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  4. South Westshore
  5. Rentals by Owner

South Westshore Rentals by Owner

Why Choose Rent By Owner for your South Westshore 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 South Westshore

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience, as understanding seasonal trends and local weather patterns ensures you find the perfect rental by owner in this vibrant destination.

Peak Season Highlights

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Spring (March to May)

During spring, the area experiences warm weather ideal for exploring and outdoor activities, making it a popular time for visitors seeking pleasant temperatures and vibrant surroundings.

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

This period attracts travelers looking to escape colder climates, as mild winter weather provides a comfortable environment for sightseeing and relaxation.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Summer (June to August)

While summer can be busy, the region still offers excellent rental options with fewer crowds, especially if you prefer quieter beaches and attractions.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 70°F to 75°F
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Fall (September to November)

This shoulder season features cooler weather and less tourist activity, providing a peaceful setting for those who enjoy a more relaxed visit without the peak-season prices.

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

Weekly Weather Forecast for South Westshore

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 a private outdoor swimming pool to relax and unwind in the warm Florida sun.
  • Make the most of spacious patios or decks perfect for outdoor dining and entertaining.
  • Take advantage of lush landscaped gardens that add beauty and tranquility to your stay.
  • Benefit from access to outdoor grilling areas for memorable cookouts with family and friends.
  • Utilize outdoor seating areas designed for lounging while soaking up the region’s sunny weather.
  • Experience the convenience of outdoor parking spaces tailored for your visit here.
  • Incorporate nearby walking trails or open outdoor spaces ideal for exploring the area’s natural scenery.
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Family Activities

  • Pinellas Trail: Explore this scenic biking and walking path that runs through the region, offering families a safe and enjoyable way to experience outdoor leisure.
  • Adventure Island Tampa: Enjoy a day of water slides and themed zones at this nearby water park, perfect for cooling off and creating lasting family memories.
  • Bay Shore Boulevard: Take a relaxing stroll or rent bikes along the waterfront, offering picturesque views and a peaceful setting for family outings.
  • Local Beaches: Unwind at the pristine beaches nearby, where you can build sandcastles, play in the surf, or simply relax with your loved ones in this coastal destination.
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Adult Activities

  • Sunset Boat Tours: Embark on a scenic boat tour to enjoy breathtaking views of the Tampa Bay sunset, perfect for a relaxing evening in this vibrant area.
  • Golfing at Westchase Golf Course: Tee off at a premier golf course in the region, offering a challenging and enjoyable experience amid lush surroundings.
  • Visit Cypress Point Park: Stroll along the shoreline, unwind on the sandy beaches, or have a picnic while taking in the picturesque waterfront scenery.
  • Dining in Waterfront Restaurants: Indulge in diverse culinary delights at local waterfront eateries that highlight fresh seafood and regional flavors here in the area.

South Westshore Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Take advantage of the area's diverse culinary scene to enjoy authentic flavors without straying far from your rental.
  • Utilize nearby transportation: Make the most of convenient transit or rental services to easily access popular attractions and beaches.
  • Plan outdoor activities: Engage in outdoor pursuits such as waterfront walks or parks, which showcase the region's natural beauty and are often close to your accommodation.
  • Research hidden gems: Discover lesser-known spots in the area that can offer unique experiences away from crowded tourist areas.

Transportation Options

  • Raymond James Stadium Shuttle: This reliable shuttle service provides convenient transportation to the nearby stadium and event venues, making it easy to explore the area without hassle.
  • Public Transit (HART Bus): The local bus system offers an affordable option for traveling around the region, connecting you to key destinations in South Westshore and beyond.
  • Rental Car Services: Several rental car agencies operate here, giving you the flexibility to explore the region at your own pace during your stay.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available, providing quick and convenient transportation to various spots within the neighborhood and nearby attractions.

Local Customs Options

  • Respect for Local Hospitality: When visiting the area, it's customary to acknowledge and appreciate the friendly approach of locals, especially during community gatherings or dining experiences.
  • Celebrating Regional Festivals: Participating in or observing local festivals shows respect for regional traditions and provides an authentic experience of this destination's cultural heritage.
  • Environmental Conservation: Visitors are encouraged to follow eco-friendly practices, such as proper waste disposal and conservation efforts, to help preserve the natural beauty of the region.
  • Greeting Customs: Greeting locals with a warm smile and polite manners reflects the welcoming spirit of this destination's community and enhances your stay.

Frequently Asked Questions About South Westshore Rentals by Owner

2. How many Rentbyowner vacation rentals are available in South Westshore?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 922 in the South Westshore 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 South Westshore. 

3. What is the cancellation policy for rentals by owner in this area?

Cancellation policies vary by property, so it’s important to review the specific listing details. Many owners offer flexible cancellation options, but always check the terms before booking to ensure they meet your needs.

4. How do I communicate with the property owner before booking?

You can contact the property owner directly through the messaging system provided on the rental platform. This allows you to ask questions about the property, clarify any details, and confirm availability before making your reservation.

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

Additional fees such as cleaning fees, service charges, or security deposits are often outlined in the listing. Be sure to review all costs associated with the rental before finalizing your booking to avoid surprises.

6. What amenities are typically included in owner-managed vacation rentals here?

Most rentals by owner include essential amenities such as Wi-Fi, kitchen access, and parking. It's advisable to check the specific listing to see which amenities are offered and if any extras are available for your stay.

7. Is it possible to extend my stay once I’ve booked in this destination?

Yes, many owners are willing to accommodate extensions if the property’s availability allows. Contact the owner directly through the platform to discuss extending your reservation and any additional costs that might apply.

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