Windsor Holiday Rentals

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Holiday Rentals in Windsor

Palmetto Cottage-1930’s Florida Cottage

10.0 out of 10, Exceptional, (22)
"This is a clean well kept house in a quiet location. The hosts were very accommodating and did an excellent job communicating check in and other details. "
The price is AU$349
includes taxes & fees
9 Feb - 10 Feb
Palmetto Cottage-1930’s Florida Cottage

Yearling Restaurant and Cabins

2.5 star property
9.2 out of 10, Wonderful, (166)
"Loved the experience of the Yearling! Spotless cabins "
The price is AU$249
includes taxes & fees
13 Feb - 14 Feb
Yearling Restaurant and Cabins

4 Bedroom Single Family home 5 mins to University!

9.4 out of 10, Exceptional, (12)
"Stayed for just one night after the UF football game. Very short drive to campus and a quick drive to go back downtown. The house was clean and spacious for our group of 4 adults "
The price is AU$443
includes taxes & fees
23 Feb - 24 Feb
4 Bedroom Single Family home 5 mins to University!

Trendy Bungalow mins to Colleges & Downtown Gainesville

8.4 out of 10, Very good, (5)
"Very comfortable bungalow close to UF. Nice amenities. Bring all necessary food and condiments though as kitchen is bare of pantry items. No olive oil or cooking spray for pan. Nice floor plan bath tub deep for nice soak.Enjoyed the location to hiking trails and parks.Many restaurants close by as well."
The price is AU$413
includes taxes & fees
10 Mar - 11 Mar
Trendy Bungalow mins to Colleges & Downtown Gainesville

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

7.8 out of 10, Good, (16)
"Quiet, spacious, clean, comfortable, easy access, friendly neighborhood, quick responses from management, plenty towels and a privacy fence that blocks out the rest of the world. Can't wait to come back. Any previous negative reviews, have since been addressed. "
The price is AU$325
includes taxes & fees
10 Feb - 11 Feb
Private pool in a spacious 3/2 NORTH FL home.

Funky MINI GOLF Home filled with Amenities

10.0 out of 10, Exceptional, (29)
"Great Trip!"
The price is AU$339
includes taxes & fees
18 Feb - 19 Feb
Funky MINI GOLF Home filled with Amenities

Tranquil Townhouse 🏡💤 - A peaceful retreat that promises restful slumber

9.4 out of 10, Exceptional, (41)
"Very well kept property and perfect for our needs. The host was awesome with communications and the property has the essentials. Very clean."
The price is AU$373
includes taxes & fees
9 Mar - 10 Mar
Tranquil Townhouse 🏡💤 - A peaceful retreat that promises restful slumber

🏝️The Oasis w/ New Salt Pool | Walk to Publix & Restaurants | 1 Mile to UF🏝️

10.0 out of 10, Exceptional, (26)
"HerMy stay was fantastic! The cozy home was perfectly located, close to everything I needed. It was thoughtfully equipped with all the right amenities, making it feel just like home. The host was incredibly responsive and genuinely caring, ensuring a comfortable and seamless experience. Recommend if staying in Gainsville!"
🏝️The Oasis w/ New Salt Pool | Walk to Publix & Restaurants | 1 Mile to UF🏝️

Peaceful renovated house centrally located

10.0 out of 10, Exceptional, (4)
"We made an overnight trip to Gainesville to pick up a puppy and stayed here. Check in was easy, house was clean."
The price is AU$461
includes taxes & fees
13 Feb - 14 Feb
Peaceful renovated house centrally located

Pet Friendly Townhouse Near I-75

9.4 out of 10, Exceptional, (9)
"The town house was clean, and had most of what we needed. We were there for two weeks. The area is very run down, and the neighbors are very loud and there was something fishy going on next door. Not the owner’s fault."
Pet Friendly Townhouse Near I-75

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

10.0 out of 10, Exceptional, (106)
"We came to Gainesville to visit the local state parks. Greg's apartment was the perfect place to stay in the area. Great neighborhood and very comfortable apartment. Highly recommend. "
Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use

❈❈ Spacious Condo with balcony mins to UF, Shands, and DOWNTOWN ❈❈

9.6 out of 10, Exceptional, (21)
"The place was clean and comfortable. The property owner went above and beyond to make our stay wonderful - including ordering a crock pot for us to use so we didn’t have to haul ours down. Appreciated the space to spread out. Nice beds, comfy couch!"
The price is AU$484
includes taxes & fees
9 Feb - 10 Feb
❈❈ Spacious Condo with balcony mins to UF, Shands, and DOWNTOWN ❈❈

The Gator Get-Away

8.4 out of 10, Very good, (7)
"Communication with the owner was great. The interior was nice and clean with the exception of minor bug issues. Stay was definitely worth the price. Location wasn’t great but we had no issues in that aspect. "
The price is AU$502
includes taxes & fees
10 Mar - 11 Mar
The Gator Get-Away

Gator Nest - Huge Backyard + 30 Min to Springs!

8.0 out of 10, Very good, (14)
"Flexible sleeping arrangements to accommodate family. Inside was clean. Outside could use some cleanup. Parking was limited but had retail center across street. "
The price is AU$482
includes taxes & fees
9 Feb - 10 Feb
Gator Nest - Huge Backyard + 30 Min to Springs!

Spacious Micanopy Farmhouse w/ Luxurious Pool!

8.0 out of 10, Very good, (2)
"Overall it was okay. This is a farmhouse in an isolated and quiet area. We arrived onto a working horse farm. It was not clear where the house was located and people just looked at us oddly without offer to help. There is no driveway up to house, you drive through the farm/grass. The farmhouse is simply finished and very rustic. It was livable clean, but not the cleanest in every corner - there were many dusty surfaces, rooms were damp because only half of the building had AC, cupboards were...
Spacious Micanopy Farmhouse w/ Luxurious Pool!

🌟 Modern House Minutes from Downtown Gainesville, UF, VA & More! 🏡✨

9.0 out of 10, Wonderful, (32)
"We had a quick one night stay. Liked the neighborhood — very close to a nice park for running in the morning and close to breweries and restaurants."
The price is AU$374
includes taxes & fees
9 Feb - 10 Feb
🌟 Modern House Minutes from Downtown Gainesville, UF, VA & More! 🏡✨

Gator Pool and Hot Tub House -1.5 miles to Stadium

10.0 out of 10, Exceptional, (9)
"This place was great, could use a few more stays sobthe house can rack up odds and ends lol...but great stay "
Gator Pool and Hot Tub House -1.5 miles to Stadium

Modern, Fully Upgraded Home with BBQ and Firepit!

10.0 out of 10, Exceptional, (37)
"This is a nice place and with a few updates I'd give it five stars. The beds were comfortable. Layout nice and though the shower isn't large it has great water pressure. There's no coffee table in the living so no place to put down your coffee or a drink. Also no tea kettle. I guess these are minor things but they would add to the rental property. We never got a chance to use the fire pit. "
Modern, Fully Upgraded Home with BBQ and Firepit!

Florida Room: Walk DNTN | Studio | Lux Bath | Pet Welcome

10.0 out of 10, Exceptional, (1)
"We absolutely loved this place, the location was great, the room was so cute, the hosts were super friendly and helpful. "
The price is AU$257
includes taxes & fees
10 Feb - 11 Feb
Florida Room: Walk DNTN | Studio | Lux Bath | Pet Welcome

Pet-Friendly 2BR Condo Next to North Florida Hospital

9.2 out of 10, Wonderful, (62)
"Clean, perfect layout for gandparents and 15-18 yr.grankids. Wanted home environment to play cards, fix meals, and reconnect. We visit once a year and this was perfect."
The price is AU$374
includes taxes & fees
9 Mar - 10 Mar
Pet-Friendly 2BR Condo Next to North Florida Hospital
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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Other types of properties in Windsor you may be interested in

Country Inn & Suites by Radisson, Gainesville, FL

3.0 star property
9.0 out of 10, Wonderful, (1219)
"Clean"
The price is AU$174
includes taxes & fees
2 Mar - 3 Mar
Country Inn & Suites by Radisson, Gainesville, FL

Hyatt Place Gainesville Downtown

3.0 star property
9.2 out of 10, Wonderful, (785)
"Somewhat noisy from street noise and parking is an issue. Other than that, nice place."
The price is AU$224
includes taxes & fees
10 Feb - 11 Feb
Hyatt Place Gainesville Downtown

Best Western Gateway Grand

3.0 star property
8.8 out of 10, Excellent, (1100)
"Very Nice& quiet "
The price is AU$185
includes taxes & fees
9 Feb - 10 Feb
Best Western Gateway Grand
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.

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?

Trendy Bungalow mins to Colleges & Downtown Gainesville: This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Paynes Prairie Preserve State Park. Hippodrome State Theatre 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.