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Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

1. Private suite with own entry in vibrant Gainesville

Private suite with own entry in vibrant Gainesville
Gainesville
9.6 out of 10, Exceptional, (27 reviews)
"We loved our weekend stay. The room is so adorable and comfortable. The host immediately replies to your messages and is so kind. The rental is just a few minutes from the stadium making it great for Gator games. We would love to return in the future."
United States
Ashley
The price is CA $84
CA $201 total
includes taxes & fees
Nov 1 - Nov 2
Private suite with own entry in vibrant Gainesville

2. Shands Hospital Guesthouse - Free Parking

Shands Hospital Guesthouse - Free Parking
Gainesville
8.0 out of 10, Very good, (14 reviews)
"It was a perfect cozy spot. Hot shower and comfortable bed. I’m in Gainesville from time to time and live in Tampa, so this was the perfect spot! Will stay here again if available next time I’m in town."
United States
Gabrielle R.
The price is CA $73
CA $228 total
includes taxes & fees
Oct 27 - Oct 28
Shands Hospital Guesthouse - Free Parking

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

Cute Condo Close to Campus - Walk to Shands/Pool!
Gainesville
9.0 out of 10, Wonderful, (52 reviews)
"Clean and close to UF which is exactly what we needed. Communication with the host was prompt and efficient. We will stay again if available."
United States
Dereka
The price is CA $91
CA $322 total
includes taxes & fees
Oct 27 - Oct 28
Cute Condo Close to Campus - Walk to Shands/Pool!

4. Serene Vintage Farm Stay

Serene Vintage Farm Stay
Gainesville
10.0 out of 10, Exceptional, (8 reviews)
"Such a cute place! We had the best time!"
United States
Diane
The price is CA $111
CA $223 total
includes taxes & fees
Nov 2 - Nov 3
Serene Vintage Farm Stay

5. Yearling Restaurant and Cabins

Yearling Restaurant and Cabins
2.5 star property
Hawthorne
9.2 out of 10, Wonderful, (220 reviews)
"Beautiful venue."
United States
Riley
The price is CA $195
CA $219 total
includes taxes & fees
Oct 27 - Oct 28
Yearling Restaurant and Cabins

6. Charming 2-bedroom Cottage in Gainesville. 10 to UF

Charming 2-bedroom Cottage in Gainesville. 10 to UF
Gainesville
9.6 out of 10, Exceptional, (11 reviews)
"the amenities were great and the ac"
United States
Teneka G.
The price is CA $113
CA $302 total
includes taxes & fees
Oct 27 - Oct 28
Charming 2-bedroom Cottage in Gainesville. 10 to UF

7. Go Gators Apartment + PS4 Console!

Go Gators Apartment + PS4 Console!
Gainesville
9.0 out of 10, Wonderful, (13 reviews)
"Excellent place to stay and great location to everything! Will definitely book again."
United States
Michelle
The price is CA $81
CA $255 total
includes taxes & fees
Nov 11 - Nov 12
Go Gators Apartment + PS4 Console!

8. Stylish Studio in B&B Locale

Stylish Studio in B&B Locale
Gainesville
8.8 out of 10, Excellent, (23 reviews)
"Great property!"
United States
Jim M.
The price is CA $75
CA $245 total
includes taxes & fees
Oct 27 - Oct 28
Stylish Studio in B&B Locale

9. Gainesville Fur Friendly Condo

Gainesville Fur Friendly Condo
Gainesville
9.6 out of 10, Exceptional, (27 reviews)
"Clean rooms, close to the Downtown area. Great place to stay if you're visiting Gainesville."
United States
Clay F.
The price is CA $108
CA $311 total
includes taxes & fees
Nov 8 - Nov 9
Gainesville Fur Friendly Condo

10. Central Studio Surrounded by Forest. Calm & Comfort

Central Studio Surrounded by Forest. Calm & Comfort
Gainesville
9.6 out of 10, Exceptional, (5 reviews)
"Amazing stay! Totally private place, very clean, and walking distance to town. Host was amazing as well and replied quickly to any questions I had"
United States
Olivia M.
The price is CA $101
CA $220 total
includes taxes & fees
Oct 28 - Oct 29
Central Studio Surrounded by Forest. Calm & Comfort

11. Victorian Apt. w/ Tailgate Spot near Stadium!

Victorian Apt. w/ Tailgate Spot near Stadium!
Duckpond
9.8 out of 10, Exceptional, (7 reviews)
"This property is clean and spacious- and within walking distance to downtown Gainesville. There’s also plenty of street parking available - even on the weekend. "
United States
Jeanna J.
The price is CA $101
CA $357 total
includes taxes & fees
Oct 27 - Oct 28
Victorian Apt. w/ Tailgate Spot near Stadium!

12. Beautiful Home Walk to UF Newly built

Beautiful Home Walk to UF Newly built
Gainesville
10.0 out of 10, Exceptional, (14 reviews)
"Great stay!"
United States
Emily L.
The price is CA $98
CA $312 total
includes taxes & fees
Nov 1 - Nov 2
Beautiful Home Walk to UF Newly built

13. Modern & Stylish Condo Near UF - Foxmoor

Modern & Stylish Condo Near UF - Foxmoor
Gainesville
9.8 out of 10, Exceptional, (7 reviews)
"Our stayed was amazing, I love the place, you have everything you need, even shampoo and conditiones that was a plus, thank you"
United States
Monica
The price is CA $99
CA $388 total
includes taxes & fees
Oct 27 - Oct 28
Modern & Stylish Condo Near UF - Foxmoor

14. 🏡Comfy & Convenient 1BR Apartment Near Oaks Mall & Medical Center Fast WIFI

🏡Comfy & Convenient 1BR Apartment Near Oaks Mall & Medical Center Fast WIFI
Gainesville
9.4 out of 10, Exceptional, (43 reviews)
"Very clean and host provides for all of the basic needs. The location was perfect and has everything you need close by. Quiet location."
United States
Anonymous traveller
The price is CA $88
CA $253 total
includes taxes & fees
Oct 27 - Oct 28
🏡Comfy & Convenient 1BR Apartment Near Oaks Mall & Medical Center Fast WIFI

15. Shaanti Living • Cozy Studio Blue

Shaanti Living • Cozy Studio Blue
Melrose
10.0 out of 10, Exceptional, (4 reviews)
"Best place ever"
United States
Kevin
The price is CA $97
CA $135 total
includes taxes & fees
Oct 28 - Oct 29
Shaanti Living • Cozy Studio Blue

16. Great Location! Walk to Shands/UF/VA/Vet

Great Location! Walk to Shands/UF/VA/Vet
Gainesville
8.8 out of 10, Excellent, (29 reviews)
"Nice place for a quick stay in Gainsville."
United States
Nicole T.
The price is CA $101
CA $173 total
includes taxes & fees
Oct 27 - Oct 28
Great Location! Walk to Shands/UF/VA/Vet

17. Neat Condo - Short Walk to UF!

Neat Condo - Short Walk to UF!
Gainesville
8.8 out of 10, Excellent, (3 reviews)
"Very clean, well maintained apt. The bed was way too soft for me. Had to sleep on the couch which was a high end, luxurious soft leather couch. Info in notebook was very helpful. It's quite a walk to UF campus . Glad I had a car."
United States
Chris C.
The price is CA $93
CA $290 total
includes taxes & fees
Oct 29 - Oct 30
Neat Condo - Short Walk to UF!

18. The Humming Bird Suite - Affordable Lakefront Fun

The Humming Bird Suite - Affordable Lakefront Fun
Keystone Heights
10.0 out of 10, Exceptional, (4 reviews)
"Nice cozy stay and exactly what we were looking for. Communication with the owner was unmatched. Very accommodating and friendly."
United States
Preston F.
The price is CA $73
CA $184 total
includes taxes & fees
Oct 27 - Oct 28
The Humming Bird Suite - Affordable Lakefront Fun

19. The Farmhouse at Oaks | Full Kitchen • Near I75

The Farmhouse at Oaks | Full Kitchen • Near I75
Gainesville
10.0 out of 10, Exceptional, (37 reviews)
"Excellent - very spacious and conveniently located!"
United States
Lawrence H.
The price is CA $108
CA $307 total
includes taxes & fees
Oct 27 - Oct 28
The Farmhouse at Oaks | Full Kitchen • Near I75

20. Cheerful 4 bedroom house 8 min away from UF

Cheerful 4 bedroom house 8 min away from UF
Gainesville
9.2 out of 10, Wonderful, (11 reviews)
"Our stay was wonderful. The place nice and well stocked"
United States
nasir s.
The price is CA $189
CA $457 total
includes taxes & fees
Oct 27 - Oct 28
Cheerful 4 bedroom house 8 min away from UF
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Private Resort-Style Oasis, Pool, Lanai & Court – Backyard Paradise w/ BBQ: This vacation home rental outside of Windsor is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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 Santa Fe Lake. Gainesville Raceway and University of Florida 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.