Windsor Holiday Rentals

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Holiday Rentals in Windsor

Yearling Restaurant and Cabins
Premium bedding, individually decorated, individually furnished
Yearling Restaurant and Cabins
2.5 star property
9.2 out of 10, Wonderful, (156)
"We needed a nice cozy quiet place to spend the evening. We are so happy we chose The Yearling. We will be back!"
The price is HK$1,005
HK$1,131 total
includes taxes & fees
24 Sept - 25 Sept
Yearling Restaurant and Cabins
Crystal Lake Retreat
Property grounds
Crystal Lake Retreat
10.0 out of 10, Exceptional, (48)
"As advertised. No issues. Clean and well equipped. Very nice hosts. "
Crystal Lake Retreat
Palmetto Cottage-1930’s Florida Cottage
Terrace/patio
Palmetto Cottage-1930’s Florida Cottage
9.8 out of 10, Exceptional, (14)
"We loved it! Cannot wait to go again! "
The price is HK$771
HK$1,684 total
includes taxes & fees
24 Sept - 25 Sept
Palmetto Cottage-1930’s Florida Cottage
✨ 2 Master Suite Apartment near North Florida Regional Med, UF Health, & Mall ✨
Outdoor pool
✨ 2 Master Suite Apartment near North Florida Regional Med, UF Health, & Mall ✨
9.4 out of 10, Exceptional, (55)
"This condo was perfect for our stay. It was clean, priced right and perfectly located to restaurants, shopping and entertainment. We booked this for a week while we worked in town and our crew loved it. We will be back for the second portion of our project. "
The price is HK$771
HK$1,938 total
includes taxes & fees
29 Sept - 30 Sept
✨ 2 Master Suite Apartment near North Florida Regional Med, UF Health, & Mall ✨
Azalea Farmhouse
Exterior
Azalea Farmhouse
9.8 out of 10, Exceptional, (32)
"it was perfectly located for our weekend couldent have been better thanks Tracy"
The price is HK$849
HK$1,786 total
includes taxes & fees
24 Sept - 25 Sept
Azalea Farmhouse
Pool + Hot Tub in SW Gainesville. Always PET FRIENDLY.
Pool
Pool + Hot Tub in SW Gainesville. Always PET FRIENDLY.
9.8 out of 10, Exceptional, (38)
"Great host and was the perfect property and location for us to attend the UM vs UF game. Peaceful neighborhood that is located near many stores. Host was responsive and accommodating. Highly recommend. "
The price is HK$834
HK$2,768 total
includes taxes & fees
26 Sept - 27 Sept
Pool + Hot Tub in SW Gainesville. Always PET FRIENDLY.
Sunrise Family-Friendly Oasis with Pool. Bring the dogs.
Fridge, microwave, oven, stovetop
Sunrise Family-Friendly Oasis with Pool. Bring the dogs.
9.6 out of 10, Exceptional, (124)
"We stayed here with our entire family when we brought our oldest to University of Florida. It was about a 30 minute drive from the airport and about 20 minutes away from her dorm. With the car, it was easy to get everywhere we needed to be. There is a grocery store less than a mile away, which was helpful.. The inside of the house was very clean and the layout was perfect for our family. The beds were premade, and the house was stocked with basic necessities, like toilet paper, paper towels,...
Sunrise Family-Friendly Oasis with Pool. Bring the dogs.
Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use
Beach
Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use
10.0 out of 10, Exceptional, (97)
"Had a wonderful, restful stay. Enjoyed a brief history from the host and when I complemented him on his garden, he kindly gifted me with a favorite plant. I enjoyed every minute in this very private apartment, very comfortable bed and spacious shower. My tire pressure was low and Greg, the host, even went out of his way to fill my tire, going way above & beyond! Highly recommend! "
The price is HK$740
HK$1,208 total
includes taxes & fees
17 Oct - 18 Oct
Convene With Nature With First Class Amenities! Create Memories! - Free Bike Use
Modern, Fully Upgraded Home with BBQ and Firepit!
Fridge, microwave, oven, stovetop
Modern, Fully Upgraded Home with BBQ and Firepit!
10.0 out of 10, Exceptional, (29)
"House was extremely clean and well stocked. House was spacious and was just like being at home for our long stay. We brought our 2 German Shepherds who loved running around in the yard and exploring. House is very close to UF and made the back and forth to there very easy. We will definitely try and book the house again when we go up for weekends to see our Gator. "
Modern, Fully Upgraded Home with BBQ and Firepit!
Private Townhouse at Foxmoor - Only Blocks to UF
Property grounds
Private Townhouse at Foxmoor - Only Blocks to UF
9.2 out of 10, Wonderful, (42)
"the house was secluded and in a nice little area near the baseball field. the beds were comfortable and was cold, which we liked. the only bad things were the lack of cleanliness in the freezer, fridge, and counters. also, the towels shedded a lot on wet bodies, but wasn’t that much of a inconvenience. overall, we’d definitely stay again when we come back"
The price is HK$672
HK$1,592 total
includes taxes & fees
24 Sept - 25 Sept
Private Townhouse at Foxmoor - Only Blocks to UF
The Gator Get-Away
Smart TV
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 HK$818
HK$2,523 total
includes taxes & fees
30 Sept - 1 Oct
The Gator Get-Away
🌟 Prime Location for UF Visitors: 2BR Condo with Pool and Fast Wi-Fi ✨
Outdoor pool
🌟 Prime Location for UF Visitors: 2BR Condo with Pool and Fast Wi-Fi ✨
9.4 out of 10, Exceptional, (44)
"Older apartment but kept nice. Has what you need for a good stay. Water pressure was excellent!"
The price is HK$701
HK$1,851 total
includes taxes & fees
29 Sept - 30 Sept
🌟 Prime Location for UF Visitors: 2BR Condo with Pool and Fast Wi-Fi ✨
Palm View ~ Newly renovated quiet home close to UF!
Fridge, microwave, oven, stovetop
Palm View ~ Newly renovated quiet home close to UF!
10.0 out of 10, Exceptional, (26)
"Very pretty updated house that is pretty close to everything. Would definitely stay here again when I come visit my son here in Gainesville."
Palm View ~ Newly renovated quiet home close to UF!
Mid-century Home 2 miles to UF/Downtown/Shands & Walk to Coffee Culture
Fridge, microwave, oven, stovetop
Mid-century Home 2 miles to UF/Downtown/Shands & Walk to Coffee Culture
9.6 out of 10, Exceptional, (54)
"Brought me back in time with older home, nice change of pace"
The price is HK$888
HK$2,507 total
includes taxes & fees
24 Sept - 25 Sept
Mid-century Home 2 miles to UF/Downtown/Shands & Walk to Coffee Culture
Private pool in a spacious 3/2 NORTH FL home.
Outdoor pool
Private pool in a spacious 3/2 NORTH FL home.
7.6 out of 10, Good, (12)
"It was the perfect house for the 5 of us. Near my in-laws. The pool is fantastic, we spent most of our time outside. The kitchen has everything you need. Clean and comfortable. Thank you!everything you need"
Private pool in a spacious 3/2 NORTH FL home.
Remodeled Family Home w/ Patio - Walk to UF!
Fridge, microwave, stovetop, dishwasher
Remodeled Family Home w/ Patio - Walk to UF!
9.6 out of 10, Exceptional, (45)
"Our group was in town for an extended work trip and had a wonderful stay! The house had everything we needed and was a quiet place to relax after a long work day. We would definitely stay here again. "
Remodeled Family Home w/ Patio - Walk to UF!
Stylish and Comfortable Escape in Gainesville
Fridge, microwave, oven, stovetop
Stylish and Comfortable Escape in Gainesville
9.6 out of 10, Exceptional, (28)
"This was a great house. I needed a place to do focus and get some work done. Perfect. The backyard is great too. Thank you "
Stylish and Comfortable Escape in Gainesville
Quiet Condo – Short Walk to UF/Shands/Downtown!
Fridge, microwave, oven, stovetop
Quiet Condo – Short Walk to UF/Shands/Downtown!
8.4 out of 10, Very good, (20)
"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 HK$564
HK$1,794 total
includes taxes & fees
6 Oct - 7 Oct
Quiet Condo – Short Walk to UF/Shands/Downtown!
University House - 8 Bedrooms - Walk to UF / Stadium
Property grounds
University House - 8 Bedrooms - Walk to UF / Stadium
8.8 out of 10, Excellent, (18)
"This home was everything we needed for our group. It was comfortable and accomodated all of us together and allowed everyone to have space. Thank you for everything."
University House - 8 Bedrooms - Walk to UF / Stadium
Cute Condo Close to Campus - Walk to Shands/Pool!
Fridge, microwave, oven, stovetop
Cute Condo Close to Campus - Walk to Shands/Pool!
9.6 out of 10, Exceptional, (13)
"The decor is beautiful, beds comfy and amenities were just right. It's obvious that the apartment is older but very well updated. Plenty of toilet paper, paper towels and a little cleaning supplies to help clean throughout our stay. Could use more than 4 plates/bowls/forks/spoons... And towels... Was hoping for a broom but not provided. Nice to have the TV in the living room but could have used one in a bedroom when traveling with children. Pool was right across the quiet little street. Laundry...
The price is HK$573
HK$1,865 total
includes taxes & fees
25 Sept - 26 Sept
Cute Condo Close to Campus - Walk to Shands/Pool!
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See all available properties in Windsor
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

DoubleTree by Hilton Gainesville
Bar (on property)
DoubleTree by Hilton Gainesville
4.0 star property
8.0 out of 10, Very good, (1008)
"We have stayed here a number of times in the past. This is the first time on the first floor. The room seemed old and dingy. Our other rooms have never had an issue with humidity, but this room did. We really like the location of the hotel but not this particular room. "
The price is HK$702
HK$789 total
includes taxes & fees
30 Sept - 1 Oct
DoubleTree by Hilton Gainesville
hom hotel + suites, Trademark Collection by Wyndham
Lobby
hom hotel + suites, Trademark Collection by Wyndham
2.5 star property
8.4 out of 10, Very good, (1516)
"Always pleased with the service and room! "
The price is HK$596
HK$671 total
includes taxes & fees
25 Sept - 26 Sept
hom hotel + suites, Trademark Collection by Wyndham
Red Roof Inn PLUS+ Gainesville
Lobby lounge
Red Roof Inn PLUS+ Gainesville
2.5 star property
7.2 out of 10, Good, (1005)
"."
The price is HK$511
HK$574 total
includes taxes & fees
24 Sept - 25 Sept
Red Roof Inn PLUS+ Gainesville
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?

Pool + Hot Tub in SW Gainesville. Always PET FRIENDLY.: This holiday home rental outside of Windsor offers an outdoor pool, a balcony 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 1 hot tub.

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. 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.