50 Best Kailua Vacation rentals on Holiday Lettings - Beach rentals

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73 Vacation rentals

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

from $139 / night

$910 / week

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from $139 / night

20

Vacation villa in Kailua

Oahu / Kailua

6 12 10 nights min

  • 6 bedrooms
  • Sleeps 12
  • 10 nights min
  • Child friendly
This is a beautiful 6 bedroom, 5 bath beachfront home reminiscent of Old Hawaii. Coconut trees abound throughout the spacious lush green lawns which leads directily on to the white sandy beach of Kailua. The home sits on one of the most breath taking beaches in the worl …see more

from $1050 / night

$7350 - $12250 / week

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from $1050 / night

(3) Excellent 

12

Vacation guest house in Kailua

Oahu / Kailua

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Private garden
Lovely Guest House with lots of upgrades Large Bathroom with paintings of Lanikai Beach California King Bed and 60inch Flat-Screen TV Super Fast High-Speed Internet up to 60MB/s with WiFi Access Full Kitchen with top of the line appliances Washer and Dryer Amazin …see more

from $179 / night

$1253 / week

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from $179 / night

23

Vacation home in Kailua

Oahu / Kailua

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Lovely hideaway two bedrooms are attached " Ohana" to the main house with two private entrances. Home provide a lovely the laid-back Kailua beach town and the Hawaiin lifestyle on the beautiful Windward side of O'ahu for your trip. Guest Access Guest have access to th …see more

from $96 / night

$651 - $1778 / week

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from $96 / night

(16) Excellent 

34

Kailua Vacation home rental

Oahu / Kailua

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Private garden
Come and play at the Beach We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance as well as downtown. And for those of you traveling without a car, a major bus line is just around the corner. Here you will be surrounded by lush …see more

from $126 / night

$840 / week

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from $126 / night

(1) Excellent 

12

Vacation home rental

Oahu / Kailua

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Charming, very clean one bedroom house is located 300 steps from Kalama Beach Park. One of the most beautiful beaches of Hawaii. Located off the street in a very quiet residential area. It is 600 sq. ft. and has a full kitchen, all linens, A/C, beach chairs, mats, coole …see more

from $145 / night

$950 / week

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from $145 / night

28

Kailua Vacation home rental

Oahu / Kailua

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
***Longer minimum stay requirements may apply.  Rates may vary depending on length of stay.  Inquire for possible DISCOUNTS*** Lanikai Beach Cottage The charming beach cottage has two separate dwellings on property that are rented together to provide 3 bedrooms and 2 ba …see more

from $650 / night

$4550 / week

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from $650 / night

(3) Very Good 

23

Kailua Vacation home rental

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It …see more

from $450 / night

$3150 / week

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from $450 / night

20

Vacation home with swimming pool in Kailua

Oahu / Kailua

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settl …see more

from $900 / night

$6300 - $9800 / week

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from $900 / night

20

Vacation home in Kailua

Oahu / Kailua

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Ke'aloha, which means “love,” is certainly appropriate for this cottage. From the moment you step inside this s …see more

from $585 / night

$4095 / week

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from $585 / night

(25) Very Good 

19

Vacation b&b with shared pool in Kailua

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.48 mi
  • Swimming pool
Located in a lovely beachside town, the Garden Studio is a ground floor attached studio with a private entrance and patio. The Studio is designed for relaxing and comes with a queen bed, dining table & chairs, ceiling fan, TV, air-conditioning and WiFi. Enjoy indoor or …see more

from $99 / night

$665 / week

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from $99 / night

(3) Very Good 

30

Vacation bungalow with swimming pool in Kailua

Oahu / Kailua

4 7 5 nights min

  • 4 bedrooms
  • Sleeps 7
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This plantation style home is located 3 blocks from Kailua beach and 2 blocks to Kailua town. It has been renovated to have open floor plan to provide comfortable living space without compromising it's Hawaiian charm. Bedrooms with A/C, ceiling fans, fully equipped kit …see more

from $400 / night

$2500 / week

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from $400 / night

(1) Very Good 

8

Vacation home in Kailua

Oahu / Kailua

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
Charming beachfront cottage right on Kailua Beach! This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room. Step out your front door and onto Kailua Beach, three mile …see more

from $350 / night

$2450 / week

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from $350 / night

(1) Very Good 

12

Vacation cottage in Kailua

Oahu / Kailua

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Holiday Palms is a newly remodeled, 600 sq ft, one bedroom private cottage, steps from beautiful Kailua Beach. Tucked away amid tropical palm trees, with your own shady patio and private gated entrance. A very quiet and private location with your own dedicated off stree …see more

from $130 / night

$910 / week

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from $130 / night

(2) Excellent 

13

Vacation home in Kailua

Oahu / Kailua

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and …see more

from $350 / night

$2450 - $3850 / week

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from $350 / night

13

Vacation b&b in Kailua

Oahu / Kailua

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Hawaii Sheffield House is in Kailua Town. is located only 10 houses to Kailua Beach. The address is 131 Kuulei Road. The closest beach access is Ka'apuni Loop.Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite is a ground …see more

from $164 / night

$1148 / week

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from $164 / night

(2) Very Good 

25

Vacation private room in Kailua

Oahu / Kailua

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.18 mi
  • Ask about children
Located in a lovely beachside town, Kailua By The Sea is a second floor detached studio with a private entrance and lanai (balcony). The room is designed for relaxing and getting into an aloha state of mind. Am easy five-minute stroll around the corner (200 yards) tak …see more

from $165 / night

$1085 / week

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from $165 / night

(4) Excellent 

16

Vacation apartment in Kailua

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Child friendly
  • Air conditioning
Very spacious and breezy apartment, a wonderful place to relax and enjoy the beautiful island. It is on a second story above the main house, has a comfortable, welcoming and sunny Lanai. The beach is just a minute walk to the beach. Fully equipped kitchenette with mi …see more

from $191 / night

$1300 / week

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from $191 / night

12

Kailua Vacation studio rental

Oahu / Kailua

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Nearest beach 0.3 mi
  • Suitable for children age 5+
  • Air conditioning
Cozy "Ginger suite" studio in private home. Private entrance and bathroom. Three blocks from the beach. 1 block from the 57 bus stop. 3 blocks to shopping, restaurants and market. Air-conditioning and ceiling fan. Small covered patio. Little kitchenette for light me …see more

from $90 / night

$565 / week

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from $90 / night

15

Kailua Vacation cottage rental

Oahu / Kailua

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Air conditioning
Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-b …see more

from $195 / night

$1365 / week

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from $195 / night

(1) Excellent 

19

Vacation apartment with shared pool, golf nearby in Kailua

Oahu / Kailua

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
My home is on the hill overlooking Lanikai Bay with 180 degree unobstructed views of the Mokulua Islands. You can observe sun and moon rises from your private patio and whales breaching just offshore in the winter! Trade winds cool the property, but there is also A/C …see more

from $155 / night

$1085 / week

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from $155 / night

(1) Very Good 

6

Home rental in Kailua with swimming pool

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. …see more

from $975 / night

$6825 / week

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from $975 / night

22

Vacation studio rental

Oahu / Kailua

Studio 2 30 nights min

  • Studio
  • Sleeps 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
Coral Room seaside studio Tax ID 7873026-01 Steps from the beach on a private lane. Large peaceful studio with cathedral ceilings, kitchenette, and private yard with barbecue. Located in the best neighborhood in Kailua, enjoy the sounds of the ocean and feel the tropi …see more

from $135 / night

$945 / week

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from $135 / night

16

Vacation home in Kailua

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Charming, Private, Hawaiian Style Home Kai Mele cottage has been featured in Coastal Living as guest house of the month, due to this private Kailua beachfront estate being nestled in among 40+ coconut trees and lush tropical gardens. With over 700 feet of an ancient lav …see more

from $550 / night

$3850 / week

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from $550 / night

10

Cottage rental in Kailua

Oahu / Kailua

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.06 mi
  • Child friendly
Enjoy a restful respite in this private cozy cottage. We are in Lanikai, across the street from the ocean and the beautiful Mokulua islands. The cottage is a separate building located on the back corner of a 10,000 sq. ft. lot. It is a comfortable roomy self-contained …see more

from $250 / night

$1750 / week

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from $250 / night

(3) Excellent 

21

Cottage rental in Kailua

Oahu / Kailua

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Air conditioning
Kailua is first and foremost a beach community. Kailua Beach Park has been named “America's Best Beach”, 'Most Beautiful; Sunrise in the World'; and the world's pre-eminent windsurfing and kitesurfing destinations. Hale Luana, meaning a house to be at leisure and …see more

from $200 / night

$1400 / week

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from $200 / night

9

Kailua Vacation home rental

Oahu / Kailua

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
The Jungle Waterfall Retreat is tucked into the rainforest of Kailua. Get the quiet relaxation of living surrounded by mountains while only being a 5 minute drive to the beach. Its just 20 minutes to the airport and Waikiki, but you will feel like you are on another isl …see more

from $260 / night

$1820 / week

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from $260 / night

23

Vacation home in Kailua

Oahu / Kailua

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Kailani Villa Nestled on a lush mountainside in Lanikai, just one block from Lanikai Beach, you will find Kailani Villa: a two-story modern and luxurious masterpiece. Kailani Villa embodies modern elegance, punctuated by Hawaiian touches throughout.  Set behind gates an …see more

from $1100 / night

$7700 / week

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from $1100 / night

(8) Excellent 

28

Vacation cottage in Kailua

Oahu / Kailua

1 2 30 nights min

  • 1 bedroom
  • Sleeps 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach t …see more

from $80 / night

$560 / week

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from $80 / night

39

Vacation b&b in Kailua

Oahu / Kailua

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 1 mi
  • Air conditioning
  • Private garden
As you step into the Maile Suite the first thing you will notice is how fresh, airy and up to date it is. The full sized bed with crisp white linens begs you to take a late afternoon nap after spending the day playing in the surf. The spacious and clean private b …see more

from $150 / night

$1050 / week

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from $150 / night

24

Kailua Vacation home rental

Oahu / Kailua

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This beautiful executive home in the wonderful Lanikai community was newly built in 2014. It boasts 3 bedrooms en suite that are generous in size and more than ample in comfort. Guests will find that the spacious living area is open and flows nicely for family gathering …see more

from $696 / night

$4866 / week

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from $696 / night

38

Kailua Vacation home rental

Oahu / Kailua

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Discover a hidden Hawaii at Lanikai Hillside Estate. Part of an exclusive gated community, the villa, whose name means ‘heavenly sea,’ offers access to a semi-private beach and views of uninhabited islands off the coast. Spacious modern Bali-inspired interiors and five …see more

from $6180 / night

$43260 - $50470 / week

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from $6180 / night

25

Vacation home in Kailua

Oahu / Kailua

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Peaceful Energy of Maluhia Let the relaxing atmosphere of Maluhia whisk you into vacation-mode! The tropical pool will make you feel like you are swimming in the middle of your own private lagoon while a heated Jacuzzi will relax your body at the end of the day. The cov …see more

from $1500 / night

$10500 / week

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from $1500 / night

21

Kailua Vacation home rental

Oahu / Kailua

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life …see more

from $600 / night

$4200 / week

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from $600 / night

5

Kailua Vacation home accommodation

Oahu / Kailua

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Air conditioning
  • Pet friendly
Attractive, ground floor, 2 bedroom unit with living room and private entry. On the island Oahu, you'll find comfort, relaxation here while on vacation. 6-8 minute walk away awaits you to world famous Kailua Beach, The busy night life of Waikiki is a short 20 minute dri …see more

from $206 / night

$1443 - $1862 / week

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from $206 / night

22

Kailua Vacation home rental

Oahu / Kailua

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Create life long memories and experience Hawaiian local living in the comfortable and beautiful "Kaimana in Kailua". Kaimana (Diamond) in Kailua is a 4 bedroom, 2 bath home, with a covered carport, front and back yard, and large porch, located in a private lane in Kai …see more

from $450 / night

$3150 / week

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from $450 / night

33

Kailua Vacation home rental

Oahu / Kailua

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Experience true island living in this stunning historic beachfront residence on the white sandy shores of Lanikai. Hale Hinano is one of the original mansions built on the best part of Lanikai Beach in the 1940's, and has been beautifully renovated with extensive upgrad …see more

from $1500 / night

$10500 / week

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from $1500 / night

53

Kailua Vacation villa rental

Oahu / Kailua

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Ask about children
  • Ask about pets
Royal Kailua Estate is a veritable Polynesian palace of unrivaled opulence located in Kailua, on Oahu’s northern coast in the great state of Hawaii. The estate spans an astonishing 11,000 square feet atop a moderate inclination. The grounds are covered in lush tropical …see more

from $7000 / night

$49000 / week

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from $7000 / night

(1) Excellent 

13

Vacation cottage in Kailua

Oahu / Kailua

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
This quiet 400-square foot cottage sits by the blue-tiled pool and offers the perfect resting spot after a full day of activities or a sleepy day on the beach. It offers a full bath and kitchenette with full-sized refrigerator, microwave, and toaster oven. The studio i …see more

from $179 / night

$1200 / week

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from $179 / night

24

Kailua Vacation apartment rental

Oahu / Kailua

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Ocean Front House, 2 Bdrm/2 Bath + Ohana Room, Sleeps 4-6. Great outdoor spaces. Honu Hale Lanikai (Honu means turtle, Hale means house) is a simple and comfortable two bedroom oceanfront vacation home in beautiful Lanikai on the island of Oahu. It has one be …see more

from $475 / night

$3325 / week

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from $475 / night

1