- USA
- Florida
- St. Petersburg - Clearwater
- Highland Oaks
- Rentals by Owner
Discover Your Ideal Highland Oaks Rental by Owner in St. Petersburg for a Comfortable Stay
Discover Your Perfect Highland Oaks Rentals by Owner
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Rentals by Owner
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Sustainable Travel
Highland Oaks Rentals by Owner
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- TV
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- TV
- Security/Safety
- Air Conditioner
- Parking
- View
- Air Conditioner
- TV
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- TV
- Security/Safety
- Parking
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
Why Choose Rent By Owner for your Highland Oaks vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Highland Oaks Rentals by Owner
Where are the best neighborhoods to stay in Highland Oaks?
When choosing a neighborhood to stay in Highland Oaks, St. Petersburg, Florida, you’ll find a welcoming community that offers convenient access to local amenities and picturesque surroundings. This area provides a peaceful atmosphere for travelers seeking comfort and relaxation, making it an ideal spot for your rental by owner. Whether you're exploring nearby parks or enjoying the laid-back coastal vibe, Highland Oaks presents a reliable and comfortable base for your visit to St. Petersburg. Booking through Rent By Owner ensures a seamless experience, connecting you with trustworthy vacation rentals designed to meet your needs.
Lake Maggiore Shore
Located just moments from the serene waters of Lake Maggiore, this area offers a peaceful retreat with easy access to nature and local amenities. Your stay here provides a perfect balance of tranquility and convenience in the heart of St. Petersburg.
View 1504+ Rentals in Lake Maggiore ShoreBest 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
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.
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.
Off-Season Highlights
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.
Fall (September to November)
Autumn brings cooler weather and less crowded attractions, providing an excellent opportunity for budget-conscious travelers seeking tranquility and value.
Weekly Weather Forecast for Highland Oaks
How to Book Your Highland Oaks vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Highland Oaks
Common Rentals by Owner Amenities
What amenities can you expect?
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.
Top Attractions Around Highland Oaks
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of outdoor activities and scenic parks just moments from your rental, offering the perfect opportunity to explore and unwind during your stay.

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.
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
1. What are the top vacation rentals in Highland Oaks?
There are a lot of options in Highland Oaks. If you plan on staying in the Highland Oaks area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland Oaks:
- Downtown! Steps to Beach Drive restaurants, shops, and gorgeous waterfront!
- (Sunny) Days of Our Lives | Includes Pool, BBQ and Bikes!
- Luxury Bungalow in Gulfport - Close to the Beaches
- Gulfport Historic Waterfront Art District - Walk to Dining & Beach
- Historic Waterfront District- Gulfport Florida, includes pool, grill and bikes!
- Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House
- Entire Bungalow, Romantic, Comfy & Cozy! On-Site Parking, 2 Baths
- Ultra-cute, newly renovated modern 2/1 home
- Charming Gulfport Town Guest Cottage Studio -Walk To Beach -Shops -Restaurants
- Fantastic Farmhouse Cottage.Best kept secret in St Pete 7 Min walk to beach
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?
4. How do I secure my booking with a rental owner in this area?
5. Are there any additional fees when booking directly with a rental owner here?
6. What amenities can I expect from rentals by owner in this destination?
7. How can I contact the property owner if I have questions before booking?
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