50 Best Hawaii Vacation rentals on Holiday Lettings - Apartments

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5,579 Vacation rentals

(3) Excellent 

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

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from $95 / night

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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

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from $299 / night

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8

Vacation apartment in Hawaii

Maui / Paia

2 4 90 nights min

  • 2 bedrooms
  • Sleeps 4
  • 90 nights min
  • Child friendly
Situated only 3min Paia, where you can find yoga rooms, restaurants, food stores and crafts shops. 3min of Ho'okipa beach and 5min from Baldwin Beach: ideal for windsurfing, surfing and kitesur. 15min from the Kahului Airport. Both rooms have large beds and are well van …see more

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from $130 / night

$780 - $1950 / week

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from $130 / night

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(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

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from $299 / night

$2093 / week

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avg. 2 hours 59 minutes

from $299 / night

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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

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from $230 / night

$1610 / week

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avg. 3 hours 7 minutes

from $230 / night

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“E komo mai (welcome, come in)”

Reviewed 18 Dec 2015

Welcome is how you will feel as soon as you step inside this charming home that is tastefully appointed with garden flowers and themed wall art. It has everything a eclectic family group might want o… More

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(13) Very Good 

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
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

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from $148 / night

$835 - $1870 / week

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from $148 / night

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(1) Excellent 

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

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from $95 / night

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(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 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

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from $150 / night

$980 - $1400 / week

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from $150 / night

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(3) 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 kitchen update …see more

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from $170 / night

$1050 / week

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Responds fast!
avg. 2 hours 23 minutes

from $170 / night

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(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

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from $495 / night

$3465 / week

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from $495 / 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 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

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from $150 / night

$980 - $1400 / week

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from $150 / night

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(1)  

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

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from $219 / night

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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

$992 / week

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avg. 2 hours 23 minutes

from $159 / 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

$1288 / week

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from $184 / night

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(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

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from $348 / night

$2436 / week

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avg. 3 hours 10 minutes

from $348 / 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 firmly booked for the week of December 10-17, 2016. It 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, la …see more

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from $320 / night

$1701 / week

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from $320 / night

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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

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from $165 / night

$1155 / week

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from $165 / night

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(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 you here o …see more

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from $165 / night

$1015 - $1715 / week

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from $165 / night

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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

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avg. 1 hour 40 minutes

from $300 / night

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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

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from $99 / 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 $145 / night

$1000 / week

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from $145 / night

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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

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from $37 / night

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(6) Very Good 

25

Apartment rental in Hawaii with shared pool

Kauai / Kapaa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
Oceanview! Experience a Vacation of a Lifetime in this Exquisite Luxury VIP Oceanview Condo at #1 Ranked Waipouli Beach Resort & Spa offering stunning Direct Oceanviews from every room. Delight in watercolor sunrises, whale watching and romantic dinners on the lanai w …see more

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from $249 / night

$1743 - $3500 / week

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Responds fast!
avg. 44 minutes

from $249 / night

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(3) Excellent 

23

Apartment rental in Hawaii with shared pool

Maui / Kihei

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located across the street from Kamaole 1 & Charley Young Beach. Its a 5 minute walk to the beach! Beautiful swimming and snorkeling beach. Ideal for taking a nice stroll and perfect for watching the sunset at night. Conveniently located within walking distance to many …see more

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from $139 / night

$973 / week

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from $139 / night

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8

Vacation home in Hawaii

Molokai / Kaunakakai

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
This private hilltop cottage is WONDERFUL! A spacious, airy, clean one bedroom/very comfy king bed. Large one bath with whirlpool tub and separate shower. Full kitchen, four burner gas stove/oven. Comfortable, spacious living area allows an abundance of ocean view throu …see more

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from $175 / night

$1225 / week

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from $175 / night

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12

Apartment rental in Hawaii 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

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from $165 / night

$1050 - $1323 / week

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Responds fast!
avg. 2 hours 9 minutes

from $165 / night

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(3) Excellent 

28

Vacation home in Hawaii

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

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from $89 / night

$567 - $847 / week

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from $89 / night

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18

Vacation home in Hawaii

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

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from $125 / night

$875 / week

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avg. 3 hours 5 minutes

from $125 / night

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21

Ewa Beach Vacation home rental

Oahu / Ewa Beach

3 8 14 nights min

  • 3 bedrooms
  • Sleeps 8
  • 14 nights min
  • Swimming pool
  • Child friendly
Location, location, location! The Hale Wai Lani (meaning "heavenly waters") townhome is quiet and secluded and situated in just the right place on the golf course to allow for peaceful enjoyment of the property and beautiful surroundings. Featuring three bedrooms, all w …see more

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from $250 / night

$1750 / week

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from $250 / night

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