1+ Vacation Rentals Near South Shore |
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Cruise Vacations - Vacation Rentals in South Shore

Large House boat located right in downtown Pittsburgh! Pricing is negotiable! From US $629
         

New
Boat Rental
Large House boat located right in downtown Pittsburgh! Pricing is negotiable!
  • Child Friendly

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Luxury Places to Stay in South Shore

Over 1921+ Luxury Places to Stay in or Near South Shore
LUX 2.3k SQFT, Game Room, Parking, Sleeps 10 Plus From US $9,999
         

New
House
LUX 2.3k SQFT, Game Room, Parking, Sleeps 10 Plus
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious 6-bedroom house in mt washington with pokerroom From US $5,734
         

9.0 (7 Reviews)
House
Spacious 6-bedroom house in mt washington with pokerroom
  • TV
  • Bedding/Linens
  • Wellness Facilities

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Walk to 2026 NFL Draft - 3 Bedroom & 3.5 Bathroom Home in Mexican War Streets From US $5,341
         

New
House
Walk to 2026 NFL Draft - 3 Bedroom & 3.5 Bathroom Home in Mexican War Streets
  • Air Conditioner
  • Parking
  • TV

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A Touchdown Location for the Draft
New
From US $5,130
         

New
House
A Touchdown Location for the Draft
  • Air Conditioner
  • Pet Friendly
  • TV

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4 BEDS Private Patio Central Modern Stay From US $4,650
         

New
Apartment
4 BEDS Private Patio Central Modern Stay
  • Air Conditioner
  • Parking
  • Pet Friendly

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5BDRM GEM with Arcade - Mt Wash From US $4,182
         

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New
House
5BDRM GEM with Arcade - Mt Wash
  • Air Conditioner
  • View
  • Balcony/Terrace

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3 KING Beds Free parking Stay close and stay cozy From US $3,060
         

New
Apartment
3 KING Beds Free parking Stay close and stay cozy
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Ultimate Fan's Retreat 5BR near all the Action From US $3,012
         

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New
House
The Ultimate Fan's Retreat 5BR near all the Action
  • Air Conditioner
  • View
  • Security/Safety

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Top-Rated Vacation Rentals with a Pool in South Shore

Over 77+ Top-Rated Vacation Rentals with a Pool in or Near South Shore
Monthly Bungalow In Green Tree From US $118
         

10.0 (52 Reviews)
House
Monthly Bungalow In Green Tree
  • Air Conditioner
  • Parking
  • Pool

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Convenient to DT, Airport, Stadiums-Free Parking! From US $132
         

10.0 (15 Reviews)
House
Convenient to DT, Airport, Stadiums-Free Parking!
  • Air Conditioner
  • Parking
  • Pool

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Drury Plaza Hotel Pittsburgh Downtown From US $136
         

|
9.6 (2210 Reviews)
Hotel
Drury Plaza Hotel Pittsburgh Downtown
  • Air Conditioner
  • Parking
  • Pool

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Explore Pittsburgh from a Modern, Hip Bungalow From US $121
         

9.6 (56 Reviews)
House
Explore Pittsburgh from a Modern, Hip Bungalow
  • Air Conditioner
  • Parking
  • Pet Friendly

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Eclectic Historic Sunny Vista Home with City Views, Northshore From US $135
         

9.6 (38 Reviews)
House
Eclectic Historic Sunny Vista Home with City Views, Northshore
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hampton Inn & Suites Pittsburgh-Downtown From US $158
         

9.4 (1314 Reviews)
Hotel
Hampton Inn & Suites Pittsburgh-Downtown
  • Air Conditioner
  • Parking
  • Pool

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Homewood Suites by Hilton Pittsburgh Downtown From US $151
         

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9.2 (1493 Reviews)
Hotel
Homewood Suites by Hilton Pittsburgh Downtown
  • Air Conditioner
  • Parking
  • Pool

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Residence Inn Pittsburgh Oakland/University Place From US $139
         

|
9.2 (924 Reviews)
Hotel
Residence Inn Pittsburgh Oakland/University Place
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in South Shore

Over 773+ Pet-Friendly Vacation Rentals in or Near South Shore
King Bed - Heart of PB - Jaw-Dropping Rooftop and Gym From US $72
         

10.0 (5 Reviews)
Apartment
King Bed - Heart of PB - Jaw-Dropping Rooftop and Gym
  • Air Conditioner
  • Pet Friendly
  • Accessibility

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Relax & Feel At Home During Your Pittsburgh Stay From US $130
         

9.4 (32 Reviews)
House
Relax & Feel At Home During Your Pittsburgh Stay
  • Air Conditioner
  • Pet Friendly
  • TV

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Sleek 2BR Downtown Retreat with Gym From US $713
         

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10.0 (7 Reviews)
Apartment
Sleek 2BR Downtown Retreat with Gym
  • Air Conditioner
  • Pet Friendly
  • TV

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Urban Retreat with Garage on Mt. Washington From US $174
         

10.0 (72 Reviews)
House
Urban Retreat with Garage on Mt. Washington
  • Air Conditioner
  • Parking
  • Pet Friendly

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View from the Top! Steps from Grandview, Sleeps 8 From US $253
         

10.0 (66 Reviews)
House
View from the Top! Steps from Grandview, Sleeps 8
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants! From US $327
         

10.0 (43 Reviews)
House
★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Two KING beds! Lots of off-street parking! Close to downtown! Pet friendly! From US $199
         

10.0 (32 Reviews)
House
Two KING beds! Lots of off-street parking! Close to downtown! Pet friendly!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Peaceful Escape Just Minutes To DT, Garage Parking From US $499
         

10.0 (28 Reviews)
House
Peaceful Escape Just Minutes To DT, Garage Parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in South Shore

Over 272+ Large Vacation Homes & Villas in or Near South Shore
City Skyline - Outside decks - Contemporary From US $407
         

10.0 (7 Reviews)
House
City Skyline - Outside decks - Contemporary
  • Parking
  • Security/Safety
  • Fireplace/Heating

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Perfect Place and Breakfast Too! From US $409
         

9.8 (41 Reviews)
House
Perfect Place and Breakfast Too!
  • Air Conditioner
  • Parking
  • TV

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Gorgeous Southside Slopes home with outdoor hot tub and city view! From US $488
         

9.8 (58 Reviews)
House
Gorgeous Southside Slopes home with outdoor hot tub and city view!
  • Air Conditioner
  • Parking
  • TV

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Entire Home Lux Master Terraces 4 Car From US $506
         

10.0 (27 Reviews)
House
Entire Home Lux Master Terraces 4 Car
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Victoria From US $318
         

10.0 (24 Reviews)
House
The Victoria
  • Air Conditioner
  • Parking
  • TV

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Luxe Campus Retreat – Sauna, Theater, Park & Walk From US $1,102
         

10.0 (18 Reviews)
House
Luxe Campus Retreat – Sauna, Theater, Park & Walk
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Pittsburgh Home with Incredible View From US $724
         

10.0 (16 Reviews)
House
Luxury Pittsburgh Home with Incredible View
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Central 5BD Getaway - Spacious Home w/BBQ From US $442
         

10.0 (10 Reviews)
House
Central 5BD Getaway - Spacious Home w/BBQ
  • Air Conditioner
  • Parking
  • TV

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Wheelchair Accessible Vacation Homes in South Shore

Over 433+ Wheelchair Accessible Vacation Homes in or Near South Shore
Etage Executive Living From US $209
         

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8.7 (420 Reviews)
Apartment
Etage Executive Living
  • Air Conditioner
  • Parking
  • Pet Friendly

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Historic 2BR Loft: Private Terrace & Free UFC Gym From US $335
         

10.0 (24 Reviews)
Apartment
Historic 2BR Loft: Private Terrace & Free UFC Gym
  • Air Conditioner
  • Pet Friendly
  • TV

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Placemakr Downtown Pittsburgh at The Pennsylvanian From US $168
         

|
8.0 (60 Reviews)
Apartment
Placemakr Downtown Pittsburgh at The Pennsylvanian
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxe 2BR Loft Retreat: Private Terrace & Free Gym From US $639
         

10.0 (3 Reviews)
Apartment
Luxe 2BR Loft Retreat: Private Terrace & Free Gym
  • Air Conditioner
  • Pet Friendly
  • TV

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Chic Apt - Amazing Three Rivers Views in PGH Heart 24-7 Parking From US $319
         

10.0 (2 Reviews)
Apartment
Chic Apt - Amazing Three Rivers Views in PGH Heart 24-7 Parking
  • Air Conditioner
  • Parking
  • TV

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Elegant 2BR in the Vibrant Heart of Pittsburgh From US $244
         

10.0 (1 Review)
Apartment
Elegant 2BR in the Vibrant Heart of Pittsburgh
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Steelers Fans’ 1BR – Downtown & Stadium Close From US $195
         

10.0 (1 Review)
Apartment
Steelers Fans’ 1BR – Downtown & Stadium Close
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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CozySuites Modern 1BR in Downtown Pitts #21 From US $155
         

10.0 (1 Review)
Apartment
CozySuites Modern 1BR in Downtown Pitts #21
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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South Shore Varoom and Airbnb Places to Stay Under $200

Over 859+ South Shore Varoom and Airbnb Places to Stay Under $200
Chic Modern 2BR Apartment in Carson by Stay Gia From US $109
         

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9.0 (4 Reviews)
Apartment
Chic Modern 2BR Apartment in Carson by Stay Gia
  • Air Conditioner
  • Parking
  • Child Friendly

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Peaceful full home in the heart of Southside Flats. From US $156
         

10.0 (29 Reviews)
House
Peaceful full home in the heart of Southside Flats.
  • Parking
  • TV
  • Security/Safety

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6 Beds Downtown Apt Very Quick Walk Everywhere From US $187
         

10.0 (2 Reviews)
Apartment
6 Beds Downtown Apt Very Quick Walk Everywhere
  • Child Friendly
  • Internet

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Cozy&Modern 2Bdr Apt PIttsburgh From US $122
         

10.0 (11 Reviews)
Apartment
Cozy&Modern 2Bdr Apt PIttsburgh
  • Air Conditioner
  • Parking
  • TV

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WC414 · Free Parking! From US $194
         

10.0 (10 Reviews)
Apartment
WC414 · Free Parking!
  • Air Conditioner
  • Parking
  • TV

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Grandview Studio | Skyline Views | Private Parking From US $191
         

10.0 (5 Reviews)
Apartment
Grandview Studio | Skyline Views | Private Parking
  • Air Conditioner
  • Parking
  • TV

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Southside Flats Cozy Quiet Luxury From US $174
         

10.0 (5 Reviews)
Apartment
Southside Flats Cozy Quiet Luxury
  • Air Conditioner
  • Parking
  • TV

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Plush 4BR Retreat Patio, Great Location From US $193
         

10.0 (4 Reviews)
House
Plush 4BR Retreat Patio, Great Location
  • Air Conditioner
  • Pet Friendly
  • TV

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Instantly Bookable Vacation Homes in South Shore

Over 1103+ Instantly Bookable Vacation Homes in or Near South Shore
Historic Home In The South Side From US $213
         

10.0 (30 Reviews)
Apartment
Historic Home In The South Side
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Stylish 2BR! Off-Street Parking! From US $243
         

10.0 (1 Review)
House
Stylish 2BR! Off-Street Parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ HostWise Stays ★ Skyline Splendor w/Private Balconies & Game Room From US $808
         

10.0 (61 Reviews)
House
★ HostWise Stays ★ Skyline Splendor w/Private Balconies & Game Room
  • Air Conditioner
  • Parking
  • TV

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Pittsburgh Pennsylvania house From US $57
         

6.0 (2 Reviews)
House
Pittsburgh Pennsylvania house
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

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1209 Ocala St Pittsburgh From US $229
         

10.0 (41 Reviews)
House
1209 Ocala St Pittsburgh
  • Air Conditioner
  • Parking
  • TV

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Clean and comfortable 3BR home in the South Side neighborhood From US $265
         

10.0 (39 Reviews)
House
Clean and comfortable 3BR home in the South Side neighborhood
  • Air Conditioner
  • Parking
  • TV

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1207 Ocala - Boat House - North Side From US $301
         

10.0 (35 Reviews)
House
1207 Ocala - Boat House - North Side
  • Air Conditioner
  • Parking
  • TV

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PGH City Home - Lovely 3 BR, 1.5 BA, Sleeps 7+ w/Ultra Suited Location From US $226
         

10.0 (34 Reviews)
House
PGH City Home - Lovely 3 BR, 1.5 BA, Sleeps 7+ w/Ultra Suited Location
  • Air Conditioner
  • Parking
  • TV

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About South Shore Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruisevacations South Shore, 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 Shore. Places to stay near South Shore with prices averaging $629 a night.

Cruisevacations makes it easy and safe to find and compare vacation rentals in South Shore 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 Shore

Type Count

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

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

Weather in South Shore

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

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