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Discover Your Perfect Oldsmar Rentals by Owner

Oldsmar Rentals by Owner

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9.3 (21 Reviews)
House
2 Bedroom , 2 Bath , Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
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10.0 (42 Reviews)
House
Beautiful home in Oldsmar
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Oldsmar Area

Why Choose Rent By Owner for your Oldsmar vacation rental?

What makes our Rentals by Owner 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.

Popular Areas for Oldsmar Rentals by Owner

Where are the best neighborhoods to stay in Oldsmar?

When exploring places to stay in Oldsmar, Florida, understanding the neighborhoods can help you find the perfect rental by owner. The area offers a variety of communities that cater to different preferences, from quiet residential streets to vibrant, family-friendly neighborhoods. Whether you're seeking a peaceful retreat or an active environment close to local amenities, each neighborhood provides unique advantages. With Rent By Owner, you'll have access to trustworthy vacation rentals in popular parts of Oldsmar, ensuring a seamless booking experience that matches your travel needs in this welcoming Floridian city.

East Lake Woodlands

In this neighborhood, you'll find a tranquil setting perfect for relaxing getaways in the region. The area offers a serene environment, ideal for travelers seeking peaceful surroundings close to outdoor recreational opportunities.

View 217+ Rentals in East Lake Woodlands

Elw Woods Landing

Here, you are surrounded by lush greenery and natural beauty that enhance your stay in the destination. This community provides a quiet, inviting atmosphere for those looking to unwind in the comfort of a cozy rental close to nature.

View 192+ Rentals in Elw Woods Landing

Quail Forest

This neighborhood offers easy access to local amenities and scenic views, making it a convenient choice for visitors exploring the region. It’s an excellent spot for enjoying a relaxed vacation while staying within reach of everything you need.

View 212+ Rentals in Quail Forest

Turtle Creek

In Turtle Creek, you’ll experience a charming community with picturesque surroundings that enhance your stay in the area. It’s an ideal setting for those seeking comfortable, private accommodations in a peaceful neighborhood.

View 139+ Rentals in Turtle Creek

Best Times to Visit Oldsmar

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience in Oldsmar, Florida, ensuring you enjoy pleasant weather and avoid peak crowds while exploring this inviting destination.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area experiences warm temperatures and is ideal for outdoor activities. Booking your rental here allows you to enjoy pleasant weather before the summer rush.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
winter
Winter (December to February)

Winter offers milder, comfortable weather perfect for escaping colder climates. This is a popular time for visitors seeking a cozy getaway in this destination.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Summer (June to August)

Summer is the low season here due to higher humidity and afternoon rain showers. It’s an ideal time if you prefer fewer crowds while exploring local rentals.

Average Temperature Daytime: 85°F to 95°F - Nighttime: 70°F to 75°F
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Fall (September to November)

During fall, the region sees a slight drop in tourist numbers. The weather remains warm, making it a peaceful period to enjoy your vacation rental without the peak crowd.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F

Weekly Weather Forecast for Oldsmar

How to Book Your Oldsmar vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Oldsmar

More Top-Rated Rentals by Owner in Oldsmar Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 swimming pools for relaxing in the warm Florida sun.
  • Benefit from private patios or decks ideal for outdoor dining and lounging.
  • Take advantage of lush gardens or landscaped yards to enhance your outdoor experience.
  • Make use of barbecue grills available for cookouts with family and friends.
  • Relax by the waterfront if your rental offers access to nearby lakes or canals.
  • Utilize shaded pergolas or cabanas for comfortable outdoor sitting areas.
  • Access outdoor recreational facilities such as tennis courts or mini golf courses often found in this region.

Top Attractions Around Oldsmar

What attractions are nearby?

Located nearby, you can enjoy a variety of outdoor activities and local attractions that showcase the best of this destination's natural beauty and community spirit, making it an ideal place to explore during your stay.

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Family Activities

  • Suncoast Trail: Explore this scenic trail that’s perfect for family-friendly biking and walking adventures within the region.
  • Oldsmar Nature Park: Discover outdoor fun with nature walks, picnicking, and wildlife viewing in this peaceful park setting close to your rental.
  • Pinellas Trail: Enjoy a day of cycling or rollerblading along this popular multi-use trail that runs through the area, offering stunning scenery and family-friendly activity options.
  • Mobbly Bayou Wilderness Preserve: Experience the natural beauty of here with kayaking, bird watching, and gentle hikes suitable for children and families alike.
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Adult Activities

  • Oldsmar Community Park: Enjoy a relaxing day outdoors by exploring scenic walking trails and engaging in outdoor activities amidst the tranquil surroundings of this popular local park.
  • Westchase Golf Course: Tee off at this renowned golf course, offering pristine fairways and challenging holes that cater to golf enthusiasts seeking leisure and recreation.
  • Pinellas Trail: Cycle or walk along this extensive trail network that passes through the area, providing an excellent way to explore the region’s natural beauty on foot or bike.
  • Oldsmar Historical Society Museum: Dive into the area's rich history by visiting this museum, which features exhibits and collections that highlight the region’s cultural heritage.

Other Places to Stay in Oldsmar, FL

Z - A Specialty Spa
Explore 268 Properties
East Lake Woodlands
Explore 217 Properties
Quail Forest
Explore 212 Properties
Elw Woods Landing
Explore 192 Properties
Oldsmar Historical Society Museum
Explore 182 Properties
Oldsmar Flea Market
Explore 173 Properties
Advanced Primary Care
Explore 164 Properties
Turtle Creek
Explore 139 Properties
More Places to Stay Near Oldsmar

Oldsmar Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature: Take advantage of the region's outdoor spaces by discovering nearby parks and nature trails to enjoy peaceful moments and scenic views during your stay.
  • Experience Regional Flavors: Savor the area's unique cuisine by visiting local eateries and markets, adding a delicious touch to your visit without leaving this destination's vicinity.
  • Utilize Nearby Amenities: Make the most of the area’s amenities including shopping centers and entertainment options close to your rental to enhance your overall experience.
  • Plan Convenient Transportation: Arrange reliable transportation methods within this region to easily explore all that the area has to offer, maximizing your time here.

Transportation Options

  • Oldsmar Trolley Service: This local trolley system provides convenient transportation around the area, making it easy to explore nearby attractions and amenities without a car.
  • Rental Cars: Numerous rental car agencies are available near here, offering flexible options for exploring the broader Tampa Bay region at your own pace.
  • Tampa International Airport Shuttle: Several shuttle services operate between the airport and the area, providing a reliable way to start or end your stay comfortably.
  • Public Transit Buses: The regional bus system connects this destination with surrounding communities, making commuting straightforward if you prefer not to drive.

Local Customs Options

  • Southern Hospitality: You will notice that warm, friendly greetings and courteous behavior are customary when engaging with locals here in the region.
  • Respect for Nature: It’s common in this area to honor outdoor spaces and wildlife, reflecting a strong appreciation for preserving the natural environment.
  • Local Food Traditions: Embracing regional flavors, many enjoy participating in community events that celebrate fresh seafood and traditional Southern cuisine.
  • Community Celebrations: Attending local festivals and events offers insight into the area's cultural values and provides a chance to connect with residents authentically.

Frequently Asked Questions About Oldsmar Rentals by Owner

1. What are the top vacation rentals in Oldsmar?

There are a lot of options in Oldsmar. If you plan on staying in the Oldsmar area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oldsmar:

2. How many Rentbyowner vacation rentals are available in Oldsmar?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 60 in the Oldsmar 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 Oldsmar. 

3. What is the cancellation policy for a rental by owner in Oldsmar, Florida?

The cancellation policy varies depending on the individual listing. You should review the specific Terms & Conditions on the property’s page or contact the owner directly for detailed information regarding cancellations and potential refunds.

4. How do I secure my booking at a rental by owner in this area?

Bookings are typically secured through the platform’s reservation process. To ensure your reservation, follow the steps outlined on the listing, which may include paying a deposit or full amount, and confirm your booking details with the owner if needed.

5. Are there any additional fees I should be aware of when booking a rental in the region?

Additional fees such as cleaning fees, service charges, or security deposits are usually specified in the listing details. Review these carefully before finalizing your reservation to understand the total cost of your stay.

6. What amenities are generally included in rentals by owner here?

Amenities can vary widely, so it’s best to check each listing for specific features such as Wi-Fi, kitchen facilities, parking, or outdoor spaces. Owners typically detail what’s included to help you plan your stay accordingly.

7. How can I communicate with the property owner before booking?

Most listings provide a direct messaging option on the platform. Use this feature to ask questions about the property, clarify policies, or request additional information to ensure the rental meets your needs.

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9.8 (9 Reviews)
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