Family-friendly holiday rentals in Plum

4.87 out of 5 average rating, 197 reviews

A large in-ground heated pool is showcased within a shaded outdoor area. Tall trees provide natural privacy, while bright blue waters reflect the clear sky. Lounge chairs are positioned along the edge of the pool, inviting relaxation in a serene setting.

Home in Monroeville

Mayberry Escape

Discover the charm of this inviting 3-bed, 3.5-bath Monroeville home! Immerse yourself in luxury with a heated pool (seasonal), rejuvenating infrared sauna, expansive decks, a private backyard, a fully equipped kitchen, a finished basement, and a delightful fire pit overlooking the pool. Experience comfort and style with off-street parking included. Enquire now to make this your own sanctuary! ***If you enjoy this space, the owners are amenable to selling. Please contact for more information***

Indoor spacesKitchenHospitality

Apartment in Downtown Pittsburgh

4.9 out of 5 average rating, 290 reviews

Cultural District new King Suite whirlpool tub

Experience Pittsburgh's Cultural District from this new king suite! You are surrounded by Pittsburgh's best restaurants, shops, steps away from the Convention Center, theaters, and more. Designed for comfort and convenience in an unbeatable location. - King bed - Whirlpool tub / shower - Equipped Kitchen & Laundry - Walk to everything - Mult garages within 5 min - 24/7 guest support Perfect for business trips, events, or weekend getaways. We're here for you before, during and after your stay!

Indoor spacesFamilyView

A rustic single-story ranch home is set against a backdrop of trees. The brick exterior is complemented by a shaded porch, with steps leading up from a grassy area. A wooden railing can be seen near the entrance, while some construction materials are visible nearby.

4.85 out of 5 average rating, 129 reviews

City-Adjacent Wooded Retreat - Peace and Wildlife

1950’s Ranch on secluded road. No other spot has so much access to private forest, this close to the city! Take a stroll, build a fire or enjoy a sunset from the porch. Only :10 from hotspots like Shadyside and L-Ville. :15-:20 from UPMC Oakland. Full & twin beds. Sparse furniture, w/ cooking utensils included. This isn’t a hotel room, it’s a home in transition and we invite you to stay simply, easily & cheap! I live close by for help in town or for anything you might need during your stay.

KitchenIndoor spacesAccuracy

4.99 out of 5 average rating, 103 reviews

The floating home is presented from an aerial view, showcasing its unique two-level structure nestled on the calm waters of the Allegheny River. The wrap-around deck and patio doors are visible, enhancing the connection to nature, with lush greenery lining the riverbank.

Houseboat in Blawnox

Allegheny River Aqua Villa

Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

Indoor spacesFamilyComfort

Apartment in East Liberty

The bedroom features a spacious bed covered in crisp white linens, highlighted by a blue accent throw. Blue curtains frame multiple windows, allowing natural light to fill the room. A small desk and chair are positioned nearby, complemented by a decorative plant and wall art.

4.96 out of 5 average rating, 227 reviews

Upscale King Bed Suite |ADA w/ Free parking!

Enjoy our spacious king-sized bed suite located in the safe, central Friendship neighborhood. This newly renovated retreat is just a short distance from all that Pittsburgh has to offer! Steps away from Whole Foods and short walk to Yinz Coffee shop! ⭐King bed (Memory foam mattress) ⭐Queen pull out bed ⭐Pack n play ⭐ADA Accessible! ⭐In-unit washer/ dryer ⭐Large desk w/ speedy wifi & extra monitor ⭐Pet friendly ⭐24/7 Guest support ⭐Free off-street parking ⭐Close to CMU/ Pitt! ⭐$0 cleaning fee!

KitchenFamilyWi-Fi

4.86 out of 5 average rating, 332 reviews

The exterior of the historic log house is visible, showcasing its rustic charm with exposed logs. Vibrant foliage in shades of red and orange surrounds a furnished porch, while fallen leaves blanket the ground. The entrance is accessible via a small set of stairs.

Home in Verona

Wyckoff-Mason Log House 1774 Historic Landmark

Stay in the historic Wyckoff-Mason House, a Pittsburgh Historical landmark. This beautifully kept log house built in 1774-75, still maintains the colonial charm of pre-revolutionary times. This property has a storied past, including local lore that it was the residence of William Penn’s brother and was visited by Benjamin Franklin. This relaxing getaway is located in one of Pittsburgh’s eastern suburbs. Get the best of the countries antiquity while visiting the city. We love all people.

KitchenIndoor spacesValue

4.99 out of 5 average rating, 108 reviews

A spacious bedroom features a wooden bed with crisp white bedding and a decorative yellow accent pillow. A bedside lamp illuminates a dark wood nightstand. A tufted bench sits at the foot of the bed, and light streams in through a nearby doorway.

Apartment in Aspinwall

Aspinwall 1 bedroom Apartment

Newly updated 1 bedroom 1 bathroom apartment in the heart of the charming town of Aspinwall. Private exterior entrance with porch and patio, new kitchen, refinished original hardwood flooring, updated bathroom, living/dining room with decorative fireplace and 50” smart TV, spacious bedroom with queen, large closets and pocket doors all warmly decorated. 2 blocks from primary business streets for dining and shopping, under 10 minute walk to both UPMC St Margaret hospital and riverfront park!

FamilyKitchenHospitality

4.98 out of 5 average rating, 120 reviews

Apartment in Bloomfield

Chic Loft Style HighEnd King Suite~ 2Parking Spots

Brand New Loft Style Apartment with 17ft. ceilings, huge windows, and 2 dedicated OffStreet Parking Spaces! Brand new KING Suite! 1 block to West Penn, short walk to UPMC! On site parking makes the short drive to Shadyside, CMU, Pitt and the Strip District/Downtown a breeze! The building was gutted and remodeled, everything is brand new! Fully stocked for long and short term stays! Steps to dozens of restaurants, shops, coffee shops, and grocery stores. Make your reservation today!

Indoor spacesFamilyQuiet

The exterior of a three-story house is shown, featuring dark siding and a peaked roof. A welcoming front entrance is accessed via a steps leading to the door. Lush green shrubs frame the house, contrasting with the bright grassy area in front.

4.91 out of 5 average rating, 554 reviews

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

FamilyKitchenHospitality

Apartment in Forest Hills

4.99 out of 5 average rating, 191 reviews

Pittsburgh Area 2 Bedroom Apt.

Comfortable, Convenient & Clean 2 bedroom apartment (1 queen bed & 1 twin size day bed). Located on a "Pittsburgh Hill" you'll remember in Forest Hills a quiet residential eastern suburb of city. Free off street parking. Downtown & Stadiums 10 mi. Universities, Medical Center, PPG Paints Arena & Carnegie Museums 8 mi. Kennywood Amusement Park, Monroeville Convention Center & Sri Venkateswara Temple 5 mi. I-76 PA Turnpike 8mi. International A/P 27 mi.

Indoor spacesKitchenLong stay

4.86 out of 5 average rating, 119 reviews

A cozy living area features two comfortable sofas, one adorned with blue cushions and a throw blanket. A dark coffee table is centered on a textured rug, surrounded by natural light from large windows dressed with gray curtains. A flat-screen TV is mounted on the wall.

Apartment in Springdale

2br gem in cute small town.

The whole group will enjoy easy access to everything from this centrally located place. Grab a book about Pittsburgh from the coffee table and find some fun things to do or have game night with the selection of board games. Sip a beverage on the back porch or make s’mores at the fire pit. Easy access to Pittsburgh, hop on 28 and be there in no time, or ride one of the busses that stop outside the door. 13 miles to PNC Park 14 miles to Acrisure Stadium

Indoor spacesFamilyLaundry

4.92 out of 5 average rating, 331 reviews

A bright living area is highlighted by a cozy sectional sofa, a coffee table, and a dining table for four. Natural light streams through three windows, illuminating the wood beams on the ceiling. A wall-mounted TV and a full kitchen are also visible in the space.

Apartment in Glenshaw

The Camera Stop

Open and bright private apartment located in the Fox Chapel area. Entire apartment was recently remodeled with all new furnishings and fixtures. We are located only 20 minutes from Downtown Pittsburgh and 15 minutes to Heinz Field, PPG Paints Arena, and PNC Park. This area is close to shopping, restaurants, grocery stores and the PA Turnpike. Jennifer is my office manager and your contact for any bookings or questions you may have. NO SMOKING

Indoor spacesKitchenAccuracy

Popular amenities for Plum family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An outdoor space is illuminated by soft string lights, featuring a hot tub surrounded by wooden decking. A gazebo with seating is nearby, and a fire pit is visible in the background, complemented by lush greenery and trees that create a private setting.

4.95 out of 5 average rating, 131 reviews

Serene Secluded Hilltop Hideaway. Hot Tub Fire Pit

KitchenFamilyCheck-in

4.93 out of 5 average rating, 137 reviews

A collage features a cozy living room with stylish furniture and artwork, a fenced backyard with a hot tub and outdoor seating, a traditional blue house exterior, and a modern kitchen showcasing stainless steel appliances and ample counter space.

Home in North Side

NEW! Luxurious 5bdr w/ a hot tub. Walk to stadiums

KitchenFamilyHot tub

4.94 out of 5 average rating, 192 reviews

Home in North Side

HotTub/Firepit/Parking! Less than 1mi PNC Park

FamilyIndoor spacesSleep quality

4.88 out of 5 average rating, 128 reviews

A richly decorated hallway is highlighted by wooden paneling and intricate ceiling details. Colorful artwork adorns the walls, including a prominent painting of a seated figure. A small table, accented with vibrant decor, contributes to the warm ambiance of the space.

Guesthouse in Pittsburgh

Luxury: Pointe Brise Retreat House

KitchenIndoor spacesGetting around

A private hot tub is nestled in an outdoor area, surrounded by softly glowing string lights and lush potted plants. Wooden steps lead to an elevated deck, creating an inviting space for relaxation and enjoyment during any season.

4.97 out of 5 average rating, 320 reviews

Gorgeous Southside slopes house w/outdoor hot tub

Indoor spacesKitchenAccess

Home in Squirrel Hill North

4.9 out of 5 average rating, 145 reviews

Gather in Style | Walk to CMU | Sleeps 13

FamilyKitchenHospitality

4.96 out of 5 average rating, 107 reviews

An inviting outdoor seating area is presented, featuring a large sectional couch with decorative pillows, a coffee table, and a patterned rug. Lush greenery surrounds the space, providing privacy, while string lights overhead create a warm ambiance.

Home in Mount Washington

Hot Tub & Fire Pit Home Near Grandview Ave

Indoor spacesKitchenSleep quality

4.96 out of 5 average rating, 135 reviews

The image captures a serene outdoor space featuring a pond with cascading water and lush greenery. A wooden pergola provides shade over hanging chairs. The landscaped area includes rocks, plants, and a glimpse of the home in the background, enhancing the tranquil atmosphere.

Home in North Side

Urban Oasis Home - Hot Tub, Pet-friendly, Koi Pond

KitchenFamilyPets

Family- and pet-friendly home rentals

The exterior of the red-brick duplex features a rounded entrance with a decorative arch and a blue front door. Symmetrical windows on either side are framed with shutters. A small staircase leads up to the entrance, which is set amidst a well-maintained outdoor area.

4.99 out of 5 average rating, 137 reviews

A Retreat Above It All

KitchenFamilyAccess

4.9 out of 5 average rating, 324 reviews

A cozy living area is highlighted by a sleek beige leather sofa, accompanied by decorative pillows. A glass coffee table sits on an ornate area rug, while natural light illuminates the space. The staircase and a softly lit hallway can be seen in the background.

Home in Duquesne

Entire home near Kennywood without extra fees.

FamilyIndoor spacesAccuracy

A warm living area features a stone fireplace gently glowing with light. Comfortable seating arrangements include a sofa and an inviting window nook with colorful cushions. Natural light enters through multiple windows, highlighting the wooden beam ceilings and rich tones of the walls.

4.94 out of 5 average rating, 71 reviews

Cottage on a hill

FamilyKitchenLocation

4.86 out of 5 average rating, 14 reviews

Stylish 1BR | Private Entrance Near Pittsburgh

KitchenIndoor spacesHospitality

Guest suite in West Mifflin

4.95 out of 5 average rating, 258 reviews

Hilltop Suite, Quiet Street

FamilyIndoor spacesComfort

4.99 out of 5 average rating, 183 reviews

Townhouse in Mt. Lebanon

Private Mt Lebanon Retreat Near Airport/Downtown

FamilyIndoor spacesTV

4.81 out of 5 average rating, 243 reviews

The exterior of the house is shown, featuring a well-maintained brick facade. The covered porch leads to the front door, framed by two windows. Lush grass surrounds the walkway, emphasizing the welcoming entry. A hint of greenery is visible in the background.

Home in Monroeville

Pittsburgh Hideaway - Pets - Private

Indoor spacesKitchenCleanliness

4.89 out of 5 average rating, 224 reviews

A bright kitchen area is furnished with modern white cabinetry and a granite countertop. The kitchen features a decorative tile backsplash and a large window, allowing ample natural light. A wooden dining table with stools is positioned in the center, enhancing the open layout.

Loft in Strip District

Lovely Strip District loft with free parking

KitchenIndoor spacesGetting around

Family-friendly home rentals with a pool

A cozy stone patio is covered with a grape arbor, offering shade and inviting seating arrangements. A small table adorned with flowers is surrounded by chairs, while potted plants and greenery add to the serene outdoor setting. The area is easily accessible and well-maintained.

4.91 out of 5 average rating, 23 reviews

1st Fl. Huge Flat on 2 Acres - Pets/Garage Parking

Getting aroundDecorAccess

4.92 out of 5 average rating, 12 reviews

Apartment in North Side

FIDO PLUS TWO 1.5 miles to Acrisure Stadium

PoolAccessAccuracy

4.65 out of 5 average rating, 17 reviews

A beautiful cozy home away from home!

Indoor spacesKitchenParking

4.81 out of 5 average rating, 105 reviews

A wooden dining table is positioned in the foreground, featuring a decorative orange fish centerpiece. The background reveals a modern kitchen with sleek granite countertops and a stylish backsplash, complemented by an overhead stainless steel range hood.

Home in Dormont

Renovated Cozy Duplex w/pool, Close to downtown

FamilyIndoor spacesBarbecue

4.57 out of 5 average rating, 61 reviews

A private pool is set within a spacious wooden deck, surrounded by lounge chairs and shaded areas. A vibrant beach ball floats on the water, and an umbrella offers shade nearby. Lush greenery is visible in the background, enhancing the outdoor space.

Home in New Kensington

Seasonal Pool Retreat | Fire Pit & Large Deck

FamilyKitchenPool

4.93 out of 5 average rating, 82 reviews

A private swimming pool is situated in a spacious outdoor area, surrounded by a secure fence. The pool features clear blue water, with steps leading into it. A well-maintained house with multiple levels is visible in the background, complemented by green trees nearby.

Home in Wexford

Spacious House w/ Pool @Wexford

KitchenFamilyQuiet

5 out of 5 average rating, 55 reviews

A newly renovated pool area features a sparkling blue pool surrounded by a spacious patio. Comfortable lounge chairs are positioned along the edge, with trees and a privacy fence providing a secluded setting. A pool house is visible in the background against a colorful sky.

Home in Coraopolis

PIT Staycation Retreat with Pool House!

FamilyKitchenEV charging