The Best Vacation Rentals - Vacation Rentals in South Side

Historic Home In The South Side From US $182
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Chic Modern 2BR Apartment in Carson by Stay Gia From US $109
         

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9.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Child Friendly
Traveler's Rest Hotel From US $148
         

9.6 (92 Reviews)
Hotel
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Perfect Place and Breakfast Too! From US $409
         

9.8 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cliffside Contemporary With Spectacualr City Views From US $707
         

Entire Home Lux Master Terraces 4 Car From US $482
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in South Side

Over 230+ Luxury Places to Stay in or Near South Side
4 Bedroom/2 Bathroom South Side I Pittsburgh From US $1,565
         

8.6 (16 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
Historic South Side Sanctuary From US $998
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in South Side

Over 20+ Top-Rated Vacation Rentals with a Pool in or Near South Side
Kasa South Side Pittsburgh From US $129
         

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8.6 (72 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Hyatt House Pittsburgh-South Side From US $193
         

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8.5 (512 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Kasa South Side Pittsburgh From US $229
         

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8.2 (105 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Kasa | Inviting 2 Bedroom with Amenity Access | Pittsburgh From US $305
         

Kasa | Welcoming Space Near South Side Marina | Pittsburgh From US $314
         

Pet-Friendly Vacation Rentals in South Side

Over 95+ Pet-Friendly Vacation Rentals in or Near South Side
Cozy Southside Pitt home w/Pool Table +Yard From US $221
         

10.0 (8 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Cozy Southside Pitt home w/Pool Table +Yard From US $198
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Pittsburgh Pennsylvania house From US $57
         

6.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
King Bed Garage Rooftop Views Sleeps 14 Game room walk to Carson St From US $325
         

Pet Friendly Southside 3-bedroom house with WiFi & AC Near Downtown From US $133
         

Elegant & Cozy Escape - 5Beds/2.5Bath - Sleeps 10 From US $389
         

Large Vacation Homes & Villas in South Side

Over 40+ Large Vacation Homes & Villas in or Near South Side
Central 5BD Getaway - Spacious Home w/BBQ From US $322
         

City Skyline - Outside decks - Contemporary From US $407
         

10.0 (5 Reviews)
House
  • Parking
  • Security/Safety
  • Child Friendly
4bd Pittsburgh Escape: BBQ, Games, 10mins to UPitt From US $376
         

Pittsburgh Gem - 5BR - Downtown Deck View From US $436
         

City Skyline - Outside decks - Contemporary From US $312
         

Amazingly Homey w/Garage + Outdoor Space! 5B/2B From US $400
         

9.6 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck From US $379
         

9.4 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in South Side

Over 23+ Wheelchair Accessible Vacation Homes in or Near South Side
Kasa | Spacious SouthSide Works Studio | Pittsburgh From US $250
         

8.8 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Traveler's Rest Hotel From US $199
         

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8.8 (55 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
HYATT house Pittsburgh-South Side From US $145
         

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8.6 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Kasa | Studio, Marina in SouthSide | Pittsburgh From US $176
         

8.6 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Kasa | Within Walking Distance of City Theatre | Pittsburgh From US $250
         

Kasa | Stay in or Go out in Steel City | Pittsburgh From US $316
         

7.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
The Josephine Villa by Luxe PGH From US $896
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

South Side Varoom and Airbnb Places to Stay Under $200

Over 90+ South Side Varoom and Airbnb Places to Stay Under $200
Cozy&Modern 2Bdr Apt PIttsburgh From US $122
         

10.0 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Southside Flats Cozy Quiet Luxury From US $196
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Southside Flats Cozy Quiet Luxury From US $164
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
2615 Jane Down - Southside From US $192
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety
City Retreat in SouthSide Flats From US $191
         

10.0 (1 Review)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
House on a hill - view of Pittsburgh From US $190
         

9.8 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in South Side

Over 95+ Instantly Bookable Vacation Homes in or Near South Side
Updated Townhome with Private Garage in South Side From US $206
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
A Perfect South Side Getaway From US $274
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Hot Tub | King Bed | Games | Free Parking From US $377
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
South Side Bicycle Home Sleeps 6 From US $375
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About South Side Vacation Rentals

With more than 239 South Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Thebestvacationrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in South Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Thebestvacationrentals South Side, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in South Side. Places to stay near South Side are 788.48 ft² on average, with prices averaging $304 a night.

Thebestvacationrentals makes it easy and safe to find and compare vacation rentals in South Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in South Side

Type Count
Vacation Homes 137
Holiday Apartments 90
Hotels with Suites 9
Villas 2

Use these Quick Filters to Find a Vacation Rental in South Side

Pro Tip: Thebestvacationrentals makes it easy to compare the best listings on Thebestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thebestvacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in South Side.

Weather in South Side

View the weather forecast for South Side before booking your South Side 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