Holiday Rentals in Windsor

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

Yearling Restaurant and Cabins
Premium bedding, individually decorated, individually furnished

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 €134
includes taxes & fees
15 Sept - 16 Sept
Yearling Restaurant and Cabins
Palmetto Cottage-1930’s Florida Cottage
Property grounds

Palmetto Cottage-1930’s Florida Cottage

9.8 out of 10, Exceptional, (38)
"The place was adorable. Loved the cemetery across the street. Very pretty area on road off the cemetery. Nice walk in the morning. Saw deer and a bunch of cattle. "
The price is €204
includes taxes & fees
3 Sept - 4 Sept
Palmetto Cottage-1930’s Florida Cottage
CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV
Pool

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

9.6 out of 10, Exceptional, (12)
"Wonderful stay here in the house. Had everything we needed. Really loved the bunk room for our teenagers. Perfect little getaway. Thank you "
The price is €413
includes taxes & fees
16 Sept - 17 Sept
CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV
4 Bedroom Single Family home 5 mins to University!
Fridge, microwave, oven, stovetop

4 Bedroom Single Family home 5 mins to University!

9.4 out of 10, Exceptional, (15)
"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 €264
includes taxes & fees
3 Sept - 4 Sept
4 Bedroom Single Family home 5 mins to University!
Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar
Luxury Apartment | In-room dining

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 €227
includes taxes & fees
3 Sept - 4 Sept
Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar
Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use
Property grounds

Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use

10.0 out of 10, Exceptional, (117)
"Greg was so friendly and made sure we had everything we needed. I would absolutely suggest staying here!"
Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use
Belong Downtown 1br 1ba
Fridge, microwave, oven, stovetop

Belong Downtown 1br 1ba

2.0 star property
9.6 out of 10, Exceptional, (7)
"Clean and perfect for my dog."
The price is €162
includes taxes & fees
3 Sept - 4 Sept
Belong Downtown 1br 1ba
Private pool in a spacious 3/2 NORTH FL home.
Outdoor pool

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

7.8 out of 10, Good, (25)
"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.
Stylish Studio in B&B Locale
TV

Stylish Studio in B&B Locale

9.6 out of 10, Exceptional, (4)
"House was a great affordable place to stay for the weekend near food, grocery, and shopping."
The price is €130
includes taxes & fees
21 Sept - 22 Sept
Stylish Studio in B&B Locale
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
Outdoor dining

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 €171
includes taxes & fees
3 Sept - 4 Sept
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
Rm Sun with two twin beds and a private bath near UF/Shands H, & B. Plaza
Fridge, microwave, oven, stovetop

Rm Sun with two twin beds and a private bath near UF/Shands H, & B. Plaza

8.4 out of 10, Very good, (6)
"The place was rather hard to find with Google maps. Room smelled like a locker room, never could figure out why. Would definitely stay there again."
The price is €98
includes taxes & fees
3 Sept - 4 Sept
Rm Sun with two twin beds and a private bath near UF/Shands H, & B. Plaza
Cute Condo Close to Campus - Walk to Shands/Pool!
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (31)
"Everything was great, convenient to campus and other amenities. "
The price is €202
includes taxes & fees
8 Sept - 9 Sept
Cute Condo Close to Campus - Walk to Shands/Pool!
Remodeled Vintage Private Home. <5 min to UF and Downtown
Terrace/patio

Remodeled Vintage Private Home. <5 min to UF and Downtown

10.0 out of 10, Exceptional, (49)
"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
Charming 2-bedroom apartment with WiFi, fitness room in terrific Gainesville
Outdoor dining

Charming 2-bedroom apartment with WiFi, fitness room in terrific Gainesville

2.0 out of 10, (2)
"Was doubled booked and left without a place to stay. Horrible communication and still haven’t received a refund."
Charming 2-bedroom apartment with WiFi, fitness room in terrific Gainesville
Gator Alumni House, 2 Miles From Campus
3 bedrooms, desk, iron/ironing board, free WiFi

Gator Alumni House, 2 Miles From Campus

9.8 out of 10, Exceptional, (80)
"Great stay and awesome location. "
The price is €362
includes taxes & fees
8 Sept - 9 Sept
Gator Alumni House, 2 Miles From Campus
Rm Moon Q-size Bed and Private bath/TV, a cozy space near I-75, UF, and Shands H
Fridge, microwave, oven, stovetop

Rm Moon Q-size Bed and Private bath/TV, a cozy space near I-75, UF, and Shands H

8.0 out of 10, Very good, (5)
"This is an affordable place for 2 w a shared kitchen and common area in a great location. Clean and furnished w pans and utensils for cooking, with full size refrigerator and stove/oven. Owners responsive and available."
The price is €99
includes taxes & fees
16 Sept - 17 Sept
Rm Moon Q-size Bed and Private bath/TV, a cozy space near I-75, UF, and Shands H
Sleek condo UF crossing
Fridge, coffee/tea maker

Sleek condo UF crossing

9.0 out of 10, Wonderful, (18)
"This condo is very clean and conveniently located to UF, restaurants, and shopping. Communication with the property manager was excellent."
The price is €160
includes taxes & fees
3 Sept - 4 Sept
Sleek condo UF crossing
Gator Den 6 Bedrooms Steps to UF
Dining

Gator Den 6 Bedrooms Steps to UF

9.6 out of 10, Exceptional, (24)
"We were in town for a wedding and this home had everything we needed. I will definitely look at this place again when I'm in town "
Gator Den 6 Bedrooms Steps to UF
2 Miles to UF & DT - Pergola, Fire Pit, Game Room
Terrace/patio

2 Miles to UF & DT - Pergola, Fire Pit, Game Room

10.0 out of 10, Exceptional, (6)
"It was a very nice place. The outside sitting area was a nice area for our family to hang out and relax. The check in and check out procedures were very easy. "
2 Miles to UF & DT - Pergola, Fire Pit, Game Room
University House - 8 Bedrooms - Walk to UF / Stadium
Property grounds

University House - 8 Bedrooms - Walk to UF / Stadium

9.0 out of 10, Wonderful, (32)
"family together for a wedding"
University House - 8 Bedrooms - Walk to UF / Stadium
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, 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 €98 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.