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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Windsor holiday rentals

A bedroom with a large bed, a ceiling fan, a desk with a chair, and a window with curtains.

1. Private suite with own entry in vibrant Gainesville

Private suite with own entry in vibrant Gainesville
Gainesville
9.6 out of 10, Exceptional, (26 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 AU$209
includes taxes & fees
16 Oct - 17 Oct
Private suite with own entry in vibrant Gainesville
A compact, modern kitchen with wooden cabinets and a central island, a cozy bedroom with a large bed and bedside tables, and a patterned rug on the floor.

2. 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.
Central Studio Surrounded by Forest. Calm & Comfort
A wooden dock with a chair, surrounded by trees and a calm water body.

3. Yearling Restaurant and Cabins

Yearling Restaurant and Cabins
2.5 star property
Hawthorne
9.2 out of 10, Wonderful, (218 reviews)
"Beautiful venue."
United States
Riley
The price is AU$224
includes taxes & fees
15 Oct - 16 Oct
Yearling Restaurant and Cabins
A small, single-story RV-style accommodation with a covered porch and a visible kitchen area, surrounded by trees.

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 AU$232
includes taxes & fees
2 Nov - 3 Nov
Serene Vintage Farm Stay
A cozy room with a red sofa, a small table with books, and a potted plant.

5. 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 AU$313
includes taxes & fees
21 Oct - 22 Oct
Charming 2-bedroom Cottage in Gainesville. 10 to UF
A modern building with multiple floors, large windows, and a water feature in the foreground.

6. 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 AU$267
includes taxes & fees
9 Nov - 10 Nov
Go Gators Apartment + PS4 Console!
A modern kitchen with wooden cabinets, a central island, and pendant lighting.

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

Cute Condo Close to Campus - Walk to Shands/Pool!
Gainesville
8.8 out of 10, Excellent, (51 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 AU$331
includes taxes & fees
19 Oct - 20 Oct
Cute Condo Close to Campus - Walk to Shands/Pool!
A campfire in a grassy area with chairs and a tree nearby.

8. 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 AU$141
includes taxes & fees
22 Oct - 23 Oct
Shaanti Living • Cozy Studio Blue
A modern living room with a sofa, coffee table, and a dining area with a chair and table. There is a ceiling fan and a view of the outdoors through a sliding glass door.

9. 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 AU$393
includes taxes & fees
15 Oct - 16 Oct
Modern & Stylish Condo Near UF - Foxmoor
A kitchen with a sink, a microwave, and cabinets.

10. The Humming Bird Suite - Affordable Lakefront Fun

The Humming Bird Suite - Affordable Lakefront Fun
3.0 star property
Keystone Heights
The price is AU$176
includes taxes & fees
19 Oct - 20 Oct
The Humming Bird Suite - Affordable Lakefront Fun
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 AU$363
includes taxes & fees
15 Oct - 16 Oct
Victorian Apt. w/ Tailgate Spot near Stadium!
A modern museum building with a circular central section, a glass facade, and a sign reading 'CADE museum'.

12. 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 AU$284
includes taxes & fees
15 Oct - 16 Oct
Gainesville Fur Friendly Condo
Interior

13. 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 AU$458
includes taxes & fees
15 Oct - 16 Oct
Cheerful 4 bedroom house 8 min away from UF
A modern living room with a white dresser, a grey sofa, a TV, and a dining area with a table and chairs.

14. 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 AU$255
includes taxes & fees
19 Oct - 20 Oct
Stylish Studio in B&B Locale
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 AU$172
includes taxes & fees
19 Oct - 20 Oct
Treehouse Suite: Walk DNTN | Lux Apt | Pet Welcome
A large, elegant house with a symmetrical facade, multiple entryways, and a well-maintained lawn.

16. 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, (62 reviews)
"Great location to downtown and campus! "
United States
Aubrey L.
The price is AU$453
includes taxes & fees
16 Oct - 17 Oct
Cheerful 2-BDRM/2.5 Bathroom Home Near DWTN & UF
A living room with a sofa, a coffee table, a lamp, and a ceiling fan.

17. 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 AU$180
includes taxes & fees
15 Oct - 16 Oct
Great Location! Walk to Shands/UF/VA/Vet
A porch with two Adirondack chairs, a wooden door, and a sign reading "Downtown Studio Depot Village".

18. 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)
"We liked the location and the fact that we could walk to restaurants. We were able to have our little dog with us. Would stay again. The property managers were very nice and accommodating."
United States
Carolyn
The price is AU$152
includes taxes & fees
19 Oct - 20 Oct
Pet friendly studio on 2nd level with a full bathroom and kitchen
A modern kitchen with stainless steel appliances, granite countertops, and a tiled floor.

19. Funky MINI GOLF Home filled with Amenities

Funky MINI GOLF Home filled with Amenities
Gainesville
9.8 out of 10, Exceptional, (41 reviews)
"Clean, cosy and comfortable. My family had a great stay for a weekend trip!"
United States
Hussein B.
The price is AU$365
includes taxes & fees
15 Oct - 16 Oct
Funky MINI GOLF Home filled with Amenities
A swimming pool with a clear blue water feature, surrounded by a concrete deck and palm trees.

20. Botanical Retreat: King Comfort & Poolside Peace

Botanical Retreat: King Comfort & Poolside Peace
Gainesville
9.6 out of 10, Exceptional, (11 reviews)
"Apartment very clean, great location, safe and host is very responsive"
United States
Doug B.
The price is AU$315
includes taxes & fees
21 Oct - 22 Oct
Botanical Retreat: King Comfort & Poolside Peace
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

Hotel Indigo Gainesville-Celebration Pointe by IHG

Hotel Indigo Gainesville-Celebration Pointe by IHG

10/10 Excellent
"L"
Award Antonio 1-night trip
Posted 9 hours ago
Hotel Indigo Gainesville-Celebration Pointe by IHG

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$172 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Resort-Style Oasis, Pool, Lanai & Court – Backyard Paradise w/ BBQ: This holiday home rental outside of Windsor is located in the city centre, and has a patio, a garden 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 stovetop and a microwave, 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.