Discover Your Perfect Ole Vacation Homes

Why Choose Rent By Owner for your Ole 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 Ole Vacation Rentals

Where are the best neighborhoods to stay in Ole?

When planning your getaway to Ole in Naples, Florida, choosing the right neighborhood can greatly enhance your vacation experience. Located in a prime area of southwest Florida, Ole offers convenient access to beautiful beaches, vibrant shopping districts, and charming local attractions. Whether you prefer a peaceful retreat or an active, lively atmosphere, the neighborhoods within Ole provide a variety of options to suit your preferences. By selecting a well-situated area in Ole, you can enjoy seamless connectivity to all that Naples has to offer, ensuring your stay is both relaxing and memorable. Find the perfect vacation rentals in Ole that align with your travel desires and experience the best of Naples, Florida."

Flamingo Fairways

Located within this sought-after area, Flamingo Fairways offers a peaceful retreat with easy access to the region's beautiful golf courses and natural scenery. Here, you can enjoy a relaxing stay in a well-connected neighborhood that combines comfort with convenience.

View 1029+ Rentals in Flamingo Fairways

Best Times to Visit Ole

When should you plan your Vacation Rentals stay?

Finding the best time to visit here can greatly enhance your experience, as seasonal variations in Ole, Naples, Florida, USA, influence the climate and overall atmosphere of this destination.

Peak Season Highlights

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Winter (December to February)

During the winter months, the region experiences its peak travel period as visitors flock here for warm weather and sunny skies, making it an ideal time to secure your preferred vacation rentals.

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

Spring attracts many travelers eager to enjoy pleasant temperatures and beautiful scenery, ensuring demand for vacation rentals remains high during this lively season.

Average Temperature Daytime: 80°F - Nighttime: 60°F

Off-Season Highlights

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Summer (June to August)

While summer can bring higher temperatures, the region tends to see fewer visitors, offering a more relaxed atmosphere and potentially better deals on vacation rentals.

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

Late fall sees a slowdown in tourism, providing an excellent opportunity to enjoy quieter surroundings and attractive rates on accommodations in this destination.

Average Temperature Daytime: 82°F - Nighttime: 65°F

Weekly Weather Forecast for Ole

How to Book Your Ole 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 Ole

More Top-Rated Vacation Rentals in Ole 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 refreshing dip in the private outdoor swimming pool.
  • Relax under the shaded lounge area designed for leisure and outdoor gatherings.
  • Take advantage of the outdoor grilling station for enjoyable cookouts.
  • Spend time on the outdoor patio or deck, perfect for morning coffee or evening conversations.
  • Benefit from lush landscaped gardens surrounding your stay for added privacy and beauty.
  • Utilize the community's outdoor sports courts for tennis or basketball games.
  • Discover scenic walking or jogging paths nearby to explore the natural surroundings of the region.

Top Attractions Around Ole

What attractions are nearby?

Within this charming destination, you can enjoy a variety of outdoor activities and explore scenic beaches just moments away from your travel accommodations here in Naples, Florida.

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Family Activities

  • Clam Pass Park: Spend a day exploring the scenic boardwalk and relaxing on the pristine beaches, perfect for family outings in this popular outdoor area.
  • The Naples Zoo at Caribbean Gardens: Discover a variety of exotic animals and enjoy engaging educational exhibits that make for an exciting day with children.
  • Corkscrew Swamp Sanctuary: Experience nature walks through lush wetlands and observe local wildlife, ideal for family adventures immersed in the region's natural beauty.
  • Trieste Water Sports: Try stand-up paddleboarding, kayaking, or boat rentals to enjoy water-based activities suitable for all ages here in the area.
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Adult Activities

  • Golfing at the Naples Grande Golf Club: Experience world-class golf in a scenic setting that caters to both beginners and seasoned players, making it a perfect activity for your stay here.
  • Exploring Clam Pass Park: Enjoy a relaxing day on the pristine beaches or take a tram ride through the lush mangroves along the coast in this popular outdoor destination.
  • Shopping and Dining in Olde Naples: Discover charming boutiques, galleries, and delightful eateries that showcase the local flavor and vibrant atmosphere of this coastal community.
  • Visiting The Baker Museum: Immerse yourself in fine art and captivating exhibitions housed within a cultural hub that adds a touch of sophistication to your vacation experience.

Other Places to Stay in Ole, FL

Flamingo Fairways
Flamingo Fairways Vacation Rentals
More Places to Stay Near Ole

Ole Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Savor the regional flavors by trying out nearby restaurants and cafes to experience authentic cuisine during your stay.
  • Take advantage of outdoor activities: Make the most of the area's beautiful weather by participating in outdoor pursuits such as walking along scenic trails or relaxing in parks.
  • Plan day trips within the region: Discover nearby attractions and natural spots for memorable excursions that showcase the best of what this destination offers.
  • Utilize local amenities and services: Access community facilities, shops, and entertainment venues to enrich your vacation experience in the area.

Transportation Options

  • Car Rentals: You can explore the area at your own pace by renting a car, providing convenient transportation to local attractions and beaches.
  • Public Transit: The local bus system offers affordable and reliable routes that help you navigate the region comfortably without a vehicle.
  • Taxi Services: Taxis and rideshare options like Uber and Lyft are readily available, offering flexible transportation around this vibrant destination.
  • Bicycle Rentals: For a scenic and eco-friendly way to enjoy the neighborhood, bicycle rentals are a popular choice among visitors here.

Local Customs Options

  • Respect for the Beach Environment: Locals in this coastal area emphasize keeping the beaches clean and preserving the natural beauty that makes the region so special.
  • Golf Course Etiquette: The community takes pride in its golf courses, encouraging visitors to follow local customs of proper attire and respect for fellow players.
  • Holiday Celebrations: Participating in regional festivities often involves local customs like traditional parades and community gatherings that showcase the area's vibrant culture.
  • Restaurant Courtesy: Dining establishments in the region value courteous behavior and encourage guests to observe local dining manners, especially during lively social events.

Frequently Asked Questions About Ole?

1. What are the top vacation rentals in Ole?

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

2. How many vacation rentals have private pools in Ole?

There are 14 vacation rentals with private pools near Ole. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Ole are best for families?

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

4. How many Rentbyowner vacation rentals are available in Ole?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 139 in the Ole 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 Ole. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policies vary by property, so it's important to review the specific listing details before booking. For precise information on refunds and cancellation deadlines, please consult the individual property listing or contact the host directly.

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

Additional fees such as cleaning, service charges, or local taxes may apply depending on the property. These details are typically outlined during the booking process, so reviewing the listing description carefully will ensure you’re fully informed.

7. How do I know if a vacation rental is available for my travel dates?

Availability depends on current bookings and can be checked directly through the listing platform. It’s recommended to enter your preferred dates and to confirm availability with the host if necessary to secure your stay.

8. What amenities are commonly included in vacation rentals in this destination?

Most properties in this region offer amenities such as Wi-Fi, fully equipped kitchens, outdoor spaces, and laundry facilities. To verify the amenities included, refer to the detailed listing or contact the owner for specific questions.

9. What should I do if I encounter issues during my stay in a vacation rental?

If you experience any problems, contact the property owner or manager listed on the booking platform promptly. Support options are provided through the platform, ensuring a reliable and seamless resolution process.