Discover Your Perfect Sleepy Hollow Vacation Homes

Best Vacation Homes in Sleepy Hollow

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Sleepy Hollow Luxury Rentals

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Sleepy Hollow Pet Friendly Vacation Rentals

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8.6 (7 Reviews)
Condo
Shores Club
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Sleepy Hollow Large Vacation Homes

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Why Choose Rent By Owner for your Sleepy Hollow 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 Sleepy Hollow Vacation Rentals

Where are the best neighborhoods to stay in Sleepy Hollow?

When selecting a neighborhood to stay in Sleepy Hollow, Port Orange, Florida, you’ll find a variety of charming areas that offer both comfort and convenience. Each neighborhood provides a unique atmosphere, whether you prefer a peaceful residential setting or easy access to local amenities. Staying in the heart of Port Orange places you close to key attractions and the beautiful natural surroundings that define this inviting area. No matter your choice, you can enjoy the reliable and seamless experience of booking through trusted vacation rentals designed to make your trip memorable and hassle-free.

Deep Forest Village

In this peaceful area, you can enjoy the tranquility of nature while staying close to local amenities. It's an ideal spot to unwind in comfort and explore the serene surroundings of Port Orange.

View 942+ Rentals in Deep Forest Village

Best Times to Visit Sleepy Hollow

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination can enhance your experience, allowing you to enjoy its relaxed vibe and pleasant weather when the region's atmosphere is at its best.

Peak Season Highlights

spring
Spring (March to May)

During this time, the region experiences warm weather ideal for outdoor activities and exploring. It’s a popular period for visitors seeking pleasant temperatures and vibrant scenery.

Average Temperature Daytime: around 78°F - Nighttime: about 58°F
winter
Winter (December to February)

This season offers mild winter temperatures, attracting travelers looking to escape colder climates and enjoy the comfortable weather here in Florida.

Average Temperature Daytime: approximately 70°F - Nighttime: roughly 50°F

Off-Season Highlights

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Summer (June to August)

The summer months bring higher humidity and hotter days, making it less busy but perfect for those who enjoy longer daylight hours and water activities.

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

Autumn tends to see fewer visitors, offering a quieter experience with comfortable temperatures and less crowded attractions during this period.

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

Weekly Weather Forecast for Sleepy Hollow

How to Book Your Sleepy Hollow 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 Sleepy Hollow

More Top-Rated Vacation Rentals in Sleepy Hollow 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 outdoor grilling with a fully-equipped barbecue area available at many properties in the region.
  • Relax by a private or shared swimming pool, perfect for cooling off during warm Florida days.
  • Take advantage of spacious patios or decks to dine al fresco while enjoying the pleasant weather.
  • Experience the convenience of outdoor parking spaces tailored for easy access and security.
  • Make the most of scenic views with properties that feature expansive yards and landscaped gardens.
  • Participate in outdoor activities like cycling or jogging along nearby trails and pathways.
  • Utilize screened-in porches or lanais to enjoy the fresh air without the hassle of insects.

Top Attractions Around Sleepy Hollow

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of outdoor activities, leisurely walks, and recreational opportunities just moments from your vacation rental in Sleepy Hollow, Port Orange, Florida.

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Family Activities

  • Hontoon Island State Park: Discover the natural beauty of this park with family-friendly boat tours and picnic areas, offering a peaceful escape in the heart of the region.
  • Susan H. Skerritt Nature Preserve: Engage with local wildlife and explore scenic trails that are perfect for a family day immersed in Florida's diverse ecosystems.
  • Port Orange Fish Management Area: Enjoy fishing and birdwatching at this accessible spot where your family can connect with nature right here in the region.
  • Local Beaches Near here: Relax and play on pristine sands and shallow waters, making the area an ideal destination for family beach outings and water activities.
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Adult Activities

  • Golfing at the Port Orange Golf Course: Enjoy a day of leisurely golf on well-maintained courses that offer scenic views and challenging play in this vibrant region.
  • Exploring local nature trails: Discover the area's natural beauty by hiking or biking along scenic trails that wind through lush landscapes and preserve native ecosystems.
  • Visiting nearby breweries and craft breweries: Sample local brews and experience the region’s lively craft beer scene, perfect for relaxed evenings after exploring here.
  • Attending cultural events and festivals: Immerse yourself in the local culture by participating in seasonal festivals and community events held throughout the region.

Sleepy Hollow Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature: Take advantage of the region’s scenic parks and waterways to enjoy outdoor activities that showcase the area's natural beauty.
  • Visit Nearby Attractions: Discover local points of interest to enrich your stay and gain a true sense of this destination’s charm.
  • Plan Your Activities: Schedule your days around popular events or seasonal festivities to make the most of your visit here.
  • Choose the Right Accommodation: Select a well-reviewed vacation rental in Sleepy Hollow that offers convenience and comfort for your stay in the area.

Transportation Options

  • Personal Vehicles: Renting or driving your own car offers flexibility and convenience for exploring the region around Sleepy Hollow, Port Orange.
  • Public Transit: Local bus services provide budget-friendly transportation options to navigate through this part of Florida with ease.
  • Rideshare Services: Rideshare apps like Uber and Lyft are readily available here, offering a reliable way to get around without the need for personal vehicle ownership.
  • Bike Rentals: Biking is a popular choice for experiencing the area's scenic routes and local attractions at a leisurely pace.

Local Customs Options

  • Traditional Floridian Hospitality: Locals here take pride in welcoming visitors with warm, friendly gestures that reflect the region's southern charm and hospitality.
  • Celebration of Local Festivals: Participating in community events and festivals is a cherished custom that highlights the area's rich cultural heritage and communal spirit.
  • Respect for Nature and Wildlife: It’s common to observe a deep reverence for the natural surroundings, with many residents engaging in conservation efforts and outdoor activities.
  • Preservation of Historical Sites: Many locals value their history, often sharing stories and maintaining sites that showcase the area’s unique past and traditions.

Frequently Asked Questions About Sleepy Hollow?

1. What are the top vacation rentals in Sleepy Hollow?

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

2. How many vacation rentals have private pools in Sleepy Hollow?

There are 215 vacation rentals with private pools near Sleepy Hollow. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Sleepy Hollow are best for families?

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

4. How many Rentbyowner vacation rentals are available in Sleepy Hollow?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1438 in the Sleepy Hollow 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 Sleepy Hollow. 

5. What is the cancellation policy for booking vacation rentals in Sleepy Hollow, Port Orange, Florida?

Cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand the cancellation terms and any applicable fees.

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

Additional fees such as cleaning fees, service charges, or taxes may apply. Please check the detailed listing information or reach out to the owner for clarity on all costs involved.

7. How do I secure my reservation for a vacation rental in this area?

Reservations are typically secured through the online booking system with a deposit or full payment. For specific instructions or assistance, contact the property owner or the customer support team.

8. Is it possible to modify or extend my stay once booked?

Modification or extension options depend on the property's policies and availability. Contact the owner directly to discuss potential changes to your reservation.

9. What amenities are included with vacation rentals in the region?

Amenities vary between properties but often include essentials like Wi-Fi, kitchens, and outdoor spaces. Review each listing carefully or contact the owner to confirm the amenities available during your stay.

Sleepy Hollow Top Rated Vacation Rentals

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