1. USA
  2. Florida
  3. Naples
  4. Pine Woods
  5. Rentals by Owner

Discover Your Perfect Pine Woods Rentals by Owner

Pine Woods Rentals by Owner

More Top-Rated Rentals by Owner in Pine Woods Area

Why Choose Rent By Owner for your Pine Woods 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 Pine Woods Rentals by Owner

Where are the best neighborhoods to stay in Pine Woods?

When choosing a neighborhood to stay in within Pine Woods, Naples, Florida, you’ll discover a charming and peaceful community that offers both tranquility and convenient access to local amenities. This area provides the perfect setting for a relaxing getaway, with a variety of rental options available through Rent By Owner. Whether you're seeking a cozy retreat or a spacious family home, staying in Pine Woods ensures you'll enjoy a comfortable experience in a welcoming environment that captures the essence of Naples’ southern charm.

Central Naples

In this part of town, you’ll find a variety of rental options that put you close to the heart of Naples, allowing easy access to local amenities and scenic spots. The area’s convenient location makes it an ideal choice for travelers seeking comfort and accessibility in their vacation stay.

View 610+ Rentals in Central Naples

Grey Oaks

This prestigious neighborhood offers upscale rental properties within a serene and elegant setting, perfect for those looking to enjoy the region's refined lifestyle. Staying here provides a peaceful retreat while remaining close to the area's best shopping and dining experiences.

View 588+ Rentals in Grey Oaks

Hawksridge

Known for its family-friendly atmosphere and quiet streets, Hawksridge is an excellent neighborhood for relaxing getaways in Naples. You can enjoy spacious rentals in a safe environment, tailored for visitors wanting a comfortable and laid-back experience.

View 1732+ Rentals in Hawksridge

Best Times to Visit Pine Woods

When should you plan your Rentals by Owner stay?

Timing your visit to this charming destination can enhance your experience, so consider the local climate and seasonal patterns to select the ideal period for your vacation in Pine Woods, Naples, Florida, USA.

Peak Season Highlights

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Winter (December to February)

During these months, the area experiences its peak tourist season with pleasant temperatures that attract visitors seeking warm weather and outdoor activities.

Average Temperature Daytime: 75°F (24°C) - Nighttime: 55°F (13°C)
spring
Spring (March to May)

Spring brings an influx of travelers to the region, drawn by blooming landscapes and ideal weather conditions for exploring your vacation rental in Pine Woods or nearby areas.

Average Temperature Daytime: 80°F (27°C) - Nighttime: 60°F (16°C)

Off-Season Highlights

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Summer (June to August)

Although summer is hotter, fewer visitors opt for travel during this time, making it a good opportunity to book a rental by owner at more favorable rates.

Average Temperature Daytime: 88°F (31°C) - Nighttime: 75°F (24°C)
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Fall (September to November)

As the region transitions into fall, visitor numbers decline, offering you a quieter experience while still enjoying mild temperatures and sunny days.

Average Temperature Daytime: 82°F (28°C) - Nighttime: 62°F (17°C)

Weekly Weather Forecast for Pine Woods

How to Book Your Pine Woods 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 Pine Woods

More Top-Rated Rentals by Owner in Pine Woods 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 a private outdoor swimming pool to relax and unwind in the warm Florida sunshine.
  • Make the most of spacious patios or decks perfect for outdoor dining and entertaining guests.
  • Take advantage of lush, landscaped gardens that provide a serene setting right outside your rental.
  • Benefit from outdoor grilling areas to prepare delicious meals using local produce.
  • Relax in comfortable outdoor lounge furniture designed for lounging after daytime adventures.
  • If available, explore outdoor recreational spaces such as tennis courts or putting greens nearby.
  • Access to covered porches or verandas offering shaded spots to enjoy the scenic surroundings here in the region.

Top Attractions Around Pine Woods

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and local attractions that make your stay in Pine Woods, Naples, Florida, memorable and engaging.

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Family Activities

  • Nature Trails at Corkscrew Swamp Sanctuary: Explore the area's lush landscapes and diverse wildlife on family-friendly walking trails through this renowned natural preserve.
  • Naples Zoo at Caribbean Gardens: Experience a fun-filled day observing exotic animals and engaging exhibits perfect for family visits in this popular wildlife destination nearby.
  • Clam Pass Park: Relax on pristine beaches or enjoy a scenic tram ride to the Gulf of Mexico, making it ideal for families seeking outdoor recreation in the region.
  • Pelican Bay Community Park: Play in large open spaces, enjoy playgrounds, or participate in family activities within this well-maintained community park here in Naples.
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Adult Activities

  • Golfing at Naples Golf Club: You can enjoy a round of golf on the scenic courses that are just a short drive from your rental, offering a perfect way to unwind amidst lush greens.
  • Spa and Wellness Centers: Indulge in relaxing treatments at local spas that provide rejuvenating experiences, ideal for unwinding after exploring the nearby natural attractions.
  • Private Boat Tours: Explore the inland waterways and nearby islands with private boat tours that showcase the area's vibrant ecosystem and stunning coastline.
  • Fine Dining Experiences: Savor exquisite cuisine at upscale restaurants in this destination, where you can delight in fresh seafood and regional specialties in a sophisticated setting.

Pine Woods Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Ahead: Explore the area’s natural beauty and local amenities beforehand to maximize your time in this charming destination.
  • Select a Prime Rental: Choose a well-reviewed rental by owner in Pine Woods to enjoy a comfortable and authentic stay that reflects the region’s relaxed vibe.
  • Embrace the Outdoors: Take advantage of nearby parks, trails, or waterfronts to experience the region’s scenic landscapes during your visit.
  • Connect with Local Tips: Reach out to your host or locals for insider advice on hidden gems and must-visit spots around here to enhance your vacation experience.

Transportation Options

  • Rental Car Services: You can conveniently rent a vehicle locally to explore the area at your own pace, with several providers offering flexible options for visitors staying in Pine Woods.
  • Public Transportation: The region is served by public transit systems that provide affordable and reliable routes, making it easy for you to get around without a car.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft are readily available here, offering a convenient way to travel directly from your rental to nearby attractions or destinations.
  • Bicycle Rentals: For a more active exploration, bicycle rentals are popular locally, allowing you to enjoy the scenic surroundings at a leisurely pace within this peaceful neighborhood.

Local Customs Options

  • Respect for Local Nature: It is customary to honor the area's natural environment by avoiding littering and participating in conservation efforts during your stay in Pine Woods, ensuring the region's pristine beauty remains intact.
  • Greeting Etiquette: Welcoming gestures such as a friendly nod or verbal greeting are appreciated here, reflecting the region’s warm and courteous community spirit among visitors and locals alike.
  • Dining Customs: When dining out or attending gatherings, it is polite to observe local dining manners, including punctuality and modest service tips, making your experience more authentic and respectful of regional traditions.
  • Community Engagement: Participating in local events or supporting small businesses can enrich your visit, allowing you to embrace the region's close-knit community and cultural vibrancy during your stay.

Frequently Asked Questions About Pine Woods Rentals by Owner

1. What are the top vacation rentals in Pine Woods?

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

2. How many Rentbyowner vacation rentals are available in Pine Woods?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1075 in the Pine Woods 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 Pine Woods. 

3. What is the cancellation policy for a rental by owner in Pine Woods?

The cancellation policy varies depending on the specific listing you choose. It is recommended to review the cancellation terms listed with each property or contact the owner directly for detailed information.

4. How do I confirm the availability of a rental home in Pine Woods?

Availability can be checked through the booking platform by entering your preferred dates. For real-time updates and to ensure the dates are reserved, it’s best to contact the owner directly if you have specific questions.

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

Additional fees such as cleaning, service charges, or taxes may apply depending on the listing. These details are usually outlined at checkout or in the listing description, so reviewing them carefully is advisable.

6. What amenities are typically included in a rental by owner in Pine Woods?

Most rentals offer essential amenities like Wi-Fi, parking, and fully equipped kitchens. To find out about specific features such as pools or outdoor spaces, refer to the property listing or reach out directly to the owner.

7. How can I ensure my stay in this destination meets my expectations?

Reading the detailed description, reviews from previous guests, and communicating with the owner beforehand can help set clear expectations and ensure a smooth stay in the area.

More Rentals You May Like Near Pine Woods

More Top-Rated Rentals by Owner in Pine Woods Area