Discover Your Perfect Oakland Vacation Homes

Best Vacation Homes in Oakland

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Oakland Luxury Rentals

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Oakland Pet Friendly Vacation Rentals

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10.0 (2 Reviews)
Hotel
Hotel room #7
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Oakland on PetFriendly.io

Why Choose Rent By Owner for your Oakland Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Oakland

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the optimal seasons when the weather in this region is most favorable for outdoor activities and exploring local attractions.

Peak Season Highlights

spring
Spring (March to May)

This is when the area experiences pleasant weather, making it ideal for outdoor activities and exploring local attractions.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

The region offers mild temperatures and colorful scenery, perfect for enjoying the outdoors before winter sets in.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Summer (June to August)

During the hot summer months, you can expect higher temperatures that are suitable for water activities and indoor relaxation.

Average Temperature Daytime: 85°F to 95°F - Nighttime: 65°F to 75°F
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Winter (December to February)

The cold winter season brings cooler temperatures, making it a good time for cozy accommodations and off-season rates.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°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

More Top-Rated Vacation Rentals in Oakland Area

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 dining on a spacious patio or deck, perfect for savoring meals while taking in the scenic surroundings.
  • Take advantage of private or shared waterfront access for relaxing activities by the lake or river nearby.
  • Relax in a shaded backyard area equipped with outdoor seating and lounge chairs for unwinding after your adventures.
  • Make use of a fire pit or outdoor fireplace, ideal for cozy evenings under the stars.
  • Benefit from a well-maintained garden or landscaped yard that adds to the beauty of your stay here.
  • Utilize designated picnic areas set up for outdoor gatherings and family outings within the property grounds.
  • Engage in outdoor sports and recreation, such as horseshoes, lawn games, or during the warmer months, swimming or boating nearby.

Top Attractions Around Oakland

What attractions are nearby?

While staying here, you can enjoy outdoor activities such as fishing and boating at nearby lakes, along with exploring local parks and scenic spots that showcase the natural beauty of the region.

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Family Activities

  • Madill City Park: Enjoy a relaxing day outdoors with your family at this scenic park, ideal for picnics, playgrounds, and walking trails in the area.
  • Hampton Inn Madill Museum: Discover local history and culture through engaging exhibits that provide an educational experience for kids and adults alike.
  • Lake Texoma: Spend quality time fishing, boating, or swimming at this popular lake close to the region, perfect for outdoor family adventures.
  • Chickasaw Pointe Golf Course: Introduce the family to golfing on a well-maintained course, offering fun and relaxation amid beautiful surroundings nearby here.
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Adult Activities

  • Lake Texoma: Enjoy fishing, boating, or relaxing on the shores of this popular destination in the region known for its scenic beauty and outdoor recreation opportunities.
  • Foss State Park: Explore hiking trails, have a picnic, or unwind by the water at this inviting park that offers a peaceful retreat close to here’s vibrant local scene.
  • Chickasaw National Recreation Area: Experience swimming, nature walks, and wildlife viewing at this natural haven, perfect for outdoor enthusiasts visiting the area.
  • Downtown Madill: Discover charming shops, local dining options, and cultural events that showcase the authentic character of this destination in the heart of Oklahoma.

Oakland Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the area's authentic eateries to experience regional flavors that truly capture the spirit of this destination.
  • Plan Outdoor Activities: Make the most of your stay by engaging in outdoor pursuits like fishing or lakeside relaxation, which showcase the natural beauty of the region.
  • Visit Nearby Attractions: Discover local landmarks and scenic spots to enrich your visit without venturing far from your chosen vacation rentals.
  • Connect with the Community: Engage with residents and local events for a genuine experience that highlights the culture and hospitality of this area.

Transportation Options

  • Madill Transit System: This local bus service offers convenient transportation within the area, making it easy to explore your vacation rentals and nearby attractions.
  • Private Car Rentals: Renting a car provides flexibility and freedom to explore the region at your own pace, especially ideal for accessing more remote or rural destinations.
  • Taxi Services: Available throughout here, taxis provide quick and reliable transfers between your vacation rental and key points around town.
  • Shuttle Services: Several shuttle providers operate in this destination, offering cost-effective options for airport transfers and excursions around the region.

Local Customs Options

  • Southern Hospitality: Expect warm welcomes and friendly conversations, reflecting the region's tradition of Southern hospitality that visitors often experience when exploring local communities here.
  • Community Gatherings: Participating in or observing local events such as church socials or town celebrations can give you a glimpse into the area's close-knit social customs.
  • Respect for Nature: Many residents value outdoor traditions like fishing and boating, integral to understanding the region’s connection to its natural surroundings.
  • Music and Folk Traditions: Enjoying local country or folk music sessions reveals the cultural importance of music as a means of storytelling and community bonding here.

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:

2. How many vacation rentals have private pools in Oakland?

There are 1 vacation rentals with private pools near Oakland. Top-rated RBO homes that have access to a swimming pool include:

3. 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:

4. How many Rentbyowner vacation rentals are available in Oakland?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 79 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. 

5. What is the cancellation policy for booking a vacation rental in this area?

Cancellation policies vary by property, so it is important to review the specific listing details or contact the owner directly to understand the terms related to cancellations and potential refunds in this region.

6. Are there any specific house rules or restrictions I should be aware of when staying here?

Each vacation rental has its own set of house rules and restrictions, which are detailed in the listing. Be sure to read these carefully or reach out to the host for clarification before making your reservation.

7. How do I find out about the availability of a particular property in the area?

Availability calendars are typically provided on the listing page. To confirm current availability, you can also contact the property owner directly through the booking platform.

8. What amenities are generally included in the vacation rentals here?

Amenities vary per property, but common features include fully equipped kitchens, Wi-Fi, parking, and laundry facilities. Detailed information about what’s included can be found in each listing description.

9. Can I make special requests or modifications to my booking in this destination?

Special requests can often be communicated directly to the property owner. It is recommended to contact them prior to booking to discuss any specific needs or modifications.