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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Windsor vacation rentals

1 bedroom, iron/ironing board, WiFi, bed sheets

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.
$130 nightly
The price is $144
Jul 26 - Jul 27
Total with taxes and fees
Private suite with own entry in vibrant Gainesville
View from property

Yearling Restaurant and Cabins

Yearling Restaurant and Cabins
2.5 star property
Hawthorne
9.2 out of 10, Wonderful, (212 reviews)
"The Yearling Cabins are somewhat remote. I planned my stay around a guided tour at the Marjorie Kinnan Rawlings State park and dining at the Yearling Restaurant."
United States
Sarah
$139 nightly
The price is $156
Jul 25 - Jul 26
Total with taxes and fees
Yearling Restaurant and Cabins
Exterior

"La Grande" Retro Escape

"La Grande" Retro Escape
Gainesville
10.0 out of 10, Exceptional, (5 reviews)
"The host was very accommodating. Sweet place. "
United States
Deanne H.
$139 nightly
The price is $154
Jul 30 - Jul 31
Total with taxes and fees
"La Grande" Retro Escape
TV, books

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.
$177 nightly
The price is $188
Aug 3 - Aug 4
Total with taxes and fees
Stylish Studio in B&B Locale
Coffee/tea maker, fridge, microwave, toaster

The Humming Bird Suite - Affordable Lakefront Fun

The Humming Bird Suite - Affordable Lakefront Fun
Keystone Heights
10.0 out of 10, Exceptional, (3 reviews)
"Nice cozy stay and exactly what we were looking for. Communication with the owner was unmatched. Very accommodating and friendly."
United States
Preston F.
$128 nightly
The price is $142
Jul 29 - Jul 30
Total with taxes and fees
The Humming Bird Suite - Affordable Lakefront Fun
Terrace/patio

Palmetto Cottage-1930’s Florida Cottage

Palmetto Cottage-1930’s Florida Cottage
Micanopy
9.8 out of 10, Exceptional, (60 reviews)
"We have stayed here several times and have always been very satisfied. The host is very good at responding to any questions and needs. "
United States
Jayne S.
$207 nightly
The price is $228
Jul 26 - Jul 27
Total with taxes and fees
Palmetto Cottage-1930’s Florida Cottage
TV

Bass Fishing Paradise w/ Shared Dock in Hawthorne!

Bass Fishing Paradise w/ Shared Dock in Hawthorne!
Hawthorne
10.0 out of 10, Exceptional, (2 reviews)
"Thank you for letting us stay. We had a great time fishing."
United States
cheryl M.
$272 nightly
The price is $302
Aug 2 - Aug 3
Total with taxes and fees
Bass Fishing Paradise w/ Shared Dock in Hawthorne!
TV

Hawthorne Angler's Cabin w/ Lake + Dock Access!

Hawthorne Angler's Cabin w/ Lake + Dock Access!
Hawthorne
10.0 out of 10, Exceptional, (2 reviews)
"It's a beautiful property with peacocks wildlife and not too far from Gainesville very relaxing"
United States
John W.
$272 nightly
The price is $302
Jul 26 - Jul 27
Total with taxes and fees
Hawthorne Angler's Cabin w/ Lake + Dock Access!
Property grounds

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
$100 nightly
The price is $109
Aug 11 - Aug 12
Total with taxes and fees
Shaanti Living • Cozy Studio Blue
Interior

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.
$237 nightly
The price is $246
Jul 25 - Jul 26
Total with taxes and fees
Victorian Apt. w/ Tailgate Spot near Stadium!
Exterior

Go Gators Apartment + PS4 Console!

Go Gators Apartment + PS4 Console!
Gainesville
9.2 out of 10, Wonderful, (12 reviews)
"Excellent place to stay and great location to everything! Will definitely book again."
United States
Michelle
$198 nightly
The price is $210
Jul 26 - Jul 27
Total with taxes and fees
Go Gators Apartment + PS4 Console!
Interior

🌟 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, (39 reviews)
"We had cockroach issues, the door handle kept breaking off on the front door and locking after 5 seconds, no coffee pods for keurig, and lack of kitchen towels supplies.Sheets were amazing and beds were comfortable."
United States
Rebecca S.
$189 nightly
The price is $209
Jul 26 - Jul 27
Total with taxes and fees
🌟 Modern House Minutes from Downtown Gainesville, UF, VA & More! 🏡✨
Interior

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.
$284 nightly
The price is $317
Jul 25 - Jul 26
Total with taxes and fees
Cheerful 4 bedroom house 8 min away from UF
Terrace/patio

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, (5 reviews)
"Great location near University of Florida. Cute place with everything you need. "
United States
Dennis D.
$186 nightly
The price is $197
Jul 26 - Jul 27
Total with taxes and fees
Serene Place, Walk to UF, Stadium, Near Shands & Downtown
Exterior

Gainesville Fur Friendly Condo Ping Pong Table

Gainesville Fur Friendly Condo Ping Pong Table
Gainesville
9.6 out of 10, Exceptional, (27 reviews)
"So close to the University and all places I wanted to see. Communication with host was outstanding. "
United States
Christy
$210 nightly
The price is $210
Aug 4 - Aug 5
Total with taxes and fees
Gainesville Fur Friendly Condo Ping Pong Table
Smart TV, offices

Fantastic Find in Finley Woods

Fantastic Find in Finley Woods
Gainesville
9.8 out of 10, Exceptional, (65 reviews)
"Beautiful place. Very clean with all amenities needed on hand. "
United States
Marissa B.
$228 nightly
The price is $253
Jul 26 - Jul 27
Total with taxes and fees
Fantastic Find in Finley Woods
Property grounds

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

White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
Keystone Heights
9.6 out of 10, Exceptional, (19 reviews)
"Awesome location, great cabin! Had everything I needed to see my family ❤️ Will request to stay again!"
United States
Bonnie
$176 nightly
The price is $196
Jul 26 - Jul 27
Total with taxes and fees
White Sands Lake 2-bedroom Cottage, Sleeps 6, Kayaks/Fishing
Terrace/patio

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

Fish from own dock or in Palatka, Visit Ocala National Forest, FU Gators 30+ min
Hawthorne
10.0 out of 10, Exceptional, (21 reviews)
"Fantastic stay. Wonderful location for fishing in many of the lakes nearby. Well equipped property and great communication with the owner. Will likely be back next year!"
United States
Kellie S.
$253 nightly
The price is $278
Jul 25 - Jul 26
Total with taxes and fees
Fish from own dock or in Palatka, Visit Ocala National Forest, FU Gators 30+ min
Interior

Pet friendly 1bd/1b unit with living space and full kitchen

Pet friendly 1bd/1b unit with living space and full kitchen
Gainesville
9.0 out of 10, Wonderful, (31 reviews)
"Great spot and super close to everything. Would definitely stay here again."
United States
Emma
$107 nightly
The price is $118
Aug 10 - Aug 11
Total with taxes and fees
Pet friendly 1bd/1b unit with living space and full kitchen
Interior

Orange Blossom in Historic McIntosh

Orange Blossom in Historic McIntosh
McIntosh
10.0 out of 10, Exceptional, (109 reviews)
"Great cottage very comfortable and quiet. neighborhood is quaint and fun to walk around. Owners are very nice and close if issues arrive."
United States
Judy I.
$205 nightly
The price is $226
Jul 26 - Jul 27
Total with taxes and fees
Orange Blossom in Historic McIntosh
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

La Quinta by Wyndham Gainesville

La Quinta by Wyndham Gainesville

10/10 Excellent
"Hotel is clean, the staff is very friendly and the location is very convenient."
Rayner 1-night trip
Posted 1 hour ago
La Quinta by Wyndham Gainesville

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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 vacation rentals in Windsor?

Yes, you can find vacation rentals close to popular sights in Windsor, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Windsor?

5BR UF Family Retreat with Private Pool, Pond, Game Room – Sleeps 10: This vacation home rental outside of Windsor is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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 larger area.

What are vacation rentals like in Windsor?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.