Best Vacation Homes in Oakland
Apartment
10.0(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
1025 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
£216/Night
7 Nights - £1,513
House
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
247.57 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
View
£79/Night
7 Nights - £556
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
- Parking
Internet
Child Friendly
£203/Night
7 Nights - £1,420
Apartment
10.0(5 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
Air Conditioner
£148/Night
7 Nights - £1,039
Apartment
9.9(13 Reviews)
1 Bedroom
1 Bath
4 Guests
667.36 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
£143/Night
7 Nights - £998
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£223/Night
7 Nights - £1,562
Apartment
9.8(44 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£164/Night
7 Nights - £1,148
Apartment
9.8(27 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£197/Night
7 Nights - £1,379
Oakland Luxury Rentals
Apartment
7 Bedrooms
8 Baths
36 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£2,096/Night
7 Nights - £14,670
House
1 Bedroom
3 Baths
16 Guests
2421.88 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
£934/Night
7 Nights - £6,541
Apartment
9.0(12 Reviews)
3 Bedrooms
3 Baths
12 Guests
2400.35 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
£614/Night
7 Nights - £4,299
Apartment
10.0(2 Reviews)
7 Bedrooms
3 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£464/Night
7 Nights - £3,250
New
House
2 Bedrooms
3 Baths
6 Guests
1905.21 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
£450/Night
7 Nights - £3,153
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£424/Night
7 Nights - £2,970
House
8.8(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
17395 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£424/Night
7 Nights - £2,970
Apartment
10.0(1 Review)
3 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£395/Night
7 Nights - £2,763
Oakland Pet Friendly Vacation Rentals
Apartment
9.8(18 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£144/Night
7 Nights - £1,010
Apartment
9.8(17 Reviews)
1 Bedroom
1 Bath
4 Guests
667.36 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
£113/Night
7 Nights - £789
Apartment
9.8(23 Reviews)
1 Bedroom
1 Bath
- Pet Friendly
- Kitchen
- Parking
- Internet
£173/Night
7 Nights - £1,209
Apartment
9.8(17 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£140/Night
7 Nights - £978
Apartment
9.6(9 Reviews)
1 Bedroom
1 Bath
4 Guests
355.21 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
£143/Night
7 Nights - £1,000
Apartment
9.6(51 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£172/Night
7 Nights - £1,201
Apartment
9.6(34 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£254/Night
7 Nights - £1,781
Apartment
9.6(19 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£176/Night
7 Nights - £1,233
Oakland Large Vacation Homes
Apartment
9.8(57 Reviews)
3 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£337/Night
7 Nights - £2,357
Apartment
5 Bedrooms
2 Baths
10 Guests
1399.31 ft²
- Fireplace/Heating
Security/Safety
£144/Night
7 Nights - £1,008
House
9.4(21 Reviews)
5 Bedrooms
2 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£373/Night
7 Nights - £2,611
House
10.0(1 Review)
9 Bedrooms
4 Baths
29 Guests
5800 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
£873/Night
7 Nights - £6,108
House
2.0(3 Reviews)
8 Bedrooms
2 Baths
29 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
£1,153/Night
7 Nights - £8,073
New
Apartment
3 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
£847/Night
7 Nights - £5,928
House
5 Bedrooms
3 Baths
14 Guests
1900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£530/Night
7 Nights - £3,713
House
1.0(1 Review)
5 Bedrooms
2 Baths
- Air Conditioner
Laundry
TV
£167/Night
7 Nights - £1,170
Why Choose Rent By Owner for your Oakland Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Oakland Vacation Rentals
Where are the best neighborhoods to stay in Oakland?
Exploring neighborhoods in Oakland, Pittsburgh offers a diverse range of experiences for every traveler. Whether you're looking to immerse yourself in vibrant urban culture or enjoy peaceful residential streets, the area provides a variety of options to suit your preferences. Staying in this part of Pittsburgh means you can easily access local attractions and enjoy the authentic atmosphere that makes Oakland unique. When searching for your perfect vacation rental, consider neighborhoods within Oakland that balance convenience, comfort, and character to enhance your visit to Pittsburgh.
South Oakland
In this vibrant neighborhood, you'll find a lively atmosphere with easy access to local amenities, making it an ideal choice for travelers seeking convenience and proximity to the heart of the city.
View 2363+ Rentals in South OaklandNorth Oakland
Known for its diverse community and academic atmosphere, this part of the region offers a welcoming environment along with nearby cultural attractions, perfect for exploring the city’s rich history and vibrant arts scene.
View 61+ Rentals in North OaklandBluff
Perched along scenic overlooks, Bluff provides stunning views and a peaceful ambiance, making it a great place for visitors looking for a quiet retreat within close reach of urban attractions.
View 2298+ Rentals in BluffSquirrel Hill South
This charming neighborhood is celebrated for its diverse eateries and friendly atmosphere, offering a comfortable stay amid welcoming local charm and convenient access to the region's attractions.
View 1064+ Rentals in Squirrel Hill SouthBest Times to Visit Oakland
When should you plan your Vacation Rentals stay?
Choosing the right time to visit ensures you experience the best of this destination, whether you're seeking vibrant local events or peaceful seasonal scenery in Oakland, Pittsburgh, Pennsylvania, USA.
Peak Season Highlights
Summer (June to August)
During the warm summer months, the area experiences lively outdoor activities and events, making it an ideal time for you to explore local attractions and enjoy pleasant weather.
Average Temperature Daytime: around 80°F to 85°F - Nighttime: around 60°F to 65°F
Fall (September to November)
Autumn brings beautiful foliage and comfortable temperatures, attracting visitors who want to experience the region's natural beauty and seasonal festivities.
Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 50°F to 55°F
Off-Season Highlights
Winter (December to February)
The colder winter months can be quieter, offering a peaceful retreat for those seeking cozy accommodations and lower rates in this destination.
Average Temperature Daytime: around 40°F to 45°F - Nighttime: around 25°F to 30°F
Spring (March to May)
Early spring is less crowded, providing a good opportunity for you to enjoy fewer tourists while the region begins to bloom and warms up gradually.
Average Temperature Daytime: around 55°F to 65°F - Nighttime: around 35°F to 45°F
Weekly Weather Forecast for Oakland
How to Book Your Oakland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Oakland
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor seating areas perfect for relaxing or dining al fresco amidst the region’s scenic surroundings.
- Take advantage of private patios or decks to unwind and soak up the local atmosphere during your stay.
- Benefit from access to lush, well-maintained gardens or landscaped yards that enhance your outdoor experience.
- Make use of outdoor grilling facilities to prepare meals while enjoying the pleasant climate here.
- Discover spaces equipped with fire pits or fireplaces, ideal for cozy evenings outdoors.
- Explore nearby walking paths or trails that allow you to immerse yourself in the natural beauty of this destination.
- Utilize outdoor pools or hot tubs, if available, for relaxation and leisure after a day exploring the area.
Top Attractions Around Oakland
What attractions are nearby?
While staying here, you'll have the opportunity to explore a variety of nearby activities in the area, from cultural attractions to outdoor adventures, all easily accessible for a memorable visit.
Family Activities
- Children's Museum of Pittsburgh: Engage your family with interactive exhibits and hands-on activities that inspire learning and fun in this beloved local museum.
- Pittsburgh Zoo & PPG Aquarium: Discover a diverse array of animals and marine life, offering an educational adventure for the whole family right here in the region.
- Schneider's Dairy Barn: Enjoy a delightful experience with farm tours and fresh dairy products at this family-friendly farm attraction nearby.
- Oakland's parks and outdoor spaces: Relax and play in scenic parks like Schenley Park, perfect for picnics, outdoor games, and family strolls in this vibrant neighborhood.
Adult Activities
- Explore the Pittsburgh Art Museum: Immerse yourself in a diverse collection of contemporary and traditional artworks within this prominent cultural institution near your vacation rental.
- Stroll through Phipps Conservatory and Botanical Gardens: Enjoy a peaceful walk amid stunning plant displays and innovative horticultural exhibits that showcase the area's natural beauty.
- Experience the thrill at Heinz Field Tours: Take a behind-the-scenes look at this iconic sports stadium, perfect for sports enthusiasts staying nearby.
- Enjoy the nightlife along the North Shore: Discover a variety of restaurants, bars, and entertainment venues that offer vibrant evening experiences close to your lodging.
Other Places to Stay in Oakland, PA
University of Pittsburgh
Petersen Events Center
UPMC Presbyterian Hospital
UPMC Montefiore
University of Pittsburgh Medical Center
The Nationality Rooms
Pittsburgh Playhouse
UPMC Magee-Womens Hospital
Soldiers and Sailors Memorial Hall and Museum
South Oakland
Cathedral of Learning
North Oakland
Oakland Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining and cultural scenes: Take the opportunity to indulge in regional cuisines and visit cultural venues that showcase the authentic spirit of this area.
- Plan your activities around the city's natural beauty: Utilize nearby parks and outdoor spaces to enjoy scenic walks or relaxing afternoons amidst the region's lush landscapes.
- Prioritize convenience with central locations: Choose vacation rentals that place you close to key attractions, making it easier to maximize your time exploring this destination.
- Engage with the local community: Attend neighborhood events or visit local markets to gain a deeper understanding of the region’s unique character during your stay.
Transportation Options
- Public Transit (Port Authority Bus & Light Rail): You can easily navigate the area using the extensive bus and light rail network, offering a convenient way to explore local attractions from your vacation rental.
- Regional Airport (Pittsburgh International Airport): This major airport provides direct flights and quick access for travelers arriving from outside the region, making your arrival seamless.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft operate throughout here, providing flexible transportation around the region at any time.
- Car Rentals: Renting a vehicle offers you the freedom to explore the broader area at your own pace, with numerous rental agencies available near key transit hubs.
Local Customs Options
- Greeting Customs: When visiting here, it is customary to greet with a firm handshake and maintain eye contact to show respect.
- Local Dining Etiquette: Sharing meals at family-style tables is common, reflecting the area's friendly and communal spirit.
- Festive Celebrations: Participating in regional festivals often involves traditional music and dance that showcase the area's vibrant culture.
- Environmental Respect: Recycling and conservation practices are highly valued by locals, emphasizing the region’s commitment to sustainability.
Frequently Asked Questions About Oakland?
1. What are the top vacation rentals in Oakland?
There are a lot of options in Oakland. If you plan on staying in the Oakland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oakland:
- Brand New University-Themed Home ON Pitt Campus, Outdoor Dining, Free Parking
- Luxury King Suite Near Shadyside Hospital
- Industrial Loft 5 min to UPMC Shadyside CMU Pitt, sleeps 4
- 3 Story home w/11 beds! | Close to Pitt & CMU!
- 461 Melwood Suites Unit 102 Studio
- Oakland, Pittsburgh !A Modern and Stylish Private Bedroom with Shared Bathroom
- Gorgeous 4bd near universities Hot tub + Games
- *New* *Unique* 3b/3b sleeps 12 in North Oakland!
- *New* Loft 5 min Shadyside/East Liberty Sleeps 8
- 3E-*New* 5 min to UPMC Shadyside, sleeps 4
2. Which vacation homes in Oakland are best for families?
If you are looking for a family-friendly vacation home in Oakland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oakland:
3. How many Rentbyowner vacation rentals are available in Oakland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 115 in the Oakland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oakland.
4. What is the cancellation policy for vacation rentals in Oakland, Pittsburgh?
Cancellation policies vary by individual listing. You should review the specific property's cancellation terms on its page or contact the owner directly to understand the options available for your stay.
5. How do I ensure my reservation in this destination is secure and confirmed?
Reservations are typically confirmed once you complete the booking process and receive a confirmation email from the listing owner. For added assurance, verify the reservation details with the host before finalizing.
6. Are there any additional fees associated with booking in this area?
Additional fees such as cleaning, service charges, or taxes are often outlined in the listing details. Be sure to review these fees before completing your booking to avoid surprises.
7. Can I modify or cancel my reservation if my plans change in this region?
Modifications or cancellations depend on the property’s particular policies. Contact the owner directly through the platform to discuss any changes to your reservation.
8. What amenities should I expect from vacation rentals here?
Amenities vary by property, so check the listing description for details. Common features may include Wi-Fi, parking, kitchens, and other conveniences to enhance your stay in this destination.
Oakland Top Rated Vacation Rentals
Hotel
9.2(986 Reviews)
1 Bath
- Fireplace/Heating
Pool
Breakfast- Kitchen
£114/Night
7 Nights - £800
Hotel
9.0(709 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
£110/Night
7 Nights - £770
Hotel
8.5(303 Reviews)
8 Baths
488.41 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
£182/Night
7 Nights - £1,270
Hotel
8.4(799 Reviews)
10 Baths
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
£155/Night
7 Nights - £1,082
