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

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Vacation rentals Kailua-Kona
666 properties
Vacation rentals Kohala Coast
312 properties
Pahoa
104 properties
Cabins Volcano
78 properties
Cottages Waimea
75 properties
Apartments Captain Cook
65 properties
Vacation rentals Hilo
63 properties
Keaau
56 properties
Estates Keauhou
39 properties
Holualoa
22 properties
Hakalau
15 properties
Ocean View
14 properties
Pahala
13 properties
Naalehu
12 properties
Mountain View
12 properties
Honokaa
10 properties
Papaikou
9 properties
Kalapana
9 properties
Kapaau
7 properties
Hawi
7 properties

Island of Hawaii

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1,657 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

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 24 minutes

from $999 / 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
Our house is safe and open for future reservations! I will keep you posted (05/16/18) Welcome to Anthurium Alii Gardens this Hawaiian paradise in the middle of a magical rainforest near Volcano Village, 3 miles away from the Hawaii Volcanoes National Park ! This is the …see more

from $185 / night

$1,125 - $1,825 / week

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avg. 2 hours 35 minutes

from $185 / 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 56 minutes

from $150 / night

(17) 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

(2) Excellent 

30

Home rental in Hilo with swimming pool

Hilo / Hawaii Paradise Park

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • 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 45 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 56 minutes

from $150 / 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

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

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 24 minutes

from $199 / night

24

Waikoloa Vacation home rental

Kohala Coast / Waikoloa

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
❤️PiH❤️ brought to you by Paradise in Hawaii Luxury Homes Welcome to one of the newest homes in our Hawaiian Luxury Collection. Hawaiian Jewel at KaMilo is a wonderful newer 4 bedroom home. We pride ourselves on providing some of the most sought after homes on the Koh …see more

from $395 / night

$2,765 / week

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from $395 / 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

10

Vacation private room rental

Island of Hawaii / Kukuihaele

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Private garden
Waipi'o Hostel is located in the quaint village of Kukuihaele, less than a mile from majestic Waipiʻo Valley. In a place where horses and wild turkeys often wander by, this is the old Hawaiʻi. A place where neighbors are welcoming and life is sweet as the smell of sug …see more

from $55 / night

$385 / week

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from $55 / night

8

Vacation condo rental

Island of Hawaii / Kohala Coast

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
Upscale development in resort area on famed South Kohala coast. Two story condo. Located between Mauna Lani Bay Hotel and Fairmont Orchid. Walking distance to shops and beaches. Access to private beach club. Beautiful pool + exercise room. One car garage + additional pa …see more

from $260 / night

$1,820 / week

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from $260 / night

13

Vacation cottage in Kohala Coast

Island of Hawaii / Kohala Coast

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
Don't spend your entire vacation budget on a cramped hotel room with no ocean view when traveling to Hawaii. The money you save can pay for all your food, entertainment, and rental car! Spread out and enjoy sweeping Pacific ocean and Big Island mountain views in your o …see more

from $139 / night

$900 / week

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from $139 / 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

(17) Excellent 

13

Vacation home in Hilo

Island of Hawaii / Hilo

2 2 nights min

  • Sleeps 2
  • 2 nights min
  • Nearest beach 4 mi
  • Child friendly
  • Pet friendly
Studio apartment attached to a centrally located house in town, conveniently close to everything! Easy access to historic downtown, Bayfront, Saddle Road, the University of Hawaiʻi at Hilo, and the world famous Merrie Monarch Hula Festival. Gated yard, private entrance. …see more

from $59 / night

$350 / week

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avg. 2 hours 51 minutes

from $59 / night

33

Vacation home in Puako

Kohala Coast / Puako

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
❤️PiH❤️ Sweet Heaven Villa brought to you by Paradise in Hawaii Luxury Homes Welcome to the newest home in our Hawaiian Luxury Collection. Sweet Heaven Villa at KaMilo is a wonderful 4 bedroom home. We pride ourselves on providing some of the most sought after homes o …see more

from $395 / night

$2,765 / week

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from $395 / night

(1) Excellent 

39

Home rental in Kailua-Kona

Island of Hawaii / Kailua-Kona

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
❤️PiH❤️ brought to you by Paradise in Hawaii Luxury Homes Welcome to Pacific Vista Retreat, a part of our Hawaiian Luxury Collection. Pacific Vista Retreat in Kahakai Estates is a newer and wonderful 5-bedroom home, minutes away from downtown Kailua-Kona. It has some o …see more

from $495 / night

$3,465 / week

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from $495 / night

(2) Excellent 

28

Vacation home in Kapoho

Island of Hawaii / Kapoho

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
An extraordinary island adventure awaits at this quiet and surreal 2-bedroom, 2-bath Kapoho vacation rental house, which sleeps 4. Elevated 20 feet off the ground with spectacular views over a spacious private deck, this tranquil home is about as close to the ocean as y …see more

from $150 / night

$1,050 / week

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avg. 16 minutes

from $150 / night

(1) Very Good 

36

Vacation home in Captain Cook

Island of Hawaii / Captain Cook

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Child friendly
Welcome to WhaleSpirit Sanctuary, a sacred vacation and rejuvenation destination. This eco-friendly sanctuary is located within minutes of some of the island’s best waters to swim and see whales, dolphins, turtles and many other amazing marine life. Here at WhaleSpirit …see more

from $165 / night

$1,040 / week

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from $165 / night

24

Vacation home in Waikoloa

Kohala Coast / Waikoloa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
❤️PiH❤️ brought to you by Paradise in Hawaii Luxury Homes Welcome to Orchid Villa, part of 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 - overlo …see more

from $275 / night

$1,925 / week

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from $275 / night

(1) Excellent 

26

Puako Vacation home rental

Kohala Coast / Puako

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
❤️PiH❤️ brought to you by Paradise in Hawaii Luxury Homes Welcome to Beautiful Ocean Villa (or Nani Moana Hale - its Hawaiian translation), part of our Hawaiian Luxury Collection. Beautiful Ocean Villa at the Mauna Kea Resort Wai'ula'ula complex has majestic views of m …see more

from $409 / night

$2,863 / week

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from $409 / night

(8) Very Good 

14

Vacation apartment with shared pool in Kailua-Kona

Island of Hawaii / Kailua-Kona

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Serious inquiries only. We are charged for each one. Ask about discounts for Military, law enforcement, seniors, disabled, local stays. Centrally located on the Kona coast close to the town of Kailua and the Kona resort areas, Sea Village boasts lush tropical gardens t …see more

from $177 / night

$2,058 / week

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avg. 3 hours 14 minutes

from $177 / 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

22

Vacation log cabin accommodation

Island of Hawaii / Pahoa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Private garden
Charming and cozy screened in simple, off-grid cabin with a nice slice of ocean view through the Norfolk Pines. There's a lanai provided with table and chairs looking out towards the lush tropical garden of bananas, avocados and a variety of fruit trees and flowers. A t …see more

from $59 / night

$413 / week

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from $59 / night

27

Vacation home in Waikoloa

Kohala Coast / Waikoloa

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
❤️PiH❤️ brought to you by Paradise in Hawaii Luxury Homes Welcome to Hawaiian Destiny, part of our Hawaiian Luxury Collection. Hawaiian Destiny at KaMilo is a wonderful home that sleeps 12 with a stunning backyard oasis including private pool and spa with stunning view …see more

from $519 / night

$3,633 / week

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from $519 / night

(12) Excellent 

27

Vacation cottage in Pahoa

Island of Hawaii / Pahoa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 1 mi
Tranquil, Tropical, Private - Allergy Friendly - Walk to the Black Sand Beach Oliana Cottage is located away from the street & behind the owner's house. 3 hours from Kona airport, 45 minutes from Hilo airport. 50 minutes to Volcano Park. Sunlight and gentle tradewind …see more

from $99 / night

$693 / week

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avg. 2 hours 43 minutes

from $99 / night

(2) Very Good 

17

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 studio 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 waves, watch a pod …see more

from $98 / night

$686 / week

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from $98 / night

(46) Excellent 

131

Kailua-Kona Vacation home rental

Island of Hawaii / Kailua-Kona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
The historic 'Onion House,' built by the McCormick spice family, is a unique architectural treasure, with stunning visual aesthetics. With walls of screen and stained glass, light dances throughout the interior. At night, the translucent roof panels glow like twin Jap …see more

from $350 / night

$2,555 - $3,255 / week

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avg. 3 hours 22 minutes

from $350 / night

(3) Excellent 

10

Vacation condo with shared pool in Kailua-Kona

Island of Hawaii / Kailua-Kona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
When staying at Wyndham Kona Hawaiian Resort in Kailua-Kona on the Big Island’s west coast, you’ll feel as if you’re stepping back in time to a simpler, unspoiled era. The resort is designed to re-create the charming island ambiance found back in the ’30s, while still a …see more

from $179 / night

$1,299 - $2,399 / week

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from $179 / night

(22) Excellent 

30

Kailua-Kona Vacation cottage rental

Island of Hawaii / Kailua-Kona

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden
Best of both worlds! Private 2 bedroom cottage with full kitchen and bath located at a cooler elevation of 2100' in Kaloko Mauka. Close to fantastic hiking trails, but only 10 minutes to the airport and beaches, yet still only 15 minutes to Kona town. Enjoy a hike and b …see more

from $159 / night

$1,113 / week

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from $159 / night

(43) Excellent 

Certificate of Excellence

15

Kailua-Kona Vacation apartment rental

Island of Hawaii / Kailua-Kona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Kona Isle captures the very essence of old romantic Hawaii, with its manicured gardens, private beach and tropical ocean breezes. Come lounge under the palm trees and watch the dolphins and whales at play, enjoy swimming in the solar-heated pool and easy access to the s …see more

Certificate of Excellence

from $129 / night

$903 / week

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avg. 2 hours 23 minutes

from $129 / night

(11) Excellent 

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

from $60 / night

$420 / week

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avg. 3 hours 46 minutes

from $60 / night

(20) Excellent 

18

Vacation home rental

Island of Hawaii / Keaau

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Whale House has a huge wraparound lanai providing stunning ocean views. This home includes a full size kitchen with a dishwasher, two identical master suites, a large downstairs suite, free kayaks, golf clubs, bicycles, gas BBQ, washer, dryer, a hammock, snorkels, masks …see more

from $135 / night

$945 / week

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avg. 2 hours 53 minutes

from $135 / 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

Studio rental in Hilo

Island of Hawaii / Hilo

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Air conditioning
  • Private garden
Lovely beach studio located a minute walking distance to ocean with small swimming cove and tide pools. It is centrally located 5 minute drive from the airport, Richardson's Beach Park (famous for surfing, snorkeling, and swimming), downtown Hilo's famous Farmers Marke …see more

from $99 / night

$693 / week

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from $99 / night

(2) Very Good 

24

Vacation home accommodation

Kohala Coast / Waikoloa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
❤️PiH❤️ brought to you by Paradise in Hawaii Luxury Homes Welcome to Hawaiiana Escape at Kulalauni on the Big Island of Hawaii. Welcome to the newest home in our Hawaiian Luxury Collection. Hawaiiana Escape is a wonderful new exquisite 3 bedroom home in the gated Kula …see more

from $275 / night

$1,925 / week

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from $275 / night

(3) Excellent 

34

Condo rental in Waikoloa with shared pool, golf nearby

Kohala Coast / Waikoloa

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
(That’s the state fish of Hawai’i, if you didn’t know. I’ll teach you a couple more words so you don’t sound too haole when you get here.) This place is the reason my kids don’t want to stay in Canada for Christmas. It’s hard to trade all that snow-shoveling for trop …see more

from $235 / night

$1,645 / week

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avg. 3 hours 2 minutes

from $235 / night

14

Home rental in Ocean View

Island of Hawaii / Ocean View

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden
Nice Friendly place to stay. Half way from Hilo and way to Kona Set in a lovely sunny area sea views ,close to shops your host lives on site. Go to black sand beach ride the waves in the sun. Take a trip to Kona for the night live and white sand beaches You can drive …see more

from $50 / night

$325 / week

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from $50 / night