101+ Vacation Rentals & Holiday Homes in Oakland |
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Oakland Accommodations - Hotels & Rentals

About Oakland Vacation Rentals

Discover More than 101 Incredible Getaway Rentals Available in Oakland. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Oakland.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Oakland, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Oakland. The Average Size of Places to Stay Near Oakland is 835.37 ft², with Prices Averaging US $265 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Oakland. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Oakland

Type Count
Holiday Apartments 65
Vacation Homes 27

Use these Quick Filters to Find a Vacation Rental in Oakland

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Oakland with Online Reservations.

Weather in Oakland, PA

View the weather forecast for Oakland before booking your Oakland 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

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Petersen Events Center 2,012 Properties
UPMC Presbyterian Hospital 2,010 Properties
UPMC Montefiore 2,010 Properties
University of Pittsburgh Medical Center 2,003 Properties
University of Pittsburgh 1,991 Properties
The Nationality Rooms 1,991 Properties
Pittsburgh Playhouse 1,966 Properties
UPMC Magee-Womens Hospital 1,958 Properties
Soldiers and Sailors Memorial Hall and Museum 1,891 Properties
South Oakland 1,851 Properties
Cathedral of Learning 1,837 Properties
North Oakland 56 Properties

Frequently Asked Questions About Oakland?

What are the top hotels, lake houses & vacation rentals in Oakland?

We provide an array of great vacation destinations in Oakland. If you are looking to stay in or around the Oakland area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Oakland:

Which hotel, lake house, or vacation rental in Oakland is best for families?

Searching for a family-friendly getaway in Oakland? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Oakland?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 101 in the Oakland area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Oakland.

Nearby Neighborhood (4) 
Neighborhood Property Count
North Oakland Vacation Rentals in Pittsburgh, Pennsylvania 56
South Oakland Vacation Rentals in Pittsburgh, Pennsylvania 1851
Squirrel Hill South Vacation Rentals in Pittsburgh, Pennsylvania 784
Bluff Vacation Rentals in Pittsburgh, Pennsylvania 1827

People Also Ask

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