Sleepy Hollow vacation rentals
We found 16 vacation rentals — enter your dates for availability
Discover a selection of vacation rentals in Sleepy Hollow that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the best amenities for hanging out with the people that matter most, including parking and a TV. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
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Find the best place to stay - Sleepy Hollow
Welcome to your Peace and Relaxation
Sleeps 11 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Looking to Just Get Away??? Cute Cottage with Pool. Close to the Beach!
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
96 reviews(96 reviews)
Stay 5 Nights, Get 1 Night Free - 4 BR home in quiet setting close to everything
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
2-story home with outdoor pool, alfresco dining, grill, & beach chairs
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
5 reviews(5 reviews)
Perfect Location Between New Smyrna And Daytona Beach - 10 Minutes To The Beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
Newly remodeled 3-bedroom house in Port Orange close to beach & racetrack!
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Top rated rentals - Sleepy Hollow
Love this place!
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
Our third year coming here and it only gets better. The renovations were very well done and make both the inside and outside extra appealing. The backyard is private and peaceful and the pool clean and inviting. The house is close to everything you could want and the neighbourhood is safe and quiet. We will definitely be back for a fourth visit!
Wendy W.
Stayed May 2025
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental in Sleepy Hollow?
In Sleepy Hollow, vacation houses and cottages are the most popular types of rentals, with several options available throughout the area. These properties typically feature comfortable living spaces, fully equipped kitchens, and outdoor areas for enjoying the pleasant Florida weather. Many of the vacation houses provide ample room for families or groups, often including multiple bedrooms and private gardens, making them great for gatherings and relaxation.
Are there any beach house rentals in Sleepy Hollow?
In Sleepy Hollow, Florida, several beach house rentals are available, suiting those seeking a relaxed coastal getaway. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, providing all the comforts of home. Many rentals also include outdoor spaces, such as patios or decks, superb for enjoying the warm Florida climate. Nestled near the scenic shoreline, these beach houses offer easy access to the beach and local attractions, making them an ideal choice for families or groups looking to enjoy a laid-back vacation experience.
How much does it cost to rent a vacation home in Sleepy Hollow?
Prices for vacation rentals in Sleepy Hollow vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Sleepy Hollow to more spacious homes.
Are there any discounts for Sleepy Hollow vacation house rentals?
You can find great discounts on house rentals in Sleepy Hollow on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Sleepy Hollow vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Sleepy Hollow with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Sleepy Hollow?
A long-stay vacation rental in Sleepy Hollow is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Sleepy Hollow for a vacation rental?
The most popular time to visit Sleepy Hollow is in September, when the warm Florida weather invites travellers to enjoy its scenic beauty and outdoor activities. This month is particularly appealing for those eager to spend time exploring the area's lush landscapes and tranquil waterways. With temperatures typically in the high 20s to low 30s Celsius, September offers a comfortable climate for hiking, cycling, and unwinding by the water.
While the peak season runs from February to April, when visitors flock to enjoy the vibrant spring atmosphere, September strikes a lovely balance of fewer crowds and pleasant weather. This makes it an ideal time for those who appreciate a more relaxed pace while still having access to various activities and local attractions.
If you're looking for a more budget-friendly option, October presents a wonderful opportunity to experience the beauty of Sleepy Hollow during the quieter autumn months. The temperatures remain warm, and you can enjoy the changing foliage without the hustle and bustle of peak tourist traffic.
Are there any remote work vacation rentals in Sleepy Hollow?
In Sleepy Hollow, Florida, there are several remote work vacation rentals available, making it a suitable location for those looking to blend work and leisure. Properties in this area often come equipped with reliable Wi-Fi and dedicated workspaces, such as desks, allowing for a productive environment.
The charming neighbourhood offers a peaceful setting, ideal for focusing on work while also enjoying the tranquillity of the surroundings. Many rentals feature comfortable living areas, private outdoor spaces, and amenities that promote relaxation after a day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Sleepy Hollow vacation rental?
Book your Sleepy Hollow vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Sleepy Hollow home rental booking on Vrbo?
To find Sleepy Hollow vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Sleepy Hollow vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.