Hualalai Resort 5 Bedroom; Offering Short-term Special Rates!
Kaupulehu House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $1,800 - $2,200 /nt
    $12,600 - $35,000 /wk
    $54,000 - $84,000 /mth
 
 
 
 
 

3 reviews write a review

15th Fairway of Hualalai Resort- Luxury 3 bdrm/3.5 bath villa
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,000 - $1,300 /nt
    $7,000 - $19,600 /wk
    $32,900 - $39,000 /mth
 
 
 
 
 

2 reviews write a review

Elegant remodeled town home - near Four Seasons.
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,200 - $1,300 /nt
    $8,400 - $21,000 /wk
    $36,000 - $39,000 /mth
 
 
 
 
 

2 reviews write a review

Two Bedroom Ocean View - Close to Four Seasons
Kaupulehu Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $900 /nt
    $6,300 - $15,400 /wk
    $27,000 /mth
 
 
 
 
 

6 reviews write a review

Luxurious Hualalai Villa Near 4 Seasons
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 8
  • baths
  • rates (USD) $1,100 - $1,300 /nt
    $7,700 - $19,600 /wk
    $33,000 - $39,000 /mth
 
 
 
 
 

1 reviews write a review

Ideal Family Villa Near Four Seasons Resort Hualalai
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,100 - $1,300 /nt
    $7,700 - $21,000 /wk
    $33,000 - $39,000 /mth
 
 
 
 
 

5 reviews write a review

Ocean view Hainoa 19 Hualalai- access to Kapalua resort, near beach & golf
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 8
  • baths 3
  • rates (USD) $1,000 - $2,500 /nt
    $7,000 - $17,500 /wk
    $28,000 - $70,000 /mth
 
 
 
 
 

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Four Seasons Luxury 3BD Waiulu Villa, Upper Level, Flawless and Chic with Incredible Views
Kaupulehu House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,200 - $2,800 /nt
    $8,400 - $19,600 /wk
 
 
 
 
 

6 reviews write a review

Ocean View Fairway Villa - July Cancellation Special!
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 6
  • baths 3
  • rates (USD) $1,200 - $1,300 /nt
    $8,400 - $21,000 /wk
    $36,000 - $39,000 /mth
 
 
 
 
 

1 reviews write a review

Custom Luxury Residence in Exclusive Hualalai Resort
Kaupulehu House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 5
  • baths 3
  • rates (USD) $1,800 - $2,200 /nt
    $12,600 - $24,500 /wk
    $54,000 - $66,000 /mth
 
 
 
 
 

1 reviews write a review

5-Star Luxury Waiulu Villa Retreat (Upper Level)
Kaupulehu Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD)
 
 
 
 
 

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Hillside Penthouse Villa ~ Billion Dollar Ocean and Beach Views!
Kaupulehu Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $1,300 /nt
 
 
 
 
 

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Hualalai Kaulu Villa Retreat ~ Golf Carts, Maid & Shopping Service Included
Kaupulehu Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 6
  • baths 3
  • rates (USD)
 
 
 
 
 

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Hualalai Oceanfront Golf Villa with Private Spa Overlooks 18th Hole
Kaupulehu Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $1,600 /nt
 
 
 
 
 

2 reviews write a review

Maluhia Retreat at Hualalai
Kaupulehu Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

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Kahikole Kai Retreat at Hualalai
Kaupulehu House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 9
  • baths
  • rates (USD)
 
 
 
 
 

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Hualalai Luxury at Lalani Lau'eki
Kaupulehu House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $20,300 /wk
 
 
 
 
 

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Stunning Ocean Views From Expansive Lanai- Best Location At Hualalai Resort!
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 6
  • baths
  • rates (USD) $1,400 - $3,700 /nt
 
 
 
 
 

4 reviews write a review

Two Bedroom Ocean-View, Ground-Level with Lawn, Tropical Shower
Kaupulehu Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $745 - $1,650 /nt
    $5,215 - $11,550 /wk
 
 
 
 
 

14 reviews write a review

Large Hualalai Estate Home at Hualalai, Four Seasons Resort
Kaupulehu Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • owner badgeowner badge
  • sleeps 10
  • baths 6
  • rates (USD) $3,799 - $10,000 /nt
 
 
 
 
 

8 reviews write a review

Kaimupulehu Grand Estate at Hualalai - Available in December!
Kaupulehu Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • sleeps 12
  • baths
  • rates (USD)
 
 
 
 
 

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Hualalai Resort Estate Home
Kaupulehu House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $2,200 - $5,000 /nt
    $15,400 - $21,000 /wk
 
 
 
 
 

4 reviews write a review

Fabulous Location - Up Close Golf Course And Ocean Views!
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $850 /nt
 
 
 
 
 

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Fantastic Private Home At Hualalai Resort. Great Location With 2 Golf Carts
Kaupulehu House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $2,200 /nt
 
 
 
 
 

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Beautiful And Private Residence At Four Seasons Hualalai Resort
Kaupulehu House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $2,500 /nt
    $17,500 /wk
    $75,000 /mth
 
 
 
 
 

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Four Seasons Hualalai Prime Oceanfront Golf Villa
Kaupulehu Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

2 reviews write a review