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

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Vacation rentals Kailua-Kona
537 properties
Vacation rentals Kohala Coast
239 properties
Pahoa
159 properties
Vacation rentals Hilo
71 properties
Cabins Volcano
70 properties
Cottages Waimea
68 properties
Keaau
55 properties
Apartments Captain Cook
45 properties
Holualoa
28 properties
Hakalau
14 properties
Kapoho
14 properties
Pahala
13 properties
Estates Keauhou
13 properties
Naalehu
13 properties
Ocean View
10 properties
Mountain View
9 properties
Hawi
7 properties
Honokaa
6 properties
Kalapana
6 properties
Milolii
6 properties

Island of Hawaii

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1,433 Vacation rentals

(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

$3213 / week

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avg. 3 hours 0 minutes

from $299 / night

(3) Excellent 

24

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
****** FALL 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 PAPER …see more

from $109 / night

$1575 / week

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from $109 / 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
Special discount in August and September, check out our new rates! 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 drea …see more

from $148 / night

$1170 - $1520 / week

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from $148 / 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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avg. 3 hours 58 minutes

from $150 / 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

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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avg. 3 hours 58 minutes

from $150 / 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

11

Cottage rental in Kailua-Kona

Island of Hawaii / Kailua-Kona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 8 mi
This fabulously restored and redecorated cottage has its own private lanai with full ocean view overlooking Honokahou Harbor and is nested in a small quiet family farm surrounded by bananas and hapuu ferns. The cottage includes a full size private bathroom and a small k …see more

from $135 / night

$900 / week

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from $135 / night

(1) Excellent 

24

Vacation cottage in Pahoa

Island of Hawaii / Pahoa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
The Rainbow Eucalyptus tree may be one of the most stunning trees you'll ever see - and you can gaze at this beauty in a gorgeous jungle setting from your lanai at the Rainbow Cottage. There are two bedrooms each with queen sized bed, a living room, dining room, bathroo …see more

from $85 / night

$450 - $740 / week

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from $85 / night

(1) Excellent 

22

Vacation home in Waikoloa

Kohala Coast / Waikoloa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
Welcome to the beautiful Waikoloa Beach Resort, a tropical oasis amid the dramatic backdrop of virgin, black lava fields. Our mission at ******************* is to provide you with the perfect vacation destination and all the comforts of home, so sit back, relax, and cho …see more

from $179 / night

$1253 / week

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from $179 / night

(1) Excellent 

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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avg. 3 hours 14 minutes

from $165 / night

32

Vacation apartment rental

Kohala Coast / Waikoloa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Breathtaking unobstructed views--ocean, golf course, and, oh, those gorgeous sunsets! Two bedroom, 2 1/2 bath Big Island-Hawaiian retreat overlooking holes 2 and 3 of the beautiful Waikoloa Village Golf Course, designed by Robert Trent Jones Jr.  Just a pitch and a putt …see more

from $125 / night

$875 / week

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from $125 / night

(5) Very Good 

12

Vacation apartment with shared pool in Kailua-Kona

Island of Hawaii / Kailua-Kona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Keauhou Kona Surf & Racquet Club is located approx. four miles south of Kailua Kona. Surf & Racquet 1201 is a second floor two bedroom two bathroom oceanfront condo with a large wraparound lanai for watching whales or a green flash from a Kona sunset. It's turnkey furni …see more

from $165 / night

$1050 - $1323 / week

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avg. 3 hours 14 minutes

from $165 / night

12

Vacation apartment rental

Island of Hawaii / Kailua-Kona

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
NOTE, THERE IS A SEVEN NIGHT MINIMUM FOR THIS CONDO. Country Club Villas 223 is located in the Keauhou area, approx. four miles south of Kailua Kona. This beautifully furnished ocean view two bedroom (king in master, two twins in guest) two bath is located on the second …see more

from $145 / night

$1015 - $1155 / week

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avg. 3 hours 14 minutes

from $145 / night

(7) Good 

13

Apartment rental in Kailua-Kona with shared pool

Island of Hawaii / Kailua-Kona

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The owner of this condo has always dreamed of owning a submarine so this condo has the decor of his dream. Walk into this ground floor condo and be greeted by large " under water windows" depicting beautiful coral reefs and a surprise swimmer". Not your typical Island …see more

from $99 / night

$623 - $693 / week

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avg. 42 minutes

from $99 / 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

20

Kailua-Kona Vacation apartment rental

Island of Hawaii / Kailua-Kona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Ocean and Golf Course Views From Upgraded Unit! Keauhou Punahele B102 Keauhou Punahele is a Non Smoking and Non Air Conditioning condominium resort. Unit B102 is located on the ground floor of Building # B which is the first building you see in front of you as you enter …see more

from $115 / night

$805 / week

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from $115 / night

(15) Excellent 

23

Vacation home in Hilo

Island of Hawaii / Hilo

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
Lopaka's Family Lodge is a beautiful and immaculate unit in a tropical setting located 3 miles above downtown Hilo. It is a spacious (800 sq. ft.) 1 BR, 1BA and comes with everything you need including washer & dryer. The private entrance is up a short six step stairway …see more

from $125 / night

$800 - $1150 / week

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avg. 2 hours 21 minutes

from $125 / night

23

Vacation home in Kailua-Kona

Island of Hawaii / Kailua-Kona

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
You will enjoy impressive ocean views from almost every room in this home, along with amazing sunsets!  This beautiful, 2 story home with 4 bedrooms 4.5 baths  is located in the gated community of Keauhou Estates on the Big Island of Hawaii. This community is situated c …see more

from $450 / night

$3150 / week

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from $450 / night

10

Vacation b&b in Volcano

Island of Hawaii / Volcano

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
This listing is new and a good bargain! HUGE en suite private room! It has its own private entrance, automatic gate, a nice size lanai (patio), bathroom, walk-in closet, HDTV, AppleTV (Netflix, etc.), good wifi, wet bar, microwave, coffee maker, and other important esse …see more

from $82 / night

$574 / week

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avg. 1 hour 7 minutes

from $82 / night

(1) Very Good 

10

Vacation apartment in Kailua-Kona

Island of Hawaii / Kailua-Kona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
The Surf & Racquet Club is located approx. four miles south of Kailua Kona in Keauhou. Surf & Racquet 8303 is a third (top) floor two bedroom w/den garden view condo. Bedding consists of a queen in the master, a double in the loft and a queen futon in the den. It fully …see more

from $130 / night

$665 - $910 / week

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avg. 3 hours 14 minutes

from $130 / night

(1) Very Good 

13

Vacation apartment in Kailua-Kona

Island of Hawaii / Kailua-Kona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
Kanaloa 3203 is a spacious second floor two bedroom plus sleeping loft oceanfront condo. There is a king bed in the master, two twins in the guest and two twins in the loft. In addition, there is a jacuzzi in the attached master bath as well as a private office space of …see more

from $265 / night

$1750 - $1925 / week

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avg. 3 hours 14 minutes

from $265 / night

(9) Very Good 

23

Vacation home in Keauhou

Island of Hawaii / Keauhou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
This beautifully appointed Villa, built in 2005, has recently been professionally decorated with all new furnishings. It is located on the sunny west side of the Big Island of Hawaii. Na Hale O Keauhou is a gated community with well-maintained, lush tropical landscaping …see more

from $165 / night

$1155 / week

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from $165 / night

31

Vacation home in Waikoloa

Kohala Coast / Waikoloa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
Kulalani #2405 in beautiful Mauna Lani Resort, Family Friendly, Discount Golf and Free Private Access to the luxurious Mauna Lani Beach Club On the luminous Kohala Coast, Kulalani at Mauna Lani is truly a paradise. Spread over 25 lush acres along the fairways of the Cha …see more

from $219 / night

$1533 / week

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from $219 / night

(8) Very Good 

15

Apartment rental in Kailua-Kona

Island of Hawaii / Kailua-Kona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Newly remodeled unit, with ocean view, we also have a screened in Lanai, queen size bed and queen size sleeper sofa bed. Kitchen has new appliances, stove, microwave oven, refrigerator.It sleeps four very comfortably, flat screen TV, VCR, stereo, air conditioner, ceil …see more

from $79 / night

$553 - $833 / week

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avg. 2 hours 20 minutes

from $79 / night

19

Vacation apartment in Waikoloa

Kohala Coast / Waikoloa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Welcome to Waikoloa Fairways - where the VOG is less and sunshine is more. Join us in thinking that Waikoloa Fairways is the best place to stay on the Big Island - enjoy the quiet surroundings in this premier gated community. WE ARE LOCATED IN THE VILLAGE OF WAIKOLOA (n …see more

from $125 / night

$875 / week

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from $125 / 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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avg. 3 hours 15 minutes

from $125 / 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 $169 / night

$1124 - $1470 / week

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from $169 / night

22

Home rental in Kailua-Kona with swimming pool

Island of Hawaii / Kailua-Kona

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
Make lasting memories while luxuriating on your dream vacation in this custom built, eco-friendly, solar home in beautiful and secure Keauhou Estates on the Island of Hawaii. Hawaii ( also called the Big Island) has been hailed as the world's “best island for living” an …see more

from $395 / night

$2765 / week

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from $395 / night

(3) Very Good 

13

Vacation home in Pahoa

Island of Hawaii / Pahoa

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Enjoy a wonderful, Hawaiian vacation at our 'House of Sea Spray' (Hale Huna Kai) on the beautiful East Coast of Hawaii. Our two-bedroom vacation home comfortably accommodates parties of up to six people in a modern, cheerful, quiet, and relaxed setting. Convenient to H …see more

from $165 / night

$975 / week

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from $165 / night

(11) 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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avg. 3 hours 14 minutes

from $89 / night

(78) Very Good 

27

Kapoho Vacation home rental

Island of Hawaii / Kapoho

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
If you love expansive ocean views, Sunrise House is the place for you! The location of Sunrise House at the edge of the sea on quiet Kapoho Point provides all the comforts of home, and you just can't get more oceanfront than this! This private retreat features 2 bedroom …see more

from $140 / night

$930 - $1440 / week

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from $140 / night

35

Vacation villa in Hilo

Island of Hawaii / Hilo

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
Water Falling Villa is a spectacular vacation rental on the Big Island of Hawaii. Perched on a cliff along the Hamakua Coast in Ninole, Hawaii, this epic estate is positioned to take advantage of a postcard-perfect double Hawaiian waterfall that cascades majestically do …see more

from $2785 / night

$19495 / week

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from $2785 / night

(5) Excellent 

18

Kapaau Vacation cottage rental

Island of Hawaii / Kapaau

2 1 night min

  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
This unique setting, a working farm in the heart of Kohala, offers it all. The cozy cottage has expansive views of gardens and sweeping lawns, with the Kohala coast as a backdrop. Located midway between artistic Hawi and historic Kapa'au, this cottage offers convenienc …see more

from $79 / night

$553 / week

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avg. 1 hour 39 minutes

from $79 / night

(8) Excellent 

34

Vacation home with swimming pool in Keaau

Island of Hawaii / Keaau

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
The sight and sound of dramatic crashing surf greet you from every room of this luxury, 4 bedroom/2 bathroom Hawaiian prviate home on 1/2 landscaped acre with your own swimming pool and hot tub by the sea. This is Hale Mar, and you'll love it. The best of everything, …see more

from $299 / night

$2093 / week

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from $299 / night

(3) Very Good 

16

Apartment rental in Kailua-Kona with shared pool

Island of Hawaii / Kailua-Kona

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Welcome to 'Kona Bob's' Condo. This lovely first floor newly remodeled (August 2013) ocean view condo at Kona Shores is decorated Hawaiian Island style. There are many upgraded items including granite countertops in both the kitchen and bathroom, custom cabinetry, stain …see more

from $100 / night

$700 / week

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avg. 1 hour 50 minutes

from $100 / night

(2) Excellent 

25

Vacation condo in Kailua-Kona

Island of Hawaii / Kailua-Kona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Our Kona Bali Kai direct ocean front condo (Unit 219) sits 30' behind the seawall. You can't get any closer to the sea without getting wet. If you want DIRECT Ocean Front, next to the most popular Island surf break in a TOTALLY remodeled unit at a great price point loo …see more

from $149 / night

$1043 / week

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Responds fast!
avg. 1 hour 38 minutes

from $149 / night

(32) Excellent 

Certificate of Excellence

16

Vacation home in Kailua-Kona

Island of Hawaii / Kailua-Kona

2 Min stay varies

  • Sleeps 2
  • Min stay varies
  • Nearest beach 0 mi
  • Car not necessary
This studio located off Ali'i Drive walking distance to the famous White sand beach also known as Magic Sands. One block above beach in quite neighborhood in a quite cul-de-sac. Perfect for a couple. Listening to the birds in early morning and hear the waves on the beac …see more

Certificate of Excellence

from $85 / night

$595 / week

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Responds fast!
avg. 2 hours 47 minutes

from $85 / night

(1) Excellent 

34

Waimea Vacation apartment rental

Island of Hawaii / Waimea

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
KA NOHONA KAI LA'AKEA, which translates in Hawaiian to 'seaside home of sacred light/happiness' only begins to describe what you are about to experience when you stay in this lovely home. Located in the famous Mauna Lani Resort, the award winning architecture of Fairway …see more

from $219 / night

$1533 / week

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from $219 / 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 13 minutes

from $75 / night