Captain Cook Vacation Rentals

Escape to the scenic beauty of South Kona with our exclusive collection of Captain Cook vacation rentals. This peaceful area of the Big Island offers an authentic Hawaiian experience, with lush coffee farms, panoramic ocean views, and a relaxed, local vibe. Choose from charming cottages, oceanfront homes, and tropical hideaways perfect for exploring famous spots like Kealakekua Bay and Pu'uhonua o Hōnaunau National Historical Park. Our rentals provide a private retreat while keeping you close to popular beaches like Two Step Beach, ideal for snorkeling and swimming with dolphins.

Whether you're seeking adventure or tranquility, Captain Cook is the perfect base for discovering the Big Island’s wonders. Spend your mornings touring nearby coffee farms, your afternoons at Honaunau Bay, and your evenings stargazing from your private lanai. Browse our full selection of Captain Cook vacation rentals and find your dream Hawaiian escape today. With easy access to Kailua-Kona vacation rentals as well, you’ll have the flexibility to explore even more of the island’s breathtaking beauty!

Purple House in Paradise


Our 700 sq. foot 2 story home, Miloli'i Beach Bungalow, is located 33 miles south of Kona in Miloli'i. If you are looking to get away from the hustle and bustle of the city, you've come to the right place. Our little house in paradise,

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $283 
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Makai Hideaway 600ft from Ocean Giant Deck/GameroomnAsk about 10 day special

Ask about 10 day specials/ 2 person stays and 8th night free if you book a 7th night stay!!!!
https://www.youtube.com/watch?v=VigSB3M4z3w
The above is the link to a video of my house.
Makai Hideaway is quiet and peaceful. Unwind and

  • 3 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Captain Cook
from $295 
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Luxury And Aloha Await You! Relaxation, Great Snorkeling, Large Unit

South Kona Hideaway is near some of the best snorkeling Hawaii has to offer. We are situated between Honaunau (Place of Refuge) and Kealakekua Bay at an elevation of 900 ft. Your beautifully decorated suite has a living room with a queen sofa

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $174 
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Absolute Ocean Front Home at Sea Level Hale Hokulani "House of the Heavenly Star

HAWAII LAW COMPLIANT !!
We received the original and the renewals of the highly sought after short term vacation rental seal of approval/certificate from the County of Hawaii meeting all their stringent requirements. When you rent our home

  • 3 bedroom
  • 1 bathroom
  • Sleeps 5
Hawaii> Captain Cook
from $259 
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Kona Coast Original Beach Boys 9.5 acre Estate, Pool and Amazing Ocean Views

Kona recalls the Beach Boys playing their pop hits by the pool. The band left but the good vibrations linger. Situated on 9.5 gated acres, gated for with an amazing Hawaiian plantation-style home with separate sleeping quarters and a guest

  • 5 bedroom
  • 5 bathroom
  • Sleeps 12
Hawaii> Captain Cook
from $1,374 
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Maka Nui Estate private family resort style home.

Aloha,

And welcome to Maka Nui! The name means Big view which you will see when you enter the gate to our paradise. The home sits on a cliff overlooking an undeveloped and historic coastline including Kealakekua Bay and Pu'uhonua o'

  • 6 bedroom
  • 6 bathroom
  • Sleeps 10
Hawaii> Captain Cook
from $1,549 
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Private Island Style Cottage With Ocean View And Tropical Garden

Beautiful island style cottage with sunset views and tropical garden. If you want to experience true Hawaiian living in an eco-friendly natural, non smoking environment this is your place. Have a soak in the tub, pick fresh herbs, veggies and

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $204 
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Rare Beauty and Luxury at Kealakekua Bay

Your hosts Tammy and Joe are committed to providing a 5-star experience. The home is maintained in immaculate condition with the highest levels of spotless cleaning before you check in.

The property is very private with secure gated

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $624 
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Relax and Enjoy! Five Star Accommodations at Affordable Rates!

If you are adventurous and free spirited, but still require all the amenities a luxury rental home has to offer then Pu`uhonua ('Place of Refuge') is the place for you. Experience tropical Hawaii at it’s finest in this unique pole house

  • 5 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Captain Cook
from $806 
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Ocean Front Home with Pool and Spectacular Views

Aloha and Welcome to Ocean Song!
This vacation home is located right on the edge of the crystal clear waters in the Kealakekua Bay. Situated at the end of a plumeria lined lane, Ocean Song offers privacy and seclusion in a lush tropical

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $1,125 
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On the Ocean at Kealakekua Bay. Where the Dolphins Play.

'Okika Lani sits at the south end of Kealakekua Bay on a private road with spectacular views of the Pacific Ocean, the Captain Cook Monument, and crescent shaped, white sand Ke'ei Beach.

Enter the gate at 'Okika Lani and walk into an

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $952 
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Minutes From Kealakekua Bay In The Midst Of Kona Coffee Country

The property is a one-acre lot with a small mango orchard (30 trees), fruit trees (lime, lemon, orange and avocado) and a beautifully manicured landscape. The cottage is separate from the main house, so your privacy is assured. There is a

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Captain Cook
from $161 
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'We Loved This Romantic Getaway for Two !' - Testimonial.

This rustic wooden mountain cabin is situated next to a forest, in a secluded spot away from the main house, on a 3.5 acre farm. At an elevation of 2,100 feet, it avoids the summer heat at sea level ('Cool and peaceful..' - Teri), yet is close

  • 2 bedroom
  • 1 bathroom
  • Sleeps 3
Hawaii> Captain Cook
from $195 
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Ocean Beach Home In The Heart Of Authentic Old Hawaii

STVR 19-360891, NUC 19-1179

From home to ocean in under a minute! This newly built custom home is just 200 feet from the ocean and located in the heart of authentic Old Hawaii - Captain Cook locale on the Big Island of Hawaii. An

  • 2 bedroom
  • 3 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $454 
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Oceanfront Home with Pool ‘The Cove at Milolii'

Front row views of Kona sunsets

Our two-story oceanfront home has views from every room and tropical breeze flowing from roof top cupola through every window and door. The main living area is upstairs with 4 bedrooms and 3

  • 4 bedroom
  • 4 bathroom
  • Sleeps 9
Hawaii> Captain Cook
from $546 
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Incredible Views!!!

Sun Tracks Across the Water ---
Sun Tracks Cross the Water
Beautiful panoramic sunset views across the curvature of the earth. Close enough to watch whales, away from crowds and the beaten tourist path, your vacation starts here. This

  • 2 bedroom
  • 1 bathroom
  • Sleeps 3
Hawaii> captain cook
from $167 
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Sweet Mermaid Studio at Manini Beach, Kealakekua Bay

Everything you might need to enjoy an exciting or relaxing vacation right by the ocean at the beautiful and world famous, "Kealakekua Bay'.
This private location is perfect for adventuring around our quaint neighborhood, with quiet walks,

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Captain Cook
from $249 
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Cottage with Amazing View, Minutes to Dolphin Swimming, Very Private, Affordable

Please check out the main house on the same property for larger groups:
vrbo 1542506

This cottage is perfect for a couple looking to save money but still have a million dollar view. In Kealakekua Bay, just 3 minutes from some of the

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Captain Cook
from $281 
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Stunning oceanview property minutes from dolphins

Please check out our cottage on the same property for smaller groups: Vrbo 953957

This Unique property showcases a 153 foot ocean facing deck with luxurious indoor/outdoor Hawaiian style living. Everything is completely redone and

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $478 
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Ocean Views from Private Lanai 1 bed/1 bath Cottage on a 100% organic Farm!



Kona Mauna Kai is a working farm on the slopes of Mauna Loa on the Big Island of Hawaii. Mauna Kai means mountain and ocean and that’s exactly what you get on our farm. 180 degree views of the beautiful Kona coastline.
On the farm,

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Captain Cook
from $158 
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Ohia Cottage: Your Coastal Retreat near Napoopoo Beach

Ohia Cottage is a well-appointed guest house on a secluded private farm in the heart of Kona s coffee belt.

How amazing would it be to wake up and smell the coffee in Hawaii?! Our cottage is a perfect setting to host honeymooners

  • 2 bedroom
  • 1 bathroom
  • Sleeps 3
Hawaii> Captain Cook
from $306 
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Quiet Paradise on Bay w/Aircon

A true Hawaiian-style vacation rental makes you feel welcome in this fully equipped family home. Just steps to the magical blue waters of Kealakekua Bay, you'll be able to swim, snorkel, and paddle practically in your front yard. With a peekaboo

  • 4 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $438 
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Paradise at Bay View Farms w/ Private Infinity Pool, Hot Tub & Incredible Views

Bay View Farms Estate House

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Retreat to a gentler, slower-paced era in this beautifully

  • 4 bedroom
  • 7 bathroom
  • Sleeps 20
Hawaii> Captain Cook
from $2,853 
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Quiet get-away in Lush Tropical Setting- 5 min walk to snorkeling beach!

Experience spinner dolphins, sea turtles, hump-back whales (in winter), manta rays, amazing fish and coral reefs at pristine Kealakekua Bay, a protected marine sanctuary.

Enjoy glorious sunsets through the palm fronds from the lanai or

  • 3 bedroom
  • 2 bathroom
  • Sleeps 7
Hawaii> Captain Cook
from $432 
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New 2 Bedroom Guesthouse with Mountain & Ocean View!

This comfy, stylish guesthouse is located near Kealakekua Bay and the Captain Cook Monument. Here you can enjoy snorkeling, hiking, kayaking, boat tours and scuba diving. Our Guesthouse offers 2 bedrooms with queen beds, a full-size kitchen,

  • 3 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $394 
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Romantic cottage with stunning ocean and mountain views in Captain Cook, HI

Enjoy spectacular views of Kealakekua bay in the newly built Coffee Cottage in Captain Cook, Hawaii! Situated amongst the coffee trees at a pleasant 1350 ft. elevation, it’s a perfect temperature year round.
Stretch out in the California

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Captain Cook
from $339 
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Hawaiian Retreat w/ Ocean Views in Captain Cook!

Indulge in the ultimate Hawaiian getaway at this stunning 3-bed, 3-bath vacation rental house in Captain Cook. Upon arrival, you’ll be greeted by 3 manicured acres of mature fruit trees. Past the front door lies access to the ocean-view lanai,

  • 3 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $366 
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Hawaiian home with incredible ocean views, orchids, and gorgeous sunsets

Our home is in a rural area of the Big Island, on one acre of landscaped property with orchids, palms, banana plants, a koi pond and more. This is our personal residence, available the months when we are not there. The kitchen is totally

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $195 
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New Round House With Pool 180 Degree Ocean View 13% discount for 7 nights

Make this home your base camp for all of your Big Island adventures. This unique round house with spectacular ocean views is located one hour from Hawaii Volcano National Park and one hour to Kona, a midpoint location for your sightseeing

  • 2 bedroom
  • 1 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $282 
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Luxury Home With Amazing Ocean View Above Kealakekua Bay -BIG lanai with HOT TUB

Newly built LUXURY designer home including a 6-person HOT TUB and an amazing view of the ocean. The living space on the top floor is 2300 sq. ft. including a covered lanai of 1150 sq. ft. Bedrooms with attached bathrooms are 30 ft. apart with

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Captain Cook
from $589 
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Tropical Romantic S. Kona Cottage with Incredible Oceanview

Makalani (Heavenly View) Cottage is a delightfully romantic cottage surrounded by a tropical garden in South Kona's coffee-belt with a breathtaking panoramic view of the Pacific Ocean. For the adventurous traveler seeking authentic Hawaiian

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $185 
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Ocean-View Bungalow: Walk to Pebbles Beach!

On-Site Whale Watching | 4 Snorkeling Sets | Wraparound Lanai

An unforgettable Hawaiian escape begins and ends here at 'Anji's Beach House,' a 3-bedroom, 3-bath vacation rental in Captain Cook. Nestled on the picturesque Kona Coast, this

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Captain Cook
from $367 
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Kona Cliff House at Pebble Beach - a romantic getaway!

Kona Cliff House at Pebble Beach is a romantic getaway & perfect for all things ocean! Spectacular coastal views from every room in this fully remodeled penthouse. All full custom gourmet kitchen stocked with your chef needs.

Location

  • 1 bedroom
  • 1 bathroom
  • Sleeps 2
Hawaii> Captain Cook
from $305 
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Close But Far.... Cool da Heels


Aloha travlers!

I'm very happy to see that you made it through these last couple of months, it certianly has been one for the history books!
If you are feeling the urge to venture out, Hotel Pa'amalu may be the very place for

  • 2 bedroom
  • 1 bathroom
  • Sleeps 3
Hawaii> Captain Cook
from $202 
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Charming Tropical Hideaway, Best Snorkeling, Pool, Hot Tub

Tropical Hideaway is a charming Hawaii-style downstairs studio apartment in a lush garden setting, with ocean and sunset views, plus a chemical-free swimming pool with waterfall and private hot tub. Tropical Hideaway is just a three minute drive

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $197 
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AS SEEN ON HGTV BEACH HUNTERS! Oceanfront, Amazing Whale Watching and Snorkeling

Welcome to Koni Kai, Hawaiian translation: Passionate Sea. Koni Kai is a beautifully designed, very comfortable oceanfront home. Considerable time and effort has been spent to ensure Koni Kai is equipped with everything one might want/need

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $442 
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At Awapuhi Views, you can check out the surf conditions, and enjoy the breezes

Our home is located halfway down the Miloli'i Rd. We have a very large master bedroom with a King bed, the Master has bow- windows and its own door to the wrap around deck.oceanside deck. The Master bedroom has a walk-in closet, and en suite

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $215 
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Gorgeous 180 degree COASTAL VIEW Home! New SUMMER RATES!

Escape to our charming 2-bedroom, 2 full-bath vacation home in Captain Cook, where you'll be greeted by stunning beach views and a host of amenities to make your stay truly unforgettable. Imagine yourself relaxing on the wrap-around lanai, or

  • 2 bedroom
  • 3 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $262 
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Amazing Views of the Bay and Ocean, Steps to Beach

Welcome to our stunning 3-bedroom vacation home in Captain Cook!

Nestled just a 2-minute walk from the serene Kealakekua Bay, this property offers the perfect escape for your island getaway.

Golfers will appreciate the easy

  • 3 bedroom
  • 4 bathroom
  • Sleeps 7
Hawaii> Captain Cook
from $452 
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Big Island Paradise

"A Little Peace of Heaven" is an adorable picture-perfect home to experience Aloha! The sweetest place for a Romantic getaway! And just as fabulous for a family, as the second bedroom has a new Nectar queen mattress for friends or

  • 2 bedroom
  • 1 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $343 
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Hale Hanai - near Kealakekua Bay - Proximity to ocean without oceanfront price

"Pathway of the Gods" is the meaning of the name given by ancient Hawaiians to Kealakekua Bay. Five hundred feet from the bay, nestled among the palm trees and fragrant plumeria blossoms is the site of your next vacation. Let us "Big Isle"

  • 3 bedroom
  • 2 bathroom
  • Sleeps 10
Hawaii> Captain Cook
from $466 
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Exceptional Historic Home in South Kona

The very best place to gather as a family where social distancing is easy with your own gourmet kitchen and private pool! We have adopted expanded and more thorough cleaning procedures due to Covid 19.

Experience Old Hawaii but with all

  • 4 bedroom
  • 3 bathroom
  • Sleeps 6
Hawaii> Captain Cook
from $504 
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Aloha Awaits at the Southern Belle of Miloli'i

Create your own private paradise away from the hustle and bustle! Enjoy 180 degree ocean views and the comforts of a luxurious home all to yourself! Experience the scenic adventurous road first paved by Elvis to quaint Miloli’i, where the sun

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $360 
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Papa Belle 3.5 Acre Estate w/Pool, Spa, Epic Ocean Views, and Orchard

The moment you enter the Royal Palm lined driveway of this gorgeous estate, you'll know you have arrived at your new sanctuary! Papa Belle Estate is a 3.5 acre oasis on the South Kona coast offering breathtaking views, wonderful amenities, and

  • 2 bedroom
  • 3 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $762 
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Captain Cook Hide Away

About this space
1 bedroom 1 bath unit in small neighborhood.

The space

B & B style cute and homey 1 bedroom 1 bath downstairs apartment, newly remodeled, 800 sq. ft. of interior space. Has its own laundry room with washer,

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $198 
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Oceanfront sanctuary with light-filled interior, lanai, W/D, & full kitchen

Manini Beachfront Getaway

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Fill your next Hawaii vacation with an abundance of aloha when you

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Captain Cook
from $653 
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Take Your Breath Away!


Aloha and welcome to your peaceful place of eden and the answer to a relaxing visit on the Big Island of Hawaii. We are located on the west side of the Big Island of Hawaii and close to Ho'okeena Beach, Pu-uhonua o Honaunau (aka Place of

  • 3 bedroom
  • 2 bathroom
  • Sleeps 8
Hawaii> Captain Cook
from $368 
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Peaceful Miloli'i Cottage w/ Ocean & Sunset Views!

Live like a local at this solar-powered geodesic vacation rental in the Miloli’i area! Situated just 35 miles south of Kailua-Kona, this Captain Cook 1-bath studio cottage offers tranquil surroundings and proximity to beaches. Venture out to

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $210 
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Walk 3 minutes to Kealakekua Bay to see dolphins

I swim and see dolphins many times a week, the reason I chose to live at Kealakekua Bay. The "Ohana"-guest apartment for rent is on the GROUND floor. It is completely separate from the two floors where I live upstairs. You can walk down the

  • 1 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Captain Cook
from $267 
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Oceanfront - Dolphin Retreat - KAYAKS INCLUDED

On the shores of Kealakekua Bay, a Protected Marine Conservation area, is an enchanting, 4 bedroom/3 bath, water front house called the Dolphin Retreat. This open and airy private home has all the amenities one would desire for a tropical

  • 5 bedroom
  • 3 bathroom
  • Sleeps 10
Hawaii> Captain Cook
from $1,138 
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