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

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Vacation rentals Kailua-Kona
442 properties
Vacation rentals Kohala Coast
210 properties
Pahoa
148 properties
Vacation rentals Hilo
68 properties
Cottages Waimea
66 properties
Cabins Volcano
62 properties
Keaau
50 properties
Apartments Captain Cook
45 properties
Holualoa
27 properties
Hakalau
14 properties
Pahala
14 properties
Kapoho
13 properties
Naalehu
13 properties
Estates Keauhou
12 properties
Ocean View
10 properties
Honokaa
8 properties
Hawi
7 properties
Mountain View
7 properties
Kalapana
6 properties
Kawaihae
6 properties

Island of Hawaii

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1,263 Vacation rentals

24

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

$980 - $1400 / week

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from $150 / 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 - $1400 / week

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from $150 / night

(2) Excellent 

26

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 $299 / night

$2093 / week

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avg. 2 hours 59 minutes

from $299 / night

(13) Very Good 

35

Volcano Vacation home rental

Island of Hawaii / Volcano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Private garden
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 place you have dreamed of, in between the sun and the mist, among the Ohia Lehua trees …see more

from $148 / night

$835 - $1870 / week

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from $148 / night

(13) 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

$1015 - $1715 / week

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from $165 / night

9

Vacation townhouse with shared pool in Waikoloa

Kohala Coast / Waikoloa

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
3 Bed/3 Bath, gated, on golf course, tennis, lagoon pool, fitness center The Waikoloa Beach Resort is one of the most popular vacation destinations on the Big Island of Hawaii. Our Townhome offers everything you would need to enjoy your vacation directly within the res …see more

from $189 / night

$1225 - $1400 / week

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from $189 / night

(10) Excellent 

Certificate of Excellence

23

Vacation cottage in Naalehu

Island of Hawaii / Naalehu

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Private garden
If an alternative experience of Hawaii is what you're seeking then this is the place for you. Come experience this cute little cabin nestled in the woods, surrounded by tall Ohia trees and lots of tropical birds to serenade you. Situated on the edge of a National Park, …see more

Certificate of Excellence

from $75 / night

$525 / week

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Responds fast!
avg. 1 hour 48 minutes

from $75 / night

28

Pahoa Vacation home rental

Island of Hawaii / Pahoa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.001 mi
  • Child friendly
  • Private garden
Kahua Kapoho in sunny Kapoho Vacationland is a clean, classy, private and very well equipped vacation rental home at a great rate.  You'll love swimming, floating and soaking in the private tidal pond.  Plus you're just a 5 minute walk from the famous Wai Opae tidepools …see more

from $109 / night

$725 - $966 / week

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from $109 / night

(3) Excellent 

28

Vacation home in Pahoa

Island of Hawaii / Pahoa

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Private garden
Beautiful 800 sq/ft vacation house on the east shore, Hawaii. Very private custom artistic home with stunning ocean views (1000 ft from the ocean), surrounded by lush tropical wilderness. Comfortably fits 3, or 2 couples. Built in 2014, with king size bed, queen hide-a- …see more

from $89 / night

$567 - $847 / week

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from $89 / night

10

Vacation apartment with shared pool in Kailua-Kona

Island of Hawaii / Kailua-Kona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Keauhou Gardens (also known as Kona Coast Resort) is located approx. four miles south of Kailua Kona. Keauhou Gardens 11303 is a top floor (two flights of stairs) one bedroom (king plus sleeper sofa) oceanview. Its large lanai has plenty of room to spread out and watch …see more

from $135 / night

$903 - $1015 / week

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avg. 2 hours 9 minutes

from $135 / night

(6) Excellent 

11

Waikoloa Vacation apartment rental

Kohala Coast / Waikoloa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.3 mi
  • Swimming pool
  • Child friendly
Our contemporary condo is 5 minutes from the beach (Anaeho'omalu Bay: A-Bay), restaurants and shops - it's the perfect place for your stay in Hawaii. It is a short walk to the world-class Hilton Waikoloa and Marriott Waikoloa Beach Hotels. Our quiet 3rd floor condo (un …see more

from $159 / night

$1100 - $1500 / week

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from $159 / night

23

Vacation home rental

Kohala Coast / Waikoloa

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Child friendly
  • Pet friendly
Spend your next Hawaiian family retreat at this outstanding 6-bedroom, 4-bathroom Waikoloa house with room to comfortably sleep 18 guests. Everything needed to achieve ultimate relaxation can be found here, including a soothing sauna! Upon arrival, you’ll be amazed by …see more

from $349 / night

$2094 - $2905 / week

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from $349 / night

30

Vacation apartment with shared pool in Pahala

Island of Hawaii / Pahala

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Escape the stresses of your daily life and step back in time to "Old Hawaii" where the world-famous Punalu'u Black Sands Beach creates the perfect setting for your island escape. In this quiet area the trade winds blow gently, the flowers are always blooming, the mighty …see more

from $95 / night

$665 - $771 / week

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from $95 / night

(4) Excellent 

52

Vacation b&b in Naalehu

Island of Hawaii / Naalehu

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
Make your genuine Hawaii experience away from the tourist crowds and find peace and serenity surrounded by a lush tropical garden. Tucked away from the busy hustle our 1.2 acre property in the district of Ka'u, on the Island of Hawai'i ( Big Island), offers the perf …see more

from $99 / night

$693 / week

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from $99 / night

(7) Excellent 

6

Vacation apartment with shared pool, golf nearby in Pahala

Island of Hawaii / Pahala

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
This is a true one-bedroom unit, not a small studio unit that is (often) described as a one-bedroom unit. This unit at Colony One, Sea Mountain, on the Big Island, (Hawaii Island), has a king-size bed in the bedroom on the lower level, and the living room, dining and …see more

from $70 / night

$450 / week

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avg. 3 hours 51 minutes

from $70 / night

14

Home rental in Waimea

Island of Hawaii / Waimea

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
Hale Kukui is the main portion of the Waimea Guest House, a historic Hawaiian home located on the dry side of Waimea. It is located only 15 - 20 minutes from the BEST beaches on the island! There is a large and well equipped kitchen and a separate dining room and liv …see more

from $185 / night

$1295 / week

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from $185 / night

(2) Very Good 

8

Vacation home rental

Island of Hawaii / Hilo

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Enjoy Hawai'i, live local, stay close to downtown Hilo. The property is 6 miles from the airport, up mauka (the mountain) in a little plantation village. Our affordable nightly rates include all taxes and a minimal cleaning fee that permit guest to spend their resources …see more

from $110 / night

$771 / week

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from $110 / night

(10) Very Good 

10

Vacation apartment in Kailua-Kona

Island of Hawaii / Kailua-Kona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Keauhou Gardens (also known as Kona Coast Resort) is located approx. four miles south of Kailua Kona. Its walking distance to the Keauhou Shopping Village and just down the road from the Kahaluu snorkeling beach. Keauhou Gardens 3104 is a one bedroom (king) plus sleepe …see more

from $89 / night

$560 - $875 / week

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Responds fast!
avg. 2 hours 9 minutes

from $89 / night

(3) Very Good 

45

Vacation home in Milolii

Island of Hawaii / Milolii

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
If you are looking for Adventure, Romance, a moment to Relax and enjoy Hawaiian decor or just a Vacation Get-away, please come to see all that we have to offer. Dive and snorkel spot is 5 minutes walking right down the road. This unique place provides a quiet get aw …see more

from $125 / night

$735 - $1355 / week

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Responds fast!
avg. 2 hours 51 minutes

from $125 / night

(1) Excellent 

16

Vacation home in Honaunau

Island of Hawaii / Honaunau

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Private garden
Experience old Hawaii in this beautiful, beach house on Honaunau Bay and 2 steps near the City of Refuge. Walk across the street and swim, dive or snorkel, arguably, the nicest bay on the island. Honaunau is great place for kayaking, scuba diving and we have a boat laun …see more

from $189 / night

$1300 / week

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from $189 / night

(9) Excellent 

33

Vacation apartment in Kailua-Kona

Island of Hawaii / Kailua-Kona

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Na Hale O Keauhou condo description N-4 is building N, only buildings N,H and G are next to the nature preserve with unobstructed panoramic ocean views and privacy. Our home is the largest unit available in the entire gated community. Building N is closest to the oce …see more

from $184 / night

$1288 / week

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avg. 3 hours 12 minutes

from $184 / night

12

Apartment rental in Kailua-Kona with shared pool

Island of Hawaii / Kailua-Kona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in Keauhou, approx four miles south of Kailua Kona town, the Surf & Racquet Club is a frequent choice for first time as well as repeat visitors. Surf & Racquet 5102 is a first floor oceanfront two bedroom (king in master, two twins in guest), two bath condo. Fu …see more

from $165 / night

$1050 - $1323 / week

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Responds fast!
avg. 2 hours 9 minutes

from $165 / night

(8) Excellent 

18

Vacation home with swimming pool in Keaau

Island of Hawaii / Keaau

5 8 3 nights min

  • 5 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
This is a large comfortable home it sleeps up to 8 guest at 12.50 per extra guest, we have a private salt water pool and we are on ocean side. The name, House Of Love By the Sea translated to Hawaii is Hale O' Kealoha Ala Kai it sits in Hawaiian Paradise Park. Located …see more

from $200 / night

$1430 - $1934 / week

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Responds fast!
avg. 1 hour 59 minutes

from $200 / night

11

Vacation apartment accommodation

Island of Hawaii / Kailua-Kona

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
Second floor end end unit in oceanfront building provides an unobstructed panoramic marine view framed by palm trees from living/dining, kitchen and lanai areas. Full remodel completed in 2014 and stocked to meet your vacation needs. Pristinely landscaped grounds featu …see more

from $120 / night

$825 - $950 / week

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from $120 / night

26

Pahoa Vacation studio rental

Island of Hawaii / Pahoa

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
Zen Lite is a lovely, fully equipped studio home in the Kehena area of the Puna district on the Big Island of Hawaii. It may be small, but Zen Lite's clever layout provides plenty of space for a couple or a single traveler. The home is well stocked with amenities, inclu …see more

from $79 / night

$540 - $580 / week

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from $79 / night

12

Vacation bungalow in Pahoa

Island of Hawaii / Pahoa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Private garden
Romantic Bamboo Bungalow Located just of the red road within walking distance to Kehena Beach Short drive to Uncle Roberts Awa bar the Warm ponds and the Tide pools. Your Bungalow has a fully equipped kitchen, WiFi, Parking on site and a Laundry. The outdoor shower is …see more

from $100 / night

$580 / week

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from $100 / night

18

Vacation home in Captain Cook

Island of Hawaii / Captain Cook

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
Relax on the Lanai and enjoy the blue skies and panoramic ocean views. If you are here during the season, you will even see whales from this lovely ranch style home; our Stunning Kona Paradise. Snorkeling gear and boogy boards are available at property for your use. F …see more

from $125 / night

$875 / week

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Responds fast!
avg. 3 hours 5 minutes

from $125 / night

24

Vacation home in Captain Cook

Island of Hawaii / Captain Cook

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Look no further than this 2-bedroom, 2-bathroom vacation rental house for your next Hawaiian getaway! Located on the secluded Ke’ei Beach 50 feet from the ocean, this beautiful property sleeps 4 guests, making it ideal for families or friends sharing a memorable 'Old Ha …see more

from $199 / night

$1194 - $1974 / week

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from $199 / night

27

Waikoloa Vacation apartment rental

Kohala Coast / Waikoloa

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
I would like to take this opportunity to share some of the highlights of our vacation rental as well as some information about Hawaii's Best Kept Secret “THE WAIKOLOA BEACH RESORT”. Hawaii has always had wonderful places to visit and enjoy but none can surpass the wonde …see more

from $165 / night

$1000 / week

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Responds fast!
avg. 1 hour 4 minutes

from $165 / night

(4) Excellent 

25

Volcano Vacation home rental

Island of Hawaii / Volcano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
The spirit of ALOHA will touch your soul as you enter Hale Sweet Hale. So well appointed you'll think you're at home. Hale Sweet Hale was thought out with much care and love to make your stay in Volcano truly memorable.Hale Sweet Hale, a unique cedar log home, nestl …see more

from $175 / night

$1050 - $1330 / week

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from $175 / 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 $89 / night

$623 / week

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from $89 / night

9

Vacation home in Honokaa

Island of Hawaii / Honokaa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Suitable for children age 5+
This private home on the lush Hamakua Coast is a beautiful blend of past and present. Located just a block from the overlook of the sacred Waipio Valley, the house allows visitors to commune with nature and history, while enjoying all the comforts of the 21st century. …see more

from $195 / night

$1215 / week

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from $195 / night

13

Pahoa Vacation guest house rental

Island of Hawaii / Pahoa

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
Located just five minute's walk from the beautiful Champagne Ponds of Kapoho where you can swim in geo-heated tide pools with sea turtles and tropical fish. Nahele is a comfortable home just right for a couple or a family with up to two small children. It is off-grid, t …see more

from $145 / night

$1015 / week

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from $145 / night

33

Vacation home in Pepeekeo

Island of Hawaii / Pepeekeo

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Air conditioning
Between the Scenic Route and the ocean. Good ocean views in an agricultural setting. All NEW furniture and incidentals. Terrific landscaping. Gated (power) with a 2 car garage. We have four sheep and a few chickens. More photos to come. Tempurpedic! For those of y …see more

from $175 / night

$1015 / week

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from $175 / night

(22) Excellent 

9

Vacation cottage 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 $145 / night

$1015 - $1155 / week

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from $145 / night

(2) Very Good 

10

Kailua-Kona Vacation apartment rental

Island of Hawaii / Kailua-Kona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located two miles south of Kailua Kona town, this two bedroom two bath oceanfront condo is a great location for your Kona vacation. It's close enough to easily get to town for restaurants and activities as well as snorkeling and water sports in the Keauhou area to the …see more

from $155 / night

$1043 - $1323 / week

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Responds fast!
avg. 2 hours 9 minutes

from $155 / night

6

Vacation hotel apartment in Holualoa

Island of Hawaii / Holualoa

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Ask about children
Room # 10 - 1 Twin and 1Full Sized Beds - Ocean View 3 Guests Maximum Separate men's & women's bathrooms down the hall. NO KITCHEN FACILITIES - NO FOOD SERVED NO SMOKING OR OPEN FIRES ON THE HOTEL PROPERTY "SELF CHECK-IN" SYSTEM FOR AFTER HOUR CHECK-IN CHECK-IN - 3:0 …see more

from $65 / night

$455 / week

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from $65 / night

(7) Excellent 

21

Vacation studio in Hilo

Island of Hawaii / Hilo

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Enjoy the ideal location on the beautiful Hamakua Coast, the green side of the Big Island of Hawaii, on our own piece of Paradise. We have views of the Ocean & Mauna Kea mountain, but the best views are from your own balcony above the rushing waters of the Makea Stream …see more

from $97 / night

$625 / week

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Responds fast!
avg. 3 hours 56 minutes

from $97 / night

(52) Excellent 

Certificate of Excellence

37

Home accommodation in Milolii

Island of Hawaii / Milolii

3 14 Min stay varies

  • 3 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
Aloha Beach House quiet and peaceful. Unwind and relax from city life. Three bedroom, three baths, and game room. A large Lanai runs the length of the house for dolphin and whale watching. Have dinner on a beautiful Lanai and watch the incredible sunsets while enjoying …see more

Certificate of Excellence

from $85 / night

$800 - $2550 / week

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Responds fast!
avg. 2 hours 39 minutes

from $85 / night

(9) Very Good 

65

Vacation home in Hilo

Island of Hawaii / Hilo

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Spacious well-appointed home with everything you need just moments from downtown Hilo. With three bedrooms and two baths, this Reed's Island home is a wonderful place to stay while you enjoy all that the Big Island has to offer. The master bedroom with its ensuite bathr …see more

from $170 / night

$1124 - $1470 / week

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from $170 / night

1