50 Best Vacation Rentals in Island of Hawaii - Holiday Lettings - Cabins

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Vacation rentals Kailua-Kona
662 properties
Vacation rentals Kohala Coast
284 properties
Pahoa
110 properties
Cabins Volcano
77 properties
Cottages Waimea
69 properties
Apartments Captain Cook
63 properties
Vacation rentals Hilo
60 properties
Keaau
52 properties
Estates Keauhou
36 properties
Holualoa
24 properties
Hakalau
15 properties
Ocean View
14 properties
Kapoho
13 properties
Pahala
13 properties
Naalehu
11 properties
Mountain View
11 properties
Honokaa
9 properties
Kalapana
8 properties
Papaikou
8 properties
Hawi
7 properties

Island of Hawaii

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1,612 Vacation rentals

(3) Excellent 

31

Condo rental in Kailua-Kona with golf nearby

Island of Hawaii / Kailua-Kona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
****** SUMMER SALE 1ST TIME VISITORS CHECK OUR REVIEWS ****** OCEAN FRONT OVER THE POOL PANORAMIC VIEWS IN KAILUA-KONA POOL, HOT TUB ,WATCH THE DOLPHINS PLAY, WHALE WATCING DECEMBER---MARCH. ****** FREE PRIVATE WIFI****** ******WE PROVIDE BEACH GEAR PLENTY OF PAP …see more

from $105 / night

$1,400 - $1,575 / week

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avg. 22 minutes

from $105 / night

(4) Excellent 

28

Vacation guest house with swimming pool in Hilo

Island of Hawaii / Hilo

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
Enter the magnificent Royal Palm lined drive and experience Big Island history. Enjoy the unique ambiance of this one of a kind grounds of the former Ola’a Sugar Plantation residence and its directors cottage, now the guest house. It has been completely and tastefully …see more

from $150 / night

$980 - $1,400 / week

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avg. 2 hours 50 minutes

from $150 / night

23

Vacation home in Keauhou

Island of Hawaii / Keauhou

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Quintessential blend of Luxury, Privacy, and Open Air Living. This 5 bedroom, 6 bath estate is nestled on 5 extremely private acres, but just moments away from Alii Drive, minutes to White Sand Beaches, and local golf courses. This unique offering of ultra-luxury living …see more

from $999 / night

$6,783 - $8,883 / week

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avg. 1 hour 42 minutes

from $999 / night

(2) Excellent 

30

Home rental in Hilo with swimming pool

Hilo / Hawaii Paradise Park

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Hale Mar provides the best value in luxury, absolute ocean front homes in Hawaii, with private swimming pool, outdoor hot tub, resort quality furnishings, gourmet kitchen, full laundry, FREE wireless internet, and more. Close to the active Volcano for unique day and nig …see more

from $349 / night

$3,213 / week

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avg. 1 hour 38 minutes

from $349 / night

(1) Very Good 

25

Keaau Vacation cottage accommodation

Island of Hawaii / Keaau

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 16 mi
  • Swimming pool
  • Private garden
Enter the magnificent Royal Palm lined drive and experience Big Island history. Enjoy the unique ambiance of this one of a kind grounds of the former Ola’a Sugar Plantation residence and its directors cottage, now the guest house. It has been completely and tastefully …see more

from $150 / night

$1,050 / week

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avg. 2 hours 50 minutes

from $150 / night

(13) Very Good 

35

Volcano Vacation home rental

Island of Hawaii / Volcano

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 30 mi
  • Child friendly
  • Private garden
CHILDREN UNDER 12 STAY FOR FREE OCTOBER 10 - DECEMBER 15, up to 2 children under 12 at no extra cost, PLEASE LET ME KNOW WHEN MAKING YOUR RESERVATION AND I'LL MAKE THE ADJUSTMENT :) Roxane. Welcome to Anthurium Alii Gardens this Hawaiian paradise in the middle of a magi …see more

from $165 / night

$1,125 - $1,825 / week

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avg. 2 hours 35 minutes

from $165 / night

(16) Excellent 

20

Volcano Vacation cottage rental

Island of Hawaii / Volcano

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
In the Hawaiian language, a "kipuka" is a kind of oasis. It can be an island of forest surrounded by lava fields, or an opening within a forest, or even a dwelling, a home within the forest. This is our Kipuka -- a custom-designed cottage, a vacation home for you here o …see more

from $165 / night

$1,015 - $1,715 / week

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from $165 / night

16

Kailua-Kona Vacation condo rental

Island of Hawaii / Kailua-Kona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
1150 sqft Spacious comfortable in the heart of Kailua Kona In the back, small quiet building third floor , 3 minutes walk to Mc Donald restaurant or Starbucks, 6 minutes walk to Allii dr or ocean ,main tourist attractions of Kona town. Huge kitchen with gas stove and b …see more

from $199 / night

$1,662 - $1,872 / week

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avg. 1 hour 42 minutes

from $199 / night

24

Vacation apartment with shared pool in Kailua-Kona

Island of Hawaii / Kailua-Kona

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Come and enjoy your stay in this beautifully upgraded 1 bedroom condo at Kona Reef. Located on a desirable single level overlooking the pool and the ocean, you will find all the comforts you would expect in this tropical paradise. Let the sound of the crashing waves be …see more

from $175 / night

$1,225 / week

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from $175 / night

12

Private room rental in Hilo

Island of Hawaii / Hilo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
Aloha and welcome to Hale Sunrise! Our home is on 4 lush and serene acres 15 minutes from downtown Hilo and airport. This is where you can stay to soak in the feeling of real and local Hawaii away from the rush of town. You have a continental breakfast, a comfy bed, a p …see more

from $100 / night

$650 / week

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from $100 / night

(11) Excellent 

Certificate of Excellence

11

Vacation apartment in Pahoa

Island of Hawaii / Pahoa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Private garden
Aloha, E komo mai! This studio apartment is located on a paved street, in the Puna District of the Big Island. Ideally located, less than 15 miles, from Hilo & 3 miles from old Pahoa Town. Kilauea Volcano, (the most active volcano on earth) located within HVNP in Volc …see more

Certificate of Excellence

from $60 / night

$420 / week

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avg. 3 hours 46 minutes

from $60 / night

(34) Excellent 

35

Captain Cook Vacation home accommodation

Island of Hawaii / Captain Cook

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
ENJOY this peaceful, stunning two-story home surrounded by tropical landscape and 180 degree ocean view!! AWARD-WINNING Voted TOP VACATION RENTAL in CAPTAIN COOK 3 years in a row!!-- Recently voted 'EXCELLENT' by Trip Advisor and 'RECOMMENDED' by FlipKey. This unique …see more

from $195 / night

$1,365 / week

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from $195 / night

39

Vacation home in Kailua-Kona

Island of Hawaii / Kailua-Kona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
This luxury home has direct ocean sunset views from the living room, the dining room, the kitchen and the master bedroom! You can hear the surf from your bed at night! This is a 3 bedroom, 3 bath private luxury home with a panoramic (sunset) view of the Ocean. This is …see more

from $295 / night

$2,093 / week

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avg. 1 hour 36 minutes

from $295 / night

27

Pahoa Vacation home rental

Island of Hawaii / Pahoa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Named for its panoramic view of the Kapoho coastline, Kapoho View is just a 5 minute drive from the famous geothermally heated Kapoho tidepools.  Tucked away in a tiny neighborhood nestled between papaya groves, this peaceful 3 bedroom home is a perfect place to relax a …see more

from $89 / night

$592 - $1,045 / week

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from $89 / night

(1) Very Good 

14

Vacation condo in Pahala

Island of Hawaii / Pahala

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
Condo #18 is unsurpassed in regards to resort location. This corner unit is located to afford utmost privacy, unobstructed sweeping views of the ocean & the golf course’s 1st & 9th holes and maximum ease to access the swimming pool, hot tub & BBQs. This well appointed …see more

from $95 / night

$665 / week

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avg. 2 hours 54 minutes

from $95 / night

(42) Excellent 

28

Vacation home in Kapoho

Island of Hawaii / Kapoho

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
From the moment you open the beautiful custom gate and enter the lush, private grounds you will know you have found a special place. You'll enter into the great room, which lives up to its name with an open floor plan, high ceilings, wood floors, and tasteful touches ar …see more

from $150 / night

$998 - $1,939 / week

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from $150 / night

33

Vacation home in Waikoloa

Kohala Coast / Waikoloa

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
Welcome to the newest home in our Hawaiian Luxury Collection. Orchid Villa at Fairways is a wonderfully exquisite high end 3 bedroom home which is one of the best buildings for sunset and golf views - overlooking tee to green. Our specific locations provides excepti …see more

from $289 / night

$2,023 / week

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from $289 / night

(2) Excellent 

18

Vacation home with swimming pool in Ookala

Island of Hawaii / Ookala

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Whether adventure or a relaxing vacation calls, Ocean Soul is the perfect place for your next Hawaiian retreat. Perched on the cliffside of Waipunalei, Ocean Soul's 13 acre property hosts the most amazing ocean views, a lap swimming pool, multi-level home with three be …see more

from $350 / night

$2,275 - $3,325 / week

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from $350 / night

(1) Excellent 

35

Vacation home in Hilo

Island of Hawaii / Hilo

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.3 mi
  • Ask about children
  • Private garden
SPECTACULAR VIEWS await you at Kahoa House for your Hawaiian holiday. Early-birds and mainlanders adjusting to the time difference can enjoy a cup of Ka’u coffee in the comfortable living room, and watch the sun rise out of the Pacific through the large east-facing win …see more

from $285 / night

$1,820 - $3,115 / week

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from $285 / night

24

Vacation home with shared pool in Kailua-Kona

Island of Hawaii / Kailua-Kona

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Surf, swim, sunbathe, and experience serenity when you stay at this luxurious 3-bedroom, 3-bathroom vacation rental townhome that sleeps 8 in Kona. With a community pool, fitness area, and resort-like amenities, you’re sure to feel like royalty throughout your stay! Boa …see more

from $179 / night

$1,253 - $2,793 / week

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avg. 19 minutes

from $179 / night

(1) Excellent 

95

Home rental in Kailua-Kona

Island of Hawaii / Kailua-Kona

5 11 4 nights min

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
Welcome to the newest home in our Hawaiian Luxury Collection. Pacific Vista Retreat in Kahakai Estates is a wonderful newer 5-bedroom home minutes away from downtown Kailua-Kona with some of the most amazing views of the Pacific Ocean and entire coast line of any vacati …see more

from $695 / night

$4,865 / week

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from $695 / night

16

Vacation home in Honomu

Island of Hawaii / Honomu

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Suitable for children age 5+
On the slopes of Mauna Kea, at 1200' above the little town of Honomu the great waterfall of Akaka cascades down through verdant rainforest. Nearby, on top a hill is our private little piece of paradise. The house overlooks a vast swath of East Hawaii. From the blue of …see more

from $150 / night

$910 - $1,190 / week

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avg. 2 hours 43 minutes

from $150 / night

(3) Very Good 

15

Vacation apartment in Pahoa

Island of Hawaii / Pahoa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 8 mi
  • Suitable for children age 5+
  • Ask about pets
This beautiful second floor suite. 650 sqft. is just a stones throw away from the ocean . Enjoy the ocean view from the dining - living - bedroom and balcony as well as the deautiful landscape eg. Rockwalls , water - features , This is a perfect cozy getaway for a sin …see more

from $75 / night

$485 / week

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from $75 / night

(3) Very Good 

13

Cottage rental in Kapaau with golf nearby

Island of Hawaii / Kapaau

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ask about children
The Space 1 Bedroom / Living room, 1 Bathroom, Sleeps 2 only. The Big Island's North Kohala region is a travelers' delight, off the beaten path, it makes the area one of Hawaii's best-kept secrets. Experience ''Old Hawaii'' in the charming historic towns of Hawi and K …see more

from $125 / night

$795 / week

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avg. 2 hours 16 minutes

from $125 / night

16

Vacation home in Hawaii Volcanoes National Park

Island of Hawaii / Hawaii Volcanoes National Park

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Private garden
Beautiful craftsmanship abounds in our one bedroom (plus a comfy pull out couch), upgraded bath home in the beautiful Volcano community. From the carved bar to the lava rock fireplace to the Jacuzzi jetted tub, we've paid attention to every detail. French doors from the …see more

from $159 / night

$1,113 / week

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from $159 / night

12

Vacation home in Hilo

Island of Hawaii / Hilo

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
The suite is very spacious (500 sq/ft), located less than one mile to downtown Hilo on a private 1.7 acre property. The suite is accented with hardwood floors and tastefully furnished including a queen size bed and two single bed (trundal bed). The room has it's own pri …see more

from $149 / night

$1,043 / week

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from $149 / night

14

Villa rental in Puako with golf nearby

Kohala Coast / Puako

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxury villa in the Mauna Lani Resort is a terrific alternative to a luxury hotel room. You will have all the amenities of a luxury oceanfront resort, with a full kitchen and lower price. Only minutes (drive or walk) to a pristine, private, Owner's only beach uniqu …see more

from $190 / night

$1,330 / week

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from $190 / night

(2) Good 

18

Vacation studio in Kailua-Kona

Island of Hawaii / Kailua-Kona

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Ask about children
STUDIO - NEW PICS ARE HERE OF NEW REMODEL AND DECOR - CHECK IT OUT! GORGEOUS, clean, air-conditioned studio sleeps 2 comfortably with the ambience of 'old Hawaii' in the beautiful native vegetation and meandering walkways that lead to the beach and the heart of Kailua …see more

from $109 / night

$693 / week

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avg. 1 hour 5 minutes

from $109 / night

(1) Excellent 

65

Puako Vacation home rental

Kohala Coast / Puako

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Beautiful Ocean Villa (or Nani Moana Hale - its Hawaiian translation), the newest home in our Hawaiian Luxury Collection. Beautiful Ocean Villa at the Mauna Kea Resort Wai'ula'ula complex has majestic views of mountains and ocean. You will be mesmerized looki …see more

from $535 / night

$3,745 / week

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from $535 / night

(22) Excellent 

9

Vacation cottage with golf nearby in Holualoa

Island of Hawaii / Holualoa

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Private garden
Our estate is situated on the slopes of Mt. Hualalai on the Big Island of Hawaii. We are located just 15 minutes from the Kailua-Kona Keahole Airport, 10 minutes from the quaint coastal town of Kailua-Kona, 10 minutes from the artists' village of Holualoa, and also 10 m …see more

from $149 / night

$1,043 - $1,183 / week

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from $149 / night

(23) Excellent 

Certificate of Excellence

21

Volcano Vacation cottage rental

Island of Hawaii / Volcano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 50 mi
  • Pet friendly
Aloha! Welcome to Hale Hubner. Located in Volcano Village, and just 5 minutes from Hawaii Volcanoes National Park, we invite you to make our house your home away from home during your next visit. Hale Hubner is perfect for friends, couples, and small groups or families …see more

Certificate of Excellence

from $105 / night

$660 - $800 / week

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Responds fast!
avg. 3 hours 33 minutes

from $105 / night

(1) Excellent 

29

Waimea Vacation home rental

Island of Hawaii / Waimea

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
This solar powered home is located on the coast In the foothills of Hawaii Island’s oldest volcano, Kohala Mountain, with views of the coastline and ocean. This economical home is conveniently located in the eclectic neighborhood of Kawaihae Village. Set along the Kaw …see more

from $185 / night

$1,295 / week

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Responds fast!
avg. 1 hour 38 minutes

from $185 / night

(10) Excellent 

Certificate of Excellence

16

Vacation cottage in Honokaa

Island of Hawaii / Honokaa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 21 mi
  • Ask about children
Rainbow Bee is located on our formerly active, 5 acre honey bee farm with lots of fruit trees - cozy and serene with an earthy elegance that you will love. It has two glass sliding doors that open onto a large deck & overlooks a beautiful lily pond. The cottage has on …see more

Certificate of Excellence

from $109 / night

$545 / week

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Responds fast!
avg. 2 hours 42 minutes

from $109 / night

19

Vacation home in Kailua-Kona

Island of Hawaii / Kailua-Kona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
***Please note there is a 7 night minimum during the holidays. Christmas reservations must check out by 10AM on Dec. 27 and New Year's reservations can check in on Dec. 27 or after for a week. There is a 14 night minimum to book both Christmas and New Year's.*** Locati …see more

from $275 / night

$1,925 / week

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from $275 / night

(10) Excellent 

20

Vacation home rental

Island of Hawaii / Hilo

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Car not necessary
1BR/1BA, 420 sq ft ocean view property, no pets, no cigarettes 'Alani House sits on a cliff overlooking the Pacific Ocean, and Honoli'i Beach is at the end of the block. With direct access to the black sand beach and lifeguards on duty, Honoli'i is one of the Big Islan …see more

from $99 / night

$693 / week

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from $99 / night

(2) Excellent 

48

Waimea Vacation home rental

Island of Hawaii / Waimea

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Hale Kohola “The House of the Whale” is situated on 3 acres in an ideal location on the Kohala Coast, with panoramic views of the ocean and coastline. The master bedroom has a stunning ocean view. STATE GE AND TAT TAX OF 13.42% TO BE ADDED TO THE NIGHTLY RATE The Space …see more

from $159 / night

$1,113 - $1,463 / week

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from $159 / night

(5) Excellent 

14

Vacation home in Pahoa

Island of Hawaii / Pahoa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
July 2016: Currently live lava flow viewing at the nearby Kalapana Lava viewing area. Oceanfront one-bedroom apartment on the gorgeous Red Road and a short walk to a black sand beach. Quiet and serene yet modern in a natural tropical setting. Wake up looking at the wave …see more

from $125 / night

$875 / week

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from $125 / night

25

Vacation condo in Waikoloa

Kohala Coast / Waikoloa

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Beach/lakeside relaxation
Welcome to Paradise! We invite you to enjoy your next vacation on the Big Island of Hawaii from the comfort of our spacious, well equipped, 2-bedroom, 2-bath condominium. This charming vacation rental is surrounded by the lush greens and fairways of the Beach Golf cours …see more

from $195 / night

$1,365 / week

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from $195 / night

(2) Excellent 

13

Volcano Vacation cottage rental

Island of Hawaii / Volcano

2 2 nights min

  • Sleeps 2
  • 2 nights min
Charming studio in a very private, peaceful and secluded location. Just three miles from Hawaii Volcanoes National Park and six miles from the Volcano Golf Course and Volcano Winery, you can enjoy the native birds who seranade you amongst the fern forest. Our studio p …see more

from $85 / night

$595 / week

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from $85 / night

21

Home rental in Hilo

Island of Hawaii / Hilo

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
THE COQUI "GINGER HALE" COTTAGE IS A 2 Bedroom + 1 Bath PRIVATE HOME ON OVER 1/4 OF AN ACRE IN A COUNTRY SETTING- Peaceful Garden Like surroundings with fruit trees and fruit you can pick and enjoy during your stay. Welcome and enjoy our Island Cottage at the centrally …see more

from $105 / night

$675 / week

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from $105 / night