50 Best Central Oregon Vacation rentals on Holiday Lettings - House rentals

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Vacation rentals Sunriver
406 properties
Vacation rentals Black Butte Ranch
131 properties
Vacation rentals Bend
113 properties
Redmond
56 properties
Vacation rentals Sisters
26 properties
Cabins Camp Sherman
12 properties
La Pine
6 properties

Central Oregon

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757 Vacation rentals

27

Home rental in Sisters

Central Oregon / Sisters

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This rustic cabin in Sisters, OR offers access to a shared pool, tennis courts, and proximity to wilderness and conveniences for up to eight guests to feel at home! Sitting in the quiet and relaxed Tollgate community three miles outside of Sisters, a quick drive will b …see more

from $99 / night

$693 / week

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avg. 37 minutes

from $99 / night

(1) Excellent 

52

Vacation home in Redmond

Central Oregon / Redmond

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Rest assured that you'll rest comfortably in this classic lodging option that's designed for up to four guests. Discover a master bedroom with queen bed, queen sleeper sofa in living room and balcony with gas BBQ. A mini kitchen includes a double burner cooktop, full si …see more

from $108 / night

$759 - $1,053 / week

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from $108 / night

(1) Excellent 

27

Redmond Vacation home rental

Central Oregon / Redmond

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
With rustic charm, access to the Eagle Crest Resort, and plenty of space for up to six lucky guests, this sprawling, single-level townhouse in the newly-built Creekside community is the perfect home-away-from-home for your next vacation! This cozy home offers luxuriou …see more

from $91 / night

$637 / week

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avg. 37 minutes

from $91 / night

26

Home accommodation in Black Butte Ranch

Central Oregon / Black Butte Ranch

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Planning a trip to Central Oregon with your friends and loved ones? Consider staying at this memorable three-bedroom Black Butte Ranch home, which features a spacious patio, two master suites, and access to resort amenities such as a shared pool, a shared hot tub, tenni …see more

from $147 / night

$1,029 / week

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avg. 37 minutes

from $147 / night

(12) Very Good 

6

Vacation apartment rental

Central Oregon / Black Butte Ranch

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
This Central Oregon vacation rental condo has a unique design with new kitchen and bathroom. New slate floors and tile sunken soaking tub. The living room has new furniture, fireplace, a large flat screen tv with DVD and surround sound and free wi fi throughout the co …see more

from $210 / night

$1,470 / week

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from $210 / night

(2) Excellent 

15

Sunriver Vacation home rental

Central Oregon / Sunriver

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
Experience the natural beauty of Sunriver from this quiet location near the national forest. Enjoy views of the large common area and wildlife from your deck and from the many windows in the great room. Use the 3 single bikes and the tandem (in season) to bike the 30 …see more

from $185 / night

$850 - $1,400 / week

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from $185 / night

(1) Very Good 

21

Vacation home in Sunriver

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Featuring a private hot tub, access to amazing community amenities, and plenty of room for up to eight guests, this home in Sunriver might just become your new favorite vacation destination! Located near the wonderful SHARC aquatic center, this home sits on a large lot …see more

from $125 / night

$875 / week

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avg. 37 minutes

from $125 / night

(3) Excellent 

26

Vacation home in Sunriver

Central Oregon / Sunriver

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
This warm home which features many large windows is a welcome retreat for your family or friends. The home has a lovely woodland setting and features a large wood burning fireplace and large enclosed hot tub just outside the Master Bedroom.... perfect for winter evenin …see more

from $85 / night

$595 / week

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avg. 37 minutes

from $85 / night

39

Sunriver Vacation home rental

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This is a gorgeous Sunriver home right on the Woodlands Golf Course with great views of the fairways. It has a private hot tub, a gourmet kitchen, and eight available SHARC passes! Day trips to tourist darling Bend (17 miles away) and skiing mecca Mt. Bachelor (25 mile …see more

from $99 / night

$693 / week

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avg. 37 minutes

from $99 / night

(12) Excellent 

10

Vacation home in Bend

Central Oregon / Bend

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Otterhouse is a riverside, two-story chalet-style home featuring an open floor plan with natural light and vaulted cedar ceilings. In addition to the living room, it has a spacious, warm library\loft as well as a large TV entertainment room. There is a master bedroom up …see more

from $195 / night

$1,200 - $1,520 / week

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avg. 3 hours 30 minutes

from $195 / night

50

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Get ready to live like a local in this gorgeous Deschutes Landing townhome with a lovely interior and great views! Located in the middle of Bend's historic Old Mill District, enjoy Bend from its very heart and leave your worries behind you. Close to everything, with a …see more

from $121 / night

$847 / week

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avg. 37 minutes

from $121 / night

(1) Excellent 

8

Home rental in Black Butte Ranch

Central Oregon / Black Butte Ranch

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Pet friendly
A fireplace and 3 VCR’s highlight this beautiful single level golf vacation rental in Central Oregon.  The vacation home sits on the 7th fairway of the Big Meadow golf course. It has two sunken living rooms, each with their own TV and VCR - an ideal setup for two famili …see more

from $330 / night

$2,310 / week

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from $330 / night

25

Vacation home in Redmond

Central Oregon / Redmond

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Escape from reality with a retreat into the beautiful Central Oregon wilderness with a stay in this spacious three bedroom home at Eagle Crest Resort! With an open floor plan, updated amenities, and an ideal location, this home-away-from-home is sure to delight guests o …see more

from $130 / night

$910 / week

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avg. 37 minutes

from $130 / night

(2) Very Good 

12

Vacation condo accommodation

Central Oregon / Sunriver

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
Time to plan for that summer getaway to Central Oregon. Sunriver is conveniently located for a quick drive to the brew pubs and festivals in Bend, or to the mountain lakes on the Cascades Lakes Highway. Not just a 'rental' - our condo used to be our 2nd home before we m …see more

from $145 / night

$1,100 / week

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from $145 / night

33

Vacation home in Redmond

Central Oregon / Redmond

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This charming Eagle Crest vacation rental offers plenty of room for eight guests, resort attractions, and classic beauty in the heart of Central Oregon. Plan a ski trip into the Cascade Mountains, or an outdoor adventure by horseback, bicycle, or foot with the whole fam …see more

from $91 / night

$637 / week

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avg. 37 minutes

from $91 / night

(1) Excellent 

16

Bend Vacation home rental

Central Oregon / Bend

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
This home is located on the desirable, southwest side of Bend in the heart of best recreation activities that Oregon has to offer. Easy access puts Mt. Bachelor skiing, fly fishing on remote lakes, mtn. biking, rafting, kayaking or the Old Mill District & Factory Outlet …see more

from $250 / night

$1,750 - $2,730 / week

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avg. 2 hours 0 minutes

from $250 / night

14

Bend Vacation home rental

Central Oregon / Bend

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Relax into this comfortable 3 bedroom, 2 bath home on the Westside of Bend. Only one block from the river and a charming foot bridge across to downtown Bend's vibrant restaurants and shops. Only 4 blocks to 10 Barrel and Galveston Street with easy access to Century Driv …see more

from $210 / night

$1,200 - $1,700 / week

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from $210 / night

(5) Excellent 

30

Vacation log cabin rental

Central Oregon / Black Butte Ranch

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Look no further! You have found a beautifully remodeled home complete with private hot tub, wifi, Netflix, and cable TV for your next getaway! Caring and responsive owners included:). About Trail Cabin 2: Our home is located in the Golf Home section of the ranch on Gla …see more

from $99 / night

$675 - $1,500 / week

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avg. 1 hour 9 minutes

from $99 / night

(2) Very Good 

30

Sunriver Vacation home rental

Central Oregon / Sunriver

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
This spacious three-bedroom Sun River vacation rental offers a private hot tub, gas fireplace, expansive patio, and space for eight guests! Whether you're soaking up the sun or skiing the slopes, Tan Oak is the perfect destination location for the entire family! Walk t …see more

from $100 / night

$700 / week

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avg. 37 minutes

from $100 / night

27

Vacation apartment with shared pool in Redmond

Central Oregon / Redmond

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Air conditioning
********** Important! ********** This great property is one where we have to send out for availability with each request, which takes up to 24 hours - more if over the weekend. If it is still available for your dates - we would love to book your stay! The Weekly Rate …see more

from $133 / night

$549 - $1,299 / week

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from $133 / night

14

Bend Vacation home rental

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
Nestled in the pines, located adjacent to beautiful Pioneer Park and a short 2 block walk to downtown. This remodeled condo is part of the Pioneer Park Condos that are located along the Deschutes River. This second floor unit is perfectly situated. A lovely river trail …see more

from $90 / night

$585 - $1,200 / week

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from $90 / night

11

Vacation condo rental

Central Oregon / Redmond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
This amazing 3 Brm 2 Bth condo overlooks the Deschutes River valley. 6 Free Facilities Passes Included Free Wi Fi Private King Master 1 Queen Bed 1 Queen Sofa Bed 2 Twins Sleeps 8 Spend quality together time in the living room by the gas fireplace. The full kitchen …see more

from $208 / night

$1,450 / week

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from $208 / night

(10) Excellent 

18

Vacation home in Bend

Central Oregon / Bend

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden
Private country setting with mountain views just 5 miles northwest of Bend. This 12 year old home sits on 20 acres of open juniper and pine forest, surrounded by other large, open tracks of land. The setting is lovely and private - like your own, private park with a h …see more

from $250 / night

$1,750 / week

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from $250 / night

34

Vacation home in Redmond

Central Oregon / Redmond

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Experience the natural beauty of Central Oregon at this spacious home located right on the 15th fairway complete with a large back deck, private outdoor hot tub, and access to a number of resort amenities including swimming pools, tennis courts, and a fitness center. T …see more

from $124 / night

$868 / week

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avg. 37 minutes

from $124 / night

36

Home accommodation in Sisters

Central Oregon / Sisters

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This comfortable vacation rental in Sisters is a fantastic place to plan your next Central Oregon adventure. Nestled in Tollgate, an authentic western-style community, when you stay here you will have easy access to city businesses, shared amenities such as a pool, plus …see more

from $150 / night

$1,050 / week

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avg. 37 minutes

from $150 / night

34

Vacation home in Sisters

Central Oregon / Sisters

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
If you're looking for a peaceful Central Oregon getaway to share with your large group, consider staying at this stunning Sisters vacation rental. Custom built by an architect with experience designing churches, this cathedral-esque home boasts five bedrooms, a loft, a …see more

from $149 / night

$1,043 / week

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avg. 37 minutes

from $149 / night

13

Vacation home in Bend

Central Oregon / Bend

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Gorgeous home on 5 acres, quiet yet close to town. Beautiful northwest mountain views. Beautifully furnished. Luxury furnishings with granite countertops, fine cabinetry; and a modern, elegant decor. Extra large windows allow in the light and beauty of the natural surro …see more

from $150 / night

$900 - $1,400 / week

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from $150 / night

(1) Excellent 

37

Vacation home in Sunriver

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Feel refreshed and recharged after a stay in this charming vacation cottage, located in the heart of Sunriver. You'll even have your own hot tub and eight SHARC passes! Sunriver's shops and restaurants are less than two miles off, and both Mt. Bachelor's skiing (21 mil …see more

from $99 / night

$693 / week

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avg. 37 minutes

from $99 / night

15

Vacation home rental

Central Oregon / Redmond

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Situated in the high Desert of Central Oregon, this resort community is one of several that offer the guest peace, comfort and the chance to unwind. Eagle Crest has three golf courses, trails for communicating with nature, and a variety of water activities with pool, ho …see more

from $150 / night

$800 - $1,170 / week

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from $150 / night

28

Vacation home with shared pool in Sisters

Central Oregon / Sisters

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
GM#349 is a spacious 2,855 sq. foot reverse living home that sits on a quiet cul-de-sac at Black Butte Ranch. It sits on over an acre with stunning views of the #14 Fairway of Glaze Meadow! When you enter the great room of this home, you are struck by the beautiful wo …see more

from $299 / night

$2,093 - $2,933 / week

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from $299 / night

14

Sunriver Vacation home accommodation

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Ask about pets
This open, spacious cabin-style home is right on the bike path, with just a quick walk to SHARC and the Village Mall. There's lots of room for your entire family (including the four-legged members) to spread out and relax, and with three bedrooms on the ground level and …see more

from $207 / night

$1,892 / week

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from $207 / night

30

Bend ski condo to rent.

Central Oregon / Bend

2 4 60 nights min

  • 2 bedrooms
  • Sleeps 4
  • 60 nights min
  • Ski
  • Child friendly
  • Air conditioning
Firehall Condo in the heart of Bend and close to all outdoor activities Skiing, Golf, River Rafting, Hiking and more. Front Second Floor Corner Unit with the Brickhouse Restaurant downstairs. Great location walking distance to restaurants, coffee houses, bars and sto …see more

from $117 / night

$817 / week

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from $117 / night

20

Vacation condo in Sunriver

Central Oregon / Sunriver

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
This newly renovated place is one minute walk to the village. The village has shops, restaurants, ice skating, bounce houses, rock climbing and miniature golf. You will find three golf courses nearby. The sharc is a two minute drive and offers indoor/outdoor swimming po …see more

from $125 / night

$875 / week

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from $125 / night

53

Vacation home in Sunriver

Central Oregon / Sunriver

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Treat yourself to a taste of rustic luxury at this grandiose, four-bedroom log estate on the Deschutes River, just outside Sunriver. Resting on two acres of high desert land with 80 feet of premier riverfront property and stunning views of Mt. Bachelor, this Sunriver va …see more

from $395 / night

$2,765 / week

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avg. 37 minutes

from $395 / night

(8) Very Good 

25

Home rental in Bend

Central Oregon / Bend

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Plan a snowy holiday in this one-bedroom home with a loft and luxury resort attractions at Mt. Bachelor Village. The inviting space is perfect for six guests (four adults) wishing to explore Oregon by river or mountain top! This condo is surrounded by nature. The Desch …see more

from $69 / night

$483 / week

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avg. 37 minutes

from $69 / night

24

Vacation home rental

Central Oregon / Sunriver

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
This warm and inviting Sunriver home is a two-story, three-bedroom home with WiFi, A/C, a Ping-Pong table, hot tub, and bikes. The lower level kitchen, living room and dining room is an open area. The kitchen has a breakfast bar with three stools and the dining table …see more

from $109 / night

$763 / week

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avg. 37 minutes

from $109 / night

52

Vacation apartment in Redmond

Central Oregon / Redmond

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Up to six guests will find this expansive condo just perfect. There's one queen bed in master bedroom, queen sleeper sofa in living room, one queen bed or two twin beds in the guestroom, and a Murphy bed in the living room. A fully equipped kitchen features an oven, sto …see more

from $125 / night

$876 - $1,111 / week

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from $125 / night

37

Vacation home in Sunriver

Central Oregon / Sunriver

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This single-level Sunriver vacation home has a private hot tub, SHARC passes, and a relaxing great room for all guests to gather. Set in the heart of Sunriver, you'll be near the aquatic park where you can use the eight provided passes to take your kids out for the da …see more

from $99 / night

$693 / week

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avg. 37 minutes

from $99 / night

15

Vacation home in Bend

Central Oregon / Bend

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Beautiful new home on Bend's Eastside. Close to Old Mill District shopping and fine dining. Minutes to downtown and access to major arteries. Enjoy real Bend living in this lovely, well appointed, home. Granite countertops throughout. A bright gourmet kitchen has a full …see more

from $195 / night

$1,200 - $1,700 / week

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from $195 / night

(6) Very Good 

15

Sunriver Vacation home rental

Central Oregon / Sunriver

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Air conditioning
Nestled amongst the pines of Sunriver, this spectacular and luxurious craftsman style home provides all the warmth and convenience of a modern, well appointed rental property. With over 3600 sq. ft. of comfort, this home really has it all! From the gourmet kitchen to th …see more

from $351 / night

$2,457 / week

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from $351 / night