Uptown Holiday Rentals
10.0
Exceptional
(62 Reviews)
1500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R7,151/Night
For 7 Nights R50,054
10.0
Exceptional
(12 Reviews)
452.08 ft²
4 Guests
1 Bedroom
1 Bathroom
Apartment
- Private Pool
- Oceanfront
- Fireplace/Heating
R1,916/Night
For 7 Nights R13,410
10.0
Exceptional
(60 Reviews)
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
R8,869/Night
For 7 Nights R62,088
10.0
Exceptional
(1 Review)
1022.57 ft²
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
R6,306/Night
For 7 Nights R44,143
10.0
Exceptional
(52 Reviews)
441 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R4,537/Night
For 7 Nights R31,765
10.0
Exceptional
(13 Reviews)
450 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
R9,436/Night
For 7 Nights R66,051
10.0
Exceptional
(10 Reviews)
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
R4,377/Night
For 7 Nights R30,635
10.0
Exceptional
(2 Reviews)
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R11,800/Night
For 7 Nights R82,604
10.0
Exceptional
(2 Reviews)
- Chicago
- Sheridan Park
- 0.27 mi to center
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
R5,421/Night
For 7 Nights R37,954
Luxury Holiday Rentals in Uptown
Over 82+ Luxury Holiday Rentals in or Near Uptown
10.0
Exceptional
(2 Reviews)
26910 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R32,808/Night
For 7 Nights R229,655
10.0
Exceptional
(1 Review)
5000 ft²
15 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R20,445/Night
For 7 Nights R143,121
10.0
Exceptional
(4 Reviews)
2300 ft²
14 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R19,486/Night
For 7 Nights R136,408
New
645.83 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- View
- Pet Friendly
R14,905/Night
For 7 Nights R104,332
9.4
Exceptional
(12 Reviews)
1500 ft²
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R11,572/Night
For 7 Nights R81,000
10.0
Exceptional
(8 Reviews)
8 Guests
4 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R10,181/Night
For 7 Nights R71,258
10.0
Exceptional
(59 Reviews)
1500 ft²
4 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R9,786/Night
For 7 Nights R68,507
New
- Chicago
- Sheridan Park
- 0.25 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
R9,721/Night
For 7 Nights R68,048
10.0
Exceptional
(1 Review)
- Chicago
- Buena Park
- 0.19 mi to center
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
R8,836/Night
For 7 Nights R61,859
Top-Rated Holiday Rentals with a Pool in Uptown
Over 14+ The Best Private Villas and Holiday Rentals in Uptown with a Pool
New
620 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Pet Friendly
R5,649/Night
For 7 Nights R39,542
New
620 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Pet Friendly
R5,207/Night
For 7 Nights R36,447
New
624.31 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Pet Friendly
- Air Conditioner
R3,962/Night
For 7 Nights R27,737
10.0
Exceptional
(19 Reviews)
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
R3,400/Night
For 7 Nights R23,791
New
- Chicago
- Buena Park
- 0.13 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Breakfast
R3,709/Night
For 7 Nights R25,968
New
614 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Breakfast
R3,371/Night
For 7 Nights R23,594
New
614 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Breakfast
R2,812/Night
For 7 Nights R19,681
New
- Chicago
- Sheridan Park
- 0.14 mi to center
614 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Pet Friendly
- Kitchen
R2,409/Night
For 7 Nights R16,865
New
614 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Breakfast
R1,584/Night
For 7 Nights R11,085
Pet-Friendly Holiday Rentals in Uptown
Over 38+ Pet-Friendly Holiday Rentals in or Near Uptown
9.6
Exceptional
(14 Reviews)
441 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R7,328/Night
For 7 Nights R51,298
New
- Chicago
- Sheridan Park
- 0.25 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
R6,152/Night
For 7 Nights R43,062
9.0
Exceptional
(20 Reviews)
441 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R6,735/Night
For 7 Nights R47,156
9.5
Exceptional
(180 Reviews)
1001.04 ft²
6 Bathrooms
Hotel
- Fireplace/Heating
- Breakfast
- Pet Friendly
R4,126/Night
For 7 Nights R28,883
8.8
Fabulous
(15 Reviews)
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R6,927/Night
For 7 Nights R48,482
8.0
Excellent
(7 Reviews)
4844 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R3,869/Night
For 7 Nights R27,082
7.4
Very Good
(6 Reviews)
- Chicago
- Buena Park
- 0.24 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R3,363/Night
For 7 Nights R23,545
New
- Chicago
- Buena Park
- 0.33 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
R8,061/Night
For 7 Nights R56,423
9.8
Exceptional
(11 Reviews)
- Chicago
- Sheridan Park
- 0.25 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R8,402/Night
For 7 Nights R58,814
Large Holiday Rentals and Private Villas in Uptown
Over 3+ Large Holiday Rentals and Private Villas in or Near Uptown
10.0
Exceptional
(139 Reviews)
4200 ft²
21 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
R21,632/Night
For 7 Nights R151,422
8.4
Excellent
(38 Reviews)
- Chicago
- Buena Park
- 0.21 mi to center
12 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R3,546/Night
For 7 Nights R24,822
10.0
Exceptional
(1 Review)
- Chicago
- Sheridan Park
- 0.25 mi to center
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
R13,967/Night
For 7 Nights R97,766
Wheelchair Accessible Holiday Homes in Uptown
Over 15+ Wheelchair Accessible Holiday Homes in or Near Uptown
9.4
Exceptional
(20 Reviews)
441 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R4,619/Night
For 7 Nights R32,338
9.4
Exceptional
(13 Reviews)
441 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R2,945/Night
For 7 Nights R20,614
9.4
Exceptional
(13 Reviews)
646 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
R3,078/Night
For 7 Nights R21,548
New
464 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Spa
- Fireplace/Heating
- Breakfast
R3,946/Night
For 7 Nights R27,622
New
605 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R2,931/Night
For 7 Nights R20,516
New
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
R2,292/Night
For 7 Nights R16,046
New
469 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
R2,129/Night
For 7 Nights R14,900
New
588 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
R1,998/Night
For 7 Nights R13,983
New
481 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
R1,457/Night
For 7 Nights R10,201
Uptown Private Villas and Holiday Homes Under $200
Over 26+ Uptown Private Villas and Holiday Homes Under $200
9.8
Exceptional
(227 Reviews)
- Chicago
- Buena Park
- 0.29 mi to center
1700 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R3,258/Night
For 7 Nights R22,808
9.8
Exceptional
(6 Reviews)
1194.79 ft²
6 Guests
2 Bedrooms
1 Bathroom
Apartment
- Parking
- Air Conditioner
- Internet
R2,178/Night
For 7 Nights R15,244
New
- Chicago
- Buena Park
- 0.24 mi to center
1450 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,057/Night
For 7 Nights R14,409
9.8
Exceptional
(7 Reviews)
- Chicago
- Buena Park
- 0.24 mi to center
2 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
R2,537/Night
For 7 Nights R17,765
8.0
Excellent
(7 Reviews)
- Chicago
- Buena Park
- 0.24 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Breakfast
- Pet Friendly
R1,533/Night
For 7 Nights R10,725
10.0
Exceptional
(5 Reviews)
- Chicago
- Buena Park
- 0.24 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Breakfast
- Pet Friendly
R1,533/Night
For 7 Nights R10,725
9.6
Exceptional
(22 Reviews)
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Spa
- Fireplace/Heating
R2,440/Night
For 7 Nights R17,078
5.0
Average
(1 Review)
- Chicago
- Sheridan Park
- 0.07 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Kitchen
- Air Conditioner
- Internet
R2,914/Night
For 7 Nights R20,401
4.8
Average
(10 Reviews)
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Kitchen
- Air Conditioner
- Internet
R1,572/Night
For 7 Nights R11,003
Instantly Bookable Holiday Homes in Uptown
Over 18+ Instantly Bookable Holiday Homes in or Near Uptown
10.0
Exceptional
(1 Review)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
R6,352/Night
For 7 Nights R44,470
9.8
Exceptional
(69 Reviews)
650 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Parking
R5,127/Night
For 7 Nights R35,891
9.8
Exceptional
(36 Reviews)
1018 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Air Conditioner
R6,265/Night
For 7 Nights R43,848
9.4
Exceptional
(10 Reviews)
675 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R8,212/Night
For 7 Nights R57,487
New
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
R6,284/Night
For 7 Nights R43,979
9.0
Exceptional
(14 Reviews)
- Chicago
- Sheridan Park
- 0.25 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R8,730/Night
For 7 Nights R61,106
New
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
R6,000/Night
For 7 Nights R41,998
4.5
Average
(2 Reviews)
1500 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Condo
- Spa
- Kitchen
- Air Conditioner
R1,981/Night
For 7 Nights R13,868
New
- Chicago
- Buena Park
- 0.13 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Spa
- Breakfast
- Pet Friendly
R1,983/Night
For 7 Nights R13,885
Book a Last Minute Place to Stay in Uptown
About Casai's Private Villas and Holiday Rentals in Uptown
Discover more than 91 vacation rentals available in Uptown. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Uptown.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Uptown, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Uptown. On average, places to stay near Uptown offer 896.13 ft², with nightly prices averaging R5,440.
With Casai, finding and comparing holiday rentals in Uptown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Uptown
| Type | Count |
|---|---|
| Holiday Apartments | 68 |
| Vacation Homes | 11 |
Use these Quick Filters to Find a Holiday Rental in Uptown
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Uptown.
Weather in Uptown, IL
View the weather forecast for Uptown before booking your Uptown Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in Uptown, IL
Frequently Asked Questions About Uptown?
What are the top holiday rentals in Uptown?
With numerous options available in Uptown, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Uptown:
- Spacious 2-BR Condo + Free On-Site Parking
- Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- ❤️ Spacious and Airy Apartment With Parking On Site!
- Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
- Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
- Uptown Gem
- Chic apartment in marvelous Chicago with WiFi, AC
- Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
- -Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
- Ultra-modern 4BR/2.5BA Uptown/Edgewater duplex, featuring a rooftop deck with fire pit and easy access to the lake, dining, shopping, and Chicago’s cultural highlights.
Which holiday homes in Uptown are best for families?
If you're searching for a family-friendly holiday home in Uptown, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Uptown:
- Elegant 2BR Apartment w/In-Unit Laundry
- The Bright Retreat in Andersonville
- Cozy Studio Apt with In-Unit Laundry and Wi-Fi!
How many Casai.co.za holiday rentals are available in Uptown?
As of 2026, Casai boasts over 91 properties listed in the Uptown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Uptown.
Nearby Neighborhood (8)
| Neighborhood | Property Count |
|---|---|
| Lakeview Vacation Rentals in Chicago, Illinois | 244 |
| Edgewater Vacation Rentals in Chicago, Illinois | 57 |
| Ravenswood Vacation Rentals in Chicago, Illinois | 32 |
| Edgewater Beach Vacation Rentals in Chicago, Illinois | 883 |
| Andersonville Vacation Rentals in Chicago, Illinois | 1148 |
| Sheridan Park Vacation Rentals in Chicago, Illinois | 1301 |
| Buena Park Vacation Rentals in Chicago, Illinois | 1257 |
| Lakewood-Balmoral Vacation Rentals in Chicago, Illinois | 1119 |
People Also Ask
Finding the best prices in Uptown
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