Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

3.0 star property
The price is NZ$681
includes taxes & fees
26 Feb - 27 Feb
Hawthorne Angler's Cabin w/ Lake + Dock Access!
9.8 out of 10, Exceptional, (50 reviews)
"House was interesting and comfortable, location was perfect and I fell in love with Micanopy.."
United States
Robin
The price is NZ$381
includes taxes & fees
26 Feb - 27 Feb
Palmetto Cottage-1930’s Florida Cottage
2.5 star property
9.2 out of 10, Wonderful, (201 reviews)
"I stayed for one night and was happy with my cabin. It was clean and comfortable. The staff was friendly and welcoming, the check in process uncomplicated."
United States
Gabriele
The price is NZ$262
includes taxes & fees
26 Feb - 27 Feb
Yearling Restaurant and Cabins
9.6 out of 10, Exceptional, (14 reviews)
"Awesome location, great cabin! Had everything I needed to see my family ❤️ Will request to stay again!"
United States
Bonnie
The price is NZ$398
includes taxes & fees
26 Feb - 27 Feb
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing

Holiday Home in Fort McCoy

Wilderness Getaway at The Grist Mill
10.0 out of 10, Exceptional, (1 review)
"This was the cutest place to stay for our honeymoon! The staff was so kind and left us a bottle of wine. It was a quiet secluded area. If you’re ready to unplug and unwind this was perfect. Cell service works totally fine but who needs it when you’re in such a wonderful location! There was a grill and lots of extra amenities in the mill and the lodge. We had a wonderful time and wish we could have stayed longer!! "
United States
David
The price is NZ$411
includes taxes & fees
1 Mar - 2 Mar
Wilderness Getaway at The Grist Mill

Aparthotel in Newberry

Landing Apartments Newberry
4.0 star property
10.0 out of 10, Exceptional, (49 reviews)
"Great stay very clean better than any hotel around the area "
United States
Diogenes
The price is NZ$458
includes taxes & fees
22 Mar - 23 Mar
Landing Apartments Newberry
8.4 out of 10, Very good, (16 reviews)
"Work trip, good place to sleep and relax"
United States
Anonymous traveller
The price is NZ$314
includes taxes & fees
23 Mar - 24 Mar
Gainesville Cozy Pet friendly Near UF & Downtown, Family Getaway. Pet Friendly w/BBQ Grill & Patio
10.0 out of 10, Exceptional, (1 review)
"Was a great place to unwind after a long day at work. Very relaxing, very quiet"
United States
Matthew g.
The price is NZ$216
includes taxes & fees
8 Mar - 9 Mar
Charming 1-bedroom house with AC, WiFi in welcoming Melrose

Apartment in Fort McCoy

The Thoroughbred
The price is NZ$345
includes taxes & fees
9 Mar - 10 Mar
The Thoroughbred
10.0 out of 10, Exceptional, (6 reviews)
"Great location for UF families. Very clean and nice. We had everything we needed in the kitchen. Great communication from host. Would stay there again."
United States
Lene
Serene Place | Walk to UF • Free Parking • Kitchen
9.8 out of 10, Exceptional, (6 reviews)
"Great location and comfortable. Loved the pickleball court! "
United States
Jeannette T.
The price is NZ$326
includes taxes & fees
1 Mar - 2 Mar
La Casita: Charming 1-bedroom house in Gainesville w/ pickleball court!
3.0 star property
The price is NZ$510
includes taxes & fees
3 Mar - 4 Mar
3 Mi to UF: Townhome w/ Patio in Gainesville!

Holiday Home in Gainesville

Fantastic Find in Finley Woods
9.8 out of 10, Exceptional, (52 reviews)
"Great spot close to UF, quiet nice neighborhood. Spot is accurate to description and very nice. Great master tub!"
United States
Ed S.
The price is NZ$417
includes taxes & fees
10 Mar - 11 Mar
Fantastic Find in Finley Woods
10.0 out of 10, Exceptional, (33 reviews)
"Really nice place. Comfortable, clean. "
United States
Ellen S.
The price is NZ$370
includes taxes & fees
2 Mar - 3 Mar
The Farmhouse at Oaks | Full Kitchen • Near I75

Holiday Home in Fort McCoy

Relaxing Lakefront Cottage
10.0 out of 10, Exceptional, (16 reviews)
"We thoroughly enjoyed our stay!"
United States
Jennifer C.
The price is NZ$447
includes taxes & fees
1 Mar - 2 Mar
Relaxing Lakefront Cottage

Apartment in Haile Plantation

Gainesville Hideaway
9.6 out of 10, Exceptional, (12 reviews)
"Great location and a great place to stay, especially if the market is in town. "
United States
chad s.
The price is NZ$528
includes taxes & fees
10 Mar - 11 Mar
Gainesville Hideaway
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic home! Very welcoming and quaint! Loved our stay! Thank you so mich foe bwing a wonderful host!"
United States
Jessica N.
The price is NZ$453
includes taxes & fees
26 Feb - 27 Feb
Northwood Estate, 15min from UF, sleeps 9, recently renovated!

Mobile Home in Gainesville

"La Grande" Retro Escape
10.0 out of 10, Exceptional, (4 reviews)
"The host was very accommodating. Sweet place. "
United States
Deanne H.
The price is NZ$258
includes taxes & fees
10 Mar - 11 Mar
"La Grande" Retro Escape
10.0 out of 10, Exceptional, (36 reviews)
"Beautiful house, comfortable stay and the host is super responsive. Would definitely recommend staying here when in Gainesville!"
United States
Lori C.
The price is NZ$666
includes taxes & fees
11 Mar - 12 Mar
Luxurious Home in Upscale Neighborhood. EV Charger. Furnished backyard patio.
9.4 out of 10, Exceptional, (14 reviews)
"We really enjoyed the proximity to Publix and UF! The grill and outdoor space were also terrific!"
United States
Anonymous traveller
The price is NZ$519
includes taxes & fees
10 Mar - 11 Mar
Modern Home Near UF, Stadium - Private Gazebo, Pets!
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

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 favorite 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 depends 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 NZ$241 per night. Entering your travel dates in the search wizard you might find 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?

Family-Friendly Gainesville Home - Walk to UF - Pool + Sleeps 16: This holiday home rental outside of Windsor offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable 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. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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.