Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Windsor

Our top choices for Windsor vacation 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 ￥20,458
￥23,016 total
includes taxes & fees
Sep 3 - Sep 4
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 ￥16,043
￥34,170 total
includes taxes & fees
Sep 3 - Sep 4
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 ￥27,894
￥69,814 total
includes taxes & fees
Sep 17 - Sep 18
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 ￥13,982
￥40,494 total
includes taxes & fees
Sep 28 - Sep 29
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 ￥16,293
￥39,028 total
includes taxes & fees
Sep 3 - Sep 4
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 ￥12,069
￥27,284 total
includes taxes & fees
Sep 3 - Sep 4
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 ￥8,036
￥21,765 total
includes taxes & fees
Sep 21 - Sep 22
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 ￥11,922
￥28,774 total
includes taxes & fees
Sep 3 - Sep 4
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 ￥6,182
￥16,190 total
includes taxes & fees
Sep 3 - Sep 4
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 ￥9,581
￥33,998 total
includes taxes & fees
Sep 8 - Sep 9
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 ￥27,670
￥60,933 total
includes taxes & fees
Sep 8 - Sep 9
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 ￥6,623
￥16,356 total
includes taxes & fees
Sep 16 - Sep 17
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 ￥10,045
￥26,838 total
includes taxes & fees
Sep 3 - Sep 4
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. "
The price is ￥16,337
￥46,188 total
includes taxes & fees
Sep 3 - Sep 4
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

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, you can find vacation rentals close to popular sights in Windsor, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Windsor?

CHOMP HOUSE - 0.8m to Stadium, Pool, Sleeps 16, Mini Golf, Huge TV: This vacation home rental outside of Windsor offers a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 larger area.

What are vacation rentals like in Windsor?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.