50 Best Hawaii Vacation rentals on Holiday Lettings - Apartments

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Vacation rentals Maui: 2,815 properties
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7,591 Vacation rentals

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48

Vacation home in Ko Olina

Kapolei / Ko Olina

3 7 min stay varies

3 bedrooms
sleeps 7
min stay varies

Nearest beach 7 mi
Child friendly
Air conditioning

Mountain & Ocean Views! is one of the premier residences in an exclusive gated community, secure, peaceful, quiet, breeze, comfortable, cozy, convenient, only minutes away from the world famous Ko Olina Beach Aulani Disney Resort. Enjoy this 3bd. 2bth., tri-level custom …see more

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from $213 / night

$1,491 / week

Responds fast!
avg. 2 hours 17 minutes

from $213 / night

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68

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

$2,100 / week

Responds fast!
avg. 1 hour 33 minutes

from $300 / night

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23

Vacation home in Hawaii

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 living …see more

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from $999 / night

$6,783 - $8,883 / week

Responds fast!
avg. 1 hour 17 minutes

from $999 / night

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11

Vacation home in Mililani

Oahu / Mililani

1 2 3 nights min

1 bedroom
sleeps 2
3 nights min

Nearest beach 10 mi
Air conditioning

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 $85 / night

$595 / week

Responds fast!
avg. 2 hours 48 minutes

from $85 / night

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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

Update: Eruption seems to be over! Come and explore the Big Island, help local businesses recover from this adventure while discovering the remains of one of the most incredible eruption in the history of mankind!!! Kama'aina discount! The house is QUAKE SAFE and NO ASH …see more

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from $155 / night

$1,125 - $1,545 / week

Responds fast!
avg. 2 hours 39 minutes

from $155 / night

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16

Condo rental in Poipu

Kauai / Poipu

1 4 5 nights min

1 bedroom
sleeps 4
5 nights min

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

$1,393 / week

from $199 / night

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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

$1,288 / week

from $184 / night

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31

Hawaii Vacation home rental

Kauai / Hanalei

3 6 3 nights min

3 bedrooms
sleeps 6
3 nights min

Beach/lakeside relaxation
Nearest beach 0.5 mi
Child friendly

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

$1,610 / week

Responds fast!
avg. 3 hours 23 minutes

from $230 / night

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23

Vacation studio with shared pool in Ka'anapali

Maui / Ka'anapali

Studio 3 4 nights min

Studio
sleeps 3
4 nights min

Nearest beach 0 mi
Swimming pool
Child friendly

Experience breathtaking views of the ocean, tropical gardens and newly renovated garden pool from one of the best vantage points in the entire complex. If the daytime views of the ocean and the island of Lanai aren't enough, wait until sunset when you see the tiki torc …see more

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from $175 / night

$1,225 / week

from $175 / night

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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 - $1,400 / week

Responds fast!
avg. 2 hours 51 minutes

from $150 / night

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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 $198 / night

$1,351 / week

from $198 / night

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12

Vacation home in Hawaii

Maui / Huelo

2 5 5 nights min

2 bedrooms
sleeps 5
5 nights min

Child friendly
Pet friendly

A Magical Location with WATERFALL hike, Wonderful Panoramic Ocean Views from the cottage & a large very private back yard with out a neighbor in sight! Surround with nature preserve this is a taste of old Hawaii! Nature Activities & beaches 15 mins away! A Fun Nature P …see more

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from $128 / night

$896 / week

from $128 / night

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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 $166 / night

$1,161 / week

from $166 / night

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10

Kihei Vacation condo rental

Maui / Kihei

1 4 4 nights min

1 bedroom
sleeps 4
4 nights min

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 $152 / night

$1,064 / week

from $152 / night

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22

Vacation home rental

Oahu / Sunset Beach

4 10 2 nights min

4 bedrooms
sleeps 10
2 nights min

Child friendly

Beautiful house in the north of the island of Oahu, perfect to come and enjoy the beauty of the Hawaiian landscape. The house is easily accessible and you will be charmed by the incredible view and the decor of the house. With 4 bedrooms and 3 en-suite bathrooms, Wifi I …see more

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from $653 / night

$4,566 / week

from $653 / night

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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 $149 / night

$980 - $1,050 / week

from $149 / night

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12

Private room rental in Hilo

Island of Hawaii / Hilo

1 2 1 night min

1 bedroom
sleeps 2
1 night min

Aloha and welcome to Hale Sunrise! Our home is on 4 lush and serene acres 15 minutes from downtown Hilo and airport. This is where you can stay to soak in the feeling of real and local Hawaii away from the rush of town. You have a continental breakfast, a comfy bed, a p …see more

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from $100 / night

$650 / week

from $100 / night

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25

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

$1,050 / week

Responds fast!
avg. 2 hours 51 minutes

from $150 / night

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34

Vacation studio in Hawaii

Oahu / Honolulu

Studio 4 1 night min

Studio
sleeps 4
1 night min

Nearest beach 7 mi
Child friendly

Come to real paradise, 10 minutes walk to paradise park & manoa falls hike, very private and breezy, quiet, cul de sac, hear the birds singing on day time. My place is close to public transport, airport, near city center & shopping few minutes away by car. You’ll love t …see more

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from $99 / night

$625 - $975 / week

Responds fast!
avg. 2 hours 15 minutes

from $99 / night

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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

$1,015 - $1,715 / week

from $165 / night

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30

Home rental in Hawaii with swimming pool

Hilo / Hawaii Paradise Park

4 7 min stay varies

4 bedrooms
sleeps 7
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 $349 / night

$3,213 / week

Responds fast!
avg. 1 hour 45 minutes

from $349 / night

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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

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from $219 / night

$1,533 / week

from $219 / night

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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 $150 / night

$1,050 / week

from $150 / night

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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

$1,015 / week

Responds fast!
avg. 1 hour 8 minutes

from $145 / night

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25

Vacation home with swimming pool in Hawaii Kai

Oahu / Hawaii Kai

3 8 min stay varies

3 bedrooms
sleeps 8
min stay varies

Swimming pool
Child friendly
Air conditioning

Kuapa Villa Kuapa Villa is a quaint 2,000 square foot interior, marina-front home with A/C in all bedrooms and ceiling fans throught the house. Makapuu Blue tile marina front pool, large covered back deck, and amazing marina and Volcano views. You will love the l …see more

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from $375 / night

$2,625 / week

from $375 / night

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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 $400 / night

$1,990 / week

from $400 / night

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39

Vacation condo rental

Oahu / Makaha

3 7 3 nights min

3 bedrooms
sleeps 7
3 nights min

Nearest beach 2 mi
Swimming pool
Child friendly

Lovely, breeze & convenient, with 2 reserved parking stalls. Is nestled beneath the quiet majestic mountains of the Makaha Valley. It boasts of a resort style of living. The condo is on the second floor, each room is provided with a fan and it comes with everything you …see more

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from $137 / night

$959 / week

Responds fast!
avg. 2 hours 17 minutes

from $137 / night

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16

Hawaii Vacation condo rental

Island of Hawaii / Kailua-Kona

2 5 min stay varies

2 bedrooms
sleeps 5
min stay varies

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

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from $199 / night

$1,662 - $1,872 / week

Responds fast!
avg. 1 hour 17 minutes

from $199 / night

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12

Vacation apartment with shared pool in Hawaii

Maui / Ka'anapali

2 6 7 nights min

2 bedrooms
sleeps 6
7 nights min

Swimming pool
Child friendly
Air conditioning

New Westin Nanea Premium resort with full access to adjacent Westin property. 4 pools including kids pool, water slides, hot tubs, several semi private pools, etc. On the beach with private beach lounge chairs included. Snorkelling off the beach. Full service hotel with …see more

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from $450 / night

$3,150 - $4,550 / week

from $450 / night

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6

Vacation studio rental

Maui / Lahaina

Studio 4 7 nights min

Studio
sleeps 4
7 nights min

Swimming pool
Child friendly
Air conditioning

*** this is for a Studio Premium unit*** 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. …see more

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from $399 / night

$2,793 / week

from $399 / night

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33

Vacation villa in Hawaii

Oahu / Hawaii Kai

4 12 min stay varies

4 bedrooms
sleeps 12
min stay varies

Swimming pool
Child friendly
Air conditioning

Come stay at the waterfront in the residential area of Hawaii Kai, in the beautiful Villa Kenneth, for up to 12 people. Direct pontoon boat available kayaks, Wifi Internet and air conditioning, 4 bedrooms with bathrooms, large living room with fully equipped kitchen, …see more

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from $686 / night

$4,798 / week

from $686 / night

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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

$2,436 / week

Responds fast!
avg. 2 hours 13 minutes

from $348 / night

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27

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

WE WILL REQUEST COPY OF GUESTS ID'S FOR EVERYONE'S SAFETY. ************************************************************************************** THIS UNIT IS IDEAL FOR 2 COUPLES OR 3 GENERATIONAL FAMILIES *************************************************************** …see more

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from $495 / night

$3,465 / week

Responds fast!
avg. 3 hours 12 minutes

from $495 / night

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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 $165 / night

$1,155 / week

Responds fast!
avg. 1 hour 16 minutes

from $165 / night

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24

Vacation apartment with shared pool in Kailua-Kona

Island of Hawaii / Kailua-Kona

1 4 3 nights min

1 bedroom
sleeps 4
3 nights min

Swimming pool
Child friendly
Air conditioning

Come and enjoy your stay in this beautifully upgraded 1 bedroom condo at Kona Reef. Located on a desirable single level overlooking the pool and the ocean, you will find all the comforts you would expect in this tropical paradise. Let the sound of the crashing waves be …see more

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from $175 / night

$1,225 / week

from $175 / night

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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

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26

Mokuleia Vacation home rental

Oahu / Mokuleia

4 12 min stay varies

4 bedrooms
sleeps 12
min stay varies

Swimming pool
Child friendly

The LOST RANCH North Shore Oahu SPECIAL: July 15-27, & August 28-Sept. 6, 2018 Cancelation-Last minute special. Call or email for details. Located on the North Shore of Oahu, in the charming town of Mokuleia 10 minutes west from Historic Haleiwa town, this is a one of …see more

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from $400 / night

$2,800 / week

from $400 / night

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13

Vacation cottage rental

Island of Hawaii / Pahoa

1 2 2 nights min

1 bedroom
sleeps 2
2 nights min

Child friendly

Our Rental cabins are for travelers with a taste for an Eco-Zen Luxury experience. Fitted with a Queen bed and surrounded by the Hawaiian jungle in a serene atmosphere accompanied by songs of birds, chirping frogs & ocean waves. We have three cabins available for rent. …see more

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from $89 / night

$401 - $508 / week

from $89 / night

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10

Vacation cottage rental

Island of Hawaii / Pahoa

1 2 min stay varies

1 bedroom
sleeps 2
min stay varies

Child friendly

"Kualoli" the Hawaiian translation for Metamorphosis There grows an impressive crown-flower bush, home to hundreds of monarch butterflies. Transforming through their cycle, these beauties symbolize the changes in our own human development. A literal interpretation symbo …see more

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from $84 / night

$508 - $749 / week

from $84 / night

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22

Hawaii Vacation home rental

Oahu / Kailua

2 4 min stay varies

2 bedrooms
sleeps 4
min stay varies

Air conditioning

The View at Alala Point Better known in the modern era as Lanikai, the highly sought after real estate this stunning home is located on was known to the ancient Hawaiians as Ka'ohao, which translates into "tying together" or "joining together". That translation is a p …see more

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from $750 / night

$5,250 / week

from $750 / night

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