50 Best Hawaii Vacation rentals on Holiday Lettings - Apartments

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5,029 Vacation rentals

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(24) Excellent 

31

Hawaii Vacation home rental

Kauai / Hanalei

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Stay in our private home in Princeville Kauai at a fraction of what a hotel costs! Three bedrooms, 2 baths, open living room with dining room and full kitchen. The kitchen is fully equipped for eating in, plus we have 2 large lanais for outdoor dining overlooking the m  …see more

from $230 / night

$1610 / week

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from $230 / night

(1) Excellent 

20

Vacation cottage rental

Maui / Haiku

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Private garden
A romantic honeymoon/vacation retreat on Maui's beautiful north shore. Have the best of both worlds by staying away from crowds and commercialized development, yet conveniently situated for exploring the entire island. A rare combination of gracious island lifestyl  …see more

from $359 / night

$2302 - $2652 / week

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from $359 / night

(2) Very Good 

28

Vacation apartment rental

Kauai / Poipu

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Paradise Found! Secluded End Unit,#331, Partial Ocean View. Quiet, perfect retreat,pristine beaches,stunning garden paradise.Tastefully decorated condo home with lofted ceilings,louvered windows,gleaming new wood floors,large tile entry hall and kitchenupdate  …see more

from $169 / night

$1050 - $1300 / week

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from $169 / night

(2) Excellent 

26

Home rental in Hawaii 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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from $299 / night

(12) Very Good 

28

Hawaii Vacation home rental

Island of Hawaii / Volcano

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • 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 $195 / night

$1170 - $1870 / week

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from $195 / night

6

Maui / Lahaina

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $299 / night

$2093 / week

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from $299 / night

(1)  

21

Vacation condo with shared pool in Hawaii

Maui / Kihei

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Kamaole Sands is an award-winning condo complex situated just across from one of the best beaches on Maui. Kamaole Sands III beach, is recognized as one of the best beaches in Maui. Boogie board, surf, snorkel straight off the beach. We have seen turtles, Manta rays and  …see more

from $219 / night

$1533 / week

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from $219 / night

16

Vacation studio in Hawaii

Maui / Lahaina

Studio 4 7 nights min

  • Studio
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Our "Studio Premium" is the most affordable unit you can book at the luxurious Westin Kaanapali Ocean Resort and has all Westin amenities including king-size "heavenly" bed and queen-size sofa, whirlpool bath, lanai and all the facilities available a  …see more

from $320 / night

$1700 / week

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from $320 / night

(2) 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'  …see more

from $150 / night

$980 - $1400 / week

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from $150 / night

(4) Excellent 

26

Condo rental in Honolulu

Oahu / Honolulu

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
OUR CALENDAR IS UPDATED DAILY--PLEASE CHECK 'AVAILABILITY & RATES' ************************************************************************************** THIS UNIT IS IDEAL FOR 2 COUPLES OR 2 FAMILIES TRAVELING TOGETHER. **********************************  …see more

from $495 / night

$3465 / week

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from $495 / night

14

Vacation condo in Hawaii

Oahu / Honolulu

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
Located only 1 block from Waikiki Beach, this ocean facing, large corner unit with lanai and extra windows on the 36th floor, has panoramic views of the ocean, beach, pool, and Diamond Head, not to mention the sunrise and sunset views. Breathtaking! Our condo has been  …see more

from $165 / night

$1155 / week

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from $165 / night

27

Koloa Vacation apartment rental

Kauai / Koloa

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Quiet,end unit perfect retreat,pristine beaches,stunning garden paradise. Unit 331 on bldg.39Tastefully decorated condo with lofted ceilings,louvered windows,gleaming new floors,large tile entry hall and kitchen,update granite counter tops in kitchen and bath T  …see more

from $159 / night

$991 / week

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from $159 / night

49

Condo rental in Hawaii

Maui / Wailuku

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
~~~Your own private window to the whales. Conveniently situated in quaint Maalaea Village. We invite you to come aboard, and set sail into a radiant Maui sunset. You'll see whimsical turtles playing peekaboo in the gentle surf (year round) and magnificent humpba  …see more

from $300 / night

$2100 / week

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from $300 / night

19

Hawaii 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'  …see more

from $150 / night

$980 - $1400 / week

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from $150 / night

23

Vacation condo rental

Oahu / Kahuku

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This homey one bedroom / two bathroom Turtle Bay condo offers the perfect true Hawai'i get-away for up to four lucky humans! The closest condo to the beach and sitting on the 18th hole of PGA Fazio Course, we welcome you to the coveted North Shore! **The Condo**  …see more

from $184 / night

$1288 / week

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from $184 / night

(1) Excellent 

25

Vacation home accommodation

Oahu / Honolulu

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
A Beautiful high ceiling air conditioned home located on East Oahu. This eloquent home in Hawaii Kai is perched up in a nice quiet neighborhood in Kalama Valley. This 3 bedroom, 2 bathroom house features, three lanais - one outside the master bedroom with table and chai  …see more

from $348 / night

$2436 / week

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from $348 / night

29

Vacation home rental

Oahu / Waianae

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We are removing this property from this website as we are not happy with this company. Owner  …see more

from $130 / night

$910 / week

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from $130 / night

(13) Excellent 

20

Hawaii 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  …see more

from $165 / night

$1015 - $1715 / week

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from $165 / night

12

Studio rental in Haiku

Maui / Haiku

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
A romantic honeymoon/vacation retreat on Maui's beautiful north shore. Have the best of both worlds by staying away from crowds and commercialized development, yet conveniently situated for exploring the entire island. A rare combination of gracious island lifestyl  …see more

from $249 / night

$1603 - $1799 / week

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from $249 / night

20

Vacation condo rental

Maui / Kihei

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
Bright, clean and comfortable, contemporary and uncluttered with a great view of the ocean and the lush tropical gardens below. This is a very well renovated one bed/one bath unit in KA building C unit 509, nicely furnished and well outfitted. Being up higher on the f  …see more

from $99 / night

$693 / week

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from $99 / night

19

Vacation condo with shared pool, golf nearby in Hawaii

Kauai / Princeville

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Fully remodeled quality top floor luxury laid back tropical condo. All furnishings & decor coordinated professionally. Full kitchen & quality cooking appliances & supplies. Relax & enjoy quiet & views from 2 lanais. Everything in condo needed for  …see more

from $145 / night

$1000 / week

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from $145 / night

7

Vacation studio in Kailua

Oahu / Kailua

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Kailua beach is about 1 mile from Kailua town. Kailua Guesthouse is located half-way between. It's about a 10-minute walk to the beach, a 10-minute walk to town. TheBus stop is about 300 feet from our front gate. My father acquired the property in 1947  …see more

from $139 / night

$910 / week

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from $139 / night

12

Vacation hotel apartment in Honolulu

Oahu / Honolulu

2 8 90 nights min

  • 2 bedrooms
  • Sleeps 8
  • 90 nights min
  • Swimming pool
  • Air conditioning
PLEASE NOTE: ⚫️This is NOT a Private Rental ⚫️This is NOT a Private Room. ⚫️Private Beds available in a Female Shared Room, Sorry no vacancy in our CO-Ed area at this time. プリンセスパレス ::::: ELS / INTERN STUDENT CONDO HOME STAY - STUDENT SHARE  …see more

from $37 / night

$250 / week

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from $37 / night

8

Vacation apartment with shared pool in Ka'anapali

Maui / Ka'anapali

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Escape to an exotic island surrounded by glistening, white sandy shores, flourishing tropical scenery and intriguing wild life. The symphony of gently lapping waves beckons visitors to explore Maui’s many hidden wonders. Dive down to the depths of the ocean and di  …see more

from $358 / night

$2500 / week

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from $358 / night

12

Oahu / Honolulu

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool

 …see more

from $109 / night

$765 / week

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from $109 / night

24

Kohala Coast / Waikoloa

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from $349 / night

$2094 - $2905 / week

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from $349 / night

11

Kauai / Koloa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $400 / night

$2800 / week

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from $400 / night

(1) Excellent 

13

Kauai / Haena

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $425 / night

$2975 / week

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from $425 / night

(8) Very Good 

10

Island of Hawaii / Kailua-Kona

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from $89 / night

$560 - $875 / week

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from $89 / night

(1) Very Good 

45

Oahu / Kahuku

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool

 …see more

from $200 / night

$1860 - $2000 / week

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from $200 / night

50

Island of Hawaii / Kohala Coast

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

 …see more

from $370 / night

$2800 / week

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from $370 / night

12

Kauai / Koloa

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $400 / night

$2800 / week

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from $400 / night

(3) Very Good 

28

Island of Hawaii / Waimea

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly

 …see more

from $149 / night

$895 / week

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from $149 / night

14

Island of Hawaii / Kailua-Kona

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $131 / night

$920 / week

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from $131 / night

(5) Very Good 

12

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

 …see more

from $165 / night

$1050 - $1323 / week

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from $165 / night

(2) Good 

10

Maui / Kihei

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $149 / night

$1043 / week

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from $149 / night

36

Maui / Lahaina

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $140 / night

$980 / week

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from $140 / night

(3) Excellent 

49

Maui / Lahaina

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 110 mi
  • Swimming pool

 …see more

from $850 / night

$5950 / week

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from $850 / night

(1) Excellent 

43

Maui / Lahaina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $135 / night

$945 - $7903 / week

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from $135 / night

(2) Very Good 

20

Island of Hawaii / Pahoa

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Air conditioning
  • Private garden

 …see more

from $119 / night

$833 / week

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from $119 / night