Best Vacation Homes in Oakland
Cabin
10.0(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
725 ft²
Balcony/Terrace
Pet Friendly
Parking
Internet
US $257/Night
7 Nights - US $1,798
House
10.0(7 Reviews)
2 Bedrooms
1 Bath
5 Guests
904.17 ft²
Fireplace/Heating- Balcony/Terrace
View- Pet Friendly
US $198/Night
7 Nights - US $1,386
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pet Friendly
Kitchen- Parking
US $333/Night
7 Nights - US $2,328
Cabin
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Parking
- Internet
Child Friendly
Bedding/Linens
US $254/Night
7 Nights - US $1,780
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1054.86 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $160/Night
7 Nights - US $1,122
Cabin
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
420 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $175/Night
7 Nights - US $1,223
Apartment
9.8(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Kitchen
- Parking
Air Conditioner- Internet
US $182/Night
7 Nights - US $1,276
Apartment
9.4(44 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $159/Night
7 Nights - US $1,112
Oakland Luxury Rentals
House
10.0(11 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $831/Night
7 Nights - US $5,820
House
10.0(66 Reviews)
6 Bedrooms
4 Baths
14 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $717/Night
7 Nights - US $5,021
House
9.6(41 Reviews)
5 Bedrooms
3 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $691/Night
7 Nights - US $4,838
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $590/Night
7 Nights - US $4,133
House
9.0(2 Reviews)
5 Bedrooms
4 Baths
14 Guests
Hot Tub- Fireplace/Heating
- Pet Friendly
- Kitchen
US $589/Night
7 Nights - US $4,121
House
10.0(23 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $580/Night
7 Nights - US $4,063
Cabin
10.0(4 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $569/Night
7 Nights - US $3,986
House
9.2(22 Reviews)
4 Bedrooms
3 Baths
8 Guests
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $542/Night
7 Nights - US $3,794
Oakland Pet Friendly Vacation Rentals
Apartment
9.4(41 Reviews)
1 Bedroom
1 Bath
4 Guests
350 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $117/Night
7 Nights - US $822
House
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
419.79 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $169/Night
7 Nights - US $1,185
Cabin
8.8(16 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $317/Night
7 Nights - US $2,217
Cabin
10.0(47 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $309/Night
7 Nights - US $2,161
Apartment
9.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
355.21 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $130/Night
7 Nights - US $908
House
10.0(164 Reviews)
3 Bedrooms
2 Baths
6 Guests
2550 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $217/Night
7 Nights - US $1,516
Cottage
10.0(77 Reviews)
2 Bedrooms
1 Bath
4 Guests
570 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $135/Night
7 Nights - US $948
House
10.0(40 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $172/Night
7 Nights - US $1,207
Oakland Large Vacation Homes
Cabin
10.0(290 Reviews)
5 Bedrooms
4 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $455/Night
7 Nights - US $3,185
Apartment
7.4(90 Reviews)
28 Bedrooms
28 Baths
75 Guests
602.78 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
US $84/Night
7 Nights - US $588
House
10.0(41 Reviews)
3 Bedrooms
2 Baths
11 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $399/Night
7 Nights - US $2,795
House
5 Bedrooms
5 Baths
10 Guests
5747.93 ft²
Oceanfront
Spa- Fireplace/Heating
- Pool
US $485/Night
7 Nights - US $3,393
House
10.0(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $304/Night
7 Nights - US $2,125
House
10.0(8 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $333/Night
7 Nights - US $2,328
House
10.0(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $338/Night
7 Nights - US $2,363
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $226/Night
7 Nights - US $1,584
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.
Best Times to Visit Oakland
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can greatly enhance your experience, so consider planning your trip during the optimal seasons when the area's natural beauty and local events are at their best.
Peak Season Highlights
Spring (March to May)
During this time, the region experiences mild temperatures and blooming landscapes, making it an ideal season for outdoor activities and exploring local scenery.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Fall offers comfortable weather with vibrant foliage, perfect for enjoying scenic drives and outdoor adventures in the area.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Summer (June to August)
While summer brings warmer weather, it is also the busiest time for visitors seeking outdoor recreation and local events.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
Winter (December to February)
This period sees cooler temperatures and less crowding, offering a quieter experience for those looking to enjoy the region's serene winter atmosphere.
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
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 grilling stations to cook up meals while appreciating the scenic views of the region.
- Take advantage of spacious patios or decks perfect for relaxing and soaking in the fresh air.
- Benefit from access to well-maintained gardens that offer a peaceful outdoor setting.
- Experience the convenience of parking areas designed for easy outdoor access to your rental.
- Stroll through nearby walking trails or nature paths that showcase the natural beauty of the area.
- Make use of outdoor seating areas ideal for morning coffee or evening gatherings.
- Leverage outdoor recreation facilities, such as available sports courts or open green spaces for activities.
Top Attractions Around Oakland
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities, historical sites, and local attractions that showcase the best of what Oakland has to offer for a memorable stay.
Family Activities
- Oakland Wildlife Center: Discover an engaging experience here where you can observe local animals and learn about regional conservation efforts.
- Black Patch Heritage Center: Dive into the area's rich history through interactive exhibits perfect for educating and entertaining young visitors.
- Horseback Riding Tours: Explore scenic trails on horseback, offering families a memorable way to enjoy the natural beauty of this region.
- Lakefront Activities: Spend quality time outdoors with swimming, fishing, or picnicking along the tranquil waters suitable for all ages.
Adult Activities
- Visit the Kentucky Lake State Park: Engage in outdoor activities like boating, fishing, and hiking at the beautiful Kentucky Lake, a perfect spot to enjoy nature here.
- Explore local dining options: Savor regional cuisine at charming restaurants, offering a taste of the area's culinary traditions just minutes from your vacation rental.
- Experience bird watching and wildlife viewing: Take advantage of the area's natural habitats to observe diverse bird species and wildlife in their native environment.
- Attend seasonal festivals and events: Participate in community celebrations and festivals that showcase the region's vibrant culture and local artisans.
Other Places to Stay in Oakland, KY
Martinsville
Oakland Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead: Book your vacation rentals early to secure the best spots and enjoy a stress-free stay in the area.
- Explore Local Cuisine: Take advantage of nearby eateries and food markets to experience authentic regional flavors during your visit.
- Discover Hidden Gems: Ask your hosts or locals for recommendations on lesser-known attractions that showcase the true character of this destination.
- Get Outside: Make the most of the region's natural beauty by exploring outdoor activities like hiking, biking, or relaxing by the water near your rental.
Transportation Options
- Local Bus Services: The regional bus network offers convenient transportation options, allowing you to explore here and nearby areas without hassle.
- Taxi and Ride-Sharing Services: Reliable taxi companies and ride-sharing apps are available for quick, flexible travel throughout this destination and its surroundings.
- Car Rentals: Renting a car provides the freedom to explore at your own pace, ideal for visiting attractions across the region comfortably.
- Airport Shuttles: Regular shuttle services connect the area to the nearest airports, making your arrival and departure smooth and stress-free.
Local Customs Options
- Southern Hospitality: You’ll notice the warm and welcoming attitude of locals, a hallmark of the area's friendly community spirit.
- Indulge in authentic regional flavors that reflect this destination’s rich culinary traditions during your stay.
- Local Festivals and Events: Participate in seasonal celebrations and gatherings that showcase the region’s vibrant cultural heritage.
- Historical Preservation: Respect for local history is evident in the well-maintained landmarks and museums that tell the story of this destination.
Oakland Vacation Rental Frequently Asked Questions
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:
- The Kentucky Kajun! A Beautiful 5 Bed/4 Bath Cabin On Barren River Lake.
- Cozy house close to Mammoth Cave and Bowling Green
- Cozy cabin getaway - Country setting - pond with walking trail
- Beautiful cottage with AMAZING view of Barren River Lake!
- Bluegrass Vineyard B&B, nestled next to the vineyard and winery
- Peace and quiet of country living within minutes of city amenities.
- Lake front, Romantic Honeymoon Getaway.
- Simply Sailing - A Cottage In The Trees
- Firestone's @ BRL 14mi-Mammoth Cave. Fire pit!
- Nonna’s Place - Pole Barn Dwelling Near Mammoth Cave
2. How many vacation rentals have private pools in Oakland?
There are 40 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 2026 is over 331 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 vacation rentals in this area?
The cancellation policy varies by property. It is important to review the specific listing details and contact the property owner directly to understand the conditions, deadlines, and any applicable fees before finalizing your booking.
6. How do I verify the amenities included in my rental in this destination?
Amenities are detailed within each property listing. For clarifications or to confirm specific features, reach out to the property owner, ensuring all your needs are accommodated during your stay here.
7. Are there any additional fees or charges I should be aware of when booking a vacation rental?
Additional fees such as cleaning, service charges, or taxes are typically listed on the property page. To avoid surprises, review the total cost carefully and contact the owner if you have questions about extra charges.
8. What are the check-in and check-out procedures for rentals in this region?
Check-in and check-out instructions are provided in the rental listing. For any special requests or clarification, communicate directly with the property owner to ensure a smooth arrival and departure process.
9. Is there a secure way to communicate with hosts during my stay in this destination?
Yes, the platform offers a secure messaging system that allows you to contact property owners directly. Use this feature to ask questions or make arrangements before and during your visit for a seamless experience.
Oakland Top Rated Vacation Rentals
Other
10.0(119 Reviews)
4 Bedrooms
1 Bath
12 Guests
1400 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $243/Night
7 Nights - US $1,701
House
10.0(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
1560 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $263/Night
7 Nights - US $1,840
Other
10.0(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
2500 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $195/Night
7 Nights - US $1,368
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $179/Night
7 Nights - US $1,250
House
9.8(26 Reviews)
5 Bedrooms
4 Baths
10 Guests
5750 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $469/Night
7 Nights - US $3,281
Hotel
9.6(837 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $237/Night
7 Nights - US $1,659
Hotel
9.5(372 Reviews)
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $142/Night
7 Nights - US $994
US $135/Night
7 Nights - US $945
