1027+ Private Villas and Holiday Rentals in Oakland |
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Oakland Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Oakland

Discover more than 1027 vacation rentals available in Oakland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Oakland.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oakland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Oakland. On average, places to stay near Oakland offer 790.17 ft², with nightly prices averaging GB £309.

With Casai, finding and comparing holiday rentals in Oakland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Oakland

Type Count
Holiday Apartments 756
Vacation Homes 107
Villas 2
Cottages 1

Use these Quick Filters to Find a Holiday Rental in Oakland

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Oakland.

Weather in Oakland, IL

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

Other Places to Stay in Oakland, IL


Mercy Family Health Center 1,053 Properties
41st Street Beach 896 Properties
Cleaverville 47 Properties

Frequently Asked Questions About Oakland?

What are the top holiday rentals in Oakland?

With numerous options available in Oakland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oakland:

Which holiday homes in Oakland are best for families?

If you're searching for a family-friendly holiday home in Oakland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Oakland:

How many Casai.uk holiday rentals are available in Oakland?

As of 2025, Casai boasts over 1027 properties listed in the Oakland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oakland.

Nearby Neighborhood (2) 
Neighborhood Property Count
Bronzeville Vacation Rentals in Chicago, Illinois 95
North Kenwood Vacation Rentals in Chicago, Illinois 660

People Also Ask

There are 1027 Oakland, IL Holiday Rentals

Recently Booked Holiday Rentals in Oakland