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

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Vacation rentals Kailua-Kona
431 properties
Vacation rentals Kohala Coast
195 properties
Pahoa
141 properties
Vacation rentals Hilo
67 properties
Cottages Waimea
65 properties
Cabins Volcano
61 properties
Keaau
49 properties
Apartments Captain Cook
42 properties
Holualoa
26 properties
Kapoho
15 properties
Hakalau
14 properties
Pahala
14 properties
Naalehu
13 properties
Estates Keauhou
10 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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1,209 Vacation rentals

(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

(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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from $299 / night

(3) Excellent 

24

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 atmosphere of a one of a kind guest-house located in this Historic Plantation Estate. The history dates back centuries to the legend of the Hawaiian Princess La'ieika …see more

from $150 / night

$980 - $1400 / week

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from $150 / night

19

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 atmosphere of a one of a kind guest-house located in this Historic Plantation Estate. The history dates back centuries to the legend of the Hawaiian Princess La'ieika …see more

from $150 / night

$980 - $1400 / week

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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 - $1716 / week

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from $165 / night

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

(5) Excellent 

31

Vacation home in Keaau

Island of Hawaii / Keaau

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Comfortable elegance in a very private oceanfront setting awaits you at Kahikole. Enter through the lava rock wall and turtle festooned gate into your personal oasis. Designed in the round (actually 12-sided), the home provides beautiful ocean views from virtually every …see more

from $135 / night

$900 - $1610 / week

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from $135 / night

(6) 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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from $70 / 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 - $2906 / week

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from $349 / 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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from $165 / night

(48) Very Good 

33

Home rental in Hilo with shared pool

Island of Hawaii / Hilo

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
Newly remodeled and tastefully decorated, 508 is one of the nicest condos at Maunaloa Shores. Why stay in a hotel when for about the same rate you can have ocean views, 2 bedrooms, a new kitchen, and your own private outdoor lanai less than 5 miles from downtown? Start …see more

from $99 / night

$659 - $1039 / week

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from $99 / night

(8) Excellent 

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

(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

(16) Very Good 

17

Volcano Vacation home rental

Island of Hawaii / Volcano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 21 mi
  • Ask about children
"Our Hawaiian Hideaway" is Our Lovely 1-Bedroom, 1-Bath Vacation Home on 2 acres in a Beautiful Garden Setting. Our Hideaway is conveniently located halfway between Volcano National Park and Hilo in Beautiful Mountain View. Each location is approx. 30 min. away. We thin …see more

from $85 / night

$550 - $830 / week

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from $85 / night

39

Waikoloa Vacation home rental

Kohala Coast / Waikoloa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Welcome to the newest home in our Hawaiian Luxury Collection. Hawaiian Dream Villa at KaMilo is a wonderful new 3 bedroom home. ★★★★★★★★★★★★★★★★★★★★★★★★★★★★★★★★★★ Hawaiian Dream Villa provides a perfect setting for your Hawaii getaway and is designed for large grou …see more

from $290 / night

$2030 / week

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from $290 / 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

(1) Excellent 

17

Vacation apartment in Waimea

Island of Hawaii / Waimea

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Private garden
The Jade Suite is in the Waimea Guest House and it is a private & beautifully furnished apartment in a lovely historic Hawaiian home. This is on the dry side of Waimea nestled under a HUGE Ylang Ylang tree, surrounded by giant Jade plants, Kukui Nut trees, and an enorm …see more

from $125 / night

$875 / week

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from $125 / night

(31) Excellent 

28

Kailua-Kona Vacation apartment rental

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
Love to snorkel and want to see over 100 species of tropical fish & turtles? Then why not stay right across the street from Hawaii's best snorkeling beach?! Our modern beachfront unit offers gorgeous ocean/sunset views and the easiest access to the incredible snorkeling …see more

from $185 / night

$1295 / week

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from $185 / night

(26) Excellent 

11

Vacation home rental

Island of Hawaii / Volcano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
Minutes from Hawaii's #1 destination, Volcano National Park. Volcano Dancing Ferns is located on 3 square acres surrounded by the Big Islands upcountry rain forest. Lush jungle, large Ohia trees and Hapu'u ferns surround the property. This guest room is located in a bea …see more

from $115 / night

$805 / week

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from $115 / night

(8) Excellent 

20

Vacation home rental

Island of Hawaii / Hilo

1 2 2 nights min

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

from $99 / night

$693 / week

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from $99 / night

27

Vacation apartment with shared pool in Waimea

Island of Hawaii / Waimea

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Paradise awaits at this gorgeous Kamuela vacation rental condo. Offering 3 bedrooms, 3 baths, a quiet ambiance and beautiful views across the golf course with lava rock and tons of wildlife, this condo ensures a genuinely revitalizing island retreat! This exquisite Kam …see more

from $300 / night

$1950 - $3294 / week

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from $300 / 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 $110 / night

$770 / week

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from $110 / night

(5) Excellent 

26

Vacation apartment 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 2 mi
  • Swimming pool
Make the most of your vacation by staying at Kailua-Kona's premier oceanfront property, The Royal Sea Cliff. Our two bedrooms, two bathroom deluxe penthouse condominium is on the top floor where sweeping coastline and ocean views can be enjoyed from the large lanai whi …see more

from $170 / night

$1190 / week

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from $170 / night

(3) Very Good 

40

Vacation home in Milolii

Island of Hawaii / Milolii

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 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. Located on Kai Ave and Waena Ave, Milolii, …see more

from $139 / night

$815 - $1235 / week

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from $139 / 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

18

Vacation apartment in Waikoloa

Kohala Coast / Waikoloa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Located in probably the best location at the Waikaloa Beach Resort. All attractions are a short walk away. Relax and enjoy breathtaking sunsets and gentle breezes from your private lanai overlooking the 9th fairway at the beautiful Fairway Villas. Located in a lushly l …see more

from $129 / night

$839 - $1069 / week

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from $129 / night

36

Vacation home in Hilo

Island of Hawaii / Hilo

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 0.8 mi
  • Child friendly
  • Private garden
This grand, historic Victorian house is located near downtown Hilo on Reed’s Island, a hidden jewel of Hawaii on the Big Island. Long ago, royal families occupied the prestigious ‘island’ with the Wailuku River flowing in the backyard and the tropical rain forest settin …see more

from $375 / night

$2625 - $29785 / week

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from $375 / 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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from $165 / night

10

Vacation condo in Waikoloa

Kohala Coast / Waikoloa

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Spectacular Kohala Coast resort on the Big Island of Hawaii. Fully equipped, 2 bedroom/2 bathroom villa with full kitchen, spacious wrap-around private lanai, king bed and soaking tub in master suite, one queen or two full beds in second bedroom, and queen sofa bed in l …see more

from $300 / night

$2100 / week

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from $300 / 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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from $125 / 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

28

Vacation home rental

Island of Hawaii / Hilo

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool
Papa'Aloa is the ultimate in dream vacation spots! Located on the beautiful and historical Hamakua coast only 25 miles north of Hilo, Papa'Aloa is perched on this historic 1 acre with an oceanfront location that is second to none. What we consider to be the last of the …see more

from $400 / night

$2800 / week

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from $400 / 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

$904 - $1015 / week

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from $135 / night

17

Hakalau Vacation private room rental

Island of Hawaii / Hakalau

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Deluxe Palm Room The Deluxe Palm Room is a large harmonious room which offers a calming atmosphere. This spacious room is located on the ground floor and includes 1 California King size bed, full en-suite private bath, and private exterior entrance with large double met …see more

from $99 / night

$693 / week

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from $99 / night

(2) Excellent 

13

Keauhou Vacation condo rental

Island of Hawaii / Keauhou

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Peaceful one bedroom, one bath condominium in a small and quiet community. Enjoy the tropical gardens, golf course and ocean views, and two saltwater pools. The condos are surrounded by the Kona Country Club golf course. It's an easy walk in one direction to shopping …see more

from $99 / night

$693 / week

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from $99 / night

(4) Excellent 

33

Vacation home in Pahoa

Island of Hawaii / Pahoa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Our son is a Beverly Hills Architect and he designed this house as a special retirement home for his parents. The house has bamboo 23' vaulted, hand rubbed beam ceilings with floating globe pendants. There is a curved staircase with Mango steps that leads from the livin …see more

from $240 / night

$1600 - $2550 / week

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from $240 / night

(1) Excellent 

33

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
  • Swimming pool
  • Child friendly
Punahele Penthouse Condo will fast become your favorite place to stay in Kailua-Kona! Punahele Penthouse is on the 7th (top) floor of the beautiful Kona Ali'i Condo Complex which is located in the heart of Kailua-Kona. The 2b/2b luxury suite sleeps 4 adults comfortably …see more

from $199 / night

$1399 - $2499 / week

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from $199 / night

25

Vacation home in Keaau

Island of Hawaii / Keaau

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Aloha & Welcome to Mermaid's Oasis! This 4 bedroom home is directly oceanfront in spectacular Hawaiian Paradise Park. It truly is paradise here! Before you even step foot in the door you are greeted by a Hawaiian Sea turtle fountain and pond, with tropical flowers and …see more

from $295 / night

$1895 / week

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from $295 / night

(2) Very Good 

27

Vacation home in Hilo

Island of Hawaii / Hilo

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Located in one of Hilo's oldest neighborhoods, Hilo Kealoha ("the loved one" of Hilo) is a ninety-one year old plantation home that has been updated and maintained - and now shared with visitors to the east side of Hawaii. This two-bedroom, one-bathroom home is just pas …see more

from $99 / night

$595 - $805 / week

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from $99 / night

(6) Excellent 

Certificate of Excellence

34

Apartment accommodation 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 1 mi
  • Swimming pool
Aloha and Welcome to Banyan Tree 301 ~ A Hawaiian oceanfront paradise, completely remodeled with breathtaking ocean views! Our passion is to make every stay memorable for each guest and to make you feel truly welcome in our Kona Oceanfront Hawaiian Hale! Come relax an …see more

Certificate of Excellence

from $230 / night

$1534 / week

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from $230 / night

1