Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Aparthotel in Newberry

4.0 star property
10.0 out of 10, Exceptional, (45)
"Every thing was great "
United States
Michael
Landing Apartments Newberry

Cabin in Hawthorne

2.5 star property
9.2 out of 10, Wonderful, (197)
"Cabin was very comfortable and clean. Everything was in order and working. "
United States
Philip
The price is €134
includes taxes & fees
5 Dec - 6 Dec
Yearling Restaurant and Cabins

Apartment in Gainesville

4.0 star property
8.4 out of 10, Very good, (7)
"The unit was located in the perfect are, there was so much to do around within 10 minutes driving distance. The unit was was spacious and comfortable we felt like home."
United States
NANCY
The price is €224
includes taxes & fees
1 Jan - 2 Jan 2026
Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar

Holiday Home in Gainesville

9.6 out of 10, Exceptional, (15)
"House was clean and stocked with everything we needed. Host was very responsive. While we went with family and friends it seems like the perfect game day stay."
United States
Laura F.
The price is €363
includes taxes & fees
7 Dec - 8 Dec
CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV

Apartment in Gainesville

10.0 out of 10, Exceptional, (5)
"My boyfriend and I really enjoyed staying here with our dog! The neighborhood is nice and walkable, the unit was clean and had everything we needed. As a matter of information, I did not see a place where we could control the temperature, but it was very comfortable while we were here. The shower is also quite small, but there were toiletries provided and that was nice. We were close everything we could want and a short drive from downtown. The neighborhood was quiet and we felt safe. We will...
United States
Nicole S.
The price is €127
includes taxes & fees
30 Dec - 31 Dec
Private suite with own entry in vibrant Gainesville

Apartment in Gainesville

3.0 star property
10.0 out of 10, Exceptional, (1)
"Clean, great communication. Needed a pizza cutter"
United States
bethany
Cozy UF Condo Near Shands UF on Archer

Cottage in Keystone Heights

2.0 star property
9.6 out of 10, Exceptional, (14)
"Awesome location, great cabin! Had everything I needed to see my family ❤️ Will request to stay again!"
United States
Bonnie
The price is €172
includes taxes & fees
8 Dec - 9 Dec
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing

Cottage in Micanopy

9.8 out of 10, Exceptional, (44)
"It was clean, quiet and pleasant. Great experience"
United States
Ken R.
The price is €201
includes taxes & fees
7 Dec - 8 Dec
Palmetto Cottage-1930’s Florida Cottage

Holiday Home in Gainesville

10.0 out of 10, Exceptional, (3)
"This property was just what we needed for a place to stay after going to the UF game. Easy to find and located close enough to campus (not walking distamce though) for us. It was a quick turnarpund for us, but if we need to stay another time longer i would definitely want to stay here again."
United States
Christi R.
The price is €171
includes taxes & fees
3 Jan - 4 Jan 2026
La Casita: Charming 1-bedroom house in Gainesville w/ pickleball court!

Condo in Gainesville

8.8 out of 10, Excellent, (33)
"It is an okay house."
United States
Mai G.
The price is €198
includes taxes & fees
1 Jan - 2 Jan 2026
Cute Condo Close to Campus - Walk to Shands/Pool!

Holiday Home in Gainesville

9.4 out of 10, Exceptional, (8)
"We needed a two-week rental to help family with a move. We had 6 adults and one child in our group. This house was perfect for us! A small but well-equipped kitchen allowed us to cook most meals and save some money. Location was great, very central to most of Gainesville. We wish the washer/dryer were larger capacity, but they did the job. Property owner was always very quick responding to messages."
United States
Julie L.
The price is €446
includes taxes & fees
1 Jan - 2 Jan 2026
Gator Getaway - Walk to Stadium!

Holiday Home in Gainesville

9.4 out of 10, Exceptional, (54)
"The place was clean and well maintained in general."
United States
Lina
The price is €185
includes taxes & fees
4 Jan - 5 Jan 2026
Tranquil Townhouse 🏡💤 - A peaceful retreat that promises restful slumber

Holiday Home in Citra

4.0 out of 10, (2)
"The property itself is nice, the tiny home sits in the back yard of a ranch/farm, so everything is quiet.The tiny home is a little quirky - the bathroom floor is weird and unstable, and one of the ladders is a bit of a pain to use. The property is clean and tastefully decorated, with overall nice amenities.We were VERY disappointed to learn that the hot tub - the biggest deciding factor for us choosing this listing - was "out of commission". The host never communicated this to us until we were...
United States
Olan S.
Enchanted Hideaway

Holiday Home in Duckpond

10.0 out of 10, Exceptional, (1)
"We had a great stay in this house. Very cute decorations…very well done. The house is older but very comfortable. A perfect amount of space for the 3 of us. Located close enough to everything but also far enough away from the craziness. "
United States
Jason C.
The price is €234
includes taxes & fees
7 Dec - 8 Dec
Underwater Home w/Game Room ~6 min to Stadium & Downtown / 2 King Beds &Fire Pit

Holiday Home in Gainesville

6.0 out of 10, (1)
"We were looking for a budget friendly stay that accommodated our dogs. This place checked those boxes. It was located in an older apartment complex close to a park and shopping. Air conditioning worked well and the shower had hot water. "
United States
Michele S.
The price is €332
includes taxes & fees
1 Jan - 2 Jan 2026
FAMILY/PET FRIENDLY, SPACIOUS AND QUIET HOME

Apartment in Gainesville

10.0 out of 10, Exceptional, (123)
"This place is an amazing find. Host is welcoming and you can tell how much pride he takes in his property. It is a quite spot close to, but away from the crowds at the University. We saw a momma deer and her two fawns, and found the tree frogs on the windows at night amusing. Definitely plan on staying again when Iwe are Gainesville. "
United States
Ann R.
Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use

Holiday Home in Gainesville

9.0 out of 10, Wonderful, (36)
"1st stay was freshman move in. Recent stay was senior graduation. Lots of room, good value and super amenities."
United States
Rob C.
The price is €185
includes taxes & fees
4 Jan - 5 Jan 2026
🌟 Modern House Minutes from Downtown Gainesville, UF, VA & More! 🏡✨

Cottage in Keystone Heights

7.4 out of 10, Good, (13)
"This was exactly what we were looking for- a nice, clean and quiet place. "
United States
Daniel
Rustic Lake View Cottage

Holiday Home in Gainesville

9.2 out of 10, Wonderful, (19)
"This was not a vacation for my family, so it was nice to come back to this comfortable home after a long day of clearing a relative's home."
United States
Teresa P.
The price is €237
includes taxes & fees
7 Dec - 8 Dec
4 Bedroom Single Family home 5 mins to University!

Condo in Gainesville

9.4 out of 10, Exceptional, (39)
"Excellent location!"
United States
Jaya C.
The price is €166
includes taxes & fees
4 Jan - 5 Jan 2026
🏡Comfy & Convenient 1BR Apartment Near Oaks Mall & Medical Center Fast WIFI
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.
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Top Windsor Hotel Reviews

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €127 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Windsor?

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

What are some of the best holiday rentals that Windsor has to offer?

CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV: This holiday home rental outside of Windsor offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Florida Museum of Natural History, or get outside and enjoy nature at Santa Fe Lake. Gainesville Raceway and University of Florida are a couple of places you'll find in the wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.