Windsor Vacation Rentals

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

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."
$139 nightly
The price is $156
Sep 1 - Sep 2
Total with taxes and fees
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. "
$211 nightly
The price is $232
Sep 1 - Sep 2
Total with taxes and fees
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 "
$413 nightly
The price is $458
Sep 16 - Sep 17
Total with taxes and fees
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."
$245 nightly
The price is $273
Sep 28 - Sep 29
Total with taxes and fees
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."
$248 nightly
The price is $279
Sep 1 - Sep 2
Total with taxes and fees
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."
$168 nightly
The price is $186
Sep 2 - Sep 3
Total with taxes and fees
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 "
$191 nightly
The price is $212
Sep 1 - Sep 2
Total with taxes and fees
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."
$143 nightly
The price is $146
Sep 2 - Sep 3
Total with taxes and fees
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!"
$176 nightly
The price is $196
Sep 3 - Sep 4
Total with taxes and fees
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."
$100 nightly
The price is $110
Sep 2 - Sep 3
Total with taxes and fees
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. "
$208 nightly
The price is $231
Sep 1 - Sep 2
Total with taxes and fees
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. "
$457 nightly
The price is $507
Sep 1 - Sep 2
Total with taxes and fees
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."
$101 nightly
The price is $111
Sep 16 - Sep 17
Total with taxes and fees
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."
$180 nightly
The price is $184
Sep 1 - Sep 2
Total with taxes and fees
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. "
$297 nightly
The price is $318
Sep 1 - Sep 2
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Find out more about Windsor

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $110 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.