Holiday Rentals in Windsor

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Holiday Rentals in Windsor

Yearling Restaurant and Cabins

2.5 star property
9.2 out of 10, Wonderful, (162)
"The hotel and restaurant are wonderful. The location is remote so cell phones have a hard time but the rooms have TVs and WiFi. The Restaurant is amazing lots of history the menu includes some great southern food, Free Range Venison with hunter sauce is one of my favs. The location is beside Cross Creek a location to sit and watch a sunset before going to the bar. Be sure to look in the library it is something lots of books, stuffed animals and a canoe. This is a piece of history."
The price is €138
includes taxes & fees
20 Dec - 21 Dec
Yearling Restaurant and Cabins

Crystal Lake Retreat

10.0 out of 10, Exceptional, (49)
"This was a peaceful place and had beautiful views of the lake. If you're trying to get away from a busy city - stay here. The decor is nice, beds were comfy and the host was attentive. She thought of everything!"
Crystal Lake Retreat

Mid-century Home 2 miles to UF/Downtown/Shands & Walk to Coffee Culture

9.6 out of 10, Exceptional, (56)
"Brought me back in time with older home, nice change of pace"
Mid-century Home 2 miles to UF/Downtown/Shands & Walk to Coffee Culture

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

10.0 out of 10, Exceptional, (102)
"This apartment is full of culture; art of multiple mediums and historical memorabilia, passed down through generations. The grounds are beautiful and quiet. And the shower is amazing! I wish I’d booked a longer visit. Hope to stay here again."
Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use

2BR Across UF/Shands – Walk to Campus & Hospitals!

9.0 out of 10, Wonderful, (12)
"Lance was responsive and the unit was clean. A little tricky to find in the apartment complex, but Lance provided great instructions and response time. "
The price is €192
includes taxes & fees
15 Dec - 16 Dec
2BR Across UF/Shands – Walk to Campus & Hospitals!

Palmetto Cottage-1930’s Florida Cottage

9.8 out of 10, Exceptional, (16)
"Beautiful house with a nice yard. Spent the weekend there for a Gator game. Worth the stay, will be back another weekend. "
The price is €208
includes taxes & fees
15 Dec - 16 Dec
Palmetto Cottage-1930’s Florida Cottage

✨ 2 Master Suite Apartment near North Florida Regional Med, UF Health, & Mall ✨

9.2 out of 10, Wonderful, (61)
"If you are looking for a weekend trip to UF for a Gator game or other UF event this is a great place to stay. Located right of I-75 and convenient to the Oaks Mall and looks of quality restaurants. The rental unit is quiet, clean and enjoyable."
The price is €238
includes taxes & fees
15 Dec - 16 Dec
✨ 2 Master Suite Apartment near North Florida Regional Med, UF Health, & Mall ✨

Remodeled Family Home w/ Patio - Walk to UF!

9.8 out of 10, Exceptional, (49)
"We were a group of UF alumni coming back for a football game and this was a great house. The location was perfect- close to Publix, midtown, and campus. The snacks and coffee were a nice touch and the kitchen was well-outfitted with enough cups and dishes for such a large group. The lock was tricky sometimes and the futons were not very comfortable but we were able to work it out. The host was very responsive and flexible with check in. "
Remodeled Family Home w/ Patio - Walk to UF!

Azalea Farmhouse

9.8 out of 10, Exceptional, (36)
"Great place to unwind and catch the elusive largemouth bass."
The price is €220
includes taxes & fees
15 Dec - 16 Dec
Azalea Farmhouse

Modern, Fully Upgraded Home with BBQ and Firepit!

10.0 out of 10, Exceptional, (33)
"My daughters and I needed a place to stay as we were displaced from Hurricane Milton. The house was great. We had plenty of room, there are a variety of games available. The location made it easy to get onto the main roads. There is a very large backyard with a nice deck and bistro lights which made the stay even more home like. I would highly recommend it."
Modern, Fully Upgraded Home with BBQ and Firepit!

Beautiful Lake House on Cowpen Lake w/Private Fishing Pond Boat Rental Available

10.0 out of 10, Exceptional, (126)
"Beautiful property ! The outdoor kitchen is perfect ! The property owners are amazing ! "
Beautiful Lake House on Cowpen Lake w/Private Fishing Pond Boat Rental Available

Sunrise Family-Friendly Oasis with Pool. Bring the dogs.

9.6 out of 10, Exceptional, (127)
"I booked this for me and some friends to go to a Gators Football game. We didn’t use the pool but it was nice to lay outside by it. The house was clean and only a 15 minute uber to campus, which was great. It was perfect for what we needed!"
Sunrise Family-Friendly Oasis with Pool. Bring the dogs.

Four Bedroom Pool Home - Bring Your Pets!

9.8 out of 10, Exceptional, (39)
"We had a great stay. The house was VERY clean; would not have been able to tell you if many pets had been there in the past as everything was so well kept. Location was great in a quiet neighborhood. Would def stay here again in the future. "
The price is €423
includes taxes & fees
12 Jan - 13 Jan 2025
Four Bedroom Pool Home - Bring Your Pets!

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 €194
includes taxes & fees
17 Dec - 18 Dec
Private pool in a spacious 3/2 NORTH FL home.

🌊TIDE + TAILGATE 🏈 - Hot Tub, Sleeps 12, Arcades, Cowboy Pool, Mini Golf

9.8 out of 10, Exceptional, (7)
"I recently stayed at this VRBO and had a great experience. The house was exactly as shown in the photos—exceptionally clean and well-maintained. The host was very responsive and communicated well. The location was convenient for accessing UF campus and town, which I appreciated. Overall, I would recommend this property for its cleanliness and amenities."
The price is €300
includes taxes & fees
16 Dec - 17 Dec
🌊TIDE + TAILGATE 🏈 - Hot Tub, Sleeps 12, Arcades, Cowboy Pool, Mini Golf

Quiet Condo – Short Walk to UF/Shands/Downtown!

8.0 out of 10, Very good, (21)
"Close by to everything. Easy to get to. Older condo but nice. Pool on the property is small. Owner was great in responding to my messages!"
The price is €214
includes taxes & fees
19 Dec - 20 Dec
Quiet Condo – Short Walk to UF/Shands/Downtown!

3 Mi to UF: Townhome w/ Patio in Gainesville!

9.6 out of 10, Exceptional, (11)
"We came in for UF game. This place did what it needed to do. It is pretty dated but clean. They provide lots of amenities like Keurig coffee, toiletries, paper towels , nice toilet paper etc. So we didn't have to run to the store for the stay. We had trouble with the door code but that was rectified immediately. The plugs in the two bedrooms upstairs wouldn't work even after GFI push and breaker switching. They did come immediately and fix this. Overall it was all ok."
3 Mi to UF: Townhome w/ Patio in Gainesville!

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 €312
includes taxes & fees
15 Dec - 16 Dec
The Gator Get-Away

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

8.6 out of 10, Excellent, (18)
"Everything was great, convenient to campus and other amenities. "
The price is €233
includes taxes & fees
23 Dec - 24 Dec
Cute Condo Close to Campus - Walk to Shands/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 €226
includes taxes & fees
5 Jan - 6 Jan 2025
🌟 Modern House Minutes from Downtown Gainesville, UF, VA & More! 🏡✨
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

Red Roof Inn PLUS+ Gainesville

2.5 star property
7.2 out of 10, Good, (1006)
"Nice customer service and the room were clean "
The price is €75
includes taxes & fees
16 Dec - 17 Dec
Red Roof Inn PLUS+ Gainesville

Hotel Eleo at the University of Florida

3.0 star property
9.4 out of 10, Exceptional, (1186)
"One of the nicer hotels in Gainesville. Convenient to UF. Covey Kitchen restaurant is very good, especially for breakfast. Excellent omelette and grits. "
The price is €172
includes taxes & fees
16 Dec - 17 Dec
Hotel Eleo at the University of Florida

Comfort Inn University

2.5 star property
8.0 out of 10, Very good, (1004)
"I kept on hearing people let their door slam. Kinda inconsiderate, especially if it’s after 9 PM."
The price is €81
includes taxes & fees
29 Dec - 30 Dec
Comfort Inn University
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?

Mid-century Home 2 miles to UF/Downtown/Shands & Walk to Coffee Culture: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself 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 Santa Fe Lake. 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.