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 AU$242
includes taxes & fees
14 Oct - 15 Oct
Yearling Restaurant and Cabins
The Pond House! Large Pool, 10 sleeps, Pool Table, Firepit, 10 min UF
10.0 out of 10, Exceptional, (33)
"Relaxing atmosphere and well-equipped home for a crowd. "
The price is AU$974
includes taxes & fees
14 Oct - 15 Oct
The Pond House! Large Pool, 10 sleeps, Pool Table, Firepit, 10 min UF
Palmetto Cottage-1930’s Florida Cottage
9.8 out of 10, Exceptional, (39)
"Cute place. Would definitely stay here again "
The price is AU$361
includes taxes & fees
20 Oct - 21 Oct
Palmetto Cottage-1930’s Florida Cottage
Private suite with own entry in vibrant Gainesville
10.0 out of 10, Exceptional, (3)
"A great location and a great space. Very quiet house and a great bed! Highly recommend. "
The price is AU$225
includes taxes & fees
14 Oct - 15 Oct
Private suite with own entry in vibrant Gainesville
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 AU$403
includes taxes & fees
10 Nov - 11 Nov
Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar
The Lotus Suite. Newly Built, Upscale, Central
10.0 out of 10, Exceptional, (16)
"Our family stopped here for our first night back from an off the grid houseboat trip and could not have been more pleased. The decor, the appointments, the laundry, the proximity to great food… I hope the kids go to U of F so we can stay here again ;)"
The price is AU$325
includes taxes & fees
5 Nov - 6 Nov
The Lotus Suite. Newly Built, Upscale, Central
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 AU$348
includes taxes & fees
19 Oct - 20 Oct
Tranquil Townhouse 🏡💤 - A peaceful retreat that promises restful slumber
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
4 Bedroom Single Family home 5 mins to University!
9.0 out of 10, Wonderful, (17)
"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 AU$422
includes taxes & fees
19 Oct - 20 Oct
4 Bedroom Single Family home 5 mins to University!
"La Grande" Retro Escape
10.0 out of 10, Exceptional, (2)
The price is AU$165
includes taxes & fees
20 Oct - 21 Oct
"La Grande" Retro Escape
University House - 8 Bedrooms - Walk to UF / Stadium
9.0 out of 10, Wonderful, (32)
"We loved the size of the house, perfect for a large family. The pool needs some work but we didn’t use it. "
University House - 8 Bedrooms - Walk to UF / Stadium
Raceway Retreat, just 12 miles from UF/downtown, relaxing country getaway!
10.0 out of 10, Exceptional, (1)
"Property was just as listed. Just 1 one night stop over for us. Thought about going and watching some local racing, but rain prevailed. Anyone actually planning trip for a race weekend. This just might he your place"
The price is AU$347
includes taxes & fees
1 Nov - 2 Nov
Raceway Retreat, just 12 miles from UF/downtown, relaxing country getaway!
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 AU$251
includes taxes & fees
2 Nov - 3 Nov
Stylish Studio in B&B Locale
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
2.0 star property
9.4 out of 10, Exceptional, (9)
"Sweet family visit in Keystone Heights!"
The price is AU$268
includes taxes & fees
14 Oct - 15 Oct
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV
9.6 out of 10, Exceptional, (14)
"Nice location and quiet neighborhood. Property manager has great communication and was quick to respond to questions"
The price is AU$723
includes taxes & fees
28 Oct - 29 Oct
CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV
Remodeled Vintage Private Home. <5 min to UF and Downtown
9.8 out of 10, Exceptional, (51)
"Just what we needed for a weekend stay in Gainesville. We would stay again for sure. "
Remodeled Vintage Private Home. <5 min to UF and Downtown
❈❈ Spacious Condo with balcony mins to UF, Shands, and DOWNTOWN ❈❈
9.4 out of 10, Exceptional, (34)
"Check in was easy, communication was great. Perfect location for us during our stay in Gainesville."
The price is AU$468
includes taxes & fees
8 Nov - 9 Nov
❈❈ Spacious Condo with balcony mins to UF, Shands, and DOWNTOWN ❈❈
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 AU$343
includes taxes & fees
20 Oct - 21 Oct
Amazing 2br 2ba with Loft C
Great Location! Walk to Shands/UF/VA/Vet
8.8 out of 10, Excellent, (16)
"The apartment was extremely clean and perfect for a game day stay. We will definitely stay again. "
The price is AU$194
includes taxes & fees
14 Oct - 15 Oct
Great Location! Walk to Shands/UF/VA/Vet
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 AU$564
includes taxes & fees
14 Oct - 15 Oct
The Monterey -- Private Pool & Grill - 4 KING Beds
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, 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 favourite 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 depend 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 AU$165 per night. Entering your travel dates in the search wizard might find you 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?

4 Bedroom Single Family home 5 mins to University!: This holiday home rental outside of Windsor offers an outdoor pool, a balcony and air conditioning 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 and your friends and family can relax into your holiday with amenities such as an arcade/games room.

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.