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Holiday Rentals with Pools in Highland Park and nearby

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The following rentals are within 40 kilometres of Highland Park, Lake County, Illinois.

From
$798
Per Week
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1 / 40
Payment Protection
Chicago, IL
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (6) Make Enquiry
From
$5,254
Per Month
View Details
1 / 19
Payment Protection
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 1
Booking
Details Reviews (1) Make Enquiry
From
$383
Per Night
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1 / 34
Payment Protection
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
From
$352
Per Night
View Details
1 / 14
Payment Protection
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
The Tides is a great way to experience life and culture in the heart of Chicago! Featuring a modern contemporary feel, the short term rentals at The Tides offer dramatic finishes including tiled entries, granite islands and cherry cabinetry, open floor plans with captivating views from the... View all property information
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4 of 5 stars Reviewed 6 February 2015
This apartment is located in a modern, somewhat glitzy group of buildings which form their own mini-village. It is located east of Michigan Ave., almost across the street from...
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From
$243
Per Night
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1 / 12
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
2 bedroom fully furnished apartment in the heart of Gold Coast/River North, walking distance to transportation, restaurants and the lake front. The apartment comes fully furnished, has equipped kitchen, flat screen TVs, basic cable, Internet, phone and all utilities are included. The price also... View all property information
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4 of 5 stars Reviewed 26 February 2013
Viaggio in 2 coppie in occasione del congresso RSNA in Novembre. Ho trovato questa società che fitta appartamenti in diversi edifici a Chicago proprio tramite Tripadvisor; ci...
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From
$563
Per Night
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1 / 32
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (26) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Brand new luxury 2 bedroom 2 bathroom corporate housing suite with panoramic views in a building unlike anything in Chicago!! The Resort is located in Chicago's high end neighborhood, Lakeshore East, where the Chicago River meets Lake Michigan. You will enjoy exclusive access to two full-floors... View all property information
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5 of 5 stars Reviewed 3 September 2013
We arrived to a great welcome from Nadiya - everything was very straightforward and well organised. The apartment is superb, with terrific lakeside views and is very well...
5 of 5 stars Reviewed 15 March 2013
The suite was beautiful... from the furnishings, the view, the amenities, and a few surprise items! Underground free parking was a big plus. Location was perfect. Walking...
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From
$833
Per Night
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1 / 16
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
A Chicago Premier Suites property with fantastic city views, located in the heart of River North neighborhood in one of Chicago’s premier high rise buildings. City of Chicago License #2179945 This 2 bedroom/2 bath unit is over 1300 SF and well decorated with brand new furniture and luxury type... View all property information
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5 of 5 stars Reviewed 23 October 2014
We rented a unit on the 35th floor for a family visit of sisters and sister-in-law. The view was beautiful and we were happy as soon as we stepped inside! Everything was clean...
5 of 5 stars Reviewed 26 July 2013
We rented this apartment for 10 days and found it very comfortable in an excellent location. Red line station and supermarket just one block away. Chicago Premier Suites replied...
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From
$172
Per Night
View Details
1 / 11
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
1 bedroom fully furnished apartment in the heart of Gold Coast/River North, walking distance to transportation, restaurants and the lake front. The apartment comes fully furnished, has equipped kitchen, flat screen TVs, basic cable, Internet, phone and all utilities are included. The price also... View all property information
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5 of 5 stars Reviewed 27 June 2014
My husband and I stayed in a 1 bedroom apartment on the 34th floor of the AMLI River North building for 3 weeks. We rented the unit through Manilow Suites, a short term corporate...
4 of 5 stars Reviewed 16 October 2013
An excellent downtown location in a really nice part of town... It was great having my own kitchenette and being able to make my own breakfasts and, sometimes, evening meals...
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From
$8,458
Per Month
View Details
1 / 21
Payment Protection
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Pool Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
This building just opened up in July of 2014 and is the most modern building you can find in the Chicago Loop area. From the state of the art amenities to the amazing and helpful staff, you will love staying at this apartment. Located in the Loop you have access to all the tourist attractions as... View all property information
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From
$481
Per Night
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1 / 6
Payment Protection
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Private Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Location. Situated in the heart of Chicago, State and Grand by BridgeStreet is within walking distance of American Medical Association Headquarters, Wrigley Building, and Tribune Tower. Also nearby are Hancock Tower and Millennium Park. Property Features. The front desk is open 24 hours a day.... View all property information
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From
$352
Per Night
View Details
1 / 6
Payment Protection
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Housekeeping...
  • Internet Access
  • Shared Outdoor Pool...
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Experience the best Chicago has to offer with fully furnished serviced apartments located in the heart of the city. Whether staying for business or vacation, our locations allow you to live like a local and enjoy downtown Chicago to the fullest. With locations offering multiple bedrooms, complete... View all property information
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From
$1,538
Per Night
View Details
1 / 7
Payment Protection
Chicago, IL
2 Bedrooms, 4 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Amazing penthouse available with city views. This unit is like no other available and can accommodate a variety of guests, you have the flexibility of separating the unit into a 1 bed 1.5 baths unit and a studio or the entire unit for a 2 bed 2.5 bath property. The unit is conveniently located by... View all property information
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From
$333
Per Night
View Details
1 / 10
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Gym
  • Hot Tub
  • Internet Access
  • Safe
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with dramatic floor to ceiling window in the living areas and exquisite fireplace, this Penthouse gives you the ultimate in city living. It's all about the views and location. The city unfolds before you with... View all property information
Make Enquiry
From
$154
Per Night
View Details
1 / 9
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Streeter Place is a remarkable new building designed for those who enjoy the very best that Chicago has to offer. From its progressive architecture to its distinctive lobby décor, Streeter Place offers a unique concept in urban living. Located in trendy Streeterville, Streeter Place is the smart... View all property information
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From
$383
Per Night
View Details
1 / 30
Payment Protection
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 1
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Pool Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Pet: Pet Friendly AVAILABLE JANUARY 29TH!!!!!!!!!!!! Features: 100 sq. ft balcony, grill and patio furniture Newly furnished condo from Room and Board. New appliances Includes new linens, towels All kitchen appliances/table wear/pots and pans 55' LED LCD TV with DVD SURROUND... View all property information
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From
$352
Per Night
View Details
1 / 9
Payment Protection
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Housekeeping...
  • Internet Access
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
The Tides at Lakeshore East, embrace a new standard of luxury featuring a modern contemporary feel. Situated in the city's newest neighborhood, LakeShore East, you have Millennium Park and the Lakefront right outside your door, with easy access to the Loop as well. Its a little neighborhood perfect... View all property information
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From
$154
Per Night
View Details
1 / 10
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Gym
  • Housekeeping...
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Chicago’s newest addition to Lakeshore East, Coast creates a coastal retreat on the shores of Lake Michigan. This beautiful property is situated in Chicago’s most desirable location with magnificent views of the River, the Lake and the world famous Chicago Skyline. View all property information
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From
$768
Per Night
View Details
1 / 11
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to the luxury and tranquility of the Chicago Penthouse Suite, a rental residence with elegant condominium-quality interiors. The suite boasts 9.5' ceilings, floor to ceiling windows, a private balcony with grill, granite bath and kitchen, beautiful cabinetry, and stainless steel kitchen... View all property information
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From
$705
Per Night
View Details
1 / 19
Chicago, IL
2 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with dramatic two story living areas and exquisite fireplace, this Penthouse gives you the ultimate in city living. It's all about the views and location. From 20 foot floor to ceiling windows the city unfolds... View all property information
Make Enquiry
From
$2,563
Per Week
View Details
1 / 24
Payment Protection
Chicago, IL
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Great Location and amazing looking condo in the heart of River North. 3 Beds in a 2 bedroom 1.5 bathroom unit on the 2nd floor that also boasts two huge balconies. Whole Foods is across the street as well as so many other numerous places to visit, eat at, and have fun. Navy Pier is just a few... View all property information
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From
$256
Per Night
View Details
1 / 14
Payment Protection
Chicago, IL
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Housekeeping...
  • Internet Access
  • Ocean Views
  • Satellite TV
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Located in the chic New Eastside near Millennium Park, The Art Institute and fabulous Michigan Avenue shopping, this one-bedroom, lakefront condo is furnished with all the luxuries of a five-star hotel: Sleep Number queen bed, Nespresso coffee maker, digital television, pool, gym, rooftop views of... View all property information
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