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

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Vacation rentals Kailua-Kona
553 properties
Vacation rentals Kohala Coast
257 properties
Pahoa
107 properties
Cabins Volcano
76 properties
Cottages Waimea
68 properties
Apartments Captain Cook
63 properties
Vacation rentals Hilo
62 properties
Keaau
50 properties
Holualoa
21 properties
Hakalau
14 properties
Ocean View
13 properties
Kalapana
7 properties
Kapaau
7 properties
Honokaa
7 properties

Island of Hawaii

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1,437 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 $125 / night

$1,575 / week

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avg. 27 minutes

from $125 / 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. 3 hours 30 minutes

from $165 / 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 $349 / night

$3,213 / week

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Responds fast!
avg. 1 hour 13 minutes

from $349 / night

(1) Very Good 

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 - $1,400 / week

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Responds fast!
avg. 3 hours 30 minutes

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 - $1,400 / week

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Responds fast!
avg. 3 hours 30 minutes

from $150 / night

15

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 livin …see more

from $999 / night

$6,783 - $8,883 / week

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from $999 / night

7

Vacation hotel apartment with shared pool in Waikoloa

Kohala Coast / Waikoloa

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Hilton’s presence on the famous Kohala Coast increases with the Kings’ Land resort. Located on an old lava field, Kings’ Land by HGVC is the crowning jewel of Hilton Grand Vacations Club resorts in Hawaii. Discover the resort’s many luxury features and browse the availa …see more

from $239 / night

$1,671 / week

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from $239 / 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 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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 $250 / night

$1,662 - $1,872 / week

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from $250 / 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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from $177 / 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 $649 / night

$4,543 / week

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from $649 / night

(13) 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 $121 / night

$787 - $875 / week

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Responds fast!
avg. 1 hour 29 minutes

from $121 / night

42

Waikoloa Vacation home rental

Kohala Coast / Waikoloa

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
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 Kohala Coast and are thrilled to add Hawaiian Jewel Villa to …see more

from $469 / night

$3,283 / week

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from $469 / 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

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

4

Vacation home in Hilo

Island of Hawaii / Hilo

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
This is a wonderful place to relax and get away from it all- we have a beautiful outside dance pavilion, for Tango or yoga, as well as a full library for your reading pleasure. Located five minutes from Hilo airport, centrally located to downtown Hilo and the Universi …see more

from $350 / night

$2,450 / week

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from $350 / 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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Responds fast!
avg. 2 hours 32 minutes

from $150 / 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 $130 / night

$850 - $945 / week

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Responds fast!
avg. 1 hour 29 minutes

from $130 / night

(18) Very Good 

34

Vacation home with shared pool in Waikoloa

Kohala Coast / Waikoloa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Aloha! This stunning Waikoloa Beach Villa is surrounded by the sights, sounds and feel of the ocean, and features two bedrooms, two full bathrooms and accommodates up to six guests. Also included in your stay is the Hilton Waikoloa Pool Pass for stays thru December 31, …see more

from $199 / night

$1,393 / week

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from $199 / night

(3) Very Good 

12

Condo rental in Kailua-Kona with shared pool

Island of Hawaii / Kailua-Kona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
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 $169 / night

$1,199 - $1,999 / week

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from $169 / night

(10) Very Good 

30

Waikoloa Vacation home rental

Kohala Coast / Waikoloa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
The swimming pool and spa at the Waikoloa Fairway Villas will be closed Sep 14-21, 2015. Gorgeous sunset lake views close to the ocean in a perfect location immediately next to the pool and resort facilities overlooking the lights of the Kings Shops reflected off the …see more

from $179 / night

$1,253 / week

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from $179 / 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

(2) Excellent 

19

Home rental in Waikoloa with golf nearby

Kohala Coast / Waikoloa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
When you enter the front door, you'll realize you've arrived at a very special place. Please check over 40 excellent reviews on vacation rental by owner under Waikoloa Village 425793 Sleeps 6 Minimum stay 5 nights. Thank you, hope to see you soon!! Our 2,000 sq.ft. …see more

from $259 / night

$1,800 - $2,150 / week

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Responds fast!
avg. 3 hours 54 minutes

from $259 / night

(7) Excellent 

Certificate of Excellence

30

Vacation villa in Kailua-Kona

Island of Hawaii / Kailua-Kona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This lovely, spacious condo at Kahalu'u Beach (Turtle Beach) has incredible Ocean and Sunset views, and is the perfect escape for guests wanting easy access to swimming, snorkeling, surfing and golfing. Ours is an unit on the ground floor in the back with views of the …see more

Certificate of Excellence

from $145 / night

$1,015 / week

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Responds fast!
avg. 2 hours 49 minutes

from $145 / night

33

Home rental in Puako with swimming pool

Kohala Coast / Puako

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Live the Hawaiian Lifestyle in this elegant townhouse in the gated Fairways at Mauna Lani within the world class Mauna Lani Resort. With over 1,289 square feet of luxury living space; this unit comprises of two bedrooms, two full bathrooms, and comfortably accommodates …see more

from $209 / night

$1,463 / week

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from $209 / night

26

Puako Vacation villa rental

Kohala Coast / Puako

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Plenty of room to entertain family and friends at this beautiful Waikoloa Beach Villa that features two bedrooms, two bathrooms and comfortably accommodates up to six guests. Hilton Pool Pass included for stays between April 1-December 31, 2018. An inviting living room …see more

from $169 / night

$1,183 / week

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from $169 / night

(9) Very Good 

23

Vacation home with golf nearby in Mountain View

Island of Hawaii / Mountain View

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
If you enjoy the natural beauty of the outdoors, we would like to invite you to stay with us at our peaceful home. This upstairs unit with a private entrance, has two bedrooms: one with two full/double sized beds and the other with one queen bed. Sleeps 6 when sharing b …see more

from $120 / night

$720 - $1,280 / week

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from $120 / night

38

Kailua-Kona Vacation home rental

Island of Hawaii / Kailua-Kona

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Keauhou Estates Aloha Shores - 3 Master Suites, Pool & Fantastic Ocean Views! This STUNNING 3 bedroom 3.5 bathroom single level home is located in the gated community of Keauhou Estates! Enjoy panoramic views of the Kona Coastline from Kailua Kona to Keauhou and beyon …see more

from $399 / night

$2,793 / week

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from $399 / night

27

Puako Vacation townhouse rental

Kohala Coast / Puako

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This poolside/ volcanic mountain view three bedroom townhome is surrounded by the most enchanting scenery. Ideally located away from the main traffic area of the complex, your sure to enjoy the views of the spacious green belt area off your lanai. You are steps away fro …see more

from $289 / night

$2,023 / week

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from $289 / 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 $175 / night

$1,225 / week

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from $175 / night

(1) Very Good 

23

Vacation private room with golf nearby in Waikoloa

Kohala Coast / Waikoloa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
THE WAIKOLOA OASIS!!! Have your very own private resort! Comes complete with your own private solar heated pool, 2 person Hot Springs spa, Tiki Bar kitchen and putting green. Just 8 miles from the beautiful beaches of the Kohala Coast. A-Bay, Waialea Bay, and Hapuna Bea …see more

from $125 / night

$800 / week

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from $125 / night

55

Vacation home in Waikoloa

Kohala Coast / Waikoloa

3 12 4 nights min

  • 3 bedrooms
  • Sleeps 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
Welcome to the newest home in our Hawaiian Luxury Collection. Hawaiian Destiny at KaMilo is a wonderful, newly completed home (summer 2016) that sleeps 12 with a stunning backyard oasis including private pool and spa with stunning views of the golf course and suns …see more

from $695 / night

$4,865 / week

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from $695 / night

5

Vacation home in Keaau

Island of Hawaii / Keaau

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden
Centrally located cute little one Bedroom House with big screened Lanai on one acre in Paradise Park south of Hilo. Just 20 minutes north to Hilo and beaches or 20 minutes south to more beautiful Hawaiian beaches. Walk to the water and see the waves crashing against the …see more

from $59 / night

$413 / week

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from $59 / 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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Responds fast!
avg. 3 hours 44 minutes

from $235 / night

27

Waikoloa Vacation home rental

Kohala Coast / Waikoloa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
E Komo Mai! Welcome to beautiful Hali’i Kai Luxury Resort Living at its finest. Privacy, exclusivity and luxury are the coveted attributes of this beautiful two-bedroom villa, which offers approximately 1,300 square feet of lavish living space and accommodates up to six …see more

from $219 / night

$1,533 / week

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from $219 / night

15

Vacation home in Waimea

Island of Hawaii / Waimea

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
900 square foot recently renovated unit in lovely Waimea. Quality furnishings provide spaces to relax snd enjoy 48 inch TV and the wood burning fireplace. Indoor and outdoor dining tables are available as well as a four person seating area at a koa bar. You will be abl …see more

from $130 / night

$819 / week

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from $130 / night

(1) Excellent 

18

Puako Vacation home rental

Kohala Coast / Puako

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to the newest home in our Hawaiian Luxury Collection. Sweet Escape Villa at KaMilo is a wonderful new single level 3 bedroom home. We pride ourselves on provide some of the most sought after homes on the Kohala Coast. We have now partnered with the wonderful …see more

from $359 / night

$2,513 / week

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from $359 / night

(10) Very Good 

11

Kailua-Kona Vacation condo rental

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 $169 / night

$1,199 - $1,999 / week

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from $169 / 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 55 minutes

from $185 / night

34

Vacation home with shared pool in Waikoloa

Kohala Coast / Waikoloa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
On the luminous Kohala Coast, Kulalani at Mauna Lani is truly a paradise. Spread over 25 lush acres along the fairways of the Championship Francis H. I'i Brown North Course, Kulalani offers resort style living that is unparalleled. Our guests have unlimited private acce …see more

from $235 / night

$1,645 / week

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from $235 / night