Windsor Holiday Rentals

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Holiday Rentals in Windsor

Yearling Restaurant and Cabins

2.5 star property
9.2 out of 10, Wonderful, (189)
"The property was very quite and relaxing. The restaurant at the property was great."
The price is NZ$267
includes taxes & fees
23 Sept - 24 Sept
Yearling Restaurant and Cabins

Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar

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."
The price is NZ$453
includes taxes & fees
23 Sept - 24 Sept
Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar

Stylish Studio in B&B Locale

9.6 out of 10, Exceptional, (9)
"House was a great affordable place to stay for the weekend near food, grocery, and shopping."
The price is NZ$276
includes taxes & fees
25 Sept - 26 Sept
Stylish Studio in B&B Locale

"La Grande" Retro Escape

10.0 out of 10, Exceptional, (1)
"Our family enjoyed Le Grande retro escape. The kids didn’t complain about it so win win. "
The price is NZ$203
includes taxes & fees
23 Sept - 24 Sept
"La Grande" Retro Escape

4 Bedroom Single Family home 5 mins to University!

9.4 out of 10, Exceptional, (16)
"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."
The price is NZ$467
includes taxes & fees
28 Sept - 29 Sept
4 Bedroom Single Family home 5 mins to University!

Palmetto Cottage-1930’s Florida Cottage

9.8 out of 10, Exceptional, (38)
"Cute place. Would definitely stay here again "
The price is NZ$396
includes taxes & fees
29 Sept - 30 Sept
Palmetto Cottage-1930’s Florida Cottage

Cute Condo Close to Campus - Walk to Shands/Pool!

8.6 out of 10, Excellent, (32)
"This is a wonderful property and the host was extremely helpful, both before our arrival and during our time there. I stayed there with two colleagues during a conference at the university. The kitchen was perfect to have a lovely hot breakfast each morning and we were in easy walking distance from our work and restaurants. The beds are very comfortable and the surroundings are very quiet. We had a fabulous time and hope to rent again if work gets us back there. "
The price is NZ$394
includes taxes & fees
30 Sept - 1 Oct
Cute Condo Close to Campus - Walk to Shands/Pool!

Cheerful 4 bedroom house 8 min away from UF

8.8 out of 10, Excellent, (6)
"Great spot to stay with a group! We enjoyed hanging out on the patio and there was plenty of space for everyone."
The price is NZ$561
includes taxes & fees
23 Sept - 24 Sept
Cheerful 4 bedroom house 8 min away from UF

CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV

9.6 out of 10, Exceptional, (13)
"Nice location and quiet neighborhood. Property manager has great communication and was quick to respond to questions"
The price is NZ$748
includes taxes & fees
23 Sept - 24 Sept
CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV

Juniper Cottage — In the Heart of Old Florida

9.0 out of 10, Wonderful, (12)
"Great respite after hiking and exploring Devils Den and Micanopy. "
The price is NZ$395
includes taxes & fees
28 Sept - 29 Sept
Juniper Cottage — In the Heart of Old Florida

Sleek condo UF crossing

9.2 out of 10, Wonderful, (19)
"This condo is very clean and conveniently located to UF, restaurants, and shopping. Communication with the property manager was excellent."
The price is NZ$322
includes taxes & fees
23 Sept - 24 Sept
Sleek condo UF crossing

Amazing 2br 2ba with Loft C

2.0 star property
10.0 out of 10, Exceptional, (3)
"Convenient location. Good 2/2 option. "
The price is NZ$379
includes taxes & fees
25 Sept - 26 Sept
Amazing 2br 2ba with Loft C

The Monterey -- Private Pool & Grill - 4 KING Beds

2.0 star property
10.0 out of 10, Exceptional, (7)
"Great location, quite neighborhood, very nice an clean!"
The price is NZ$717
includes taxes & fees
1 Oct - 2 Oct
The Monterey -- Private Pool & Grill - 4 KING Beds

Tiny Victorian built on TV show 2br 1 ba

2.0 star property
8.4 out of 10, Very good, (9)
"Very cool property close to everything. Super cool house. Highly recommend."
The price is NZ$383
includes taxes & fees
23 Sept - 24 Sept
Tiny Victorian built on TV show 2br 1 ba

PREMIER LOCATION - UF / Shands / Gainesville. Closest Condo to Campus!

10.0 out of 10, Exceptional, (14)
"Exactly what we needed for a weekend in Gainesville. We will definitely stay here again!"
PREMIER LOCATION - UF / Shands / Gainesville. Closest Condo to Campus!

Private pool in a spacious 3/2 NORTH FL home.

7.6 out of 10, Good, (27)
"Good location close but far enough from the city, quite place, spacious with plenty of room, big pool, beds seemed fine "
Private pool in a spacious 3/2 NORTH FL home.

Hidden Lake Sprawling Home on Private Lake with optional Guest House close to UF

9.8 out of 10, Exceptional, (58)
"Stayed with several family members for graduation. Kitchen had everything you could need and main living space was great for gatherings "
Hidden Lake Sprawling Home on Private Lake with optional Guest House close to UF

Gainesville Getaway-Hot Tub

8.0 out of 10, Very good, (1)
"This is property is close to UF with 4 bedrooms and 2 bathrooms. It’s a great place to stay for UF football games etc. The hot tub is big enough for two people. The owner was responsive to questions and flexible with our check in time. It was clean with plenty of towels and linens. "
The price is NZ$625
includes taxes & fees
23 Sept - 24 Sept
Gainesville Getaway-Hot Tub

Tranquil Townhouse 🏡💤 - A peaceful retreat that promises restful slumber

9.4 out of 10, Exceptional, (54)
"The place was clean and well maintained in general."
The price is NZ$388
includes taxes & fees
28 Sept - 29 Sept
Tranquil Townhouse 🏡💤 - A peaceful retreat that promises restful slumber

The Floridian. Newly Built Dreamhome, Central

10.0 out of 10, Exceptional, (39)
"My bridesmaids and I stayed here the night before my wedding, which was held at a venue right around the corner. The host was super nice and available, and the house was very clean and organized. Perfect place!"
The price is NZ$392
includes taxes & fees
13 Oct - 14 Oct
The Floridian. Newly Built Dreamhome, Central
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

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, 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 NZ$203 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 University of Florida Bat Houses. Thomas Center and Gainesville Raceway 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.