Naramata Wineries - Vacation Rentals in Sleepy Hollow

Seychelles - Daytona Beach Condos From US $175
         

Seaside Serenity From US $235
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Just Gotta Getaway From US $185
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Sanibel 1104 From US $188
         

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10.0 (2 Reviews)
House
  • Parking
  • Pool
  • View
Ashley Penthouse 5 From US $454
         

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10.0 (1 Review)
House
  • Parking
  • Pool
  • View
Unit 102 Aruba - 3 Bedroom Ocean Front From US $407
         

Luxury Places to Stay in Sleepy Hollow

Over 176+ Luxury Places to Stay in or Near Sleepy Hollow
One of a Kind two story gated Halifax Riverfront From US $893
         

Port Orange Linda's Lizard Landing From US $842
         

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New
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Sleepy Hollow

Over 104+ Top-Rated Vacation Rentals with a Pool in or Near Sleepy Hollow
Ocean Terrace Club From US $153
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
pirates cove From US $116
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Blue Beach Pool House From US $75
         

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9.6 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
The Salty Sandcastle Townhome From US $227
         

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9.5 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sanibel 601 From US $369
         

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9.5 (4 Reviews)
House
  • Parking
  • Pool
  • View
Cozy Home Near Ocean + Daytona Int'l Speedway From US $219
         

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9.5 (4 Reviews)
House
  • Parking
  • Pool
  • Security/Safety

Pet-Friendly Vacation Rentals in Sleepy Hollow

Over 47+ Pet-Friendly Vacation Rentals in or Near Sleepy Hollow
The Blue Anchor-Walk to Beach From US $328
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • View
Seaside Hideaway From US $295
         

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9.5 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Waterfront - Private Pool - Pet Friendly From US $375
         

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9.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Surfside Shangri La From US $340
         

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9.3 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Blue Anchor Cottage From US $432
         

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9.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
NEW - Amazing Sunshine - Up 6 Guests-Private Backyard From US $138
         

Sunrise Oaks From US $291
         

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8.0 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Vintage Florida Pet-Friendly Retreat From US $132
         

8.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Sleepy Hollow

Over 13+ Large Vacation Homes & Villas in or Near Sleepy Hollow
Fantasy Island Resort, Daytona Beach Shores From US $185
         

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8.7 (101 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Unit 103 Aruba - 3 Bedroom Ocean Front From US $390
         

Sun and Fun - The Whole Shell From US $559
         

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New
House
  • Air Conditioner
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  • Pet Friendly
White Surf 701 From US $438
         

New
Apartment
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

Wheelchair Accessible Vacation Homes in Sleepy Hollow

Over 12+ Wheelchair Accessible Vacation Homes in or Near Sleepy Hollow
Unit 107 Aruba - 3 Bedroom Ocean View From US $326
         

White Surf 306 From US $269
         

9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Ashley Unit 906 From US $250
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pool
Ambros Daytona, Trademark Collection by Wyndham From US $188
         

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8.9 (96 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Country Inn & Suites by Radisson, Port Orange-Daytona, FL From US $134
         

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8.8 (422 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Residence Inn by Marriott Daytona Beach Oceanfront From US $217
         

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8.7 (502 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Atlantic Shores Motel From US $72
         

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8.2 (209 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Sleepy Hollow Vacation Rentals and Airbnb Places to Stay Under $200

Over 51+ Sleepy Hollow Vacation Rentals and Airbnb Places to Stay Under $200
Cozy one bedroom From US $95
         

9.4 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Charming & Cozy From US $99
         

9.3 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Charming Port Orange Home - Walk to Beach! From US $179
         

Sunglow Resort 305 From US $182
         

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8.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View

About Sleepy Hollow Vacation Rentals

With more than 185 Sleepy Hollow vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Naramatawineries and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Sleepy Hollow.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Naramatawineries Sleepy Hollow, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Sleepy Hollow. Places to stay near Sleepy Hollow are 1200.96 ft² on average, with prices averaging US $303 a night.

Naramatawineries makes it easy and safe to find and compare vacation rentals in Sleepy Hollow with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Sleepy Hollow

Type Count
Vacation Homes 111
Holiday Apartments 50
Hotels 17
Resorts 4
Villas 3

Use these Quick Filters to Find a Vacation Rental in Sleepy Hollow

Pro Tip: Naramatawineries makes it easy to compare the best listings on Naramatawineries homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Naramatawineries homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sleepy Hollow.

Weather in Sleepy Hollow

View the weather forecast for Sleepy Hollow before booking your Sleepy Hollow Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Sleepy Hollow Vacation Rental Frequently Asked Questions

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:

How many vacation rentals have private pools in Sleepy Hollow?

There are 1 vacation rentals with private pools near Sleepy Hollow. Top-rated homes that have access to a swimming pool include:

How many vacation rentals are available in Sleepy Hollow?

Currently, the total number of properties listed in 2026 is over 185 in the Sleepy Hollow area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sleepy Hollow.