South Side Beach Vacations 2026

Top Beach vacation packages in South Side

Price found within the past 48 hours. Click for updated prices.

DoubleTree by Hilton Pittsburgh - Green Tree

$564

per person

Nov 11 - Nov 14

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

8.6/10 Excellent! (1,175 reviews)

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$768

per person

Nov 11 - Nov 14

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!

Reviewed on Sep 14, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

$705

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

8.6/10 Excellent! (1,639 reviews)

Checking in took over 2 hours because rooms were ready.

Reviewed on Sep 24, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

$742

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

8.6/10 Excellent! (228 reviews)

Fairmont Pittsburgh

Downtown Pittsburgh

$677

per person

Nov 11 - Nov 14

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

8.8/10 Excellent! (1,003 reviews)

Tired property. Needs a facelift and some new energy. Reading light over the bed was burnt out. The water flow at the sink was a drizzle. Mini-bar was not refilled. Maid knocked at 8:40 am even though I was scheduled for a noon checkout. Great location and views but should be called the Foulmont…. The Kimpton Hotel Monaco up the street is exponentially better.

Reviewed on Sep 22, 2026

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3 Night Beach vacations in South Side

Price found within the past 48 hours. Click for updated prices.

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

$705

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

8.6/10 Excellent! (1,639 reviews)

Checking in took over 2 hours because rooms were ready.

Reviewed on Sep 24, 2026

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$768

per person

Nov 11 - Nov 14

found 23 hours ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

Reviewed on Sep 14, 2026

The Inn on Negley

Shadyside

$772

per person

Oct 30 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (QLA) to Pittsburgh (PIT)

10/10 Exceptional! (221 reviews)

So clean! A beautiful house and an amazing breakfast! Staff were wonderful. Short walk to shops and restaurants. Highly recommended.

Reviewed on Sep 23, 2026

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4 Night Beach vacations in South Side

Price found within the past 48 hours. Click for updated prices.

Stay Pittsburgh

Downtown Pittsburgh

Save 100% on your flight

$811

per person

Dec 17 - Dec 21

found 18 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Pittsburgh (PIT)

8/10 Very Good! (325 reviews)

Apartment was on a very busy street next to a 24 hr store and had a lot of people just standing around on the corner all day and night. Not the safest spot after dark. You could hear everything on the street all night, so hard to fall asleep. Building and hall smelled like weed but the apartment was fine. I texted the number that gave me the code and they said they would check the floor, address the issue and keep me posted. Never heard back from them. No thrills but didn’t expect any given the cost. Parking was supposed to be $25/day with in and out privileges in the assigned parking lot but there was never an attendant there so no in and out and charged $30/day.

Reviewed on Sep 20, 2026

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

Save 100% on your flight

$1,008

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

Reviewed on Sep 14, 2026

Etage Executive Living

Downtown Pittsburgh

$1,019

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Pittsburgh (PIT)

9.2/10 Wonderful! (1,895 reviews)

Super location! Great amenities, especially the athletic club. Friendly, helpful staff. Would definitely stay again.

Reviewed on Sep 24, 2026

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How do I book the best South Side beach vacation packages?

Life’s a beach when you dive into our brilliant South Side beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in South Side?

A rental steps from the shore creates an amazingly affordable South Side beach vacation. Seaside sojourns during low season start from $564. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in South Side?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a South Side beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a South Side vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find South Side beach vacation deals?

Sort your search results by deals to delight in amazing South Side beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a South Side beach trip with free cancellation and/or flexible dates?

Just like the South Side tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my South Side beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in South Side. (OK, maybe not that last part.)

Top Beach South Side Hotels

Pittsburgh’s Tropicana with outdoor year round hot tub. Fantastic location!

Pittsburgh PA

14 min walk from Rex Theater

Book a stay at this family-friendly vacation home in Pittsburgh. Enjoy free WiFi, laundry facilities, and patios. Popular attractions PPG Paints Arena and PNC ...

10/10 Exceptional! (62 reviews)

"Great place!"

Reviewed on Sep 8, 2026

King Bed | Free Parking | BBQ | Fire pit | Arcade

Pittsburgh PA

1 min walk from Rex Theater

Stay at this vacation home in Pittsburgh. Enjoy a garden, laundry facilities, and patios. Popular attractions PPG Paints Arena and PNC Park are located ...

9.8/10 Exceptional! (70 reviews)

"This property was amazing! The Southside Flats area is a great location! Brandon the host was very responsive to questions and concerns prior to and during our stay. The backyard patio was a nice feature! The appliances were top notch! It had an elegant Bohemian feel to it! Will definitely book in ..."

Reviewed on Aug 4, 2026

Pittsburgh House with Hot Tub, Patio & Free Parking!

Pittsburgh PA

2 min walk from Rex Theater

Book a stay at this family-friendly vacation home in Pittsburgh. Enjoy a garden, laundry facilities, and water skiing on site. Popular attractions PPG Paints ...

10/10 Exceptional! (8 reviews)

"My family loved the walkable neighborhood and the hot tub and the hours spent at nearby Kennywood Park!"

Reviewed on Aug 8, 2026

See all 2,045 properties in South Side

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.