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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Windsor holiday rentals

A wooden dock with a chair, surrounded by trees and a calm water body.

1. Yearling Restaurant and Cabins

Yearling Restaurant and Cabins
2.5 star property
Hawthorne
9.2 out of 10, Wonderful, (215 reviews)
"Beautiful venue."
United States
Riley
The price is HK$1,090
HK$1,226 total
includes taxes & fees
22 Aug - 23 Aug
Yearling Restaurant and Cabins
A bedroom with a large bed, a ceiling fan, a desk with a chair, and a window with curtains.

2. Private suite with own entry in vibrant Gainesville

Private suite with own entry in vibrant Gainesville
Gainesville
9.8 out of 10, Exceptional, (23 reviews)
"What a great place to stay! Clean and in an absolutely beautiful neighborhood Bonus was the super friendly outdoor catWill definitely plan on staying again "
United States
Chris H.
The price is HK$470
HK$1,127 total
includes taxes & fees
24 Aug - 25 Aug
Private suite with own entry in vibrant Gainesville
A small, single-story RV-style accommodation with a covered porch and a visible kitchen area, surrounded by trees.

3. "La Grande" Retro Escape

"La Grande" Retro Escape
Gainesville
10.0 out of 10, Exceptional, (7 reviews)
"The host was very accommodating. Sweet place. "
United States
Deanne H.
The price is HK$580
HK$1,162 total
includes taxes & fees
31 Aug - 1 Sept
"La Grande" Retro Escape

4. Cheerful 4 bedroom house 8 min away from UF

Cheerful 4 bedroom house 8 min away from UF
Gainesville
9.0 out of 10, Wonderful, (9 reviews)
"The home was adorable and had plenty of room for the children to play. "
United States
Ni B.
The price is HK$1,058
HK$2,583 total
includes taxes & fees
22 Aug - 23 Aug
Cheerful 4 bedroom house 8 min away from UF
A porch with two chairs and a birdhouse.

5. Palmetto Cottage-1930’s Florida Cottage

Palmetto Cottage-1930’s Florida Cottage
Micanopy
9.8 out of 10, Exceptional, (60 reviews)
"Cute 1930’s cottage about 25 minutes from Gainesville."
United States
Michele W.
The price is HK$855
HK$1,820 total
includes taxes & fees
31 Aug - 1 Sept
Palmetto Cottage-1930’s Florida Cottage
A large, elegant house with a symmetrical facade, multiple entryways, and a well-maintained lawn.

6. Cheerful 2-BDRM/2.5 Bathroom Home Near DWTN & UF

Cheerful 2-BDRM/2.5 Bathroom Home Near DWTN & UF
Pleasant Street
10.0 out of 10, Exceptional, (61 reviews)
"Great location to downtown and campus! "
United States
Aubrey L.
The price is HK$612
HK$2,418 total
includes taxes & fees
22 Aug - 23 Aug
Cheerful 2-BDRM/2.5 Bathroom Home Near DWTN & UF
A cozy room with a red sofa, a small table with books, and a potted plant.

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

Charming 2-bedroom Cottage in Gainesville. 10 to UF
Gainesville
9.4 out of 10, Exceptional, (10 reviews)
"the amenities were great and the ac"
United States
Teneka G.
The price is HK$678
HK$1,745 total
includes taxes & fees
23 Aug - 24 Aug
Charming 2-bedroom Cottage in Gainesville. 10 to UF
A small, single-story house with a stone facade, a green porch, and a brick chimney.

8. GNV CHERT HOUSE - 1.5 miles to UF - 3 miles to Shands

GNV CHERT HOUSE - 1.5 miles to UF - 3 miles to Shands
Gainesville
9.0 out of 10, Wonderful, (4 reviews)
"Great place for our UF event"
United States
Jason
The price is HK$1,334
HK$1,941 total
includes taxes & fees
1 Sept - 2 Sept
GNV CHERT HOUSE - 1.5 miles to UF - 3 miles to Shands
A modern kitchen with stainless steel appliances, blue cabinets, and a wooden floor.

9. Underwater Home w/Game Room ~6 min to Stadium & DT

Underwater Home w/Game Room ~6 min to Stadium & DT
Duckpond
10.0 out of 10, Exceptional, (12 reviews)
"Enjoyed staying here with our family "
United States
umasudhan P.
The price is HK$855
HK$2,194 total
includes taxes & fees
25 Aug - 26 Aug
Underwater Home w/Game Room ~6 min to Stadium & DT
A cozy living room with a sofa, a dining area with chairs, a kitchen with a refrigerator, and a TV mounted on the wall.

10. Bass Fishing Paradise w/ Shared Dock in Hawthorne!

Bass Fishing Paradise w/ Shared Dock in Hawthorne!
Hawthorne
10.0 out of 10, Exceptional, (3 reviews)
"Thank you for letting us stay. We had a great time fishing."
United States
cheryl M.
The price is HK$761
HK$2,200 total
includes taxes & fees
23 Aug - 24 Aug
Bass Fishing Paradise w/ Shared Dock in Hawthorne!
A corner room with wooden flooring and large windows with white curtains.

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 HK$565
HK$2,016 total
includes taxes & fees
22 Aug - 23 Aug
Victorian Apt. w/ Tailgate Spot near Stadium!
A porch with two Adirondack chairs, a wooden door, and a sign reading "Downtown Studio Depot Village".

12. Pet friendly studio on 2nd level with a full bathroom and kitchen

Pet friendly studio on 2nd level with a full bathroom and kitchen
Gainesville
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for an overnight stay. We went to a Gator football game, so this was a good place to get some rest before the next days travel. Host was extremely quick to respond when contacted and was quite pleasant and helpful. "
United States
Pamela S.
The price is HK$582
HK$811 total
includes taxes & fees
23 Aug - 24 Aug
Pet friendly studio on 2nd level with a full bathroom and kitchen
A living room with a flat-screen TV mounted on the wall, a wooden entertainment unit below, and a glass coffee table with a decorative bowl.

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

🌟 Modern House Minutes from Downtown Gainesville, UF, VA & More! 🏡✨
Gainesville
9.0 out of 10, Wonderful, (41 reviews)
"Communication was great with host and house was very clean. Very close to Shands and the Swamp. Plenty of beds."
United States
Willie B.
The price is HK$670
HK$1,640 total
includes taxes & fees
23 Aug - 24 Aug
🌟 Modern House Minutes from Downtown Gainesville, UF, VA & More! 🏡✨
A covered outdoor seating area with wooden furniture and a table with fruit.

14. Serene Place, Walk to UF, Stadium, Near Shands & Downtown

Serene Place, Walk to UF, Stadium, Near Shands & Downtown
Gainesville
10.0 out of 10, Exceptional, (6 reviews)
"Great location near University of Florida. Cute place with everything you need. "
United States
Dennis D.
Serene Place, Walk to UF, Stadium, Near Shands & Downtown
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden ceiling.

15. Treehouse Suite: Walk DNTN | Lux Apt | Pet Welcome

Treehouse Suite: Walk DNTN | Lux Apt | Pet Welcome
Gainesville
9.0 out of 10, Wonderful, (30 reviews)
"The Depot Village Family were very responsive to my questions before arriving and for things needed while we were there! The location was super convenient to downtown and the campus. Would definitely stay again!! "
United States
Laura M.
The price is HK$2,150
HK$2,677 total
includes taxes & fees
19 Sept - 20 Sept
Treehouse Suite: Walk DNTN | Lux Apt | Pet Welcome
A breakfast tray with fruit, chocolate, and juice on a bed in a hotel room with a view of trees through a window.

16. The Canopy on 10th | Game Room • Pets • Pergola

The Canopy on 10th | Game Room • Pets • Pergola
Gainesville
10.0 out of 10, Exceptional, (13 reviews)
"Nice property, great location and good value."
United States
Sandra
The price is HK$870
HK$2,463 total
includes taxes & fees
23 Aug - 24 Aug
The Canopy on 10th | Game Room • Pets • Pergola
A modern kitchen with wooden cabinets, a glass dining table, and yellow chairs. There is a living area with a gray sofa and a blue chair.

17. Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar

Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar
4.0 star property
Gainesville
8.8 out of 10, Excellent, (11 reviews)
"Only would be improved if the blinds were darker. Some street noise but slept just fine."
United States
Bradley
The price is HK$965
HK$2,188 total
includes taxes & fees
23 Aug - 24 Aug
Grand Two Bedroom Two Bathroom Apartment with Balcony by The Scholar
A tree with a small door labeled "Welcome" and miniature figures including a gnome and a mushroom.

18. Duck Pond Getaway

Duck Pond Getaway
Duckpond
10.0 out of 10, Exceptional, (2 reviews)
"Great spot"
United States
Dayapradipa B.
The price is HK$907
HK$1,721 total
includes taxes & fees
24 Aug - 25 Aug
Duck Pond Getaway
A modern bedroom with two beds, a bedside table, a mirror, and a wardrobe.

19. Beautifully Designed Oasis - Blocks to UF Stadium!

Beautifully Designed Oasis - Blocks to UF Stadium!
Gainesville
9.8 out of 10, Exceptional, (22 reviews)
"House was absolutely perfect for our graduation weekend! Very clean and very cute! Location is outstanding!"
United States
Cherie J.
Beautifully Designed Oasis - Blocks to UF Stadium!
A two-story house with a porch, surrounded by trees and plants.

20. Juniper Cottage — In the Heart of Old Florida

Juniper Cottage — In the Heart of Old Florida
Micanopy
9.4 out of 10, Exceptional, (17 reviews)
"A charming cottage and town!"
United States
MARY
The price is HK$855
HK$1,821 total
includes taxes & fees
31 Aug - 1 Sept
Juniper Cottage — In the Heart of Old Florida
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

Drury Inn & Suites Gainesville

Drury Inn & Suites Gainesville

10/10 Excellent
"We stayed in a suite and it was so spacious. The hotel had very helpful staff. They offer happy hr and breakfast each day and the location was good"
Elyssa 2-night trip
Posted 5 hours ago
Drury Inn & Suites Gainesville

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

Private Beach & Dock! North Florida Lake House: This holiday home rental outside of Windsor is located on the waterfront, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 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.