Best Vacation Homes in Oakland
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $186/Night
For 7 Nights US $1,305
796.53 ft²
2 Guests
1 Bedroom
1 Bathroom
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $190/Night
For 7 Nights US $1,330
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $338/Night
For 7 Nights US $2,366
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $372/Night
For 7 Nights US $2,603
796.53 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $214/Night
For 7 Nights US $1,498
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $212/Night
For 7 Nights US $1,485
1568 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $306/Night
For 7 Nights US $2,140
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Kitchen
- Parking
- Air Conditioner
US $621/Night
For 7 Nights US $4,344
Oakland Luxury Rentals
12 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $2,778/Night
For 7 Nights US $19,443
2830.91 ft²
16 Guests
6 Bedrooms
4 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- Pool
US $2,075/Night
For 7 Nights US $14,528
10 Guests
4 Bedrooms
4 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $1,863/Night
For 7 Nights US $13,038
34 Guests
9 Bedrooms
9 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Kitchen
- Parking
US $1,781/Night
For 7 Nights US $12,466
4300 ft²
21 Guests
7 Bedrooms
1 Bathroom
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,764/Night
For 7 Nights US $12,348
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,629/Night
For 7 Nights US $11,405
18 Guests
9 Bedrooms
7 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,575/Night
For 7 Nights US $11,028
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Kitchen
US $1,310/Night
For 7 Nights US $9,173
Oakland Pet Friendly Vacation Rentals
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $174/Night
For 7 Nights US $1,215
753.47 ft²
3 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $204/Night
For 7 Nights US $1,426
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $548/Night
For 7 Nights US $3,833
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $152/Night
For 7 Nights US $1,066
2002.09 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $359/Night
For 7 Nights US $2,513
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $75/Night
For 7 Nights US $523
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $164/Night
For 7 Nights US $1,147
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $159/Night
For 7 Nights US $1,113
Oakland Large Vacation Homes
550 ft²
100 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
US $177/Night
For 7 Nights US $1,237
2346.53 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Parking
US $261/Night
For 7 Nights US $1,827
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $587/Night
For 7 Nights US $4,110
3724.31 ft²
16 Guests
5 Bedrooms
4 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
US $738/Night
For 7 Nights US $5,163
2300 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $441/Night
For 7 Nights US $3,089
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $409/Night
For 7 Nights US $2,865
2100 ft²
10 Guests
5 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $249/Night
For 7 Nights US $1,744
2100 ft²
14 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $316/Night
For 7 Nights US $2,211
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?
Choosing the ideal time to visit here can enhance your experience, as the region offers different attractions and climates throughout the year, making it important to consider seasonal factors when planning your stay in Oakland, Iowa.
Peak Season Highlights
Spring (March to May)
During this time, the area experiences mild temperatures and blossoming landscapes, making it an ideal season for enjoying outdoor activities and exploring the region’s natural beauty.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Summer (June to August)
This peak season offers warm weather and longer daylight hours, perfect for making the most of your stay and engaging in various outdoor pursuits in this destination.
Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
Off-Season Highlights
Fall (September to November)
As temperatures begin to cool, the region becomes quieter. This is a great time to enjoy the changing foliage and experience a more relaxed atmosphere here.
Average Temperature Daytime: 55-65°F - Nighttime: 35-45°F
Winter (December to February)
The colder months see fewer visitors, offering a peaceful retreat with the chance to embrace cozy indoor amenities and the winter landscape.
Average Temperature Daytime: 30-40°F - Nighttime: 15-25°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 a private outdoor patio or deck perfect for relaxing and outdoor dining.
- Take advantage of spacious yard areas ideal for barbecues and family gatherings.
- Benefit from access to scenic walking trails and nature spots nearby.
- Make use of outdoor fire pits for cozy evenings under the stars.
- Relax in well-maintained gardens that add charm and tranquility to your stay.
- Utilize available outdoor recreational equipment such as bikes or kayaks, if provided.
- Experience the convenience of ample parking space with easy access to local attractions.
Top Attractions Around Oakland
What attractions are nearby?
Discover a variety of outdoor activities and local attractions just moments from your accommodations in this welcoming destination, offering you the perfect opportunity to explore the region’s natural beauty and cultural sites during your stay.
Family Activities
- Oakland City Park: Spend quality time outdoors with your family at this scenic park, offering playgrounds, picnic areas, and beautiful walking trails perfect for a relaxing day in the region.
- Prairie Wind Community Center: Participate in engaging indoor activities and community events designed to keep everyone entertained and active during your visit here.
- The Oakland Public Library: Discover local history and enjoy storytimes or family-friendly programs that foster learning and fun for visitors of all ages.
- Local Heritage Tours: Explore the area's rich history through guided or self-guided tours that showcase its unique heritage and small-town charm.
Adult Activities
- Explore the Oakland County Historical Museum: Discover local history and artifacts that showcase this area's rich heritage, providing an engaging experience during your stay.
- Enjoy outdoor recreation at Lake Ahquabi State Park: Take advantage of the scenic trails, fishing, and picnicking options right here in the region for a relaxing day outdoors.
- Visit the nearby golf courses: Tee off at well-maintained golf courses in the area, perfect for a leisurely round surrounded by picturesque landscapes.
- Attend local events and festivals: Immerse yourself in community celebrations and seasonal festivals that highlight the vibrant culture of this destination.
Oakland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take advantage of the region's dining options to enjoy authentic flavors and make your stay more memorable.
- Plan Outdoor Activities: Make the most of nearby parks and outdoor spaces for leisurely walks or recreational activities that highlight the area's natural beauty.
- Visit Seasonal Events: Check out local festivals or events happening during your visit to immerse yourself in the area's vibrant community life.
- Choose a Central Location: Opt for a vacation rental in the heart of the area to easily access popular attractions and experience the local ambiance.
Transportation Options
- Local Bus Services: You can rely on local bus routes that connect the area with surrounding towns and cities, making your travel within Oakland straightforward and affordable.
- Private Shuttle Services: Private shuttles offer convenient transportation options for travelers looking to easily reach nearby destinations from this region.
- Rental Cars: Renting a car here provides you with the flexibility to explore at your own pace and access more remote attractions around Oakland and beyond.
- Taxis and Rideshare Services: Taxis and rideshare options are readily available for quick, direct trips within the area, ideal for short-distance travels during your stay.
Local Customs Options
- Local Festivals and Community Events: Participating in neighborhood festivals offers a genuine glimpse into the area's warm hospitality and vibrant traditions.
- Respect for Agricultural Heritage: Embracing farm-to-table practices and rural customs reflects the region’s deep-rooted agricultural history.
- Traditional Dining Etiquette: Being courteous during local meals, such as sharing dishes and engaging in friendly conversation, enhances your connection with residents.
- Celebration of Local History: Visiting community landmarks and museums helps you appreciate the area's unique story and cultural identity.
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:
- Early 1900's - Big Blue of Little Italy - Within minutes of TD Ameritrade - CWS
- Haven in Midtown's Historic Morton Meadows
- Beautifully restored home in historic Blackstone District
- ZOO Old Market CHI Charles Schwab Field Cozy Downtown House
- Classic Bungalow Modern w/a Splash of Glam ZOO AKSARBEN UNMC UNO Bergan Mercy
- Steps from Downtown Omaha! Rooftop firepit & luxury accommodations
- Luxury 3BR/4BA Townhome Rooftop Deck, Porch 5 Min to Downtown
- Cozy and comfortable Home in the heart of Omaha
- 1890's Craftsman Home 5BR 4BA, Sleeps 16+ w 6 TVs.
- Omaha’s #1 Unique Tiny House Experience
2. How many vacation rentals have private pools in Oakland?
There are 42 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 1212 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 vacation rentals in Oakland, Iowa?
The cancellation policy varies by property. To ensure a smooth experience, please review the specific policy listed on the rental's page or contact the property owner directly for detailed information.
6. How do I request additional amenities or special accommodations during my stay?
If you need extra amenities or special arrangements, reach out to the property owner before booking to confirm availability and discuss your needs. This helps ensure your comfort during your visit to this region.
7. Are there any specific check-in and check-out procedures in Oakland vacation rentals?
Check-in and check-out procedures are typically outlined in the rental listing. For a hassle-free stay, review these details beforehand or contact the host to clarify any questions about your arrival or departure.
8. Is parking available with vacation rentals in the area?
Many properties in this destination offer parking options. To avoid any inconvenience, verify the parking details in the rental description or ask the property owner directly when booking.
9. What should I do if I encounter issues during my stay at a vacation rental?
In case of concerns or issues, contact the property owner or local support immediately. Details for assistance are usually provided in the rental listing, ensuring prompt help during your time here.
Oakland Top Rated Vacation Rentals
1800 ft²
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $448/Night
For 7 Nights US $3,136
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $347/Night
For 7 Nights US $2,430
2836 ft²
16 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,302/Night
For 7 Nights US $9,117
US $174/Night
For 7 Nights US $1,218
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $109/Night
For 7 Nights US $761
1 Bathroom
Family Friendly
Hotel
- Pool
- Kitchen
- Parking
US $95/Night
For 7 Nights US $663
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $124/Night
For 7 Nights US $870
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $112/Night
For 7 Nights US $784
