Pleasantville Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Pleasantville, New York, USA

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10.0 (2 Reviews)
1 Bedroom 12 Guests
From US $253 per night
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8.2 (412 Reviews)
1 Bedroom 2 Guests
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9.5 (2 Reviews)
5 Bedrooms 11 Guests
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New
1 Bedroom 2 Guests
From US $198 per night
10.0 (5 Reviews)
2 Bedrooms 6 Guests
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7.3 (3 Reviews)
5 Bedrooms 12 Guests
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9.0 (1001 Reviews)
1 Bedroom 2 Guests
9.8 (14 Reviews)
1 Bedroom 4 Guests
From US $269 per night
9.6 (61 Reviews)
1 Bedroom 2 Guests
9.6 (5 Reviews)
1 Bedroom 2 Guests
From US $104 per night
New
4 Bedrooms 8 Guests
8.6 (4 Reviews)
2 Bedrooms 4 Guests
From US $104 per night
New
1 Bedroom 2 Guests
From US $3,564 per night
New
2 Bedrooms 2 Guests
From US $214 per night
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9.1 (11 Reviews)
244 Bedrooms 10 Guests
From US $312 per night
New
1 Bedroom 8 Guests
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8.5 (186 Reviews)
148 Bedrooms 47 Guests
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8.3 (587 Reviews)
145 Bedrooms 10 Guests
10.0 (2 Reviews)
3 Bedrooms 4 Guests
From US $199 per night
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8.2 (170 Reviews)
444 Bedrooms 52 Guests
From US $159 per night
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8.0 (263 Reviews)
150 Bedrooms 41 Guests
10.0 (5 Reviews)
4 Bedrooms 8 Guests
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7.9 (1358 Reviews)
101 Bedrooms 20 Guests
From US $140 per night
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7.7 (922 Reviews)
214 Bedrooms 14 Guests
9.6 (10 Reviews)
4 Bedrooms 12 Guests
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6.8 (254 Reviews)
156 Bedrooms 18 Guests
9.4 (8 Reviews)
5 Bedrooms 12 Guests
From US $116 per night
6.6 (545 Reviews)
101 Bedrooms 18 Guests
6.4 (459 Reviews)
136 Bedrooms 13 Guests
9.2 (12 Reviews)
4 Bedrooms 8 Guests
8.8 (5 Reviews)
5 Bedrooms 13 Guests
8.0 (11 Reviews)
5 Bedrooms 11 Guests
2.5 (2 Reviews)
7 Bedrooms 13 Guests
From US $229 per night
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6.3 (582 Reviews)
235 Bedrooms 41 Guests
8.8 (874 Reviews)
1 Bedroom 2 Guests
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5.9 (399 Reviews)
48 Bedrooms 14 Guests
From US $236 per night
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8.8 (391 Reviews)
1 Bedroom 2 Guests
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8.3 (454 Reviews)
28 Bedrooms 14 Guests
From US $230 per night
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8.6 (31 Reviews)
1 Bedroom 2 Guests
New
1 Bedroom 2 Guests
New
1 Bedroom 2 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
5.0 (2 Reviews)
4 Bedrooms 2 Guests
From US $394 per night
New
4 Bedrooms 14 Guests
New
1 Bedroom 3 Guests
From US $776 per night
New
4 Bedrooms 10 Guests
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8.4 (1005 Reviews)
1 Bedroom 2 Guests
8.2 (1428 Reviews)
1 Bedroom 2 Guests

About Pleasantville Vacation Rentals

With more than 106 Pleasantville vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) 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 an RBO property in Pleasantville.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Pleasantville, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO 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 (RBOs), and other popular Airbnb-style properties in Pleasantville. Places to stay near Pleasantville are 1046.95 ft² on average, with prices averaging US $520 a night.

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

Pleasantville Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Pleasantville?

How many Rentbyowner vacation rentals are available in Pleasantville?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 106 in the Pleasantville 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 Pleasantville.