Highland Oaks Rentals by Owner

Why Choose Rent By Owner for your Highland Oaks 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.

Best Times to Visit Highland Oaks

When should you plan your Rentals by Owner stay?

Choosing the optimal time to visit this destination ensures you can enjoy its relaxed atmosphere and abundant sunshine, making your rental by owner experience here both enjoyable and memorable.

Peak Season Highlights

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Spring (March to May)

During spring, you’ll experience warm temperatures and vibrant local events that make this time ideal for enjoying the area's outdoor spaces and activities.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
winter
Winter (December to February)

Winter offers mild weather perfect for escaping colder climates elsewhere, allowing you to enjoy the region’s attractions comfortably with fewer crowds.

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

Off-Season Highlights

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Summer (June to August)

Summer can be hot and humid, but it’s a great time to find deals on rentals by owner as the area sees a dip in overall visitor numbers.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 75°F to 80°F
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Fall (September to November)

Autumn brings cooler weather and less crowded attractions, providing an excellent opportunity for budget-conscious travelers seeking tranquility and value.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F

Weekly Weather Forecast for Highland Oaks

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.

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 that provide a refreshing retreat during your stay.
  • Relax in lush, landscaped gardens or scenic outdoor seating areas perfect for unwinding.
  • Take advantage of private patios or verandas to enjoy the pleasant Florida weather.
  • Utilize barbecue grills available for hosting outdoor cookouts with family and friends.
  • Make the most of well-maintained tennis courts or other sports facilities nearby.
  • Benefit from shaded picnic areas ideal for outdoor dining and social gatherings.
  • Explore shared walking paths or jogging tracks nestled within the community’s outdoor space.
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Family Activities

  • St. Pete Pier Park: Enjoy a family day out exploring the scenic views, playgrounds, and open spaces at this popular waterfront destination.
  • The Dinosaur World Museum: Discover fascinating fossils and interactive exhibits that make learning about prehistoric creatures both fun and educational for kids.
  • Sunken Gardens: Stroll through lush, tropical gardens filled with exotic plants and peaceful walkways, providing an ideal outing for families seeking nature experiences.
  • South Straub Park: Relax and have a picnic in this beautifully maintained park featuring green spaces, shaded areas, and access to nearby beaches for added fun.
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Adult Activities

  • Golfing at Mangrove Bay Golf Course: Enjoy a relaxing day on the links, just a short drive from here, where you can perfect your swing amidst scenic surroundings.
  • Sailing and boating along Tampa Bay: Explore the region’s beautiful waterways with a boat rental or guided tour to experience the area's aquatic charm firsthand.
  • Visiting local art galleries and studios: Discover the vibrant arts scene nearby by browsing unique works created by talented regional artists.
  • Enjoying waterfront dining experiences: Relish fresh seafood and panoramic views at nearby restaurants that showcase the region’s culinary delights.

Highland Oaks Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local amenities and attractions: Take the time to discover nearby shops, restaurants, and parks to enhance your stay in this welcoming area.
  • Communicate with your host: Maintain clear and friendly communication with your rental owner to ensure a smooth and enjoyable experience during your visit.
  • Plan your transportation: Consider your options for getting around, whether by car or public transit, to make the most of your time here and access key points of interest easily.
  • Respect the property and neighborhood: Follow house rules and be mindful of the quiet surroundings to enjoy a harmonious stay in this inviting destination.

Transportation Options

  • St. Petersburg-Clearwater International Airport: Located conveniently nearby, it offers domestic flights to and from major hubs, making travel easy for visitors staying in Highland Oaks.
  • Local Bus Services: The regional transit system provides accessible bus routes throughout the area, providing an economical transportation option for exploring here.
  • Rideshare Services: Companies like Uber and Lyft operate extensively in the region, offering flexible and convenient door-to-door transportation for guests at local rentals.
  • Car Rentals: Numerous rental agencies are available within the area, giving you the freedom to explore the region at your own pace during your stay here.

Local Customs Options

  • Respect for Southern Hospitality: Visitors appreciate the friendly and welcoming attitude that is a hallmark of the local culture here in Highland Oaks, often reflected in polite greetings and neighborly interactions.
  • Embracing Casual Coastal Living: The area values a relaxed approach to dress and behavior, embodying the laid-back Florida lifestyle that residents and travelers alike enjoy during their stay.
  • Celebration of Local Arts and Crafts: Supporting handcrafted goods and artistic expressions is customary, with community events emphasizing regional creativity that visitors may wish to partake in.
  • Environmental Respect and Conservation: Here, environmentally conscious practices are encouraged, aligning with the region's dedication to preserving its natural beauty for future generations.

Frequently Asked Questions About Highland Oaks Rentals by Owner

2. How many Rentbyowner vacation rentals are available in Highland Oaks?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1503 in the Highland Oaks 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 Highland Oaks. 

3. What is the cancellation policy for a rental by owner in Highland Oaks?

The cancellation policy varies depending on the individual listing. Please review the specific terms detailed on the property listing or contact the owner directly to understand the refund eligibility and timeframes.

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

Booking is typically secured through the Rent By Owner platform with a reservation deposit or full payment, as specified by the host. Be sure to read the listing’s reservation and payment policies carefully before confirming your stay.

5. Are there any additional fees when booking directly with a rental owner here?

Additional fees such as cleaning charges, service fees, or local taxes may apply and will be outlined in the listing details. Confirm these costs during the booking process to avoid surprises.

6. What amenities can I expect from rentals by owner in this destination?

Amenities vary by property but often include essentials like Wi-Fi, parking, and fully equipped kitchens. Check each listing for specific features and amenities available during your stay.

7. How can I contact the property owner if I have questions before booking?

You can reach out directly to the owner through the messaging feature on the Rent By Owner platform. This allows you to ask specific questions about the property, policies, or availability before finalizing your reservation.

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