Discover Your Perfect Highland Oaks Vacation Homes

Best Vacation Homes in Highland Oaks

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Highland Oaks Luxury Rentals

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Highland Oaks Pet Friendly Vacation Rentals

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Highland Oaks Large Vacation Homes

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Why Choose Rent By Owner for your Highland Oaks Vacation Rental Homes?

What makes our Vacation Rentals 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 Highland Oaks Vacation Rentals

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 it offers a peaceful and welcoming atmosphere ideal for a relaxing getaway. Located within easy reach of the area's attractions, Highland Oaks provides convenient access to local amenities while maintaining a quiet, residential charm. Whether you're seeking a comfortable base for exploring the vibrant city or a tranquil retreat to unwind, this neighborhood combines comfort and accessibility seamlessly. Booking your vacation rental here ensures a dependable and enjoyable stay in one of Florida's most inviting communities.

Lake Maggiore Shore

Situated along the tranquil shores, this neighborhood offers a serene environment ideal for relaxing getaways in St. Petersburg. Here, you can enjoy easy access to beautiful waterfront views and peaceful surroundings, making it a perfect spot for your stay.

View 1504+ Rentals in Lake Maggiore Shore

Best Times to Visit Highland Oaks

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, allowing you to enjoy the region’s pleasant climate and vibrant local atmosphere whenever you're planning your getaway.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination experiences its peak season with pleasant weather that attracts visitors seeking to escape colder climates.

Average Temperature Daytime: 75°F - Nighttime: 60°F
spring
Spring (March to May)

Spring is another busy period when travelers come to enjoy the region’s mild temperatures and vibrant local atmosphere.

Average Temperature Daytime: 80°F - Nighttime: 65°F

Off-Season Highlights

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Summer (June to August)

In summer, the area sees fewer visitors due to higher humidity and warmer temperatures, offering a quieter environment for your stay.

Average Temperature Daytime: 88°F - Nighttime: 75°F
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Fall (September to November)

Autumn brings a slower pace with cooler temperatures and less crowded attractions, making it an ideal time for peaceful getaways.

Average Temperature Daytime: 78°F - Nighttime: 62°F

Weekly Weather Forecast for Highland Oaks

How to Book Your Highland Oaks 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 Highland Oaks

More Top-Rated Vacation Rentals in Highland Oaks Area

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 swimming pool to relax during your stay in this welcoming area.
  • Take advantage of a spacious patio or deck for outdoor dining and entertaining with friends and family.
  • Benefit from lush landscaped gardens that provide a peaceful outdoor setting right at your rental.
  • Make use of outdoor grilling facilities to prepare delicious meals in the fresh air.
  • Spend leisure time on a furnished balcony or veranda overlooking scenic views of the region.
  • Access nearby walking trails or parks for outdoor recreation and exploration.
  • Utilize secure, private yard space perfect for outdoor activities or pet-friendly stays.

Top Attractions Around Highland Oaks

What attractions are nearby?

During your stay in Highland Oaks, you can enjoy a variety of outdoor activities and local attractions that showcase the vibrant spirit of this area, making it an ideal destination for relaxing or exploring nearby Florida scenery and leisure options.

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Family Activities

  • Suncoast Seabird Sanctuary: Spend a family day exploring this renowned sanctuary dedicated to bird rescue and rehabilitation, offering educational exhibits and encounters with native Florida seabirds.
  • Vinoy Park: Enjoy outdoor family activities at this scenic park along the waterfront, perfect for picnics, playground fun, and picturesque views of the region’s coastline.
  • The Dali Museum: Discover inspiring art and engaging interactive exhibits that make this cultural gem an enjoyable visit for families interested in creativity and history.
  • South Straub Park: Relax and unwind in this charming downtown park featuring lush greenery, open spaces, and easy access to nearby attractions, ideal for family outings.
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Adult Activities

  • Golfing at the nearby courses: Enjoy a day on the greens at some of the region’s top golf courses, perfect for relaxing and socializing in a scenic setting.
  • Sailing and water sports: Experience the thrill of sailing or paddleboarding on the calm waters around here, offering an adventurous way to explore the area’s coastal beauty.
  • Exploring local art galleries: Discover vibrant local culture by visiting art galleries that showcase regional talents in this welcoming destination.
  • Dining at acclaimed restaurants: Indulge in delicious cuisine at highly-rated eateries nearby, making every meal a memorable part of your stay here.

Highland Oaks Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Day Around Local Highlights: Take advantage of the nearby attractions and scenic spots to maximize your experience in this charming area.
  • Utilize the Convenient Location: Choose a holiday home close to key transportation routes to make exploring the region hassle-free.
  • Enjoy the Neighborhood Amenities: Make the most of local parks, shops, and eateries to fully immerse yourself in the community vibe here.
  • Book Early for Popular Seasons: Secure your preferred vacation rentals well in advance during peak travel times to ensure availability and the best options.

Transportation Options

  • St. Petersburg-Clearwater International Airport: This regional airport offers convenient flights for travelers arriving or departing from the area, making your journey smooth and accessible.
  • Public Transit via PSTA Buses: The local public bus system provides eco-friendly and budget-conscious transportation around this part of Florida's Gulf Coast.
  • Rental Cars: Numerous rental agencies operate nearby, giving you the flexibility to explore at your own pace while staying close to your Highland Oaks stay.
  • Taxi and Rideshare Services: Taxis and popular rideshare apps are readily available here, providing quick and reliable options for local travel within the region.

Local Customs Options

  • Local Seafood Dining: Visiting here, you'll notice that fresh seafood is a cornerstone of the area's culinary customs, reflecting its proximity to the Gulf Coast.
  • Community Celebrations: Participating in neighborhood events and festivals is customary, fostering a welcoming atmosphere among residents and visitors alike.
  • Respect for Nature: Emphasizing environmental conservation, many locals prioritize eco-friendly practices that preserve the region’s natural beauty.
  • Casual Coastal Attire: Embracing relaxed fashion standards, it’s common to see residents and guests dressed comfortably, especially during outdoor activities and seaside outings.

Frequently Asked Questions About Highland Oaks?

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:

2. How many vacation rentals have private pools in Highland Oaks?

There are 84 vacation rentals with private pools near Highland Oaks. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Highland Oaks are best for families?

If you are looking for a family-friendly vacation home in Highland Oaks, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland Oaks:

4. 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 1867 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. 

5. What is the cancellation policy for vacation rentals in Highland Oaks?

The cancellation policy varies by property. To understand the specific terms, please review the listing details or contact the property owner directly for the vacation rental you are interested in.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning, service charges, or taxes may apply. For precise information, it’s best to check the listing details or reach out to the host before confirming your reservation.

7. How do I ensure my booking is secure and reliable?

Booking through trusted platforms that verify listings and host identities helps ensure a secure reservation. Always read reviews and confirm the payment process through the official booking system to protect your personal information.

8. What amenities are typically included in these vacation rentals in this part of Florida?

Most rentals offer essential amenities like Wi-Fi, air conditioning, and fully equipped kitchens. For specific amenities available at each property, refer to the individual listing or contact the owner directly.

9. How can I communicate with the property owner if I have questions before booking?

You can generally message the owner through the platform's messaging system. Contacting them prior to booking allows you to clarify any details about the vacation rental to ensure it meets your needs.

Highland Oaks Top Rated Vacation Rentals

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