Windsor Holiday Rentals

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Holiday Rentals in Windsor

White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing

2.0 star property
Keystone Heights
9.6 out of 10, Exceptional, (13)
"Awesome location, great cabin! Had everything I needed to see my family ❤️ Will request to stay again!"
United States
Bonnie
The price is NZ$345
includes taxes & fees
17 Nov - 18 Nov
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing

Yearling Restaurant and Cabins

2.5 star property
Hawthorne
9.2 out of 10, Wonderful, (195)
"Cabin was very comfortable and clean. Everything was in order and working. "
United States
Philip
The price is NZ$276
includes taxes & fees
15 Nov - 16 Nov
Yearling Restaurant and Cabins

Fish from own dock or in Palatka, Visit Ocala National Forest, FU Gators 30+ min

Hawthorne
10.0 out of 10, Exceptional, (19)
"Everything was great. Owner of the property is the best."
United States
Brian R.
The price is NZ$533
includes taxes & fees
23 Nov - 24 Nov
Fish from own dock or in Palatka, Visit Ocala National Forest, FU Gators 30+ min

Palmetto Cottage-1930’s Florida Cottage

Micanopy
9.8 out of 10, Exceptional, (41)
"The place was adorable. Loved the cemetery across the street. Very pretty area on road off the cemetery. Nice walk in the morning. Saw deer and a bunch of cattle. "
United States
Joan
The price is NZ$408
includes taxes & fees
16 Nov - 17 Nov
Palmetto Cottage-1930’s Florida Cottage

Juniper Cottage — In the Heart of Old Florida

Micanopy
9.2 out of 10, Wonderful, (13)
"Great respite after hiking and exploring Devils Den and Micanopy. "
United States
Sharone
The price is NZ$403
includes taxes & fees
17 Nov - 18 Nov
Juniper Cottage — In the Heart of Old Florida

Private suite with own entry in vibrant Gainesville

Gainesville
10.0 out of 10, Exceptional, (4)
"I came down from NY to spend time with my bf for my birthday, and this place was spectacular! It's spacious and clean. They had given us coffee and tea for the espresso maker! Even had shampoo and soap in the bathroom for me! If there was anything I needed, they responded very quickly and we're super helpful. The entire stay was private and if I saw them I got to waive and say hello. The place was very secure with good locks. The little stone path was super cute. Like going to a cozy cabin....
United States
Kristen J.
The price is NZ$254
includes taxes & fees
19 Nov - 20 Nov
Private suite with own entry in vibrant Gainesville

Relaxing Lakefront Escape with Hot Tub, Fire Pit, Kayaks & Paddle Boards

Interlachen
10.0 out of 10, Exceptional, (4)
"Perfect stay! The home was spotless, cozy, and had everything we needed. Great location, beautiful views, extremely clean and a fantastic host. Highly recommend!"
United States
Francisco J.
The price is NZ$699
includes taxes & fees
17 Nov - 18 Nov
Relaxing Lakefront Escape with Hot Tub, Fire Pit, Kayaks & Paddle Boards

Orange Blossom in Historic McIntosh

McIntosh
10.0 out of 10, Exceptional, (103)
"Great property, good for a private get away. A bonus if you are a fisherman with its relative location to surrounding lakes! Highly recommended. "
United States
Stefan
The price is NZ$408
includes taxes & fees
16 Nov - 17 Nov
Orange Blossom in Historic McIntosh

3Bd 2Bath home 5 miles to Stadium/Campus/Downtown!

Gainesville
9.2 out of 10, Wonderful, (11)
"Property is very nice and clean in a quiet neighborhood. I will certainly book with this host again whenever possible"
United States
Shannon M.
The price is NZ$637
includes taxes & fees
16 Nov - 17 Nov
3Bd 2Bath home 5 miles to Stadium/Campus/Downtown!

Go Gators Apartment + PS4 Console!

Gainesville
9.0 out of 10, Wonderful, (2)
"Pros: David was very responsive. The unit itself was clean, and the location was close to the university and restaurants/shopping. Cons: The apartment complex is very old and the area felt a little sketchy. "
United States
Carmen C.
The price is NZ$346
includes taxes & fees
18 Nov - 19 Nov
Go Gators Apartment + PS4 Console!

Modern & Stylish Condo Near UF - Foxmoor

Gainesville
9.6 out of 10, Exceptional, (5)
"It was nice, would definitely come back. "
United States
Owen M.
The price is NZ$499
includes taxes & fees
19 Nov - 20 Nov
Modern & Stylish Condo Near UF - Foxmoor

Neat Condo - Short Walk to UF!

Gainesville
10.0 out of 10, Exceptional, (1)
"This condo was in the perfect location for an easy walk to and from UF campus. Response from the property manager was excellent, timely, and offered assistance when needed. Nightly rate was phenomenal in comparison to other lodging around and I would book this condo again in a heartbeat over everything else in the area!"
United States
Heather
The price is NZ$339
includes taxes & fees
16 Nov - 17 Nov
Neat Condo - Short Walk to UF!

Gainesville Game Day Home with Patio and Grill!

Gainesville
9.0 out of 10, Wonderful, (20)
"We stayed there for a softball tournament and it was perfect. Super close to U of F field. Communication with host was great and we even extended our stay! Highly recommend!!"
United States
Nikki P.
The price is NZ$1,524
includes taxes & fees
27 Nov - 28 Nov
Gainesville Game Day Home with Patio and Grill!

Spacious 3BR/2Bath Downtown Gem w/ HUGE Yard • Firepit • Grill

Gainesville
10.0 out of 10, Exceptional, (2)
"Check in was seamless, great place for the price! The beds were very comfortable, owner Jeff was very attentive and accommodating!The place was spotless & much bigger than we expected. Quiet neighborhood, close to everything. Will definitely stay there again !"
United States
paige b.
The price is NZ$380
includes taxes & fees
17 Nov - 18 Nov
Spacious 3BR/2Bath Downtown Gem w/ HUGE Yard • Firepit • Grill

Chic Condo w/ Community Pool - Under 10 mins to UF

Gainesville
8.0 out of 10, Very good, (4)
"Very nice, location was great, owner was quick to answer messages, will definitely rent again."
United States
Chris C.
The price is NZ$479
includes taxes & fees
16 Nov - 17 Nov
Chic Condo w/ Community Pool - Under 10 mins to UF

Hidden Retreat with Yard, Patio, and BBQ Close to UF or Downtown Gainesville

Gainesville
10.0 out of 10, Exceptional, (32)
"We will definitely try to stay here again! Very clean and comfortable."
United States
Jerry D.
The price is NZ$684
includes taxes & fees
30 Nov - 1 Dec
Hidden Retreat with Yard, Patio, and BBQ Close to UF or Downtown Gainesville

La Casita: Charming 1-bedroom house in Gainesville w/ pickleball court!

Gainesville
10.0 out of 10, Exceptional, (1)
"This property was just what we needed for a place to stay after going to the UF game. Easy to find and located close enough to campus (not walking distamce though) for us. It was a quick turnarpund for us, but if we need to stay another time longer i would definitely want to stay here again."
United States
Christi R.
The price is NZ$343
includes taxes & fees
16 Nov - 17 Nov
La Casita: Charming 1-bedroom house in Gainesville w/ pickleball court!

Beautiful Home | Walk to UF | Newly built

2.0 star property
Gainesville
10.0 out of 10, Exceptional, (3)
"This property was as described. We had a great stay. Disha was a fantastic host."
United States
Tara C.
The price is NZ$398
includes taxes & fees
19 Nov - 20 Nov
Beautiful Home | Walk to UF | Newly built

Azalea Farmhouse

McIntosh
9.8 out of 10, Exceptional, (47)
"This is a great spot for a couple to stay while visiting Orange Lake."
United States
Quinn B.
The price is NZ$403
includes taxes & fees
18 Nov - 19 Nov
Azalea Farmhouse

Hidden Cabin Retreat with Private Deck & Firepit

2.5 star property
Gainesville
9.4 out of 10, Exceptional, (6)
"We had a great stay. House is exactly as described. It was perfect for our family and dog. Awesome secluded neighborhood. Great communication with host, very responsive. Will stay here again!"
United States
Joe C.
The price is NZ$533
includes taxes & fees
20 Nov - 21 Nov
Hidden Cabin Retreat with Private Deck & Firepit
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$233 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?

The Pond House! Large Pool, 10 sleeps, Pool Table, Firepit, 10 min UF: This holiday home rental outside of Windsor is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 patio, 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 University of Florida Bat Houses. Thomas Center 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.