Title: Far Southwest Side Vacation Rentals from CA $130: Short-Term Rentals for 2026 | Expedia.ca

[Far Southwest Side Travel Guide](https://expedia.ca/Far-Southwest-Side.dx553248635976475353)[Hotels in Far Southwest Side](https://expedia.ca/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Flights to Far Southwest Side](https://expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Far-Southwest-Side.d553248635976475353.Car-Rental-Guide)[Far Southwest Side Vacation Packages](https://expedia.ca/Far-Southwest-Side.d553248635976475353.Destination-Travel-Guides)

![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976475353&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Far Southwest Side vacation rentals

![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/58291697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/83f39cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sentral Michigan Avenue

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

Downtown Chicago

9.2/10

Wonderful

(1,081 reviews)

"Best full kitchen multi-room family lodging"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lee

CA $149

CA $215 total

includes taxes & fees

Feb 24 - Feb 25

[](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Single Bed, City View | Living area](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/d03e88da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(427 reviews)

"Clean, nice amenities and great staff."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sydnee

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![Lounge](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/0480d64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/825d44e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Apartment, 1 King Bed with Sofa bed, Pool Access (Self Check-in with Virtual Front Desk) | Living area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/2969f0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/67000000/66430000/66425400/66425311/f7e5c565_edited_04eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kasa River North Chicago

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(183 reviews)

"Awesome stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sally

CA $172

CA $330 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e1fd538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/6dcfa9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/3e6dada5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/105000000/104320000/104315700/104315648/7b407b40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wrigleyville Suites

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

Lakeview

9.2/10

Wonderful

(29 reviews)

"Nice place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Barry

CA $162

CA $190 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Suites.h104315648.Hotel-Information)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/8abcd27a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Interior](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/7547fb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Shared kitchen](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/cf45226f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/a6832f09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Oak Park Home

[](https://www.expedia.ca/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Wanted a house in oak park and this was such a pleasant, comfortable and convenient place. Really comfortable beds too. Even a lovely piano. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

judith

CA $188

CA $366 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/9b9f65df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor)](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/5beac5cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Lounge](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/13874d20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/3a1a2525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Oak Park Residence

[](https://www.expedia.ca/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

Oak Park

9.6/10

Exceptional

(12 reviews)

"Absolutely awesome "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erik

CA $202

CA $383 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

![Comfort Double Room](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/4e4fcb6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/81879fe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/11a11fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/113000000/112310000/112306500/112306435/7a3c031a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn Chicago Southland I-80 & I-294 Near Casino

[](https://www.expedia.ca/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

Harvey

4.2/10

(72 reviews)

"Under renovations so some rooms have missing appliances, even through an app they require a deposit. Utter wise nice room and workers"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Destin

CA $115

CA $130 total

includes taxes & fees

Feb 20 - Feb 21

[](https://www.expedia.ca/Chicago-Hotels-Comfort-Inn-Chicago-Wind-Creek-Casino.h112306435.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/c487cf4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/4016d076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/faa6dc46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88910000/88902400/88902334/52817ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chicago Third Floor Studio by 747 Lofts

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

West Town

9.8/10

Exceptional

(7 reviews)

"Clean, easy to check in, all the household items you’d expect"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jason

[](https://www.expedia.ca/Chicago-Hotels-Walk-To-Local-Hot-Spots-Or-Public-Transit-Prime-Location-In-The-Heart-Of-The-Windy-City-747-Lofts-Cabin-301-Hotel-Room.h88902334.Hotel-Information)

![Design Apartment, Private Bathroom (The Oak Park Loft)](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/dfb80f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/167883c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/733d465a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Design Apartment, Private Bathroom (The Oak Park Loft)](https://images.trvl-media.com/lodging/108000000/107630000/107622700/107622605/023c5e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oak Park Loft

[](https://www.expedia.ca/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

Oak Park

10/10

Exceptional

(5 reviews)

"Good location, nice neighborhood, restaurants close"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda

CA $173

CA $350 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Chicago-Hotels-The-Oak-Park-Loft.h107622605.Hotel-Information)

![Apartment, Private Bathroom | Lounge](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/75db7b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/b9d0f86f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom | Interior](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/d23bf6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Private Bathroom | Terrace/patio](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/2e2b5c00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### At Home in Oak Park

[](https://www.expedia.ca/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

Oak Park

9.4/10

Exceptional

(9 reviews)

"Great place, clean, and very accommodating! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Theresa

CA $180

CA $358 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04&regionId=553248635976475353&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

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## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Far+Southwest+Side%2C+Illinois%2C+United+States+of+America&regionId=553248635976475353&latLong=41.720804%2C-87.679959&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=COTTAGE)

Private vacation homes

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## Top Far Southwest Side Hotel Reviews

![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg)

### The Royal Sonesta Chicago Downtown

10/10 Excellent

"Wonderful stay and amazing staff. Satara at the front desk was super helpful and the bellman Charles greeted me with a kind word and warm smile everyday! Juan in the restaurant was very delightful! It’s time for upkeep and maintenance in the bathroom (vanity and toilet). Other than that we had a lovely visit with you. "

[](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg)

### Hotel Riu Plaza Chicago

10/10 Excellent

"The room was excellent "

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg)

### Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"Everything was very good "

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg)

### Hyatt Regency Chicago

10/10 Excellent

"It was great"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information)

![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg)

### Courtyard by Marriott Chicago Magnificent Mile

10/10 Excellent

"The hotel was in a perfect location for our weekend getaway! Real nice hotel and staff made it great!"

[](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg)

### theWit Chicago, a Hilton Hotel

10/10 Excellent

"It was a great place to stay, food was great, staff was great. Prices were moderately high. I did like that we were able to use the resort fee towards food in drinks. "

[](https://expedia.ca/Chicago-Hotels-TheWit-Chicago-A-DoubleTree-By-Hilton-Hotel.h2463437.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg)

### Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"Yes"

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg)

### Hilton Chicago

10/10 Excellent

"It was great "

[](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information)

![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg)

### Palmer House a Hilton Hotel

10/10 Excellent

"Service, history, "

[](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information)

## Find out more about Far Southwest Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Far Southwest Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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