Stay If You Dare - Vacation Rentals in Squirrel Hill South

City Skyline - Outside decks - Contemporary From US $407
         

10.0 (5 Reviews)
House
  • Parking
  • Security/Safety
  • Child Friendly
461 Melwood Suites Unit 101 2Bed/2Bath From US $343
         

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10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Accessibility
Historic Home In The South Side From US $182
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Perfect Place and Breakfast Too! From US $409
         

9.8 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Beautiful 3BR Home with Cozy Front & Back Porches! From US $121
         

9.4 (28 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV

Luxury Places to Stay in Squirrel Hill South

Over 965+ Luxury Places to Stay in or Near Squirrel Hill South
Sleeps 36 8bd/8ba 7 sofa beds. Big enough! From US $2,159
         

Entire House-City life, bring your pup! From US $1,177
         

Luxury Condo Near Shady side Hospital | King Bed From US $1,054
         

Top-Rated Vacation Rentals with a Pool in Squirrel Hill South

Over 35+ Top-Rated Vacation Rentals with a Pool in or Near Squirrel Hill South
PBR - Pittsburgh Bloomfield Rowhouse From US $200
         

10.0 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Residence Inn Pittsburgh Oakland/University Place From US $139
         

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9.2 (917 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hyatt House Pittsburgh/Bloomfield/Shadyside From US $162
         

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9.0 (1018 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Courtyard by Marriott Pittsburgh University Center From US $139
         

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
Hyatt House Pittsburgh Bloomfield Shadyside From US $217
         

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8.4 (293 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Squirrel Hill South

Over 324+ Pet-Friendly Vacation Rentals in or Near Squirrel Hill South
Walk to Walnut St: Pet-Friendly Pittsburgh Home! From US $165
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Southside Pitt home w/Pool Table +Yard From US $198
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
424 Gold Way-Apt. 302 From US $217
         

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9.8 (23 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Entire Home Lux Master Terraces 4 Car From US $482
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hydee's Hideaway From US $364
         

10.0 (25 Reviews)
Apartment
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
Luxe Campus Retreat – Sauna, Theater, Park & Walk From US $521
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Free Parking+Netflix+`BBQ+Games Near Bakery Square From US $492
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Squirrel Hill South

Over 105+ Large Vacation Homes & Villas in or Near Squirrel Hill South
Family-Friendly Shadyside Gem Near Dtwn Pittsburgh From US $365
         

Family-Friendly Shadyside Gem Near Dtwn Pittsburgh From US $638
         

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10.0 (1 Review)
House
  • Parking
  • Accessibility
  • Security/Safety
Central 5BD Getaway - Spacious Home w/BBQ From US $322
         

City Skyline - Outside decks - Contemporary From US $312
         

Free Parking+9Bedrooms+BBQ+Netflix Near Bakery Sq. From US $597
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Squirrel Hill South

Over 238+ Wheelchair Accessible Vacation Homes in or Near Squirrel Hill South
Industrial Loft 5 min to UPMC Shadyside CMU Pitt, sleeps 4 From US $200
         

LUX Studio King Bed Free Parking PITT CMU From US $233
         

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9.4 (5 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
424-Apt. 403 From US $188
         

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9.6 (33 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
HULU+Parking+GYM Near UPMC|Universities|Shopping From US $161
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
PARKING+HULU+GYM Near Universities|UPMC|Shopping From US $156
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
HULU+PARKING+GYM Near Universities|UPMC|Shopping From US $155
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
1BR/1BA with Gym Access Near UPMC & Carnegie Uni. From US $135
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Shadyside Gem King Bed Gym Free Parking Walk to UPMC, CMU & Pitt From US $132
         

Squirrel Hill South Varoom and Airbnb Places to Stay Under $200

Over 499+ Squirrel Hill South Varoom and Airbnb Places to Stay Under $200
Melwood Suites Unit 107 Studio From US $152
         

9.4 (40 Reviews)
Apartment
  • Parking
  • Child Friendly
  • Internet
1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area From US $97
         

Secret Garden by Frick Park with Garage Parking From US $188
         

10.0 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Squirrel Hill South

Over 484+ Instantly Bookable Vacation Homes in or Near Squirrel Hill South
King Bed | Free Parking | Arcade | Fire Pit From US $224
         

10.0 (23 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Pittsburgh Delight - Cozy 2B/1B Apt w/Private Parking, Second Floor Unit From US $212
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Modern 4BR Home, Fully Equipped Kitchen & Parking From US $395
         

About Squirrel Hill South Vacation Rentals

With more than 974 Squirrel Hill South vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Stayifyoudare 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 Squirrel Hill South.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Stayifyoudare Squirrel Hill South, 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 Squirrel Hill South. Places to stay near Squirrel Hill South are 725.4 ft² on average, with prices averaging $246 a night.

Stayifyoudare makes it easy and safe to find and compare vacation rentals in Squirrel Hill South 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 Squirrel Hill South

Type Count
Holiday Apartments 560
Vacation Homes 366
Hotels with Suites 33
Cottages 6
B&B 2
Villas 2
Hostels 1

Use these Quick Filters to Find a Vacation Rental in Squirrel Hill South

Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare 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 Squirrel Hill South.

Weather in Squirrel Hill South

View the weather forecast for Squirrel Hill South before booking your Squirrel Hill South 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