50 Best Hawaii Vacation rentals on Holiday Lettings - Apartments

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Vacation rentals Maui: 2,586 properties
Island of Hawaii: 1,435 properties
Vacation rentals Oahu: 1,434 properties
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Vacation rentals Molokai: 88 properties

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6,521 Vacation rentals

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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

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from $299 / night

$3213 / week

Responds fast!
avg. 3 hours 0 minutes

from $299 / night

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

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from $109 / night

$1575 / week

from $109 / night

35

Hawaii 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

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from $148 / night

$1170 - $1520 / week

from $148 / night

6

Vacation apartment rental

Maui / Lahaina

1 4 7 nights min

1 bedroom
Sleeps 4
7 nights min

Swimming pool
Child friendly
Air conditioning

This property is 3 minutes walk from the beach. Set between North Ka’anapali Beach and the mountains of West Maui, this Lahaina, Hawaii resort features 6 outdoor pools. It has spacious villas with views of the ocean or island. Westin Ka’anapali Ocean Resort Villas offe …see more

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from $299 / night

$2093 / week

from $299 / night

8

Vacation apartment in Hawaii

Maui / Paia

2 4 90 nights min

2 bedrooms
Sleeps 4
90 nights min

Child friendly

Located only 3m to Paia, where you can find yoga studios, restaurants, shopping boutiques and art galleries. 3m to Ho'okipa beach and Baldwin beach where are perfect for surfing, wind surfing and kite surfing. 15m to Kahului airport. The upstairs of the house has two ro …see more

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from $130 / night

$780 - $1950 / week

from $130 / night

124

Vacation home in Haiku

Maui / Haiku

3 8 2 nights min

3 bedrooms
Sleeps 8
2 nights min

Beach/lakeside relaxation
Child friendly
Private garden

Aloha! The perfect location, perfect amount of privacy, perfect aloha spirit, perfectly natural....perfectly luxurious! Please make sure to see if your questions are asked already here before emailing. Mahalo! If you want to have a relaxing, fun, vacation, and are kind …see more

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from $95 / night

$665 / week

from $95 / night

21

Vacation condo with shared pool in Hawaii

Maui / Kihei

2 8 1 night min

2 bedrooms
Sleeps 8
1 night min

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

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from $219 / night

$1533 / week

from $219 / night

4

Hawaii Vacation home rental

Oahu / Mililani

1 2 3 nights min

1 bedroom
Sleeps 2
3 nights min

My place is close to all major Freeway, highways ( H2 , 99 ), Restaurants, shopping, entertainment. One Queen Bed Private room SM accommodation : * private refrigerator in your room with drinks North Shore ........ 20 minutes ( Best Surf in Hawaii ) "Amazing place if yo …see more

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from $39 / night

$273 / week

from $39 / night

14

Vacation condo in Hawaii

Oahu / Honolulu

1 4 Min stay varies

1 bedroom
Sleeps 4
Min stay varies

Beach/lakeside relaxation
Swimming pool
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

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from $165 / night

$1155 / week

Responds fast!
avg. 3 hours 37 minutes

from $165 / night

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

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from $150 / night

$980 - $1400 / week

Responds fast!
avg. 3 hours 58 minutes

from $150 / night

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 you here o …see more

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from $165 / night

$1015 - $1715 / week

from $165 / night

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24

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 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

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from $150 / night

$980 - $1400 / week

Responds fast!
avg. 3 hours 58 minutes

from $150 / night

142

Vacation home in Hawaii

Maui / Haiku

4 8 1 night min

4 bedrooms
Sleeps 8
1 night min

Beach/lakeside relaxation
Child friendly
Private garden

Aloha! The perfect location, perfect amount of privacy, perfect aloha spirit, perfectly natural....perfectly luxurious vegetarian home! Please make sure to see if your questions are asked already here before emailing. Mahalo! If you want to have a relaxing, fun, vacati …see more

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from $95 / night

$665 / week

from $95 / night

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 kitchen update …see more

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from $169 / night

$1050 / week

Responds fast!
avg. 2 hours 41 minutes

from $169 / night

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

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from $348 / night

$2436 / week

Responds fast!
avg. 2 hours 35 minutes

from $348 / 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 at the resort. A wint …see more

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from $320 / night

$1700 / week

from $320 / night

10

Vacation condo with golf nearby in Hawaii

Oahu / Honolulu

1 2 3 nights min

1 bedroom
Sleeps 2
3 nights min

Nearest beach 0 mi
Child friendly
Car not necessary

This is a Studio unit not 1 bedroom. Step out of the elevator and on to the warm sands of Waikiki Beach. You can not find a better location! Walk to restaurants, shopping, and all that Waikiki has to offer. You don't walk to the beach, you are on the beach! This Suite …see more

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from $145 / night

$1015 / week

Responds fast!
avg. 1 hour 12 minutes

from $145 / night

9

Vacation townhouse with shared pool in Hawaii

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

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from $189 / night

$1225 - $1400 / week

from $189 / night

29

Vacation home rental

Oahu / Waianae

1 4 7 nights min

1 bedroom
Sleeps 4
7 nights min

Nearest beach 1 mi
Swimming pool
Child friendly

Spectacular, One Bedroom Ocean View , Pool, Internet, Cable TV. Like all tourists, we came here to experience the Aloha Spirit in the west side of Oahu, and we found the paradise. As we fall in love with everything here, we decided to make this home and now we would lik …see more

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from $168 / night

$1174 / week

from $168 / 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.39 Tastefully 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

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from $159 / night

$991 / week

Responds fast!
avg. 2 hours 41 minutes

from $159 / night

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

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from $395 / night

$2765 / week

from $395 / night

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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

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from $230 / night

$1610 / week

Responds fast!
avg. 2 hours 49 minutes

from $230 / 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 humpback wh …see more

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from $300 / night

$2100 / week

Responds fast!
avg. 1 hour 40 minutes

from $300 / 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** New …see more

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from $184 / night

$1288 / week

from $184 / night

6

Vacation home in Mililani

Oahu / Mililani

1 2 3 nights min

1 bedroom
Sleeps 2
3 nights min

My place is a house and is close to all major Freeway, highways ( H2 , 99 ), Restaurants, shopping, entertainment. One bedroom Suite: * AirCondition Room * Free Wifi and Parking * Internet 42" TV * North Shore ........ 20 minutes ( Best Surf in Hawaii ) "Amazing place i …see more

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from $80 / night

$560 / week

from $80 / night

5

Vacation home rental

Oahu / Mililani

1 2 4 nights min

1 bedroom
Sleeps 2
4 nights min

My place is close to all major Freeway, highways ( H2 , 99 ), Restaurants, shopping, entertainment. One Queen Bed Private room SM accommodation : * private refrigerator in your room with drinks North Shore ........ 20 minutes ( Best Surf in Hawaii ) "Amazing place if yo …see more

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from $39 / night

$273 / week

from $39 / 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

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from $99 / night

$693 / week

from $99 / night

6

Vacation private room in Hawaii

Maui / Paia

1 2 2 nights min

1 bedroom
Sleeps 2
2 nights min

Nearest beach 0.5 mi
Car not necessary

SUMMARY: No car? Don't feel like driving on vacation? Want to save on car rental? This is THE PERFECT place for you. My place is 5min walking distance to the Beach, restaurants and dining, town center, art and culture, great views, family-friendly activities. You’ll lo …see more

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from $129 / night

$801 / week

from $129 / night

16

Condo rental in Poipu

Kauai / Poipu

1 4 Min stay varies

1 bedroom
Sleeps 4
Min stay varies

Swimming pool
Child friendly

A little slice of paradise - Our unit is #227 in building #35. It is a top floor, one bedroom condo, with a lofted ceiling. The bedroom has a comfortable king size bed and the living room couch converts to a comfortable queen size bed. The condo is perfect for 2 guests. …see more

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from $199 / night

$1393 - $1575 / week

from $199 / 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 CONDO - ELS - KCC - HPU ♚ …see more

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from $37 / night

$250 / week

from $37 / night

7

Private room rental in Hawaii

Maui / Paia

1 2 2 nights min

1 bedroom
Sleeps 2
2 nights min

Nearest beach 0.5 mi
Car not necessary

SUMMARY: No car? Don't feel like driving on vacation? Want to save on car rental? This is THE PERFECT place for you. My place is 5min walking distance to the Beach, restaurants and dining, town center, art and culture, great views, family-friendly activities. You’ll lo …see more

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from $127 / night

$801 / week

from $127 / 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 and b …see more

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from $139 / night

$910 / week

from $139 / night

4

Vacation home in Hawaii Kai

Oahu / Hawaii Kai

3 10 Min stay varies

3 bedrooms
Sleeps 10
Min stay varies

Child friendly
Pet friendly

Kuapa Villa is a quaint 2,000 square foot marina-front home with pool, large back deck, and amazing marina & Koko Head Volcano views. You will love the location of this home, as it is very close to tons of amazing sights, great shopping and restaurant options, and loads …see more

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from $550 / night

$3500 - $7000 / week

from $550 / 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 your special Hawaii …see more

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from $145 / night

$1000 / week

from $145 / night

10

Kihei Vacation condo rental

Maui / Kihei

1 4 Min stay varies

1 bedroom
Sleeps 4
Min stay varies

Child friendly

Welcome to this home away from home. This is a lovely, well-maintained 1 bedroom condo in the family friendly complex of Hale Kamaole. Walking distance to Kamaole II and III, shopping, restaurants, and parks. Complex has 2 pools, gas and coal BBQs, and a tennis court, a …see more

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from $100 / night

$700 / week

from $100 / night

11

Cottage rental in Hawaii

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

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from $135 / night

$900 / week

from $135 / 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 discover …see more

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from $358 / night

$2500 / week

from $358 / night

23

Hawaii Vacation condo rental

Oahu / Kailua

2 4 5 nights min

2 bedrooms
Sleeps 4
5 nights min

Beach/lakeside relaxation
Nearest beach 0.1 mi
Child friendly

Sandbar Cottage is an immaculate and beautifully appointed 2 bedroom / 2 bath unit located just a short stroll to one of the most beautiful beaches in the world, Kailua Beach. The unit is fully furnished with A/C in all rooms, cable TV, DVD player, Wi-Fi, washer/dryer, …see more

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from $250 / night

$1600 / week

from $250 / night

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

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from $85 / night

$450 - $740 / week

from $85 / night

26

Hawaii Vacation apartment accommodation

Kauai / Kapaa

2 6 Min stay varies

2 bedrooms
Sleeps 6
Min stay varies

Swimming pool
Ask about children

Oceanfront! Priceless and Tranquil Waipouli Beach Resort an Oceanfront 2 bedroom, 3 bath condo at the beautiful #1 Ranked Waipouli Beach Resort & Spa on the island of Kauai. There is Central AC in this condo as well as a full size washer and dryer for laundry! Enjoy …see more

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from $295 / night

$2065 - $3465 / week

Responds fast!
avg. 47 minutes

from $295 / night

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Vacation rentals Maui
Island of Hawaii
Vacation rentals Oahu
Vacation rentals Kauai
Vacation rentals Molokai