Tarrytown Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Tarrytown

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
10.0 out of 10, Exceptional, 65 reviews
"Very nice and clean very close to all of the amenities that the villages offer"
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly w/NEW GAS GOLF CART, BBQ & BICYCLES
9.6 out of 10, Exceptional, 10 reviews
"This rental property was a great place to stay. Nicely located near activities."
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly w/NEW GAS GOLF CART, BBQ & BICYCLES
New 3/2 Patio Villa, BEST VALUE, Golf Cart Included!
9.8 out of 10, Exceptional, 6 reviews
"Awesome place to stay, would definitely stay again very clean and loved the garage for keeping the motorcycles in"
New 3/2 Patio Villa, BEST VALUE, Golf Cart Included!
Save an average of 15% on thousands of hotels when you're signed in
St. Catherine home, Walking distance to Sawgrass Grove! Great location!
9.8 out of 10, Exceptional, 7 reviews
"Owner very responsive to any issue that came up. First time to visit the Villages. Great experience."
St. Catherine home, Walking distance to Sawgrass Grove! Great location!
Water Front house.
10.0 out of 10, Exceptional, 66 reviews
"This is pur second time staying at James place. Such a nicely maintained property and all the basics are taken care of. Great rental and experience."
Water Front house.
A short stroll to Clermont & a quick bike/drive to Lake Minneola trails & beach.
10.0 out of 10, Exceptional, 15 reviews
"This condo is very clean and comfortable. It is in an older complex but, very quiet. We would stay here again."
A short stroll to Clermont & a quick bike/drive to Lake Minneola trails & beach.
Upto 45 Guests Sleep At This Unique Private Island 62 Acre Estate!
10.0 out of 10, Exceptional, 21 reviews
"Great place with wonderful ownership and the most helpful staff. Definitely a place everyone should stay!!!"
Upto 45 Guests Sleep At This Unique Private Island 62 Acre Estate!
Cozy 2 bedroom downtown Clermont . Lake views by the West Orange Bike Trail.
9.4 out of 10, Exceptional, 3 reviews
"Was very good, everything easy and was the way I like"
The price is NZ$529
includes taxes & fees
1 Jun - 2 Jun
Cozy 2 bedroom downtown Clermont . Lake views by the West Orange Bike Trail.
Pet-Friendly Home w/ Lanai + Resort Amenities!
10.0 out of 10, Exceptional, 13 reviews
"Great Location!"
Pet-Friendly Home w/ Lanai + Resort Amenities!
The Sweet Escape Mansion Candy House Near Orlando
9.8 out of 10, Exceptional, 24 reviews
"Had a great time here. The place was better than the picture. Would highly recommend."
The Sweet Escape Mansion Candy House Near Orlando
Charming and Historic Southern Homestead
10.0 out of 10, Exceptional, 4 reviews
"We stayed at this home for a few days while we were in town for my son’s wedding. The home was super cute, we loved the updated, old feel to this home. You could feel the history there! The owners of the property were super responsive and very helpful! Definitely recommend this home!"
Charming and Historic Southern Homestead
The Bridgehampton pet Friendly tiny house, no extra fees!
10.0 out of 10, Exceptional, 8 reviews
"Great place to stay! Very functional and super clean. Would definitely stay here again!"
The price is NZ$285
includes taxes & fees
1 Jul - 2 Jul
The Bridgehampton pet Friendly tiny house, no extra fees!
Sleep *Up To* 45! - Florida's GAME House On 10 Very Private Lakefront Acres
10.0 out of 10, Exceptional, 29 reviews
"There was a ton to do. It was a ton of fun. I would definitely go back."
Sleep *Up To* 45! - Florida's GAME House On 10 Very Private Lakefront Acres
Ranch with pool/Lake fishing kayak Paddleboard Soccer Motocross 30 min to Disney
10.0 out of 10, Exceptional, 25 reviews
"Wonderful outdoor experience with s’mores, pool time, nature walks!"
Ranch with pool/Lake fishing kayak Paddleboard Soccer Motocross 30 min to Disney
The PERFECT location on the quiet corner!
10.0 out of 10, Exceptional, 15 reviews
"This home is exceptionally clean, stocked well, and in a perfect location. The owner is very responsive. We would highly recommend this home to anyone looking for a vacation getaway to the villages."
The PERFECT location on the quiet corner!
Home in The Villages: Golf Cart & Amenity Access
9.8 out of 10, Exceptional, 19 reviews
"The pictures accurately reflect the property. Located in a newer section of the Villages, about 5 miles from Brownwood square. Grocery, restaurants and gas stations nearby."
Home in The Villages: Golf Cart & Amenity Access
BRAND NEW BEAUTIFULLY Decorated 3/2 VILLA in Lake Denham Villages
8.0 out of 10, Very good, 2 reviews
BRAND NEW BEAUTIFULLY Decorated 3/2 VILLA in Lake Denham Villages
Come discover your Oasis in The Villages: A relaxing retreat in Lake Denham!!
10.0 out of 10, Exceptional, 1 review
"We enjoyed our stay. The home is very clean. The owner has put much detail into the decor and furnishings. I highly recommend this property."
Come discover your Oasis in The Villages: A relaxing retreat in Lake Denham!!
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly Villa w/GAS GOLF CART & GAS BBQ
9.8 out of 10, Exceptional, 10 reviews
"This villa is just beautiful! So very comfortable and welcoming. Decorated very nice and super clean. We loved the location, and really loved the Fenny area. Thank you for the wonderful stay!"
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly Villa w/GAS GOLF CART & GAS BBQ
Florida Family Home w/ Private Pool + Dock!
9.8 out of 10, Exceptional, 21 reviews
"Beautiful home, extremely clean, variety of outside fun!! We rented the home to enjoy our granddaughter’s graduation. It was perfect even with the hiccups we had. Amy was extremely responsive."
Florida Family Home w/ Private Pool + Dock!
Don't see what you're looking for?
See all available properties in Tarrytown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Tarrytown you may be interested in

Days Inn by Wyndham Brooksville/Dade City
2.0 star property
6.8 out of 10, 1,003 reviews
"This location is being renovated. We had a nice room near the lobby. The free breakfast made it a great value! They had good coffee, too. It’s very easy to access from the highway. "
The price is NZ$121
includes taxes & fees
23 Jun - 24 Jun
Days Inn by Wyndham Brooksville/Dade City
Microtel Inn & Suites by Wyndham Brooksville
2.0 star property
8.4 out of 10, Very good, 1,002 reviews
"The room itself was very clean. Also the dining area. What we didn’t like was having to move rooms our second night because the tv was not working! The third night there was a large group at the picnic area drinking, smoking food and being loud. It was 11:30. Tried calling the front desk but the phone was not working so my daughter had to get dressed to go down to the front desk!! They cleared them out right away. Just an inconvenience!!"
The price is NZ$184
includes taxes & fees
3 Jun - 4 Jun
Microtel Inn & Suites by Wyndham Brooksville
Quality Inn & Suites Brooksville I-75/Dade City
2.5 star property
7.0 out of 10, Good, 582 reviews
"The bed was comfortable I had a great night sleep "
The price is NZ$131
includes taxes & fees
12 Jun - 13 Jun
Quality Inn & Suites Brooksville I-75/Dade City
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Tarrytown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Tarrytown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Tarrytown. Seeing all the best attractions is bound to make you fall in love with Tarrytown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Tarrytown short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Tarrytown?

Yes, there are holiday rentals close to the most popular sights in Tarrytown, or you can select a more secluded option if you're looking for a relaxing stay.

What can I see and do in Tarrytown?

While exploring the area, visit family-friendly sights like Giraffe Ranch, or get outside and enjoy nature at Withlacoochee Trail State Park. Webster Westside Flea Market and Florida National Cemetery are a couple of places you'll find in the wider area.

What are holiday rentals like in Tarrytown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Tarrytown. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for families.

Recent reviews of Tarrytown properties
Expedia verified reviews